Inside the Machine

A Coach’s Guide to Selling to Organizations

Corey Stewart

2025

Inside the Machine

1. Inside the Machine

2. Introduction

3. Chapter 1: Why coaches fail in organizations

1. The gap between coaching skill and organizational know-how

2. Common ways coaches fail (and why)

3. What this book is (and isn’t)

4. How to use this book

5. A note on complexity

4. Chapter 2: Decoding the Org Chart - Where Do People Functions Live?

1. The Chief People Officer Universe

2. The Two Core Functions You Need to Understand

3. Talent Management: The People Lifecycle

4. Organizational Development: The System’s Health

5. How TM and OD Relate (And Compete)

6. Common Organizational Structures

7. Who Else Sits in the People Organization?

8. Variations by Company Size

9. Variations by Industry

10. Practical Exercise: Map an Organization

11. Key Takeaways

5. Chapter 3: Adjacent territory, the functions that influence people decisions

1. The misconception: “It’s an HR decision”

2. Finance: the gatekeepers of budget

3. Legal: the risk assessors

4. Procurement: the process police

5. Business unit leaders: the actual customers

6. IT and Security: sometimes relevant, sometimes not

7. Executive leadership: the strategic arbiters

8. The stakeholder web: how these functions interact

9. Practical strategies for navigating the ecosystem

6. How money flows

1. The fundamental truth about organizational budgets

2. Budget planning: when money gets allocated

3. Types of budgets: where money lives

4. Decision rights: who can actually say “yes”

5. Common budget scenarios and how to navigate them

6. Budget timing strategy: when to engage

7. Procurement and RFPs

8. Budget red flags: when to walk away

7. Chapter 5: The buyer landscape

1. The fundamental question: who has the problem and the budget?

2. The buyer spectrum

3. The CHRO

4. Business unit leaders

5. The VP of talent management

6. The VP of organizational development

7. Heads of learning and leadership development

8. The CEO and executive team

9. Individual executives and HRBPs

10. Project sponsors

11. When there are multiple buyers

12. Figuring out who you’re actually talking to

8. Reading the signals: when organizations need coaching

1. Why signals matter more than outreach volume

2. Rapid company growth

3. New CEO or executive leadership

4. Organizational restructuring

5. Mergers and acquisitions

6. Retention, engagement, and leadership pipeline gaps

7. Culture transformation initiatives

8. Digital transformation and technology adoption

9. Geographic or market expansion

10. Performance issues and business struggles

11. Leadership failures and scandals

12. Regulatory or compliance pressure

13. Combining signals: where the real opportunities live

14. Monitoring for signals

15. Responding to signals

16. Signal timing

9. The wrong door problem

1. Why this happens

2. How to recognize you’re at the wrong door

3. Finding the right door

4. Navigating organizational politics without overstepping

5. Common wrong door scenarios

6. Using LinkedIn to find decision-makers

7. When you’re internal

10. Positioning your coaching beyond “coaching services”

1. The positioning formula

2. Why generic positioning doesn’t work

3. Choosing your buyer

4. Naming the outcome

5. Adding context

6. Putting it together

7. Before and after

8. Testing your positioning

9. Common positioning mistakes

10. Evolving your positioning

11. Applying your positioning

11. The language of impact

1. The translation that matters

2. The “so what?” test

3. The metrics buyers actually care about

4. How to measure

5. Build measurement in from the start

6. Communicating impact

7. Mistakes that undermine your credibility

8. The real point

12. Scoping the work

1. Is coaching the right intervention?

2. Five diagnostic questions

3. Scoping different types of coaching

4. The scoping conversation

5. Thinking beyond coaching

6. When to say no

13. The proposal that gets approved

1. What a proposal actually does

2. The approval journey

3. Proposal structure

4. What not to include

5. Pricing strategy

6. Common objections and how to address them

7. Following up after you send the proposal

14. Delivering excellence

1. The core tension

2. What organizations expect

3. The quality bar

4. Handling difficult situations

5. Common mistakes

6. Building long-term relationships

15. The invisible coach problem

1. Why coaching stays invisible

2. What’s at stake

3. Translate impact into business language

4. Aggregate and anonymize

5. Client testimonials

6. Quarterly impact reports

7. Connect coaching to strategic priorities

8. Other approaches worth using

9. Visibility mistakes to avoid

10. The long game

11. Internal versus external coaches

16. From project to program

1. Why pilots die (even successful ones)

2. Before the pilot

3. During the pilot

4. After the pilot

5. What makes programs stick

6. From program to institution

17. Surviving reorgs, budget cuts, and leadership changes

1. Organizations are always changing

2. Reading the signals

3. Be valuable during the transition

4. Diversify your stakeholder relationships

5. Know when to hold on and when to let go

6. Four coaches, four disruptions

7. From stability to adaptability

18. Expanding your scope

1. The altitude ladder

2. Why coaches get stuck

3. Developing pattern recognition and business acumen

4. Building strategic relationships and offering insights

5. Asking for and delivering at bigger scope

6. Common mistakes

7. How long this takes

8. Internal versus external coaches

19. The business cycle and your coaching practice

1. Coaching is pro-cyclical

2. Why coaching gets cut early

3. Reading the signals

4. Diversify your client base

5. Position for essentials, not discretionary

6. Build financial reserves

7. Positioning across the cycle

8. Coaches through economic cycles

9. The quarterly organizational calendar

20. Building a sustainable practice

1. The reality of what you’re building

2. Business models

3. The build phases

4. Getting and keeping clients

5. Operations basics

6. Common pitfalls

21. Expanding coaching inside your organization

1. The challenges of being internal

2. The growth path

3. Strategies for expanding influence

4. Common pitfalls

5. Special situations

6. Career progression examples

22. When organizations get coaching wrong

1. How organizations get coaching wrong

2. How to course-correct

3. When to walk away

4. Coaches navigating dysfunction

5. Conclusion

1. Title Page

2. Table of Contents

Inside the Machine

Copyright © 2026 by Corey Stewart

All rights reserved. No part of this book may be reproduced in any form or by any electronic or mechanical means, including information storage and retrieval systems, without permission in writing from the author, except by a reviewer who may quote brief passages in a review.

First Edition

Published by Most Learned, LLC

For Caitlin,

who has never once questioned

why I need to start another random project.

Introduction

I spent over a decade building out talent management and organizational development functions at a large North American company. That experience showed me how organizations really work, not the neat org charts in presentations, but the messy reality of where budgets live, who controls decisions, and how things actually get done. I designed competency models and leadership programs, managed succession planning and talent reviews, restructured reporting lines, launched performance management systems, and sat through more budget cycles and stakeholder meetings than I can count.

Later, I joined the International Coaching Federation to start up the Coaching in Organizations business unit. Working with companies of all sizes, across industries, meant helping them think through how to structure and fund coaching initiatives. I got to see firsthand how organizations build internal coaching programs and turn coaching into something more than a perk for senior leaders.

What I kept seeing was the same pattern: both internal and external coaches struggled to navigate organizations. Talented, experienced coaches would get stuck at the wrong door, pitch to the wrong person, or speak the wrong language. They’d frame their work in ways that made perfect sense to other coaches but landed flat with business leaders. They’d get excited about a potential partnership, only to watch it die in budget planning because they didn’t understand the funding cycles.

The coaches who succeeded weren’t necessarily better at coaching. They were better at understanding how organizations work. They knew where talent management and organizational development sat in the structure. They understood the difference between operating budgets and discretionary funds. They could translate “this will build self-awareness” into “this addresses retention risk in our leadership pipeline.” They knew how to find the actual decision-makers, not just the friendly HR contact who took the meeting.

This book puts that organizational knowledge into a practical guide for coaches at any stage.

If you’re an external coach trying to win work with organizations, you’ll learn where budgets live, who makes decisions, and how to position your services so they actually land. If you’re an internal coach trying to expand your impact, this will help you navigate the politics and build partnerships that stick.

You don’t need an MBA or years of corporate experience. You need to understand the terrain you’re operating in. That’s what this book is for.

Chapter 1: Why coaches fail in organizations

Sarah had been coaching executives for eight years when she got the call. A Fortune 500 company wanted to explore bringing in executive coaching for their senior leadership team. The conversation went well. They loved her credentials, her approach resonated, and they asked for a proposal.

Six months later, after countless emails and three revised proposals, the project went nowhere. Sarah never quite understood what happened. The HR contact who brought her in was enthusiastic throughout. The proposal seemed solid. The pricing was competitive. But somehow, it just dissolved.

What Sarah didn’t know: her contact was an HR Business Partner with no budget authority. The actual decision-maker was the VP of Talent Development, who had already committed that year’s coaching budget to a different vendor. The HRBP genuinely believed the proposal would get approved. She just didn’t understand her own organization’s decision-making process.

Sarah didn’t fail because her coaching was inadequate. She failed because she didn’t understand the organization she was trying to work within.

The gap between coaching skill and organizational know-how

You might be an extraordinary coach. You might have impeccable credentials, powerful testimonials, and a methodology that genuinely changes people. None of that guarantees you’ll succeed inside organizations.

Organizations aren’t just collections of individuals who need coaching. They’re systems with their own logic, language, power structures, and decision-making processes. Most coaches, even experienced ones, never learn to navigate any of this.

There’s an irony here that’s hard to ignore: coaches are trained to help individuals see systems and understand dynamics. But when it comes to the organizational systems they’re trying to work within, many coaches operate blind.

This book exists to close that gap.

Common ways coaches fail (and why)

Let’s be specific about how this plays out.

The wrong door problem

You connect with someone in HR, maybe through a referral, maybe through networking. They’re enthusiastic about coaching. You have great conversations. You send a proposal. Then nothing happens.

What you didn’t know: you were talking to someone who loves the idea but can’t buy it. They’re not the decision-maker. They don’t control the budget. They can’t make it happen, no matter how much they want to.

This happens because organizations are hierarchical and specialized. The person who recognizes the need often isn’t the person who can authorize the spend. And coaches don’t know how to identify who actually has decision-making authority.

The scope mismatch problem

An organization reaches out because they’re struggling with “leadership effectiveness.” You propose 1:1 executive coaching. They thank you and go quiet.

What you didn’t know: they wanted a solution that addressed the entire leadership team or supported a broader organizational change they were navigating. They were hoping you’d diagnose the actual need and propose the right intervention. When you defaulted to your standard offering, they concluded you couldn’t help them.

Coaches tend to propose what they already do rather than diagnosing what the situation actually requires. When you only have a hammer, everything looks like a nail. Organizations need coaches who can think beyond their own toolkit, even if that means recommending interventions outside their expertise or partnering with others to address the full scope.

The language barrier problem

You talk about “increased self-awareness,” “authentic leadership,” and “transformative conversations.” They nod politely. Your proposal emphasizes “creating space for reflection” and “deepening emotional intelligence.”

They go with a competitor who talked about “reducing time-to-productivity for new executives,” “improving retention in high-potential populations,” and “building leadership bench strength for the next phase of growth.”

Coaching language and business language are different dialects. Coaches speak in terms of process and personal growth. Organizations make decisions based on business outcomes and strategic priorities. If you can’t translate between the two, you lose deals to people who can.

The timing problem

You reach out to an organization in March with a compelling proposal. They’re interested but say the timing isn’t right. You follow up in June. Still not ready. You give up, assuming they weren’t serious.

What you didn’t know: their fiscal year runs July to June, and all training budgets were allocated the prior December. If you’d reached out in Q4, you might have gotten into the next year’s plan. By March, you were asking them to find money that had already been committed.

Coaches don’t understand organizational budget cycles and planning processes. They treat outreach as random rather than strategic.

The invisible coach problem

You’re an internal coach, hired to support leadership development. You do excellent work. Your coaching clients rave about you. But when budget cuts come, your role is eliminated.

What you didn’t know: nobody in senior leadership really understood what you did or the value you created. You were coaching individuals, but you weren’t making your impact visible at the organizational level. When they needed to cut costs, you were in the “nice to have” category.

Internal coaches focus on delivery excellence but neglect stakeholder management and internal marketing. In organizations, perception of value matters as much as actual value. If the people making budget decisions can’t articulate what you do, you’re vulnerable.

The wrong problem problem

An organization hires you to coach a struggling executive. You work with them for six months. They make progress, but the underlying performance issues persist. Your contract isn’t renewed.

What you didn’t know: the executive was struggling because of a toxic culture, impossible workload, and unclear expectations from their boss. Individual coaching couldn’t fix systemic problems. You should have diagnosed this upfront and either addressed the system or declined the engagement.

Coaches are trained to work with individuals, not to diagnose organizational systems. They take the presenting problem at face value rather than questioning whether coaching is even the right intervention.

What this book is (and isn’t)

This book is not about making you a better coach. It’s about making you organizationally literate: able to navigate corporate people functions, understand how decisions get made, speak the language of business impact, and position your work so it actually lands.

It’s written for two audiences. External coaches who want to win work inside organizations, and internal coaches who want to expand coaching’s influence within their own. The contexts are different, but the core knowledge is the same: understanding how organizations work, how decisions get made, and how coaching creates value inside them.

This book assumes you’re a competent coach with solid skills and ethics. It does not assume you have corporate experience, understand how organizations work, or speak business language fluently. If you don’t know what an HRBP is or how budget cycles work, that’s exactly why this book exists.

How to use this book

You don’t have to read it linearly.

If you’re external and trying to land your first organizational client, start with Part 2 (Finding Your Entry Point) and Part 3 (Making the Case), then circle back to Part 1 for deeper understanding.

If you’re internal and trying to expand influence, start with Part 1 (Understanding the Terrain), then Part 4 (Doing the Work and Getting Credit) and Part 5 (Navigating Change and Growing Influence).

If you’re experienced but hitting walls, skip to the specific problem you’re facing:

- Can’t find the right buyers? Chapter 7

- Proposals not converting? Chapter 11

- Work not sticking? Chapter 14

- Impact invisible? Chapter 13

Think of it as a field guide, not a textbook. You don’t need to master everything before you start. You’ll get better one interaction at a time, one conversation with a potential buyer, one proposal, one coaching engagement.

A note on complexity

Organizations are messy. Every company is different. There are exceptions to every pattern in this book.

But there are underlying structures, predictable dynamics, and common patterns. Understanding these won’t make you omniscient, but it will make you far more effective, even when the situation doesn’t perfectly match what’s described here. The goal isn’t to memorize every detail. It’s to develop pattern recognition that improves with each interaction.

Chapter 2: Decoding the Org Chart - Where Do People Functions Live?

When Maria joined a tech company as an internal coach, she spent her first month completely confused. She reported to “Talent Development,” which sat under “People Operations,” which reported to the CHRO. But when she needed to partner on a leadership program, she worked with someone in “Organizational Effectiveness,” which was a different team. When executives wanted coaching, requests came through “HR Business Partners,” who were yet another group. And learning programs were managed by “L&D,” which seemed to be different from her Talent Development team, even though both worked on development.

After three months, Maria took the company’s org chart and annotated it with who actually did what, who controlled which budgets, and how decisions really got made. It saved her countless hours of confusion and wrong conversations.

Most coaches never create this map. They operate in organizational fog, never quite understanding the terrain.

This chapter gives you that map.

The Chief People Officer Universe

In most medium-to-large organizations, there’s a C-level executive responsible for all people functions. The title varies:

- Chief Human Resources Officer (CHRO)

- Chief People Officer (CPO)

- VP of People

- VP of Human Resources

- Head of People & Culture

For simplicity, we’ll use CHRO throughout this book, but know that the function is the same regardless of title.

The CHRO typically oversees everything related to employees: hiring, development, compensation, benefits, culture, employee relations, and organizational effectiveness. Under the CHRO, you’ll find various functions organized in different ways.

There’s no single “right” structure—every company organizes differently based on size, industry, and philosophy. But there are common patterns.

The Two Core Functions You Need to Understand

Within the people organization, two functions matter most for coaches:

Talent Management (TM)

Organizational Development (OD)

Before you object that your company doesn’t have both departments: you’re probably right. Many organizations combine these functions under one team or leader. Some smaller companies don’t formally separate them at all—one person or team does both.

But understanding these as distinct conceptual approaches matters because all companies perform both types of work, even if the org chart doesn’t show it. The work exists; it’s just a question of who does it and what budget pays for it. Think of TM and OD less as departments and more as mindsets and functions that exist in every organization.

Understanding the difference is critical because:

- They have different budgets

- They buy different things

- They speak different languages

- They have different measures of success

Let’s break each one down.

Talent Management: The People Lifecycle

Core Question: How do we acquire, develop, deploy, and retain the talent we need?

Talent Management treats employees as assets that need to be strategically managed throughout their lifecycle with the organization. It’s largely transactional and process-driven.

What Talent Management Does

Talent Acquisition / Recruiting

- Finding and hiring people

- Employer branding

- Candidate experience

- Recruiting operations

Coaching connection: Sometimes coaches work on interviewing skills, hiring manager effectiveness, or onboarding. Budget owner: Talent Acquisition leader or Head of Recruiting.

Learning & Development (L&D)

- Training programs

- Skills development

- Learning platforms and content

- Training delivery (in-house or vendor-managed)

Coaching connection: This is where most coaching budgets traditionally sit. L&D often owns “leadership development,” which includes coaching. Budget owner: Head of L&D or Director of Learning.

Performance Management

- Performance review processes

- Goal-setting frameworks (OKRs, MBOs, etc.)

- Performance improvement plans

- Calibration and rating processes

Coaching connection: Coaching is often positioned as support for performance improvement or leadership effectiveness. Budget owner: Usually the CHRO or Talent Management VP directly, since it’s a company-wide process.

Succession Planning

- Identifying high-potential employees

- Creating development plans for future leaders

- Mapping talent to future organizational needs

- Leadership pipeline development

Coaching connection: High-potential programs often include executive coaching as a development tool. Budget owner: VP of Talent Management or CHRO, sometimes the CEO’s office for executive succession.

Talent Analytics

- Workforce planning

- Talent metrics and dashboards

- Predictive analytics (retention risk, promotion readiness, etc.)

- Data-driven talent decisions

Coaching connection: Rare, but coaches who can demonstrate measurable impact on talent metrics become more valuable. Budget owner: Head of People Analytics or Talent Management VP.

How Talent Management Thinks

Talent Management has a structured, pipeline-oriented mindset:

- “How do we build a pipeline of leaders for the next 5 years?”

- “What capabilities do we need to develop to execute our strategy?”

- “How do we retain our top 10% performers?”

- “What’s our bench strength for critical roles?”

They think in terms of:

- Programs (structured, repeatable, scalable)

- Cohorts (groups moving through development together)

- Capability gaps (what skills/competencies are missing)

- ROI and metrics (what’s the return on development investment)

Language they use:

- Leadership pipeline

- High-potential (HiPo)

- Talent density

- Flight risk

- Bench strength

- Development plans

- Career pathing

When they buy coaching:

- As part of leadership development programs

- For high-potential employee development

- For new executive onboarding

- For performance acceleration

- As a benefit for senior leaders

Organizational Development: The System’s Health

Core Question: How do we make the organization itself more effective, adaptable, and healthy?

OD focuses on the organization as a system. It’s more diagnostic, relational, and focused on how work gets done, not just who does it.

What Organizational Development Does

Change Management

- Supporting organizational transformations

- Change strategy and communication

- Stakeholder engagement for major initiatives

- Adoption and sustainment of change

Coaching connection: Change coaching for leaders navigating transformation, team coaching for groups going through change. Budget owner: Head of OD or Change Management, sometimes project budgets from the initiative itself.

Organizational Design / Effectiveness

- Designing org structures

- Role clarity and decision rights

- Process improvement

- Operating model design

Coaching connection: Team effectiveness coaching, helping leadership teams redesign how they work together. Budget owner: Head of OD or Organizational Effectiveness.

Culture & Engagement

- Defining and evolving culture

- Employee engagement initiatives

- Values integration

- Culture measurement (surveys, pulse checks)

Coaching connection: Leadership coaching focused on culture-building, team coaching to shift team culture. Budget owner: Head of Culture or OD leader.

Leadership Development (Sometimes)

- In some orgs, this sits in OD rather than L&D

- Focus is often more strategic/systemic than L&D’s programmatic approach

- Emphasis on leadership as a cultural capability, not just individual skill

Coaching connection: Executive and leadership team coaching, often more systemic and less programmatic than L&D coaching. Budget owner: Head of Leadership Development or OD.

How OD Thinks

OD has a systems-thinking, diagnostic mindset:

- “What’s really going on beneath the surface here?”

- “How do we shift this culture?”

- “What’s blocking this team’s effectiveness?”

- “How do we design an organization that can adapt to uncertainty?”

They think in terms of:

- Interventions (targeted actions to shift the system)

- Diagnosis (understanding root causes, not symptoms)

- Culture and dynamics (the invisible forces that shape behavior)

- Systemic change (changing patterns, not just individuals)

Language they use:

- Organizational health

- Systems thinking

- Culture change

- Psychological safety

- Team effectiveness

- Change readiness

- Org design

When they buy coaching:

- For team effectiveness and leadership team coaching

- To support major change initiatives

- For culture transformation

- For conflict resolution and team dynamics

- As part of organizational diagnostic work

How TM and OD Relate (And Compete)

In a perfect world, Talent Management and OD work seamlessly together:

- TM provides the talent, OD makes sure the system uses that talent effectively

- TM builds individual capability, OD builds organizational capability

- TM focuses on people, OD focuses on people + structure + culture

In reality, there’s often tension:

Budget competition: They’re competing for the same pool of people development dollars. When budgets are tight, TM and OD may fight over what gets funded.

Philosophical differences: TM tends to be more structured and programmatic. OD tends to be more emergent and diagnostic. They can talk past each other.

Overlapping territory: Leadership development, culture, team effectiveness—these can live in either function. Turf battles happen.

Different metrics: TM measures things like “# of high-potentials” and “training completion rates.” OD measures “engagement scores” and “change adoption.” They optimize for different outcomes.

For coaches, this means:

- Don’t assume TM and OD are aligned—they might not be

- Understand which function you’re working with and what they care about

- Be careful positioning work that could be seen as “OD work” to a TM buyer or vice versa

- Look for opportunities to bridge both (e.g., a leadership program that combines TM structure with OD systems focus)

Common Organizational Structures

Here are four common ways companies organize their people functions:

Structure 1: Separated TM and OD

CHRO

├── Talent Management

│   ├── Recruiting

│   ├── Learning & Development

│   ├── Performance Management

│   └── Succession Planning

├── Organizational Development

│   ├── Change Management

│   ├── Org Design

│   ├── Culture & Engagement

│   └── Team Effectiveness

└── HR Operations

├── Compensation & Benefits

├── HR Systems

└── Employee Relations

Characteristics:

- Clear separation between people pipeline (TM) and system health (OD)

- Usually found in larger, more mature organizations

- Coaching could be bought by either function depending on use case

Coaching implication: You need to know which function owns the problem you’re solving. Executive coaching might sit in TM, while team coaching sits in OD.

Structure 2: Combined “Talent & Development”

CHRO

├── Talent & Organizational Development

│   ├── Talent Acquisition

│   ├── Learning & Leadership Development

│   ├── Organizational Effectiveness

│   └── Change Management

└── HR Operations

├── Compensation & Benefits

├── Performance Management

└── HR Business Partners

Characteristics:

- TM and OD combined under one leader

- Common in mid-size companies (500-5000 people)

- Often there’s still internal distinction between TM and OD work

Coaching implication: Single point of contact makes buying easier, but you still need to understand which budget (TM or OD) your work comes from.

Structure 3: “People & Culture” Model

Chief People Officer

├── People Operations (HR stuff)

│   ├── Recruiting

│   ├── Comp & Benefits

│   └── HR Systems

├── People Development

│   ├── Learning & Development

│   └── Leadership Development

└── Culture & Engagement

├── Culture Programs

├── Engagement Initiatives

└── Change Management

Characteristics:

- Common in tech companies and startups

- “Culture” is elevated as strategic priority

- Less emphasis on traditional HR structures

Coaching implication: “Culture” and “People Development” are your main entry points. Coaching is often positioned as part of culture-building.

Structure 4: Distributed Model

CHRO

├── Centers of Excellence (CoE)

│   ├── Talent Acquisition CoE

│   ├── Learning & Development CoE

│   └── Total Rewards CoE

└── HR Business Partners (HRBPs)

├── HRBP for Engineering

├── HRBP for Sales

├── HRBP for Operations

└── HRBP for Corporate Functions

Characteristics:

- Large, complex organizations (often 10,000+ employees)

- Centers of Excellence own strategy and programs

- HRBPs are embedded in business units and execute locally

Coaching implication: This is the most complex structure to navigate. You might pitch to a CoE but get hired through an HRBP. Or vice versa. Understanding the interplay is critical.

Who Else Sits in the People Organization?

Beyond TM and OD, you’ll usually find:

HR Business Partners (HRBPs) - Generalists embedded in business units - Act as liaison between business leaders and HR functions - Don’t usually control budgets but have significant influence - Critical relationship for coaches because they’re close to business leaders

Compensation & Benefits - Pay structures and philosophy - Benefits design and administration - Rarely buy coaching, but sometimes care about coaching costs when budgets are tight

Employee Relations / HR Compliance - Handling employee issues, investigations, terminations - Ensuring legal compliance - Important for coaches to understand boundaries (when does coaching become an ER issue?)

People Analytics / HR Systems - HRIS and people technology - Workforce analytics and insights - Growing importance, especially for coaches who can demonstrate data-driven impact

Diversity, Equity & Inclusion (DEI) - Sometimes separate function, sometimes embedded in OD or Culture - Often buys coaching for underrepresented groups or inclusive leadership development

Variations by Company Size

The structure varies dramatically by company size:

Small companies (< 500 people):

- Might have 1-2 “HR people” who do everything

- TM and OD aren’t separated—it’s just “people stuff”

- Coaching is often bought by founders or executives directly, not formal HR

Mid-size companies (500-5000 people):

- Starting to separate TM and OD

- Might have an L&D function and someone focused on “culture”

- Coaching bought through L&D or by business unit leaders

Large companies (5000-50,000 people):

- Fully separated TM and OD functions

- Multiple layers within each

- Coaching bought through formal programs and procurement processes

Enterprise companies (50,000+ people):

- Highly complex, often with regional variations

- Centers of Excellence + HRBP model common

- Coaching might be managed by dedicated internal coaching team or vendor management function

Variations by Industry

Industry also shapes structure:

Tech companies:

- Often “People & Culture” framing

- Elevated focus on engagement and culture

- Talent density and high performance emphasized

Financial services:

- Traditional CHRO structure

- Heavy emphasis on compliance and risk

- Succession planning and leadership pipeline are critical

Manufacturing / Industrial:

- Often focus on operational excellence and safety

- TM focused on skills development and workforce planning

- OD focused on continuous improvement culture

Healthcare:

- Complex due to clinical vs. administrative tracks

- Focus on both patient outcomes and employee wellbeing

- Coaching often focused on leadership in high-stress environments

Professional services (consulting, law, etc.):

- Talent is THE business

- Heavy investment in development

- Coaching often available to all senior professionals

Practical Exercise: Map an Organization

Pick a company you’re interested in working with (or your own company if you’re internal). Use LinkedIn, the company website, and any connections you have to answer:

1. Who is the CHRO/CPO? What’s their background?

2. How are TM and OD structured? Separate? Combined? Can you find an org chart?

3. Who leads L&D? Who leads OD/Change? Who leads Culture?

4. What do their job titles tell you? “VP of Talent Development” suggests TM focus. “Head of Organizational Effectiveness” suggests OD focus.

5. How large is the company? What structure would you expect based on size?

6. What industry? How might that shape priorities?

Even partial answers to these questions put you ahead of 90% of coaches. You now know where to look and who might be relevant to your work.

Key Takeaways

- Talent Management focuses on the people lifecycle: acquiring, developing, deploying, retaining talent. It’s programmatic and process-driven.

- Organizational Development focuses on system health: culture, change, effectiveness, design. It’s diagnostic and systems-oriented.

- They have different budgets, languages, and measures of success. Coaching can be bought by either, depending on the use case.

- Structure varies by company size, industry, and philosophy. There’s no universal org chart, but there are common patterns.

- Don’t assume you know the structure. Do the research. Look at LinkedIn. Ask questions. Map the terrain before you navigate it.

In the next chapter, we’ll zoom out and look at the adjacent functions that influence people decisions—because TM and OD don’t operate in isolation. Understanding the broader ecosystem is critical for strategic navigation.

Chapter 3: Adjacent territory, the functions that influence people decisions

Marcus had finally connected with the VP of Learning & Development at a major retail company. They loved his proposal for an executive coaching program. The VP was ready to move forward. Then she said, “I just need to get Finance to approve the budget, run it by Legal for the contract terms, and make sure the business unit leaders are on board. Should be quick.”

Four months later, Marcus was still waiting.

What Marcus didn’t understand is that people decisions in organizations are rarely made by “people functions” alone. Every significant people initiative touches other parts of the organization, each with their own priorities, processes, and power to say “no.”

Most coaches focus entirely on HR, missing the broader ecosystem that shapes whether their work happens or not.

The misconception: “It’s an HR decision”

Here’s what coaches often think:

“I need to convince HR that coaching is valuable. Once they’re on board, we’re good to go.”

Here’s the reality:

HR might champion your work, but they can’t make it happen alone. Depending on the scope and cost, you might need approval or buy-in from Finance (budget approval), Legal (contract review, liability concerns), Procurement (vendor management, contracting process), business unit leaders (participation and prioritization), IT or Security (if your work involves any technology or data), and executive leadership (strategic alignment, final approval).

Each of these functions has different concerns, different decision-making authority, and different veto power.

Coaches who don’t understand this ecosystem waste months in conversations that can’t convert.

Finance: the gatekeepers of budget

Finance is where more coaching deals die than anywhere else, and most coaches never see it coming. Your HR champion can love everything about your proposal, but if Finance doesn’t approve the expense, nothing happens.

This is especially true for large contracts (typically over $100K, though thresholds vary), new budget lines for things that weren’t already planned, multi-year commitments, and anything that affects headcount or looks like “hiring.”

Finance thinks in terms of return on investment. They want to know what business outcome your coaching will create, how success gets measured, what the payback period looks like, and whether the company could get similar impact for less money. If you can’t answer those questions in their language, you’re dead on arrival.

And timing matters enormously. Finance operates on strict planning cycles. Annual budgets are typically set three to six months before the fiscal year starts. Once budgets are locked, getting new spend approved is genuinely difficult. Unspent budget at year-end often gets reallocated. The best time to pitch is during budget planning season (typically Q3 or Q4 for calendar-year companies). Mid-year budget reviews are possible if they exist. Random timing outside planning cycles is the hardest path.

Speaking Finance’s language

The single most important shift: stop talking about coaching outcomes and start talking about business outcomes.

Don’t say “this will increase self-awareness and emotional intelligence.” Do say “this addresses retention risk in our leadership pipeline, where replacement costs average $250K per executive.”

It also helps to understand the different budget types. Operating budget (OpEx) covers ongoing expenses and is easier to get approved for programs. Capital budget (CapEx) covers investments in assets and rarely applies to coaching. Discretionary budget is flexible money for strategic initiatives, the easiest to access but limited. And department budgets belong to business units directly, sometimes making them easier to tap than the central HR budget.

Reading the signals from Finance

When Finance tells you “we don’t have budget for this,” they’re really saying it’s not in the plan and they’re not adjusting. “What’s the ROI?” means they want hard business outcomes, not soft skills development. “Can we do a pilot first?” means they’re not confident in the value and want proof at a small scale before committing. And “can this wait until next fiscal year?” means it’s simply not a priority right now. None of these are necessarily a “no forever,” but each requires a different response.

Who to know in Finance

The CFO has ultimate budget authority but is rarely involved in coaching decisions unless the engagement is large. The FP&A team (Financial Planning and Analysis) builds and manages budgets, making them a key relationship for understanding budget cycles. Finance Business Partners are like HRBPs but for finance, embedded in business units, and they can help you find budget pathways that aren’t obvious from the outside. The Controller manages accounting and financial controls but is less relevant for coaching decisions.

Legal: the risk assessors

Every external coaching engagement requires a contract, and Legal reviews every contract. They’re looking at liability and indemnification (who’s responsible if something goes wrong), confidentiality and data privacy (how coaching data is protected), termination clauses, and standard terms and conditions for consistency with company policies.

Legal also worries about scope boundaries. Is this coaching or therapy? If coaches exceed scope, there’s liability. They care about confidentiality: what can and can’t be shared, and when confidentiality must be broken. If coaching surfaces performance problems, what are the legal obligations? And for EU companies especially, how is coaching data stored and protected under GDPR?

Legal often sets the rules for required vendor insurance, background checks for coaches, contract approval thresholds, and vendor onboarding requirements.

How to navigate Legal

The best approach is to anticipate their concerns before they raise them. Be clear about coaching vs. therapy boundaries, have solid confidentiality protocols, carry appropriate insurance (E&O, professional liability), and be prepared to sign standard agreements or negotiate specific clauses.

What slows Legal down is custom contract terms (they prefer standard agreements), unusual liability provisions, vague scope of work (they want clear boundaries), and missing insurance or certifications.

You can speed up the process by asking HR what Legal typically needs and getting ahead of it. Use standard contract templates when possible. Highlight your professional credentials and insurance. Be responsive to contract redlines.

When Legal says “we need to review your contract,” expect two to eight weeks depending on their backlog. “We can’t accept this liability clause” means negotiations are ahead, so be prepared to compromise. If they ask whether you have professional liability insurance and you don’t, that might be a deal-breaker. And if they need background checks on all coaches, that’s standard in many industries; build it into your timeline.

Your main point of contact will usually be the contracts team that handles vendor agreements. The Associate General Counsel often reviews coaching contracts. The General Counsel is rarely involved unless it’s a major engagement. Employment lawyers sometimes weigh in on coaching-related employee issues.

Procurement: the process police

Procurement (also called “Purchasing” or “Vendor Management”) handles vendor selection, onboarding, contract negotiations, compliance, spend management, and RFP processes. In larger companies, you can’t just “start working.” You must register as a vendor in their system, provide business documentation (W-9, insurance certificates, etc.), sometimes go through diversity certification, and accept their vendor terms and conditions.

Many companies have spend thresholds that determine who gets involved. Below $25K, a business unit can often approve directly. Between $25K and $100K typically requires procurement involvement. Above $100K, a formal RFP process may be required.

Some organizations maintain “preferred vendor” lists for coaching. If you’re not on the list, you face an uphill battle. And for large engagements, Procurement may require a formal Request for Proposal where multiple vendors compete against structured evaluation criteria on long timelines (three to six months is not unusual), with the process often prioritizing price over relationship.

How to navigate Procurement

The most important thing to understand: Procurement doesn’t decide if you get hired, they manage how. They’re not the enemy. They’re following process to protect the company, and they care about cost, compliance, and risk, not coaching quality.

Play by their rules. If there’s a vendor registration process, do it early. If they ask for documentation, provide it immediately. If there’s an RFP, participate professionally (or know when to skip it).

Some coaches proactively reach out to Procurement before they need anything: “I work with a lot of companies in your industry. What’s your process for bringing on coaching vendors?” This prevents surprises later and builds goodwill.

It’s also worth knowing when Procurement doesn’t apply. Very small engagements often don’t trigger their involvement. Executive discretionary spending sometimes bypasses them. Strategic consulting (vs. training services) sometimes falls outside Procurement’s scope entirely.

When Procurement tells you “you’ll need to go through our RFP process,” expect a three to six month timeline where your existing relationship matters less than your proposal. “We need you in our vendor system before we can pay you” can take two to four weeks, so plan accordingly. “What’s your best and final pricing?” means they’re negotiating, so have your floor price ready. And if they need diversity certifications, that’s common in large companies and can slow things down if you don’t have them.

The Category Managers who own specific spend categories like “Professional Services” or “Training” are your key relationship if coaching falls in their domain. Procurement Analysts process vendor onboarding and contracts and are worth building relationships with. The Chief Procurement Officer sets policies but is rarely involved in coaching decisions.

Business unit leaders: the actual customers

This is the section most coaches skip, and it’s the one that matters most after Finance.

Business unit leaders run the parts of the company that make money or deliver services. We’re talking about the VP of Sales or Chief Revenue Officer, the VP of Engineering or CTO, the COO or VP of Operations, the Chief Product Officer, the CMO, and other functional leaders. These are the people who actually experience the impact of your coaching, or don’t.

HR might buy coaching, but business leaders are usually the ones who nominate people for it, approve participation time, determine if it’s working based on performance changes, and decide whether it’s worth scaling. They are your real customers even when they’re not your buyer.

They also control discretionary budget. Many large companies have central HR budgets for standard programs, but business units have their own money for team-specific development, executive coaching for their teams, and custom interventions. A savvy VP might hire a coach directly from their department budget, avoiding HR processes altogether. When this happens, it’s often the fastest path to getting work.

Why business leaders are skeptical of coaches

Business leaders care about business outcomes, not development for its own sake. They’re time-constrained and operationally focused. They want practical solutions that create fast impact. They don’t care about your coaching methodology unless it connects to results.

This means you need to translate everything into their world. Don’t talk about “transformative conversations” and “authentic leadership.” Talk about “accelerating time-to-impact for new leaders” and “improving team performance.” The language shift isn’t cosmetic. It’s the difference between getting a meeting and getting ignored.

Recognize what they’re dealing with. They can’t afford to have their people spending hours in coaching if it doesn’t yield business results. They’re judged on quarterly and annual performance, not long-term development. Many of them have been burned by “HR initiatives” that felt disconnected from business reality. Your job is to show you understand their business challenges, connect coaching to their specific priorities (revenue, retention, product delivery, operational excellence), and deliver visible results quickly. They need wins to keep supporting the work.

Reading the signals from business leaders

When a business leader says “this sounds great, but my team doesn’t have time,” they don’t see the value as worth the time investment. You haven’t connected it to something they care about yet. “Can HR figure this out and let me know?” means they’re delegating because it’s not a priority for them, which is a bad sign. “Let’s start with a pilot for a few people” means they’re testing whether this actually works, which is actually a reasonable response you should welcome. And “what will this do for our Q3 results?” tells you they need immediate business impact, not long-term development promises.

Who to know

This varies by company, but typically you want relationships with C-level executives (CEO, CFO, CTO, COO, CMO), SVPs and VPs who lead major business units or functions, and Directors who run teams or departments. Directors are often the first level where coaching is seriously considered.

IT and Security: sometimes relevant, sometimes not

Most coaches doing straightforward one-on-one coaching with no technology platform won’t encounter IT or Security at all. But if your coaching involves a platform or app, video conferencing tools outside the company-approved list, assessment tools that collect employee data, or any system that touches employee information, you may trigger their involvement.

When they do get involved, they’ll want to know how coaching data is stored, where servers are located (especially for EU companies under GDPR), who has access, and how data is encrypted. Some companies require security reviews for any vendor handling employee data, which can take four to eight weeks and can be a deal-breaker if your tools don’t meet their standards.

The practical advice here is simple: know your data security practices, understand where your data is stored and how it’s protected, and have documentation ready. If IT tells you they need to do a security review, add four to eight weeks to your timeline. If your tool isn’t on their approved list, you might need to use theirs instead.

Executive leadership: the strategic arbiters

The CEO, executive team (direct reports to CEO), and occasionally the Board of Directors matter for coaching when the initiative is large enough to require strategic alignment or significant budget approval.

Large-scale coaching initiatives need executive sponsorship. Executives are asking whether this aligns with strategic priorities, whether it’s the best use of resources, and whether it supports where the company is trying to go. Very large contracts (thresholds vary from $250K to $1M or more) often need executive sign-off, as do multi-year commitments.

There’s also a cultural dimension. If the CEO gets coached, coaching becomes high-status. If executives don’t participate, coaching can feel remedial.

How to navigate executive leadership

You usually don’t start here, except when you’re doing executive coaching for the CEO or their direct reports. For broader programs, you typically work through HR, who brings it to executives.

Executives have very limited time and attention. They need crisp, clear business cases. They won’t dive into operational details. They care about strategic impact, cultural transformation, leadership capability, and risk mitigation. And they’re often swayed by external benchmarks: “what are our competitors doing?”

When an executive says “let’s see how the pilot goes,” they’re not fully convinced, so your job is to prove it works. “Is this really the priority right now?” is a strategic alignment question, and they’re skeptical. “What are other companies doing?” means they’re looking for external validation before committing.

The stakeholder web: how these functions interact

Here’s what a real engagement looks like when all these functions come into play.

Say you’re proposing a $200K executive coaching program for 30 high-potential leaders. HR and L&D champion the program, believe in the value, and want to move forward. So far so good.

Then Finance asks for an ROI analysis. They note that $200K is above the discretionary spending threshold and require a budget justification showing impact on retention and the leadership pipeline. Meanwhile, Legal is reviewing your coaching agreement, pushing back on your confidentiality clause because they want reporting on high-risk situations, and requiring proof of professional liability insurance.

Procurement requires you to enter their vendor system and asks for competitive pricing from two other coaching firms. They also want payment terms changed from upfront to milestone-based. Three VPs whose teams will participate need to approve: one is enthusiastic, one is neutral, one is skeptical (“we have business goals to hit, is this the right time?”). Your coaching platform needs a security review from IT because it stores employee assessment data, which takes six weeks and requires changes to your data storage approach. And the CFO must sign off because it’s over $100K, while the CEO wants to see how this connects to the company’s “Future of Leadership” initiative announced last quarter.

Each of these stakeholders can slow things down or kill the deal. Coaches who only focus on HR often get blindsided.

Practical strategies for navigating the ecosystem

Map the stakeholders early

When you first connect with HR, ask: “Who else needs to be involved in this decision?” and “What’s your typical approval process for something like this?” Ask whether there are budget thresholds that trigger additional approvals and whether Legal or Procurement needs to be involved. The answers to these questions will save you months of confusion later.

Build your business case for multiple audiences

Your proposal needs to resonate with HR (development impact, employee experience), Finance (ROI, cost-effectiveness, measurable outcomes), business leaders (business results, performance improvement, strategic alignment), and executives (strategic importance, competitive positioning, culture impact). Don’t write one flat proposal. Write one proposal with sections tailored to different audiences.

Anticipate and accelerate process steps

If you know Legal review takes four weeks, Procurement onboarding takes two weeks, and IT security review takes six weeks, build that into your timeline and proposal. Better yet, offer to do some of that work upfront: “I’ve attached our standard coaching agreement in case Legal wants to review early” or “I can start the vendor registration process now while we finalize the scope.”

Find champions in adjacent functions

Don’t only build relationships in HR. Cultivate Finance Business Partners who can help navigate budget approval, Procurement Category Managers who can smooth vendor processes, and Business Unit Leaders who can advocate for the work.

Understand where the real decision power sits

Sometimes HR “owns” coaching but doesn’t control the budget. Sometimes Finance can block even if HR loves it. Sometimes an executive champion can override the procurement process. Ask questions to understand: “Who has the final say on this?” and “What would cause this to not get approved?”

Know when you’re stuck in process vs. stuck in a decision

There’s an important difference between process delays and decision delays. “We’re waiting for Legal review” means the timeline is extended but the decision is still yes. “We’re still evaluating whether this is the right approach” means the decision itself is uncertain. Process delays are frustrating but manageable. Decision delays require you to re-sell the value.

The coaches who consistently land organizational work aren’t necessarily better coaches than the ones who don’t. They’re the ones who understand that HR is a champion, not a sole decision-maker, and who treat Finance, Legal, Procurement, and business leaders as part of the same sale. If you can map the stakeholders early, speak each function’s language, and build your timeline around the process rather than fighting it, you’ll stop getting stuck in those endless “we’re interested but…” conversations.

How money flows

Jennifer spent two months refining her coaching proposal. The Head of Leadership Development loved it. The pricing was competitive. The program design was solid. Then, in their final meeting before she thought she’d get a contract, he said: “This is great. I just need to find the budget for it. Let me get back to you.”

Six months later, no budget had been found. The work never happened.

Jennifer made the most common mistake coaches make: she assumed that enthusiasm equals buying power. She never asked the critical question that would have saved her months of wasted effort: “Do you have budget for this, and when would it need to be allocated?”

This chapter is about the thing that determines whether coaching work actually happens: money. How organizations budget for people development, when those decisions get made, and who actually has authority to spend.

The fundamental truth about organizational budgets

Here’s what you need to understand: organizations don’t have “money.” They have budgets, which are pre-allocated pools of money designated for specific purposes, managed by specific people, released at specific times, governed by specific approval processes.

The money exists. But whether you can access it depends on whether there’s a budget line for what you do, when that budget was allocated, who controls it, whether they have spending authority, and what approval process governs it.

Coaches who don’t understand this operate in a fantasy where “if they like my work, they’ll find a way to pay for it.”

That’s not how it works.

Budget planning: when money gets allocated

Most organizations plan budgets annually, following a process that looks roughly like this.

The annual budget cycle

In Q3 of the prior year (July through September), finance sets budget guidelines for the next fiscal year. Business units submit budget requests. People functions like HR, L&D, and OD submit their budget proposals. Strategic initiatives get funding priority.

In Q4 (October through December), budget negotiations happen as requests get weighed against available funds. Tradeoffs get made: this program yes, that program no. The CFO and executive team give final budget approval, and the budget locks for the next year.

When Q1 of the current year arrives (January through March), budget execution begins. Departments start spending against their allocated budget. Changes at this point are difficult because they require re-approval.

Some companies do a mid-year budget review around June or July, which creates an opportunity to adjust for the second half of the year, but typically only for strategic shifts or major changes.

Then year-end (October through December) brings the “use it or lose it” mentality, since unspent budget often gets reallocated. There’s a rush to spend remaining budget before the fiscal year closes. And at the same time, planning for next year’s budget has already begun.

What this means for coaches

The best time to influence budget is Q3 and Q4 of the prior year, when next year’s budget is being planned. If you want to be in someone’s 2027 budget, you need to be in conversations by Q3 2026.

The hardest time to get budget is Q1 and Q2 of the current year, after budget is locked. You’re now asking them to “find” money that’s already been allocated to other things. There are possible windows (mid-year budget reviews, discretionary budget that wasn’t pre-allocated, year-end surplus spending), but they’re narrow.

Here’s the painful reality: if you show up in March asking to be hired in April, and they don’t already have budget for coaching, you’re probably out of luck until the following fiscal year. That’s why so many “interested” conversations go nowhere.

Variations by fiscal year

Not all companies follow a January-through-December calendar year. Retail companies often run February to January to avoid the holiday season. Education typically follows the academic year, July to June. Government and public sector organizations often use October to September (the US federal fiscal year). Many tech companies do follow the calendar year.

Always ask: “When does your fiscal year start?” This tells you when budget planning happens.

Types of budgets: where money lives

Organizations don’t have one big pot of money. They have many different budget pools, each with different rules.

Operating budgets

Operating budgets (OpEx) cover day-to-day operational expenses: programs, services, ongoing costs. This is the largest pool of money for people development, and it’s where most coaching budgets come from. L&D has an operating budget, OD has one, and so do individual business units like Sales and Engineering.

Operating budget is spent throughout the year and is relatively easier to access compared to other budget types. Approval usually follows threshold rules. A department head might be able to approve up to $50K without escalation, for example. If your coaching engagement falls under that threshold, you may only need one person to say yes.

This is the budget type you’ll encounter most often, so understand how it works at your target organizations. When someone says “we have budget for coaching,” they almost always mean operating budget.

Project budgets

Project budgets are where the big opportunities live. When an organization launches a major strategic initiative (a digital transformation, an M&A integration, a culture change program, a reorganization), that initiative gets its own dedicated budget, often substantial. Large transformations can have millions in budget, and that money is managed separately from ongoing operational budgets.

What makes project budgets so valuable for coaches is that they’re cross-functional. They’re not trapped inside HR. A project sponsor at the executive level controls the budget, with a dedicated project manager handling day-to-day allocation. If you can position coaching as essential to the success of a major initiative, you’re accessing money that was never part of the L&D budget at all.

The key is finding these projects. Watch for company announcements, reorganizations, leadership changes, mergers. Then connect with the project sponsors and make the case that coaching supports the transition.

Discretionary and uncommitted budget

Some budget exists but hasn’t been pre-allocated to specific programs. Executives often hold these discretionary pools for strategic opportunities that come up during the year. The pools are typically smaller, but they’re flexible and can be accessed outside normal budget cycles.

This is where you can sometimes get work when you’ve missed the budget cycle. But you need access to the senior leaders (VPs, C-level) who control that discretionary money. The approval process is often just a single person, which can make things move fast if you have the relationship.

Departmental budgets

Individual departments (Sales, Engineering, Marketing) often have their own development budgets, managed locally rather than centrally by HR. Many coaches successfully bypass HR entirely by working directly with business unit leaders who have their own money for team development. The approval sits with the department head, sometimes with HR notification but not always HR involvement.

Capital budgets and executive development funds

Capital budgets (CapEx) cover investments in assets with multi-year value: buildings, equipment, major IT systems. They rarely apply to coaching unless you’re building a coaching platform or major infrastructure, so you can mostly ignore them.

On the smaller end, many organizations allocate individual development budgets to executives, often $5K to $25K per person per year for coaching, conferences, and courses. The executive decides and expenses it, so approval is minimal. These are great for getting your foot in the door or building testimonials, but they won’t scale to larger programs.

Decision rights: who can actually say “yes”

Here’s the brutal truth: enthusiasm doesn’t equal authority.

Someone can love your proposal, champion your work, and genuinely want to hire you. But if they don’t have spending authority, none of that matters.

Spending authority thresholds

Most organizations have approval thresholds like this (amounts vary):

Amount

Who Can Approve

Under $5K

Department manager

$5K - $25K

Director or department head

$25K - $100K

VP or functional leader

$100K - $500K

C-level executive (CHRO, CFO, etc.)

Over $500K

CEO or executive team

These are illustrative; your target company might have different thresholds. But the principle is universal: the larger the spend, the higher the approval authority required.

Budget holders vs. recommenders

This distinction is where coaches lose months of their lives. Pay attention.

Budget holders are people who control a budget line and can authorize spending from it. The VP of Learning and Development with a $2M L&D budget. The VP of Sales with a departmental development budget. The CHRO with strategic people initiatives budget. These people can say yes and make it stick.

Recommenders are people who can advocate for spending but don’t control the budget. HR Business Partners almost never have budget authority. Neither do program managers in L&D, internal OD consultants, or many directors and senior managers. They can champion your work internally, and that’s valuable, but they cannot sign a purchase order.

The mistake coaches make, over and over, is spending months cultivating a recommender while thinking they’re talking to the decision-maker. You have wonderful meetings. You refine the proposal. You go back and forth on scope. And then one day your contact says, “I just need to get my VP to approve the budget,” and you realize you’ve been selling to someone who was never going to buy. You could have been in front of the actual budget holder three months ago.

How to identify who has authority

Ask these questions tactfully. You can be direct: “Do you have budget allocated for this type of work?” or “What’s the approval process for bringing in external coaches?” or “Who would need to sign off on a project like this?”

If direct feels too blunt for the relationship, go indirect: “How have you typically hired coaches in the past?” or “When you’ve done similar work, what was the process?” or “Who else should be part of this conversation?”

Then watch for the signals. “I’ll need to check with [name]” means they’re not the decision-maker. “Let me see if I can find budget” means they don’t currently have allocated budget. “I’ll have to get approval from [name]” means there’s someone above them with actual authority. And “I can approve up to $X, anything beyond that needs…” is them telling you their threshold directly.

Common budget scenarios and how to navigate them

“We don’t have budget for this”

This can mean several things. Maybe they didn’t plan for coaching and the budget is fully allocated. Maybe there’s no budget in this specific bucket but money exists elsewhere. Maybe they’re not convinced of the value enough to reallocate. Or maybe it’s a polite no.

Your job is to figure out which one. Ask when they typically plan budget for next year, so you can time your follow-up. Ask whether other budget sources could cover it, like project budgets or department budgets. Float the idea of a smaller pilot that might fall under a lower approval threshold. And offer to stay in touch and reconnect during budget planning season.

What you shouldn’t do: push aggressively, offer huge discounts out of desperation, or assume they’re lying. Sometimes there really is no budget. Respect that and play the long game.

“Let me see if I can find budget”

This one is tricky. They might have discretionary funds they could tap. They might try to get budget reallocated, which is hard but possible. Or they might be kicking the can down the road, and this will never happen.

Ask for a realistic timeline. Offer to help make the case with ROI data or case studies. And whatever you do, set a specific follow-up date. Don’t leave it open-ended. “Should I check back in two weeks?” gives both of you a deadline.

“This will come out of the Q3 discretionary budget”

This is actually a good signal because they’ve identified a specific budget source. Discretionary means it’s flexible but probably limited, so ask how much is typically available and whether other priorities are competing for the same pool. Your work is competing with other initiatives for that discretionary money, so help them understand why coaching should win.

“We have budget, but we need to go through procurement”

Budget exists, which is great. But the process will be slow. Ask about the typical procurement timeline and what documentation they’ll need from you. Offer to start the vendor registration process immediately. Procurement can add four to eight weeks to your timeline. Don’t fight it, just plan for it. (Chapter 3 covers procurement processes in detail.)

“We can do a small pilot first”

They’re interested but not fully convinced, and they want proof of value before committing to a larger investment. This is reasonable. Embrace it.

The key is designing the pilot strategically. Define clear success metrics upfront, before you start. Ask what the path to scaling looks like if the pilot goes well. Make sure the pilot is large enough to show real impact but small enough to be approvable at a lower budget threshold. And make sure the metrics are actually achievable. If you accept vague success criteria, you’re setting yourself up for “the pilot didn’t prove enough value” no matter what happens.

Budget timing strategy: when to engage

There are four basic approaches to budget timing, and the right one depends on the size of what you’re selling and where you are in the relationship.

Get in the budget

This is the most reliable approach for large programs, ongoing coaching, or anything requiring significant budget allocation. The tradeoff is that it requires patience: you need to engage six to nine months before you want to start work.

The rhythm goes like this. In Q3 of the prior year, you begin conversations and build relationships. During Q3 and Q4, you share your proposal while budget planning is active. In Q4, you help them make the case internally for the budget. By Q1 of the current year, budget is approved and contracting begins. Work starts in Q2.

To make this work, you need to be building credibility (through articles, talks, referrals) well ahead of budget season. You need to be networking to find companies that are in budget planning mode. And you need to be willing to help build the business case for their internal budget request. That’s not free work; it’s investment in a relationship that leads to a signed contract.

Tap discretionary budget

This is real-time and opportunistic. It works for smaller engagements, quick-start projects, and individual executive coaching. The approach is straightforward: identify decision-makers who control discretionary budget (VPs, executives), build the relationship, and when an opportunity surfaces, move fast. Have a proposal ready in days, not weeks. Deliver results that justify future budget allocation.

The work you do between opportunities matters. Stay visible through networking, referrals, and thought leadership. Be top-of-mind when a need arises.

Attach to a project budget

When a company announces a major initiative (a reorg, an acquisition, a digital transformation, a culture change), there’s project budget attached to it. Monitor company announcements through press releases, LinkedIn, and earnings calls. Build relationships with change management and transformation teams. Develop clear “coaching for change” offerings so you can position coaching as essential to the project’s success, not a nice-to-have.

Project budgets can be substantial, and they’re often controlled by executive sponsors outside of HR. This is where coaching work can scale quickly.

Catch year-end surplus

In Q4 of the fiscal year (October through December for most companies), organizations often have surplus budget they need to spend before the fiscal year closes. The “use it or lose it” mentality makes people more willing to try new things.

Time your outreach for Q4. Have proposals ready to go with no long discovery process. Emphasize fast starts and quick wins. The goal isn’t just to land the year-end work; it’s to deliver enough value that you get written into next year’s budget.

Procurement and RFPs

Chapter 3 covers the mechanics of how organizations buy (vendor registration, legal review, purchase orders, and the rest of it). The short version: small purchases under $25K take one to four weeks, medium purchases up to $100K take four to eight weeks, and anything over $100K can take three to six months. Plan your timeline accordingly and start vendor registration early.

What’s worth adding here is guidance on RFPs, which come up specifically when budget is large enough to require a competitive process.

Should you respond to an RFP?

For large engagements, organizations often issue formal RFPs. The process (from RFP issued to contract signed) takes three to four months minimum, and writing a quality response takes real time. So be selective.

Respond if you have an existing relationship and know you’re a strong contender, the scope genuinely fits your expertise, you have time to craft a quality response, and the contract size justifies the effort. A good rule of thumb: only respond if the potential contract value is more than ten times the time you’ll invest in the response.

Skip it if you’ve never talked to the organization before. You’re likely “RFP fill,” meaning they need a minimum number of vendors to satisfy procurement policy but have already chosen someone. Also skip if the RFP is extremely detailed and prescriptive (often means the same thing), the scope doesn’t fit your expertise, or you don’t have relationships inside the organization. Cold RFP responses almost never win.

Budget red flags: when to walk away

Sometimes the budget situation is telling you the deal won’t happen, and the best thing you can do is stop investing time.

If someone says “we’re very interested, but we don’t have budget and won’t for the foreseeable future,” that’s a polite no. They like you. They can’t or won’t find money. Thank them, stay in touch, and move on.

If you’re being asked to do extensive free work to “build the business case” for budget, be careful. It’s reasonable to share a sample ROI analysis or some case studies. It’s not reasonable to do weeks of unpaid consulting so they can justify the investment to their boss. That’s their job, not yours. Offer limited help and draw the line.

If you’ve been having budget conversations for six months or more with no progress, there’s either no budget or no real commitment. Set a deadline. “I need to know by [date] if this is moving forward. If not, let’s reconnect next budget cycle.” This isn’t aggressive; it’s respectful of both your time and theirs.

Watch for budgets that keep shrinking through negotiation. If the number keeps getting smaller, they’re either not sold on the value or they genuinely can’t afford you. Decide your minimum viable engagement and stick to it. Below that number, you’re better off walking away.

And be especially wary of “we’ll find budget if the pilot works” when the success metrics for the pilot are vague. That’s a setup. If they won’t define what success looks like before you start, you’ll never be able to prove you achieved it. Insist on clear criteria upfront. If they won’t commit to that, don’t do the pilot.

Understanding how money flows through organizations, when it’s allocated, who controls it, and how decisions get made, is the difference between coaches who consistently land work and those who are perpetually “in conversations that go nowhere.” The single most important habit you can build is asking, early and directly, whether budget exists and who controls it. Everything else follows from that.

Chapter 5: The buyer landscape

Tom had been coaching for fifteen years, mostly working with individual clients who found him through referrals. When he decided to expand into organizational work, he assumed the buyer would be “HR.” He spent months networking with HR professionals, building relationships with HRBPs and recruiters.

After a year of effort, he’d landed exactly zero organizational coaching contracts.

What Tom didn’t understand: “HR” isn’t a buyer. HR is a category containing dozens of different roles, each with different priorities, different budgets, and different reasons for hiring coaches. The CHRO buys coaching for completely different reasons than a Learning & Development manager. An HRBP has different needs than an Organizational Development consultant.

And sometimes, the real buyer isn’t in HR at all. It’s a business unit leader, a CEO, or a board member.

This chapter maps the buyer landscape: who actually hires coaches, what each buyer cares about, what authority they have, and how to recognize which buyer you’re talking to.

The fundamental question: who has the problem and the budget?

In organizations, coaching gets bought when two conditions align: someone has a problem that coaching could solve, and that someone has budget and authority to hire coaches. Miss either condition, and you don’t have a buyer.

The mistake coaches make is finding someone with the problem but no budget, or someone with budget but no compelling problem. You need both. Let’s map who has what.

The buyer spectrum

Buyers exist on a spectrum from strategic to tactical. At the strategic end, you have the CHRO, VP of Talent Management, VP of Organizational Development, and the CEO or executive team. These buyers move slowly, work with large budgets, and think in terms of systems and long-term organizational capability. A coaching engagement sold to a strategic buyer will take months to close but could be worth hundreds of thousands of dollars.

In the middle, you have heads of Learning & Development and Leadership Development, along with directors in talent management and OD. They have moderate budgets, moderate speed, and tend to think programmatically. They’re looking for coaching that fits into an existing architecture of development programs.

At the tactical end are business unit leaders, individual executives buying coaching for themselves, HRBPs, and project sponsors. These buyers move fast, work with smaller budgets, and care about solving a specific, concrete problem. You can close a deal with a tactical buyer in a week, but the engagement will typically be smaller in scope.

Each buyer type operates differently. Let’s look at the ones that matter most.

The CHRO

If you want to build a substantial coaching practice inside organizations, the CHRO (or Chief People Officer) is the buyer you most need to understand. This is the person who thinks about the entire people strategy. They care about organizational capability for the future, leadership pipeline and succession, culture and engagement, and how all of it aligns to business strategy.

CHROs hire coaches for executive coaching at the C-suite level, leadership team coaching, strategic culture transformation, supporting major organizational change, and sometimes building internal coaching capability. Their budgets are large, often $500K or more for people initiatives, and they can frequently access CEO or board-level budget for executive coaching.

Selling to a CHRO requires patience. They are slow and deliberate. They need a strong business case and strategic rationale. They’re concerned about scalability and sustainability, and they want proof of impact. What gets a CHRO to say yes is alignment to company strategy, executive sponsorship or board interest, competitive intelligence (“our competitors are doing this”), clear ROI, and a proven track record with similar companies. What makes them pass is anything that doesn’t feel strategically important right now, or anything where the ROI isn’t convincing.

The most common mistake coaches make with CHROs is leading with their coaching methodology. CHROs don’t care about your model or your certification. They care about business impact and strategic outcomes. Reference work with similar companies. Demonstrate that you understand their industry and its challenges. If you sound like a coach selling coaching, you’ve already lost. You need to sound like a strategic partner who happens to use coaching as the delivery mechanism.

To reach CHROs, you need referrals from other CHROs or executives, visibility at CHRO-level events, thought leadership that demonstrates strategic thinking, or board-level connections. Cold outreach almost never works at this level.

Watch for these signals that a CHRO isn’t actually going to buy. “Let me think about it,” repeated over months, means this isn’t a real priority. “Talk to my team and they’ll figure it out” means they’re delegating, which tells you they don’t see this as strategic enough to own personally. “We’re focused on other initiatives right now” is a polite no.

Business unit leaders

Business unit leaders (VPs, directors running a function or division) are the other buyer type you need to deeply understand, because they buy coaching for fundamentally different reasons than HR leaders do, and the sales process is completely different.

A business unit leader cares about one thing: their team’s performance and results. They want to develop their direct reports, fix team dynamics, address specific people challenges, and hit their business goals. They’re pragmatic, results-oriented, and impatient. They don’t want to hear about coaching philosophy. They want to know: can you help, how fast, and what will it cost?

Business unit leaders often have discretionary development budgets in the range of $25K to $100K or more, and they can sometimes approve spending quickly without going through HR. This is one of their great advantages as buyers. Where a CHRO engagement might take six months to close, a business unit leader might say yes in a single meeting if you’ve demonstrated that you understand their problem and can solve it.

What makes them say yes: clear business outcomes relevant to their goals, the ability to start quickly, trust that you can deliver, reasonable cost, and (this is critical) not requiring tons of their time. That last point trips up many coaches. Business leaders are busy. If your engagement design requires extensive meetings with the sponsor, lengthy intake processes, and elaborate reporting, you’ll lose them. Make it easy.

What makes them say no: too expensive for the perceived value, too slow to start, requires too much of their involvement, or they simply don’t trust that you can deliver.

The best way to reach business unit leaders is through referrals from people they trust (peers, their direct reports, other vendors they work with), introductions from HRBPs, or networking in their industry. When you do connect, lead with business outcomes rather than coaching process. Show that you understand their business and their industry. Be fast, responsive, and flexible.

Two red flags to watch for. “HR usually handles this” means they’re delegating to HR, which turns a fast process into a slow one and may mean the leader isn’t invested enough to make the engagement work. “I don’t have budget but I’m sure we can find it” sounds optimistic but often means they don’t actually have access to budget for this.

The VP of talent management

The VP of Talent Management thinks programmatically. They care about leadership pipeline, high-potential development, succession planning, talent retention, and capability building at scale. When they hire coaches, it’s usually for HiPo development programs, leadership development cohorts, new leader acceleration, or retention of critical talent.

Their budgets range from $200K to over $1M depending on company size. They can usually approve up to a certain threshold without CHRO sign-off. But their decision-making style is fundamentally different from a business unit leader’s. They think in cohorts, curricula, and scalable systems. They’re metrics-focused (completion rates, satisfaction scores, promotion velocity). They’re risk-averse and will often require a pilot before scaling.

What gets a VP of Talent to say yes is a clear tie to talent metrics, a scalable approach that isn’t just boutique executive coaching, fit within their existing development architecture, measurable outcomes, and competitive pricing. They will pass if your approach doesn’t scale, can’t be measured, doesn’t fit with existing programs, or if the budget is already allocated for the year.

The teams that report to them (talent management directors, program managers) are often the people you’ll actually work with day-to-day. These directors have smaller budgets, typically $25K to $150K, and more limited authority. They’re tactical and program-focused, budget-conscious, and they value responsiveness and flexibility. When a director says “I love this but I’ll need to get approval,” and says it more than once, that’s a signal they don’t have real authority. You may need to help them build the internal business case for their VP.

To reach VPs of Talent, attend talent development conferences, build your presence on LinkedIn with relevant content, share case studies from similar companies, or get referrals from vendors they already work with.

Here are the red flags that tell you something is off with a talent management buyer. “We need you to fix our underperformers” means they think coaching is remedial performance management rather than development. You need to clarify that distinction early or you’ll end up in an impossible engagement. “We’ll need weekly reports on what each person is working on in their sessions” means they don’t understand confidentiality boundaries, and you need to establish those upfront before signing anything. “What’s your per-coach hourly rate?” with no other questions means they’re price shopping and don’t care much about the relationship or business impact. You can still win that work, but know what you’re walking into.

The VP of organizational development

The VP of OD thinks differently from everyone else on this list. As we covered in Chapters 2 and 3, OD professionals think in systems. They care about organizational effectiveness, culture, change management, team dynamics, leadership team effectiveness, and strategic organizational design. When they hire coaches, it’s for team coaching, change coaching, culture change interventions, conflict resolution, and executive team effectiveness.

Their budgets are moderate, typically $100K to $500K, and often tied to specific strategic initiatives. They may also have access to project budgets for large organizational changes.

Selling to a VP of OD requires demonstrating that you think systemically. They use a diagnostic approach and want to understand root causes before designing interventions. They value customization over standard programs, and depth over scale. If you pitch them a standard coaching package, they’ll lose interest. If you talk about diagnosing the organizational dynamics first and co-designing an intervention, you’ll have their attention.

Their teams (OD directors, change management leads) are often doing the hands-on work of organizational change. These team members can be a path to the VP, and they’re worth building relationships with in their own right.

Two red flags worth noting. “The last three coaches we hired couldn’t help us” suggests a pattern. It might mean the organization has systemic issues that no coach can solve, or expectations that are simply unrealistic. Proceed with caution. “Just so you know, the leadership team doesn’t know they’re getting coaching yet” means you’re walking into an ambush. The participants will resist, and you’ll be the one dealing with it.

Reach OD buyers through OD networks and conferences (the OD Network, NTL, and similar communities), by publishing in OD-focused venues, through referrals from other OD practitioners, or by demonstrating systems thinking in your thought leadership.

Heads of learning and leadership development

In many organizations, the Head of Learning & Development and the Head of Leadership Development are either the same role or adjacent roles that overlap significantly. Both care about developing people at scale, both think programmatically, and both buy coaching as a component of broader development initiatives.

The L&D-focused buyer thinks about learning programs, skills development, learning platforms, and training ROI. They buy coaching as part of blended learning, manager development, or new leader onboarding. Their budgets typically run $50K to $300K. The leadership development buyer is more focused on leadership capability, leadership pipeline, and succession readiness, with budgets of $100K to $500K that sometimes overlap with talent management.

Both types are programmatic and structured in their decision-making. They want clear outcomes, scalable delivery, measurable results, and reasonable cost relative to other options. They need coaching to fit within an existing architecture. If you can integrate with their LMS or platform, demonstrate clear learning outcomes, and show cost-effectiveness compared to other development modalities, you’re in good shape.

Watch for scope creep with these buyers. “Can you also facilitate our leadership offsite as part of this?” is a classic attempt to get extra work without additional budget. And “We need three coaching sessions to complete the certification program” tells you they see coaching as a compliance checkbox rather than genuine development. You can still do the work, but know that the engagement will feel more like a delivery contract than a coaching relationship.

The CEO and executive team

CEOs hire coaches for themselves (executive coaching), for their leadership team, as a strategic thinking partner, for support during major transformation or crisis, and for succession planning. They can access large budgets, often $100K to $500K or more, and can find budget even outside formal planning cycles. CEO coaching sometimes comes from the board’s budget.

The sales process with a CEO is unlike any other buyer. It’s fast when they want something, driven entirely by relationship and trust, and involves very little formal process. They value confidentiality and discretion above almost everything else. What gets them to say yes is personal connection, credibility through track record and reputation, understanding of their industry, and sometimes external validation from the board or investors. What turns them off is feeling “pitched” rather than understood.

You reach CEOs through referrals from other CEOs or board members, executive peer networks (YPO, EO, Vistage), board connections, or introductions from investors and advisors.

Two red flags. “We’re probably getting acquired but need to show we’re investing in development” means you’re window dressing for a deal. The program will die after the acquisition closes. And “Don’t document anything from the sessions, we need this completely off the record” is a serious ethical and political risk. Someone is asking you to be part of something they don’t want documented. Think carefully before accepting.

Individual executives and HRBPs

Individual executives buying coaching for themselves are covered in earlier chapters, but the key point for the buyer landscape is simple: chemistry is everything. They decide fast if they like you, they pay from personal development budgets ($5K to $50K) or sometimes their own funds, and they find you through referrals and reputation. Be a thinking partner, not a service provider.

HRBPs, as we discussed in Chapter 2, are connectors more than buyers. They usually have limited or no budget of their own and need to get funding from the business unit or central HR. Their value is as an introduction to the real buyer, not as a buyer themselves. If an HRBP says “Let’s get started and I’ll figure out the approval later,” that’s a red flag. They’re going rogue without real buy-in from above. If they say “I need to check with several people,” that confirms they don’t have authority. Work with HRBPs as allies, but always identify who actually controls the budget.

Project sponsors

Project sponsors are a special case worth knowing about. When an organization is going through a major initiative (a reorg, transformation, M&A integration, or culture change), there’s usually a project sponsor with a substantial budget. These project budgets can be large, sometimes $500K to $5M or more, and they often include budget for change management and enablement that coaching fits within.

Project sponsors are outcome-focused and timeline-driven. They care about whether coaching will contribute to project success, whether you can start quickly and align with the project timeline, and whether you have a track record with similar projects. They’re less concerned about methodology.

Frame coaching as change enablement rather than development. Align to their project success metrics. Be responsive to their timeline.

If they say “We’re still scoping the project,” that means it’s premature. They don’t know what they need yet, and you’ll waste time trying to sell something when the requirements haven’t been defined. If they say “We have change management covered,” they may not see coaching as adding value beyond what their change consultants already provide.

When there are multiple buyers

In practice, large coaching initiatives rarely have a single buyer. You’ll often need multiple people to say yes, and understanding how these multi-stakeholder decisions work is one of the most important skills for selling coaching to organizations.

Here’s what this looks like in practice. A CHRO champions a coaching program, but still needs the CFO to approve the budget, business unit leaders to buy in on participation, and board awareness if it involves executive coaching. Or a VP of Talent wants to launch a coaching program, but needs strategic approval from the CHRO, budget sign-off from Finance, and vendor management through Procurement (we covered what Finance and Procurement care about in Chapter 3). Or a business unit leader wants coaching for their team, but needs the HRBP to coordinate, HR or OD to partner on delivery, and sometimes the CHRO to be aware.

The way to navigate these situations is straightforward, even if it takes patience. Map all the stakeholders early. The single most useful question you can ask is “Who else needs to be part of this decision?” Understand what each stakeholder cares about, because the CFO’s concerns are completely different from the CHRO’s. Tailor your messaging accordingly. And find the champion, the person who will orchestrate the others through the decision process. Without a champion, multi-buyer deals stall.

You don’t need to sell to every stakeholder yourself. Your champion will often handle the internal selling. But you do need to arm them with the right arguments for each audience, and you need to be available when a skeptical stakeholder asks to meet you directly.

Figuring out who you’re actually talking to

When you’re in a conversation with someone about coaching and you’re not sure whether they’re a real buyer, there are a few categories of questions to work through in your own head (or, when appropriate, to ask directly).

On the budget side: do they control a budget line for development or coaching? What’s their spending authority threshold? Has this year’s budget already been allocated? Do they have discretionary funds? If the answers are unclear or negative, you may be talking to an influencer rather than a buyer.

On authority: can they approve this directly, or do they need permission? Who else needs to say yes? What’s the approval process? Have they hired coaches before, and if so, what did that process look like? Someone who has bought coaching before and has the authority to do it again is your ideal buyer. Someone who has never done it and isn’t sure how it would work is going to take much longer to close.

On problem ownership: is this their problem to solve, or someone else’s? How urgent is it to them? What happens if they don’t solve it? Are they measured on this outcome? A buyer who personally owns the problem and will be judged on the result is far more motivated than someone doing a favor for a colleague.

On coaching readiness: have they bought coaching before? Do they understand how coaching works? Do they have realistic expectations? Can they manage and support the engagement? Buyers who are new to coaching need more education up front, which isn’t necessarily a dealbreaker, but it does change the sales process.

If you’re talking to someone who doesn’t control budget, doesn’t have authority, doesn’t own the problem, and hasn’t bought coaching before, you probably don’t have a real buyer yet. That doesn’t mean the conversation is wasted. They might connect you to the real buyer. But don’t invest months cultivating a relationship with someone who can’t actually say yes.

The buyer landscape is more complex than most coaches realize when they first start selling to organizations. But the complexity is manageable once you learn to quickly assess who you’re talking to, what they care about, and whether they have the authority and budget to act. The profiles in this chapter will look different at every company, and titles alone are unreliable. Pay attention to the signals, ask the right questions, and you’ll figure out who the real buyer is faster than you expect.

Reading the signals: when organizations need coaching

Elena had been cold-emailing companies for months with her coaching services. Her emails were professional, her credentials strong, but her response rate was dismal. Most emails went unanswered. Those that got replies were polite variations of “not right now.”

Then she changed her approach. Instead of blasting generic outreach, she started monitoring companies for specific signals: leadership changes announced on LinkedIn, transformation initiatives mentioned in earnings calls, funding rounds reported in tech news. When she saw these signals, she reached out with specific, relevant messages: “I saw you just appointed a new CTO. I work with technology leaders navigating their first 90 days…”

Her response rate tripled, and she started landing conversations that converted into engagements.

The lesson: coaching isn’t always needed. It’s needed at specific moments when organizations face specific challenges. Learning to read these signals is the difference between random outreach and strategic positioning.

Why signals matter more than outreach volume

Organizations don’t hire coaches because coaching is nice. They hire coaches when they’re experiencing pain that needs to be addressed, or when they see an opportunity they want to capitalize on, and coaching feels like the right intervention. Your job is to recognize these moments and position yourself accordingly.

The signals that indicate coaching need fall into three broad categories. Growth signals appear when an organization is expanding and that expansion strains leadership capacity. Change signals show up when the organization is transforming, because transformation creates coaching needs at every level. And crisis signals emerge when the organization is struggling, which creates urgency around leadership support.

Let’s look at the signals that matter most, starting with the ones that consistently produce the best coaching opportunities.

Rapid company growth

This is the single most reliable signal for coaching work. When a company’s headcount is increasing 30% or more year over year, when they’re opening new locations, closing funding rounds, or preparing for an IPO, leadership development needs multiply faster than the organization can fill them.

Here’s why. The people who built the company from ten to fifty employees are suddenly managing managers. The founder who was brilliant at product is now supposed to run a 200-person organization. New executives hired from the outside need to onboard into a culture they didn’t build. The leadership team that used to fit around a conference table now needs to function at a completely different level of complexity. And the culture that made the company special is at risk of diluting with every new hire.

The buyers in these situations are usually the CHRO (if they have one yet), the CEO or founders directly, or the VP of People or Talent. Sometimes it’s an individual executive who’s privately struggling with the jump from “doing the work” to “leading the people who do the work.”

You can spot rapid growth through funding announcements on Crunchbase or TechCrunch, LinkedIn hiring patterns (watch for clusters of new roles posted in a short window), company press releases, and earnings calls that mention “significant growth” or “scaling.”

When you see this, your outreach might sound like: “I noticed [Company] just raised a Series C and is expanding rapidly. I work with high-growth companies helping new executives accelerate their impact and leadership teams scale effectively. Would it make sense to explore how coaching could support your growth?”

The positioning that lands here centers on scaling leadership capacity for growth, accelerating new leader effectiveness, executive team alignment during hyper-growth, and preserving culture while scaling.

New CEO or executive leadership

A leadership change at the top is one of the clearest, most time-sensitive signals you’ll find. When a company announces a new CEO, CTO, COO, or other C-level executive, coaching needs emerge on multiple fronts.

The new executive needs support navigating their first 90 days. The leadership team needs to gel around a new leader with a different style and different expectations. The people reporting to the new executive need coaching to adapt. And in the case of a new CEO, the board often sponsors coaching directly because they want to protect their leadership investment.

What makes this signal so valuable is the timing pressure. New executives are most open to coaching support early in their tenure, when they’re still forming their approach and building relationships. After six months, they’ve settled into patterns (good or bad) and the window narrows. Reach out within the first 30 days if you can.

You’ll find these signals through press releases, LinkedIn job changes, industry news, and board announcements. The buyers are the board of directors (for CEO coaching), the CEO (for executive team coaching), the CHRO (for new executive onboarding support), and sometimes the new executive themselves.

Your outreach here should be direct and congratulatory: “Congratulations on your new role as [title] at [Company]. The first 90 days are critical, and I work with executives navigating significant leadership transitions. Would you be open to a brief conversation about how coaching could support your success?”

Organizational restructuring

Reorgs are messy, and they create coaching needs at every level. When a company announces restructuring, department mergers or splits, new operating models, or significant role changes, people throughout the organization are suddenly doing jobs they didn’t sign up for, reporting to people they don’t know, and working in structures they don’t yet understand.

Leaders need to navigate new roles and responsibilities. Teams are forming and reforming. People are adapting to new managers. Anxiety and uncertainty run high. All of this is coaching territory.

The buyers tend to be VPs of Organizational Development, change management teams, business unit leaders directly affected by the reorg, and the CHRO. You’ll spot these signals in company announcements, LinkedIn posts from employees about “exciting changes” (a reliable euphemism), news articles about reorgs, and earnings calls mentioning “organizational simplification” or “efficiency initiatives.”

Your outreach should acknowledge the complexity: “I saw [Company] announced a significant restructuring. Reorgs are challenging, and I work with leaders and teams navigating these transitions. I’d be happy to share what’s worked for other organizations going through similar changes.”

Mergers and acquisitions

M&A creates some of the richest, most complex coaching engagements you’ll find. The integration of two leadership teams, two cultures, two sets of expectations, and two groups of people who may not have chosen to work together is a challenge that lasts months or years.

Leaders from the acquired company often need support processing what amounts to a career-level disruption. Retained talent is at flight risk. The newly combined leadership team needs alignment. And whoever is running the integration is managing a level of complexity that few leaders have experienced before.

The buyers here include integration leaders, the CHRO, business unit leaders, and (increasingly) private equity firms that recognize coaching as an integration accelerator. You’ll find M&A signals through press releases, SEC filings, industry news, and private equity portfolio announcements.

The best window for outreach is 30 to 90 days post-announcement, when integration planning is underway but before things get chaotic. Your message might be: “Congratulations on the [acquisition/merger]. Integration is complex, and I work with leadership teams navigating post-M&A dynamics. I’ve supported several companies through similar integrations and would be happy to share what worked.”

Retention, engagement, and leadership pipeline gaps

These two signals are closely related and often show up together. When an organization has high turnover, poor Glassdoor reviews mentioning burnout or bad management, engagement survey results that are driving urgent action, or difficulty recruiting and retaining talent, there’s almost always a leadership effectiveness problem underneath.

Similarly, when you see a company promoting lots of people into leadership roles, posting many manager and director positions, frequently hiring senior leaders externally (because they can’t develop them internally), or publishing blog posts about “building our leadership team,” the pipeline is thin and they know it.

The common thread is that people leave managers, not companies. Coaching that improves manager effectiveness directly addresses retention. And coaching that accelerates first-time managers directly addresses pipeline gaps.

These signals tend to be slower-burning than a new CEO appointment or an M&A announcement. They’re “ongoing cultivation” opportunities rather than “respond this week” opportunities. You build relationships, share relevant thinking, and position yourself so that when budget is allocated for a development initiative, you’re already in the conversation.

The buyers are the CHRO, VP of Talent Management, VP of People, and business unit leaders dealing with the problem directly. You can monitor for these signals through Glassdoor review patterns, LinkedIn (watch for clusters of people leaving the same company), industry reports on turnover, and company announcements about engagement initiatives.

When you reach out, keep it observational rather than diagnostic: “I noticed [Company] has had some turnover in [department/level]. Retention often comes down to manager effectiveness and development opportunities. I work with organizations using coaching to address these issues. Would it make sense to explore?”

Culture transformation initiatives

When a company announces a culture change, values refresh, inclusion initiative, or responds to poor engagement survey results with a transformation effort, coaching is a natural fit. Culture changes through behavior, behavior changes through leaders, and leaders change through coaching.

The buyers are usually the VP of Culture (or Chief Culture Officer), VP of Organizational Development, CHRO, or Chief Diversity Officer. You’ll see these signals in company blog posts about culture, DEI reports and announcements, Glassdoor review patterns, and awards or recognition for culture initiatives.

Your outreach might sound like: “I saw [Company]’s announcement about your culture transformation initiative. Culture change happens through leadership behavior change, and I work with leaders developing the capabilities your new culture requires. Would you like to discuss how coaching could support this?”

Digital transformation and technology adoption

When companies announce major technology implementations, “digital transformation” initiatives, AI adoption, or shifts to new ways of working like agile or DevOps, leaders often need to lead differently than they have before. The technical change is usually well-managed; the human change is where things break down.

Buyers here include the Chief Digital Officer or CTO, VP of Organizational Development, change management teams, and project sponsors. You’ll find these signals in company announcements, job postings for “Digital Transformation” roles, earnings calls mentioning technology investments, and industry conferences.

Geographic or market expansion

When companies open offices in new cities or countries, enter new markets, or internationalize operations, leaders who’ve never managed distributed teams suddenly need to do so. Cultural complexity, matrix structures, and integration challenges all create coaching needs. Watch for company press releases about expansion, job postings in new locations, and news about entering new markets.

Performance issues and business struggles

This is real but sensitive territory. Declining revenue, layoffs, hiring freezes, earnings misses, executive departures, and negative press all signal that coaching could help, particularly around turnaround leadership, performing under pressure, and addressing leadership gaps.

But approach with care. Companies in crisis are sensitive, and appearing opportunistic will burn bridges you’ll never rebuild. Often the best approach is to wait for stabilization (a new leader in place, restructuring decisions made) rather than reaching out mid-crisis. When you do reach out, frame it as support: “I know [Company] is navigating some challenging times. I’ve worked with leaders in similar situations, and coaching can be valuable during turnarounds. If executive support would be helpful, I’d be glad to share what’s worked elsewhere.”

The buyers in turnaround situations are typically the CEO or board, the CHRO, new executives brought in to fix problems, and sometimes private equity firms or activist investors.

Leadership failures and scandals

Executive misconduct, toxic leadership issues gone public, harassment cases, ethics violations: these all create coaching needs around remediation, rebuilding credibility, addressing systemic issues, and culture repair. The buyers are usually the board, the CHRO, sometimes General Counsel, and the new CEO brought in to clean up.

But here’s the thing: this is almost never a cold outreach opportunity. Don’t reach out proactively when you see a company in the news for a leadership scandal. It reads as ambulance-chasing regardless of your intentions. This is referral territory. If you’re contacted, position as confidential support for leadership development. If you’re not contacted, let it go.

Regulatory or compliance pressure

New regulations, compliance failures, governance changes, and risk management initiatives can create coaching needs around decision-making in regulated environments, building compliance culture, and ethics leadership. The buyers are typically the Chief Compliance Officer, General Counsel, Chief Risk Officer, or CHRO. Watch industry news, company announcements about compliance, and regulatory filings.

Combining signals: where the real opportunities live

Everything above describes individual signals. But the most powerful coaching opportunities almost always involve multiple signals appearing at the same company at the same time. This is where pattern recognition becomes your greatest asset.

Consider a tech company that just closed a Series C, hired a new CTO, and is posting openings for 100 engineers. Each of those signals alone suggests a coaching need. Together, they paint a vivid picture: this company is scaling fast, has a new technology leader who needs to hit the ground running, and is about to onboard a wave of new people who will need managers who don’t exist yet. The opportunity here isn’t just executive coaching for the CTO. It’s CTO coaching plus team coaching for the engineering leadership team plus a leadership development program for the new managers they’re about to promote.

Or take a retail company with declining sales that just brought in a new CEO and announced a culture transformation. That’s turnaround pressure plus leadership change plus a strategic culture initiative. The CEO needs coaching. The executive team needs team coaching. Leaders throughout the organization need support modeling the new culture while delivering results under pressure.

A professional services firm that just completed an acquisition, is dealing with integration challenges, and is seeing retention concerns among key talent is sitting on a different kind of compound need. Integration coaching for the combined leadership team, retention-focused coaching for leaders they can’t afford to lose, and alignment work for the newly merged entity.

A healthcare company facing new regulations while simultaneously going through a digital transformation and experiencing executive turnover is dealing with overlapping complexity that no single intervention can address. Coaching for the new executives, support for leaders navigating both the regulatory and technology changes, and team coaching for the groups trying to hold it all together.

A financial services firm that just went through a public compliance failure, brought in a new Chief Risk Officer, and launched a “culture of accountability” initiative needs coaching at multiple levels: for the new CRO, for leaders who need to change their behavior, and for teams rebuilding trust with regulators and the public.

When you see multiple signals converging, the need for coaching is amplified, the budget is more likely to be available, and your pitch becomes more compelling because you can address the full picture rather than a single symptom. Train yourself to look for clusters, not isolated events.

Monitoring for signals

The signals above are only useful if you actually see them. That means building a monitoring system that surfaces relevant information without consuming your entire week.

LinkedIn is your most versatile tool. Follow your target companies, set alerts for leadership changes, monitor job postings for hiring patterns (a burst of manager-level postings tells you something different than a burst of individual contributor roles), and watch for company updates about growth or change.

Google Alerts are simple and effective. Set them up for your target company names combined with terms like “funding,” “CEO,” “reorg,” “transformation,” “layoffs,” and “acquisition.” Do the same at the industry level: your industry plus “leadership,” “change,” or “growth.”

Industry publications and news sources matter too. Subscribe to the ones relevant to your target sectors, set up RSS feeds for key topics, and follow industry analysts and journalists who break news early.

If you work with public companies, earnings calls and investor relations pages are gold mines. Read the transcripts (available on company IR sites or Seeking Alpha) and listen for mentions of “leadership development,” “culture,” “transformation,” and “growth.” These are signals that rarely show up in press releases.

Crunchbase and similar funding databases let you track funding rounds, monitor M&A activity, and follow company growth metrics for private companies.

Glassdoor and company review sites reveal patterns that indicate leadership or culture issues. Watch for sharp declines in ratings, which often signal a crisis in progress.

And don’t underestimate your network. Stay connected with people inside target organizations. Cultivate relationships with HR business partners, talent leaders, and consultants who see signals before they become public. The best coaching opportunities often come through people who spotted a need early and thought of you.

Responding to signals

When you spot a signal, the question is what to do with it. Here’s a practical sequence that takes about an hour or two per signal, which is far more efficient than random outreach.

Start by spending a few minutes assessing the opportunity. Is this a signal that genuinely indicates a coaching need? Who’s the likely buyer? Do you have relevant experience and credibility for this particular situation?

If it passes that filter, spend 15 to 30 minutes researching the context. What else is happening at this company? Are there other signals you missed? Who are the key leaders involved? Do you have any connections, even indirect ones?

Then craft your outreach, which should take about 15 minutes. Reference the specific signal. Connect it to coaching value. Personalize it to the individual you’re reaching out to.

Next, find the right contact. Use LinkedIn to identify the likely buyer. Look for mutual connections who could make an introduction. Research the best channel to reach them.

Finally, reach out quickly, ideally the same day or the next. Timing matters. A signal that was fresh and relevant on Monday becomes stale by Friday, and someone else may have already made the call.

Signal timing

Not all signals call for the same response speed. Some demand that you move within days. Others require patience.

New executive appointments, funding announcements, and M&A announcements are immediate-response signals. The window is one to seven days. These are time-sensitive because the organizational moment passes quickly and other coaches are watching for the same signals.

Organizational restructuring, culture initiatives, and significant growth indicators call for a quick response within two to four weeks. There’s urgency, but the organization needs a moment to absorb the change before they’re ready for outside support.

Crisis situations and major transformations require patience, often one to three months. Wait for stabilization. Wait for a new leader to be in place or for the planning phase to begin. Reaching out mid-chaos rarely produces good conversations.

Retention and engagement issues, leadership pipeline gaps, and general growth patterns are ongoing cultivation opportunities. There’s no single moment to respond, so instead you build the relationship over time and stay visible so that when budget appears, you’re already known.

The key is matching your response to the signal. Don’t rush in too early (they’re not ready) or too late (someone else already got the meeting).

Learning to read these signals changes your entire approach to business development. Instead of hoping someone needs you, you know when they need you and why. Instead of generic outreach that gets ignored, you send specific, timely messages that start real conversations. It takes discipline to build the monitoring habits and patience to wait for the right moments. But once you do, you’ll never go back to cold emailing into the void.

The wrong door problem

Rachel had finally gotten a meeting with someone at her dream client, a major financial services firm. The HR Business Partner she met with was enthusiastic. They had three conversations, shared a detailed proposal, and the HRBP seemed confident it would move forward.

Four months later, Rachel was still waiting. The HRBP kept saying “we’re working on it,” but nothing was happening. Eventually, Rachel learned the truth: the HRBP had no budget authority, no decision-making power, and had been trying (unsuccessfully) to convince others to approve the work.

Rachel had knocked on the wrong door.

This is one of the most common, and most frustrating, problems coaches face. You connect with someone who genuinely likes your work, wants to help, and tries to make it happen. But they simply don’t have the authority or budget to buy coaching.

Why this happens

You meet people through networking, referrals, LinkedIn, and conferences. These people tend to be junior to mid-level HR professionals, HRBPs, program managers in L&D, individual contributors in OD. They’re accessible, they respond to outreach, and they’re interested in coaching. But they can’t buy it. The actual decision-makers (VPs, CHROs, executive leaders) are harder to reach. They don’t attend the same networking events. They’re not as responsive to cold outreach. They’re busy. So coaches naturally gravitate toward accessible people, not necessarily the right people.

It gets worse when you do reach a senior leader, because they often delegate. “Talk to my HR team, they handle coaching.” “Connect with our Learning & Development director.” “Reach out to our HRBP for that business unit.” This feels like progress, but it’s usually misdirection to a non-decision-maker. The senior leader is too busy to engage, not personally interested, or (rarely) genuinely delegating to someone who can move things forward.

And as we covered in earlier chapters, organizations are complex. The person with the title that sounds like they should buy coaching might not actually have that authority. The org chart doesn’t always reveal who really makes decisions. You can’t always tell from the outside who the real buyer is.

How to recognize you’re at the wrong door

The clearest sign is when every conversation ends with “I’ll need to check with my boss” or “Let me run this by [name].” Once or twice is normal. But if you’re three meetings in and they’re still checking with someone else before anything can move, you’re talking to a recommender, not a decider.

Closely related: “Let me see if I can find budget.” When someone says they need to find budget, it means they don’t control a budget line for this work. They’re trying to cobble together money from somewhere, and that rarely works. Now, if they have a specific plan (“I’m going to request discretionary funding from my VP next quarter”), that’s different. But vague promises to “find” money are a red flag.

Watch for the conversation loop. You have the same conversation multiple times. You provide information they’ve already asked for. New stakeholders keep appearing who need to be convinced. Timelines keep slipping: “Let me get back to you in two weeks,” repeated every two weeks for months. When this happens, they’re either stuck in their own organization or they don’t have a clear path to approval.

Another telltale sign is enthusiasm paired with vagueness about process. “I love this! Let me figure out how we’d do this.” “We definitely need this. I just need to understand how procurement works here.” If someone doesn’t know the buying process, they probably haven’t bought services like yours before, which means they probably don’t have the authority to do so now. In smaller or less formal organizations this matters less, but in large established companies, not knowing the process is a giveaway.

Pay attention to titles, but don’t trust them blindly. “HR Business Partner” sounds senior but often comes with limited authority. “Senior” anything could mean senior individual contributor, not manager. “Program Manager” means they manage programs, not that they buy them. “Consultant” or “Advisor” (internal ones) often don’t have budget. And the reverse is also true: sometimes VPs don’t have authority and sometimes Directors do. Title alone won’t tell you everything, so ask about their spending authority directly (tactfully) or about their role in procurement.

Finally, beware the endless “socializing.” When someone keeps saying they need to socialize your proposal internally, build support, share it with a few people, they don’t have unilateral authority. They’re trying to build consensus from the bottom of a long chain. In highly matrixed or consensus-driven organizations, socializing is genuinely part of the process. But if it goes on for months with no progress, you’re stuck.

Finding the right door

Ask direct questions early

This is the single most important thing you can do, and most coaches avoid it because it feels awkward. Early in your conversations, ask about budget: “Do you have budget allocated for coaching?” “What’s your budget planning process like?” Ask about authority: “What’s the typical approval process for bringing in external coaches?” “Who would need to sign off on something like this?” “Have you hired coaches before? What was that process like?” And ask about timeline: “If we were to move forward, what are the steps between us talking and actually starting work?”

These questions feel blunt, but they’re respectful of everyone’s time. They help you quickly identify whether you’re talking to a decision-maker or a recommender. And they signal that you understand how organizations work, which actually builds credibility.

Ask to be introduced up

If you realize you’re talking to a non-decision-maker, ask to be introduced to the person who does have authority. You can do this tactfully: “This sounds like it would need [VP’s] approval. Would it make sense for me to connect with them directly?” Or: “Who ultimately makes the decision on coaching? I’d be happy to present to them directly.”

Best case, they introduce you and you get access to the real buyer. Sometimes they’ll say they’ll “present it” to the decision-maker, which means you’re still filtered through them but at least moving up. If they resist the introduction entirely, that’s a red flag. Either they’re protective of the relationship, or the decision-maker isn’t actually interested, or both.

Build a parallel path

While you’re talking to the accessible person, also try to reach the decision-maker through other channels. Message the VP or CHRO on LinkedIn, mentioning that you’ve been talking with their team. Ask your contact who else you should be talking to. Ask your broader network if they know the CHRO at the company. Attend conferences where decision-makers will be. Publish content that senior leaders in that space might see. You’re not going around anyone, you’re widening your approach.

Position yourself as a resource

Instead of only selling coaching, offer value that helps your contact succeed. Share what’s worked at other companies, send resources that help them build the internal case, offer a business case template. This builds goodwill, positions you as an expert rather than a vendor, and makes them want to introduce you to their boss because you make them look good.

Ask who holds the budget

A simple, direct question: “Just so I understand the process, who typically holds the budget for coaching initiatives?” Or: “Would this come from your budget or from another department?” This gets you to the actual decision-maker quickly and shows you understand organizational dynamics.

Know when to pivot

If you’re clearly at the wrong door and can’t get access to the right one, you have a few options. You can ask your contact to be your champion internally, giving them materials and support to sell on your behalf. You can stay connected but deprioritize, checking back during budget planning season. You can look for a different door at the same company, maybe a different business unit or geography. Or you can walk away gracefully, thank them for their time, leave the door open, and focus your energy on opportunities more likely to convert.

Navigating organizational politics without overstepping

You need to find the real buyer, but you also need to avoid offending your initial contact, going over people’s heads inappropriately, or creating political problems for yourself. This is a balancing act, and it’s worth getting right.

The most important principle: include, don’t bypass. When you get access to a decision-maker, bring your original contact along. “I’d love to set up a conversation with you and [original contact] to discuss this.” When talking to decision-makers, give credit. “[Name] has been incredibly helpful in shaping this proposal.” This costs you nothing and earns real loyalty.

Be transparent about your outreach. If you’re going to reach out to someone above your contact, tell them first. “I’m going to reach out to [VP] directly to see if this aligns with their strategic priorities. Is there anything I should know?” And never say or imply that your contact isn’t the right person. Not “You’re not the decision-maker, I need to talk to your boss.” Instead: “This might benefit from [VP]’s perspective as well. Would it make sense to include them?”

When it’s OK to go direct

Sometimes you do need to go around your contact. This is reasonable when your contact explicitly tells you they can’t help and points you to someone else. It’s reasonable when months have passed with no progress and going direct is a last attempt before walking away. It’s reasonable when the opportunity is time-sensitive (new exec, reorg, budget window closing). And it’s reasonable when someone in your network offers to introduce you to the decision-maker directly.

Even then, inform your original contact. “I wanted to let you know I’m going to reach out to [decision-maker] as well. I’ll keep you in the loop.” Frame it as additive, not replacement.

Common wrong door scenarios

The most common one is the enthusiastic HRBP. You connect with an HRBP who loves your work and wants to bring you in for their business unit. The problem is that HRBPs usually don’t have budget. They influence business leaders, but they don’t control development spending. The move here is straightforward: ask whether this would come from their budget or the business unit leader’s budget, then request an introduction. “It sounds like [Business Unit VP] would benefit from this. Would you be comfortable introducing us?” Offer a joint meeting with all three of you.

Similar situation with program managers in L&D. They run leadership programs and want to add coaching, but they manage programs, they don’t buy them. Ask who makes decisions about coaching vendors for those programs. Ask if it makes sense to loop in the Head of L&D.

Then there’s the junior person who reached out. Someone found you on LinkedIn, loves your work, wants to bring you into their company. Their enthusiasm is genuine, but they don’t have decision-making authority and may not even know how the buying process works. Appreciate their interest, but assess quickly: “Tell me about your role and how coaching decisions typically get made at [company].” If there’s a path, help them build the internal business case. If there isn’t, be realistic about how much time you invest.

The delegator is trickier. You reached out to a CHRO or VP, and they said “Talk to my team about this.” The question is whether that’s genuine delegation or a polite decline. You can tell the difference. Real delegation sounds like: “Yes, I care about this. Talk to [name], they have budget and authority for coaching.” Deflection sounds like: “Sure, reach out to HR.” Vague, no specific person, no indication of budget or authority. When you get delegated, try to clarify: “I’d be happy to talk with your team. Is this something you’re personally interested in?” And try to stay connected: “I’ll connect with them. Would it be OK to update you on our progress?”

Finally, there’s the multiple stakeholder maze, where every conversation reveals another person who needs to be involved. Legal, Procurement, Finance, more people you haven’t met yet. When this happens, try to map it early: “Help me understand, who are all the people who need to be involved in this decision? Who ultimately makes the final yes or no?” And be honest with yourself about whether it’s worth it. Complex buying processes can take six months or more. Is the contract size large enough to justify that investment of your time?

Using LinkedIn to find decision-makers

When you’re stuck at the wrong door, LinkedIn can help you find the right one. Start by looking at your contact’s profile to figure out who they report to (sometimes it’s listed, sometimes you can infer it from mutual connections or by searching “[Company] [Function]” to see who’s senior). Then search for the functional leader directly: “[Company] CHRO,” “[Company] VP Talent,” “[Company] Head of Learning.”

Check whether you have mutual connections with that person. If you do, reach out to those mutual connections and ask for an introduction. Before you message the decision-maker, look at their activity. What do they post about? What articles do they share? What seems to matter to them? This gives you the material you need to write outreach that actually lands.

When you do reach out, don’t send a generic InMail. Reference something specific about the company, something about their role or interests, and why coaching is relevant to them right now. Something like: “Hi [Name], I’ve been in conversation with [contact] about coaching support for [initiative]. Given your role leading [function], I wanted to reach out directly to see if this aligns with your priorities. [One specific value proposition relevant to them]. Would you be open to a brief conversation?”

When you’re internal

If you’re an internal coach, the wrong door problem looks different. You report to someone who doesn’t have strategic authority, but you need access to senior leaders or different parts of the organization. Maybe you report to L&D but need to work with OD or business units. Maybe your manager can’t get you senior executive access. Maybe you’re seen as tactical support, not strategic capability.

The most important thing you can do is build your own relationships. Offer value to senior leaders directly (without overstepping your boss), attend cross-functional meetings, volunteer for strategic projects. Your credibility comes from excellent work, and excellent work creates its own introductions. Partner across functions too. Collaborate with OD, HRBP teams, business units. Don’t wait for your boss to open doors. Find allies who can introduce you where you need to go.

Make your impact visible. Share success stories (with permission), report metrics that resonate with senior leaders, present at leadership meetings when you get the chance. If people don’t know what you’re accomplishing, they can’t advocate for you.

At some point, you may need to have the career conversation with your boss about expanding your scope and getting introductions to senior stakeholders. And if your reporting structure fundamentally limits your impact, if your boss is actively blocking your growth, if the organization doesn’t value coaching strategically, it may be time to change jobs. That’s not failure. That’s recognizing which doors will never open no matter how hard you knock.

Getting to the right door, the person with both the problem and the budget, is often the difference between landing work and spinning your wheels in conversations that can never convert. Learn to recognize the signs early, ask the direct questions, and don’t be afraid to navigate toward the person who can actually say yes.

Positioning your coaching beyond “coaching services”

David had impeccable credentials: ICF Master Certified Coach, 20 years of experience, glowing testimonials. His website positioned him as an “Executive and Leadership Coach providing transformative coaching experiences.”

He wasn’t getting much traction.

His colleague Jennifer had the same ICF credentials and similar experience, but positioned herself differently: “I help technology executives accelerate their impact in the first 90 days of new roles.” Her calendar was full.

The difference? David positioned himself as a coach. Jennifer positioned herself as a solution to a specific business problem. Both had strong credentials. Jennifer just added strong positioning.

Organizations don’t buy “coaching.” They buy solutions to problems: accelerating new executives, improving team effectiveness, supporting change, developing leadership pipelines, retaining high-potential talent.

This chapter is about how to position your coaching work in ways that resonate with business buyers and stand out in a crowded market.

Before we go further, a word about credentials. Professional credentials like ICF certification matter, a lot. They signal competence, ethical standards, and commitment to the profession. Organizations want to know you’re qualified, and designations like MCC, PCC, or ACC build real credibility and trust. But credentials alone won’t differentiate you in a crowded market. Strong positioning shows buyers why they should choose you specifically, for their specific problem, right now. Think of credentials as your license to practice. Positioning is your reason to be chosen.

The positioning formula

Effective positioning follows a simple formula:

I help [specific buyer] [achieve specific outcome] [in specific context/situation].

A few examples:

- “I help newly promoted executives accelerate their impact in the first 90 days.”

- “I help leadership teams navigate major organizational transformations.”

- “I help technology companies retain high-potential technical leaders through targeted development.”

- “I help sales leaders build high-performing, collaborative teams.”

Each of these names a specific buyer, a specific outcome, and a specific context. That’s what makes them work. “Executive and leadership coach” does none of those things.

The rest of this chapter walks through each element of that formula, then shows you how to put it together and test it.

Why generic positioning doesn’t work

When you position yourself as a generic “executive coach” or “leadership coach,” you become interchangeable with thousands of other coaches. You’re forced to compete on price and credentials. You’re easy to say “not right now” to. Statements like “I provide executive coaching to leaders” or “transformational coaching for growth-oriented individuals” aren’t wrong. They’re just not compelling. They don’t answer the buyer’s question: why you, why now, what specific problem do you solve?

There’s also a language gap. Coaches tend to describe their work in coaching terms: creating awareness, holding space, powerful questioning, transformative conversations. Buyers think in business terms: reducing time-to-productivity, improving retention, accelerating the leadership pipeline, driving team performance. If you describe your work in language buyers don’t use, they can’t see the value.

And generic positioning makes coaching feel optional. A nice perk, a luxury. When budgets tighten, luxuries get cut first. You need to position coaching as something strategic, not something nice to have.

Choosing your buyer

The first element of the formula is who you serve. Don’t try to serve everyone. You can segment buyers by seniority level (C-suite, senior leaders, mid-level leaders, emerging leaders), by function (technology, sales, operations, finance, HR), by industry, or by company stage.

Each of these dimensions matters for a different reason. Seniority level matters because CEO coaching is bought differently than first-time manager coaching, with different buyers, different budgets, and different success criteria. Functional expertise matters because a coach who understands technology leadership challenges is more credible to a CTO than a generalist. Industry experience signals you understand their world, and a healthcare executive is more likely to hire a coach who has worked in healthcare. Company stage matters because coaching a startup founder looks nothing like coaching a Fortune 500 executive.

You don’t need to pick one narrow segment and stay there forever. But you do need to make a choice. Some coaches go deep (“I only work with first-time CTOs in Series B software companies”). Others choose two or three related segments (“technology executives in growth-stage companies”). Others organize around a problem that cuts across segments (“newly appointed executives across industries during their first 90 days”). All of these work. “I work with everyone” does not.

Naming the outcome

The second element is the outcome you deliver. Here, the most important distinction is between coaching outcomes and business outcomes.

Coaching outcomes are things like increased self-awareness, better emotional intelligence, and authentic leadership presence. These are real, and they matter. But they’re not what buyers are buying. Business outcomes are things like faster time-to-impact for new leaders, higher retention of high-potential talent, improved team performance, and successful navigation of organizational change. Lead with business outcomes. Coaching outcomes are how you get there, but buyers care about the destination, not the route.

The range of business outcomes you might position around is wide: performance acceleration (“reduce time-to-full-productivity”), talent retention (“retain high-potential leaders who are at flight risk”), leadership pipeline development, change enablement, team effectiveness, strategic capability, culture impact. The point isn’t to pick from a menu. It’s to get specific. “Leadership development” is generic. “Reduce time-to-full-productivity for new executives from 12 months to 6 months” is specific. That specificity is what makes a buyer pay attention.

Adding context

Context is the third element, and it’s what makes your positioning feel relevant to a buyer’s actual situation. Coaching during rapid growth is different from coaching during a turnaround. Coaching someone in their first 90 days is different from coaching someone navigating an acquisition.

The most common contexts are transitions (new role, promotion, succession), change (transformation, M&A, restructuring), growth (scaling, entering new markets, hypergrowth), performance challenges (turnarounds, team dysfunction), and development (high-potential programs, pipeline building).

Compare “I coach sales leaders” with “I coach sales leaders navigating the transition from player to coach.” Compare “I provide team coaching” with “I help executive teams align during major strategic shifts.” The context is what makes the second version land.

Putting it together

Here’s the practical advice: pick a combination of who you serve, what problem you solve, and what outcome you deliver. You don’t need to choose between a “role-based approach” and a “problem-based approach” and an “outcome-based approach.” These aren’t competing frameworks. They’re ingredients. The best positioning uses several of them at once.

“I help first-time CEOs in tech startups navigate their first year successfully” combines role, industry, situation, and outcome. “Accelerating sales leader effectiveness during rapid growth” combines function, outcome, and context. The formula (buyer + outcome + context) is your guide.

One note: some coaches want to lead with methodology, something like “systems-oriented team coaching” or “neuroscience-based leadership coaching.” This only works if buyers already understand and value the methodology, and most don’t. For most buyers, lead with the problem and outcome. If they want to know your approach, they’ll ask.

Before and after

This is where the abstract becomes concrete.

Compare “executive and leadership coach” with “I help technology executives accelerate their impact in new roles, reducing time-to-full-productivity from 12 months to 6 months.” The second version names a buyer (technology executives), a situation (new roles), and a measurable outcome (cut ramp time in half). The first version could describe any of ten thousand coaches.

Compare “coach specializing in transformative, values-based coaching” with “I help organizations retain high-potential leaders who are at flight risk, using coaching to address their development and engagement needs.” The first version leads with methodology that means nothing to a buyer. The second leads with a problem (retention risk) and an outcome (keeping your best people).

Compare “team and organizational coaching for companies seeking to improve culture and performance” with “I help executive teams in fast-growth tech companies move from dysfunction to high trust and performance.” The first is broad enough to be meaningless. The second names a level (executive teams), an industry context (fast-growth tech), a problem (dysfunction), and an outcome (high trust and performance).

Compare “applying adult learning theory and neuroscience research to executive development” with “I help new executives build the strategic thinking and executive presence required at the C-suite level.” The first leads with academic methodology. The second leads with what the executive actually needs. The methodology becomes supporting evidence, not the headline.

Testing your positioning

Once you have a positioning statement, pressure-test it. Ask yourself: can someone outside your field understand what you do? Is it clear who you serve? Would a buyer recognize themselves in your description? Does it differentiate you from a generic “executive coach,” or could any coach copy and paste it? Is the outcome valuable enough that someone would pay for it, and can you credibly deliver it? Is the segment you’ve chosen large enough to sustain your practice, and can you actually reach those people? Do you have the experience, case studies, or proof points to back up what you’re claiming?

If you can’t answer yes to most of those questions, keep refining.

Common positioning mistakes

The most common mistake is trying to be everything to everyone. “I work with individuals and teams across all industries and all levels.” This says nothing. It doesn’t differentiate you. It makes you invisible in a market where buyers are looking for someone who understands their specific situation. You can always expand later. Start focused.

The second most common mistake is leading with credentials. “ICF PCC-certified coach with 500 hours of training and a PhD in organizational psychology.” Credentials like ICF certification absolutely matter. They build trust and credibility. But buyers care about outcomes first. They want to know what problem you solve before they ask what certifications you have. Credentials validate you after a buyer is interested; they don’t create the interest. Lead with the outcome you deliver, then back it up with credentials. For example: “I help technology executives accelerate their impact in new roles. I’m an ICF Master Certified Coach with 20 years of experience working with tech leaders.”

Other mistakes follow a pattern. Using coaching jargon (“I create a safe container for transformative conversations”) instead of business language (“I help executives gain clarity on complex decisions and take decisive action”). Being vague about outcomes (“I help leaders become more effective”) instead of specific (“I help leaders reduce meeting time by 30% while improving team alignment and decision quality”). Leading with methodology that buyers don’t understand (“somatic coaching and polyvagal theory”) instead of leading with the outcome and explaining the methodology if they ask. And positioning yourself for a market you don’t have experience in, like claiming to be a coach for healthcare CEOs when you’ve never worked in healthcare. Aspirational positioning doesn’t work in coaching. Position based on actual experience.

Evolving your positioning

Your positioning doesn’t have to be permanent. Most coaches start broader and get more specific as they build expertise, moving from “executive coach” to “coach for tech executives” to “coach for first-time CTOs in growth-stage SaaS companies.” Markets change too. What works in a growth economy (scaling leadership teams for rapid expansion) may need adjusting in a downturn (leadership effectiveness through restructuring). Test different positioning with different segments. Pay attention to what converts. Double down on what works.

The key is to be intentional. Don’t drift. Make conscious choices about how you position yourself, and revisit those choices regularly.

Applying your positioning

Once you’ve clarified your positioning, apply it consistently. Your website headline, your LinkedIn profile, your proposals, the way you introduce yourself at a networking event, the topics you write and speak about, your outreach emails. Every touchpoint should tell the same story. Consistency amplifies positioning. Mixed messages dilute it.

Strong positioning makes everything else in this book easier: finding the right buyers, having relevant conversations, commanding premium pricing, and standing out in a market full of coaches who all describe themselves the same way.

The language of impact

Lisa’s coaching engagement with a technology company had been transformative. The executives she coached reported profound shifts in their leadership effectiveness. Their self-awareness had deepened. They were more emotionally intelligent, more authentic, more present.

When the CHRO asked for a report on the coaching program’s impact, Lisa proudly shared these outcomes. The CHRO read the report, nodded politely, and said, “This is nice. But what’s the business impact? Are these leaders performing better? Are their teams more productive? Has retention improved?”

Lisa couldn’t answer those questions. Despite excellent coaching outcomes, she couldn’t demonstrate business impact. The program wasn’t renewed.

Organizations don’t invest in coaching for self-awareness. They invest for business results. If you can’t speak the language of business impact, and demonstrate it, your coaching work will always be vulnerable to budget cuts and seen as “nice to have.”

The translation that matters

Most coaches measure what happens inside the coaching engagement: increased self-awareness, better emotional intelligence, improved communication, more authentic leadership. These are real. They matter. But buyers don’t care about them directly.

What buyers care about is what changes in the business as a result. Faster onboarding for new leaders. Improved team performance. Higher engagement. Lower turnover. Better decision-making. Stronger culture metrics.

Your job is to translate from one world to the other. Here’s what that looks like in practice.

A coach says, “The executive developed greater self-awareness about their leadership style.” The buyer version: “The executive’s team engagement scores increased by 15 points, and voluntary turnover in their org decreased from 18% to 9%.”

A coach says, “The leadership team built trust and improved communication.” The buyer version: “The leadership team reduced decision-making time from 6 weeks to 2 weeks, and alignment scores improved from 3.2 to 4.5 out of 5.”

A coach says, “The CEO gained clarity about strategic priorities.” The buyer version: “The company narrowed from 12 strategic initiatives to 4, resulting in faster execution and 30% improvement in on-time delivery.”

The coaching outcomes are the mechanism. The business outcomes are the result. Every time you describe your work, you need to complete that chain.

The “so what?” test

Here’s a simple discipline that will sharpen every conversation you have with a buyer. Whenever you state an outcome, ask yourself: “So what? Why does this matter to the business?”

You tell a buyer that coaching increased emotional intelligence. The buyer thinks, “So what? How does that help us?” What you should be saying is that coaching increased emotional intelligence, which led to better conflict resolution, faster decision-making, and higher team engagement. That’s a sentence a buyer can act on.

You tell a buyer that leaders gained self-awareness through coaching. So what? What you should be saying is that leaders gained self-awareness about their impact on others, which reduced team friction and improved retention of high performers.

You tell a buyer the executive team built trust. So what? What you should be saying is that the executive team built trust, which enabled them to have difficult conversations earlier, make decisions faster, and present a unified front to the organization.

Always complete the chain from coaching outcome to business impact.

The metrics buyers actually care about

Different buyers care about different metrics, and knowing which ones matter to your buyer is half the battle. The metrics fall into four broad categories.

Talent metrics

Talent management buyers live and breathe retention, time-to-productivity, engagement, and promotion readiness. Replacing someone costs one to two times their annual salary, and losing high performers is even more painful because of the institutional knowledge that walks out the door.

Coaching impacts these numbers directly. Better managers retain people. Developed leaders stay longer. Teams with trust and psychological safety have lower turnover. When you’re working with a talent-focused buyer, these are the kinds of statements that land: “Turnover in coached leaders’ teams decreased from 22% to 11%.” “Retention of coached high-potentials was 95% versus the 78% company average.” “Average time-to-full-productivity dropped from 12 months to 7 months for coached executives.”

Engagement scores and promotion readiness matter here too. Teams led by coached managers often show significant improvement in engagement surveys. Coached high-potentials get promoted at notably higher rates. Internal fill rates for senior roles climb. These are the numbers that make a talent management VP’s career, and if you can move them, you’ll have a long-term buyer.

Performance metrics

When your buyer is a business leader (a division president, a VP of product, a CTO), they care about team output, individual performance, and decision-making speed. Did the project ship on time? Did quality improve? Are we making decisions faster?

Coaching touches these through multiple channels. Team coaching improves collaboration, accountability, and the willingness to surface problems early. Leader coaching improves how someone manages, delegates, and sets direction. The measurement examples that resonate here are things like: “On-time delivery improved from 60% to 85% after team coaching.” “360 scores increased an average of 0.8 points across all dimensions.” “The executive team reduced average decision cycle from 8 weeks to 3 weeks.”

Decision-making speed deserves special attention because it’s often invisible but enormously expensive. When a leadership team takes six weeks to make a decision that should take two, the cost ripples through the entire organization. If your coaching helps a team decide faster and execute better, that’s worth quantifying.

Change and transformation metrics

Transformation sponsors care about whether the change is actually taking hold. Are people adopting the new way of working? Is resistance decreasing? Are we hitting milestones?

Change initiatives fail more often than they succeed, and the failure is usually about people, not strategy. Coaching helps leaders navigate transitions, manage resistance, build the psychological safety needed for people to try new behaviors, and sustain momentum when things get hard. Culture metrics fall here too: psychological safety scores, values alignment, inclusion and belonging.

When you’re reporting to a transformation sponsor, statements like these carry weight: “Change adoption scores increased from 55% to 82%.” “Psychological safety scores improved from 3.1 to 4.3 in coached teams.” “The transformation achieved key milestones three months ahead of schedule.”

Financial metrics (use carefully)

Some buyers want to see the money. Revenue impact, cost savings, ROI. You can go there, but go carefully.

Revenue attribution is tricky because so many factors influence revenue. You can credibly say “sales team performance improved 18% after sales leader coaching,” but claiming you drove that revenue increase single-handedly will cost you credibility.

Cost savings are easier to defend. Retention improvements have a direct dollar value (avoided replacement costs), and productivity improvements can be estimated. An ROI calculation might look like this:

- Coaching investment: $200K

- Retention savings (3 avoided executive replacements at $250K each): $750K

- Estimated productivity gains: $300K

- Total estimated benefit: $1,050K

- ROI: 5.25x

But here’s what matters more than the math: be transparent about your assumptions. Every ROI calculation involves estimates and judgment calls. If you present your ROI as hard fact, savvy buyers will poke holes in it and question your credibility. If you present it as a reasonable estimate with clear assumptions, you come across as honest and rigorous. The transparency matters more than the precision.

How to measure

You don’t need a PhD in research methods to measure coaching impact. Here are the practical approaches, roughly ordered from most accessible to most rigorous.

The simplest approach is pre-post assessment. Measure something before coaching starts, measure it again afterward, and compare. This works with 360 feedback, engagement surveys, performance ratings, team metrics, whatever data you can access. The limitation is that you can’t prove coaching caused the change (other things were happening too), but it gives you a clear before-and-after picture that most buyers find compelling.

Goal achievement tracking is equally accessible. Set three to five specific performance goals at the start of coaching, track progress quarterly, and report on achievement rates. This has the advantage of being clearly tied to coaching, though it depends on setting good goals up front.

Stakeholder feedback gives you the qualitative side. Gathering observations from the coachee’s manager, peers, and direct reports rounds out the picture with specific behavioral changes that numbers alone can’t capture. A manager saying “Sarah’s ability to manage conflict has improved dramatically” adds meaning to an engagement score increase.

Business metrics tracking connects coaching to the numbers the organization already watches: team engagement scores, retention rates, on-time delivery, quality metrics. The challenge is attribution (many factors influence these numbers), but if you track them consistently, patterns emerge.

For more rigorous evidence, control group comparison (coached group versus similar uncoached group) and longitudinal tracking (following metrics over 12 to 24 months) provide stronger evidence of coaching’s impact. These require more organizational support to set up, but they’re powerful when you can do them. Most coaches won’t use these on every engagement, but if you’re running a large program and want to make the case for expansion, they’re worth the effort.

Build measurement in from the start

Don’t wait until the end of a coaching engagement to think about measurement. The single most important thing you can do is establish baselines before coaching begins.

Include measurement in your proposal. Specify what you’ll measure, how you’ll measure it, when you’ll measure it, and what success looks like. Here’s an example of what that looks like in practice:

“Success will be measured through pre-post 360 feedback (before coaching starts, 6 months after coaching ends), team engagement scores (quarterly tracking), retention of coached leaders (tracked over 18 months), and goal achievement (quarterly review of specific performance goals). Success criteria: average 360 scores improve by 0.5 or more points, team engagement scores increase by 10 or more points, 90%+ retention of coached leaders, 80%+ achievement of agreed-upon performance goals.”

Once coaching is underway, do quarterly check-ins on progress and a mid-point review. This lets you course-correct if something isn’t working and gives you a progress narrative, not just a final snapshot.

After coaching ends, repeat your assessments, compare to baseline, and gather stakeholder feedback. Then follow up again three to six months later. Sustained impact is the strongest argument for coaching’s value, and it distinguishes your work from a short-term bump that fades.

Communicating impact

Once you have data, you need to tell the story well. But there’s a tension here that you need to navigate carefully.

Organizations want to understand the value coaching created. Coaches must protect the privacy of coaching conversations. The way through is to report on aggregate outcomes, business metrics, and stakeholder feedback rather than disclosing what happened in individual sessions. Focus on the results coaching enabled (team performance, engagement scores, promotion readiness) rather than the personal content of conversations. When sharing individual stories or testimonials, always get explicit permission from the coachee first.

The impact report

For a formal report, lead with an executive summary that covers the program overview, key outcomes, and bottom line. Follow with context (why coaching was initiated, what problems you aimed to solve), your approach, results with both quantitative and qualitative data, and your recommendations for what’s next. Put detailed data in an appendix. The scope should match the engagement: a pilot with five participants doesn’t need the same depth as a year-long program with a hundred leaders.

Pair numbers with stories

Quantitative data provides credibility. Qualitative stories provide meaning. You need both.

Here’s what a good impact story looks like. John was promoted to VP of Engineering but was struggling with the transition. His team engagement scores were 2.8 out of 5, and he’d lost two senior engineers in his first 90 days. Through six months of executive coaching, John developed his strategic communication skills, learned to delegate effectively, and built trust with his team. By the end of coaching, his team engagement scores had improved to 4.2 out of 5. Turnover stopped. His boss rated him as “meeting expectations” rather than “needs improvement.” John was able to deliver his roadmap on time and present it confidently to the executive team. In his own words: “The coaching helped me see that my instinct to be in the weeds was actually disempowering my team. Once I shifted my approach, everything changed.”

That’s a story a buyer can retell to their CFO. Data alone can’t do that.

Good testimonials vs. bad ones

Testimonials matter, but quality varies enormously. “The coaching was wonderful. I really enjoyed working with my coach” does nothing for you. Compare that to: “Before coaching, I was overwhelmed and struggling to prioritize. My coach helped me develop a strategic framework for decision-making that’s transformed how I lead. My team’s performance has improved significantly, and I feel confident in my role.” The second is specific, outcome-focused, and credible. Gather testimonials from coached individuals, their managers, their teams, and your HR sponsors. Push for specifics.

When you don’t have perfect data

Sometimes you won’t have clean before-and-after metrics. That’s OK. You can point to goal achievement (“We set five specific performance goals; the leader achieved four fully and made significant progress on the fifth”). You can use stakeholder perception (“We gathered feedback from eight stakeholders; 100% reported significant improvement”). You can track milestones (“The executive team made decisions on twelve critical issues that had been pending for months”). You can use comparative framing (“New executives typically take 12 to 18 months to reach full productivity; with coaching, this cohort averaged eight months”). Or you can point to problem resolution (“The team coaching was initiated due to significant conflict; post-coaching, the team delivered their strategic initiative on time”).

Be honest about what you can and can’t claim. Don’t oversell or fabricate data. But don’t undersell your impact either.

Mistakes that undermine your credibility

The most common mistake coaches make is the one Lisa made in the opening story: reporting coaching outcomes without connecting them to business results. Satisfaction scores and “increased self-awareness” don’t mean anything to a buyer who needs to justify the budget. Always complete the translation to business impact.

The second most damaging mistake is claiming too much credit. Coaching is rarely the only factor in someone’s improvement, and buyers know that. When you attribute all improvement to coaching, you lose credibility with exactly the people you need to trust you. Use language like “contributed to” or “supported” rather than “caused.” Honest attribution actually makes your case stronger, not weaker.

The third mistake, and it’s more common than you’d think, is not measuring at all. Assuming your impact is obvious and not bothering to document it. Even imperfect data beats no data. Even a few stakeholder quotes and a before-and-after engagement score give you something to point to.

Beyond these three, watch out for cherry-picking data (report honestly, even when some participants didn’t benefit), using jargon (“enhanced metacognitive capacity” means nothing to a business buyer, but “better strategic thinking” does), and drowning your audience in 20 pages of charts with no narrative thread. Lead with the story and key findings. Put the detailed data in the appendix.

The real point

Learning to speak the language of business impact transforms coaching from “nice to have” to strategic investment. You don’t need perfect data or sophisticated analytics. You need the discipline to translate what happens in coaching into what changes in the business, and the honesty to report it credibly. That discipline, sustained over time, is what builds lasting client relationships and a coaching practice that grows.

Scoping the work

Michael was excited. A major consulting firm wanted to hire him to coach their partners on “leadership effectiveness.” The fee would be substantial. He eagerly accepted.

Three months in, he realized the problem. The partners weren’t struggling with leadership skills. They were struggling because the firm’s incentive structure rewarded individual performance over collaboration, creating a toxic competitive culture. No amount of individual coaching could fix a systemic problem.

Michael delivered good coaching, but it didn’t move the needle. The engagement wasn’t renewed. Both sides felt disappointed.

Michael had failed to do something critical: diagnose whether coaching was actually the right intervention for the problem at hand.

Is coaching the right intervention?

Not every people problem is a coaching problem. Sometimes the issue is structural (broken processes, wrong org design, misaligned incentives). Sometimes it’s a capability gap that needs training, not coaching. Sometimes nobody has clarified the strategy, goals, or roles, and what’s needed is leadership direction, not development. Sometimes the team is just understaffed or under-resourced. Sometimes the culture is so broken that individual coaching can’t make a dent. And sometimes the person is simply wrong for the role.

Coaching works when someone has the capability but needs to apply it differently, when the challenge requires behavior change rather than just knowledge, when the person is motivated and the system will actually let them change. Coaching doesn’t work when the system is fundamentally broken, when someone lacks the basic capability for their role, when nobody can articulate what success looks like, or when political and structural factors override anything one person can do.

Your job is to figure out which situation you’re in before you agree to coach. The rest of this chapter gives you a framework for doing that.

Five diagnostic questions

What’s the real problem?

The surface problem is almost never the real problem. They’ll tell you “our executives need better communication skills,” but the executives are fine at communicating; they just have no clear strategy to communicate. They’ll say “this leader needs executive coaching,” but the leader is in the wrong role and no coaching will fix that. They’ll ask for help making a team “more collaborative,” but the team is plenty collaborative; competing priorities from above are creating the conflict.

Your first job is to dig beneath the presenting problem. Ask what’s happening that makes them think coaching is needed. Ask what they’ve tried already, what worked, what didn’t. Ask what would be different if this problem were solved. Ask what else might be contributing to the issue. And don’t just talk to HR. Talk to the business leader, the person being coached, their team. Different perspectives reveal different dimensions of what’s actually going on.

Look for patterns. Is this an isolated individual issue or something showing up across multiple people? Has this role had turnover or repeated performance issues? If three people have failed in the same job, the job might be the problem.

Here’s what this looks like in practice. A client told me they needed coaching for their VP of Sales because “he’s not strategic enough.” After asking questions, a different picture emerged. The CEO kept changing direction, making it impossible for anyone to execute strategy. The VP was spending 60% of his time on tactical work because he was understaffed. The sales team had outdated tools and processes. Coaching alone wasn’t going to solve any of that.

The honest response was: “Coaching could help with strategic thinking skills, but I’m concerned it won’t address the core issues, which are unclear direction from leadership, insufficient staffing, and tool gaps. Can we talk about addressing those first, or in parallel with coaching?”

That kind of honesty might feel like you’re talking yourself out of work. You’re not. You’re building the kind of credibility that leads to bigger, better work down the road.

Is the person coachable?

Coaching requires some baseline ingredients: self-awareness (or at least willingness to develop it), motivation to change, enough psychological safety to be vulnerable, time and energy to engage, and basic capability to build on. When those ingredients are missing, coaching stalls.

The red flags are usually obvious once you know to look for them. Someone who blames everyone else for their problems, rejects all feedback, and believes they’re already excellent is going to be a tough coaching engagement. So is someone who doesn’t see a problem, doesn’t care about improving, and is only showing up because HR or their boss made them. People in genuine crisis mode, barely keeping their heads above water, need triage, not development. And someone who simply lacks the fundamental skills for their role needs training or a different job, not a coach.

The best way to assess coachability is to talk to the person before you agree to the engagement. Ask them what they’d like to work on, what’s important to them, and listen carefully. Are they curious about themselves or defensive? Do they take ownership or deflect? You can also look at how they respond to feedback through a 360 review, talk to their manager about why they think coaching would help, or offer a trial session to test the chemistry and see how they engage.

When someone isn’t coachable, be honest. Don’t take the engagement just for the fee. “Based on our conversations, I’m not confident coaching is the right intervention at this time. Here’s what I think might be more helpful…” That’s a hard sentence to say when you need the revenue. Say it anyway.

Does the system allow for change?

Individual coaching happens inside an organizational system. If the system actively works against the change you’re coaching toward, you’re setting everyone up for failure.

Think about it in terms of enablers and blockers. Coaching can work when the person’s manager supports the change, when the organization rewards the new behaviors, when the person has autonomy to try new approaches, and when the culture allows for growth and learning. Coaching will struggle when the manager undermines the change, when the organization punishes or ignores new behaviors, when the person is micromanaged with no room to experiment, and when the culture treats vulnerability or mistakes as career-ending.

The questions that surface this are direct. Ask the coachee: “Does your manager know you’re getting coaching? Are they supportive?” Ask: “If you started leading differently, how would the organization respond?” Ask: “What gets rewarded here? What gets punished?” Ask: “How much freedom do you have to try new approaches?” The answers tell you whether coaching has room to work or whether you’re pushing against a wall.

One of the clearest examples I’ve seen: a client wanted coaching for a manager to “empower their team” and “delegate more.” Sounds like a straightforward coaching engagement. But after digging in, the manager’s boss turned out to be a micromanager who didn’t allow delegation. The culture rewarded being in the weeds, not strategic leadership. The manager had actually tried delegating before and was criticized for “not being hands-on enough.”

The right response was: “I can coach on delegation skills, but I’m concerned the system won’t support it. Can we involve your boss in this conversation? Or should we reframe this as ‘managing up in a micromanagement culture’ instead?”

This is one of the most important diagnostic questions you can ask, because it determines whether your coaching will stick or evaporate the moment sessions end.

What’s the scope of impact needed?

Sometimes the request is for individual coaching, but the real need is systemic. The key diagnostic questions here are simple: “How many people are affected by this issue?” and “If we coached this one person, would that solve the problem, or would others still struggle?” One question I find particularly revealing: “If this person left and someone new came in, would they face the same challenges?” If the answer is yes, the problem isn’t the person.

Individual coaching is right when one person needs to shift their behavior and the issue is genuinely isolated to them. A new CTO struggling with the transition from VP, first time at C-level, needs to develop strategic leadership. The team is fine. That’s a coaching engagement.

Team coaching is the better fit when multiple people need to change and the issue is relational. A leadership team that can’t make decisions because of conflict and lack of trust between members isn’t an individual problem. It’s the dynamic between them.

Sometimes the scope is clearly organizational. Twenty new managers all struggling with the same transition (promoted for technical skills, no management training, no development infrastructure) need a manager development program, not twenty individual coaching engagements. And when the problem is a culture of fear and blame driven by toxic leadership at the top, individual coaching for the people underneath won’t change the system. That requires organizational intervention.

What does success look like?

If you can’t define success clearly, don’t start coaching. “Improved leadership effectiveness,” “better communication,” “more strategic,” and “increased emotional intelligence” are not success criteria. They’re vague aspirations that guarantee disappointment, because nobody will agree on whether they happened.

Clear success criteria are specific and observable: “Able to make strategic decisions within two weeks instead of two months.” “Team engagement scores improve by 10+ points.” “Successfully onboards and retains three direct reports in first year.” “Presents confidently to the board and receives positive feedback.”

To get there, ask the sponsor (HR, boss, buyer): “If this coaching is wildly successful, what will be different? How will you know it worked? What would you observe?” Then ask the coachee the same questions from their perspective: “What would make this coaching valuable for you? What changes would you like to see?”

The critical step is aligning those two sets of expectations. Here’s an example of how that plays out.

A client said: “We want coaching for our VP of Product. She needs to be more strategic.” After clarifying questions, the sponsor described success as the VP spending less time in product details and more time on vision and roadmap, being able to present product strategy to the board confidently, and having her team understand the strategic direction well enough to make aligned decisions. The VP herself described success differently but compatibly: feeling confident in the strategic direction instead of constantly second-guessing, trusting her team to handle details without micromanaging, and having the exec team see her as a strategic partner rather than just an operator.

Together, we turned those into aligned, measurable criteria: the VP shifts 50% of her time from tactical to strategic work (measured by time audit), presents product strategy to the board in month six and receives positive feedback, team clarity on strategy improves on an internal survey, 360 scores on strategic thinking improve from 3.2 to 4.0+, and the exec team’s perception shifts from tactical to strategic. Now everyone knows what we’re working toward and how we’ll know if we got there.

Scoping different types of coaching

Not all coaching engagements scope the same way. The type of coaching shapes the duration, intensity, structure, and the questions you need to ask before saying yes. Here’s how to think about the most common types.

Executive coaching is typically a six-to-twelve month engagement, meeting every two to four weeks for 60 to 90 minutes, usually with a 360 at the start and stakeholder check-ins along the way. The scoping questions that matter most are about transitions and challenges: What is this executive facing right now? What support do they have from their boss, team, and peers? What does success look like for them and their stakeholders? Watch out for engagements where there’s no clear development goal (“it would just be nice to have a coach”), where the executive was forced into coaching, or where the boss is toxic and won’t support the change. Those are setups for failure.

Leadership team coaching runs six to twelve months, usually with monthly or bi-monthly half-day or full-day sessions with the whole team together. The focus is team effectiveness: trust, collaboration, decision-making, alignment. The critical scoping question is whether the team lead is willing to change themselves, not just have their team coached. If the leader is the problem and won’t engage, don’t take the work. Also check whether the team has actual decision-making authority. A team that can’t implement changes will get frustrated fast, and so will you.

New leader coaching covers the first 90 to 180 days, usually meeting every two weeks initially and then shifting to monthly. The type of transition matters for scoping: promoted from within is different from external hire, which is different from a lateral move. Ask about 90-day success criteria, critical stakeholder relationships, and anticipated landmines. The red flag here is when the person wasn’t set up for success in the first place (bad hire, wrong fit, impossible job). Coaching can’t fix a bad selection decision.

High-potential development coaching is typically nine to twelve months, often part of a broader development program with a cohort of leaders. The key scoping question is what “high-potential” actually means in this organization and what these people are being developed for. If there’s no clear development plan or career path, or if the organization doesn’t actually promote from within, the coaching becomes a nice perk with no real impact.

Team dysfunction coaching is shorter and more intensive, usually three to six months with weekly or biweekly sessions. Before scoping, figure out whether the dysfunction is a people issue or a system issue. Is the team lead part of the problem or part of the solution? What’s already been tried? If the system is actively creating the dysfunction through bad incentives or impossible workloads, coaching the team’s behavior won’t fix anything.

Change coaching runs for the duration of the change initiative, typically six to eighteen months, and is often integrated with a broader change management plan. Multiple leaders may need coaching simultaneously. The scoping risk here is being brought in as a band-aid for bad change management. If the change strategy is unclear, if leadership isn’t actually committed, or if there aren’t enough resources to support the change, coaching the people in the middle won’t help.

The scoping conversation

When someone approaches you about coaching, don’t jump to a proposal. Have a real conversation first. A good scoping conversation covers four things, and while it doesn’t need to follow a rigid structure, you want to make sure you get to all of them.

Start by understanding the context. Ask what’s happening that made them think about coaching, what problem they’re trying to solve, what they’ve tried already, and why now. Get them talking about the person or team: strengths, struggles, level of awareness, openness to coaching. And ask about the organizational context. How does the organization view coaching? What support will the person have? What could get in the way?

Then clarify expectations. This is where you ask the question that matters most: “If this coaching is wildly successful, what will be different?” Follow up with how they’ll know it worked, what success looks like at six months and twelve months, how they want to measure progress, and who will evaluate success. Also clarify scope: is this an individual issue or a team issue? Who else might need to be involved?

Assess fit before you commit. Is now the right time, or should you wait? What needs to be in place for coaching to succeed? And ask the practical questions: who needs to approve this, what’s the timeline for a decision, what’s the budget?

Finally, and this is what separates good coaches from order-takers, share your point of view. Tell them what you’re hearing, what you think would work, and what concerns you. Recommend a scope: the type of coaching, duration, frequency, focus areas, and how you’d measure success. Flag risks honestly. Then set next steps: do they want a proposal? Should you talk to the person being coached or their boss? This is where you demonstrate that you’re a thought partner, not just someone waiting to be told what to do.

Thinking beyond coaching

When you diagnose that coaching alone won’t solve the problem, you need to be able to recommend something broader. This means knowing what other interventions exist, even if you don’t deliver them yourself.

On the talent management side, organizations commonly run leadership development programs (multi-month cohort programs combining training, action learning, peer coaching, and executive coaching), high-potential development tracks with stretch assignments and mentoring, new manager programs for first-time managers, and succession planning initiatives. On the organizational development side, you’ll encounter change management programs using frameworks like Kotter or Prosci, team effectiveness interventions built on models like Lencioni’s Five Dysfunctions, culture change initiatives that span multiple years, and organizational design projects that restructure to align with strategy.

You don’t need to be an expert in all of these. But you need to know enough to recognize when they’re needed. When you can say, “Coaching could be valuable for the senior leaders, and I’d also suggest pairing it with stretch assignments so they have real situations to practice new behaviors in,” you position yourself as someone who thinks strategically about solutions, not just someone selling coaching hours. You become a trusted advisor rather than a vendor.

Knowing enough to recommend partners or internal functions who can provide these interventions, even when you can’t deliver them yourself, is what separates coaches who get called back from coaches who don’t.

When to say no

Sometimes the right thing to do is decline the work. This is hard, especially when you need the revenue, but taking engagements you can’t succeed at is worse than turning them down.

Say no when the person isn’t coachable (unwilling, resistant, defensive, or simply incapable of engaging). Say no when the system will block success (toxic boss, broken organization, no support for change). Say no when coaching isn’t the right intervention, whether because the person needs training rather than coaching, because structural issues need to be addressed first, or because the person needs to be moved out of the role, not developed in it. Say no when expectations are unrealistic: they expect coaching to fix everything, the timeline is impossibly short, or nobody can define what success looks like. Say no when there’s an ethical issue, like coaching being used punitively, confidentiality being compromised, or being asked to coach someone out of the organization. And say no when you’re simply not the right coach, whether because the work is outside your expertise, the chemistry isn’t there, or there’s a conflict of interest.

Declining gracefully isn’t complicated. “Thank you for thinking of me. Based on our conversation, I don’t think I’m the right fit for this engagement. Here’s why, and here’s what I’d recommend instead.” Then refer them to another coach, recommend a different intervention, suggest addressing systemic issues first, or offer to revisit when conditions are better.

Saying no protects your reputation (don’t take engagements you can’t succeed at), your client (don’t take their money if you can’t help), the person being coached (don’t waste their time), and the profession (don’t create evidence that coaching doesn’t work).

Diagnostic thinking and proper scoping aren’t glamorous. They don’t feel like “real coaching.” But they’re the foundation of every engagement that actually creates value. Rush past this step and you’ll end up where Michael did: delivering good coaching that doesn’t move the needle, leaving everyone disappointed. Invest in diagnosis, and you’ll do work that truly matters.

The proposal that gets approved

Nathan had submitted dozens of coaching proposals over the years. They were thorough, sometimes 20+ pages detailing his methodology, credentials, and coaching philosophy. His conversion rate was terrible. Maybe 1 in 10 proposals led to actual work.

Then he changed his approach. He started with a one-page executive summary focused on business outcomes, followed by a crisp 5-page proposal. His conversion rate jumped to 6 in 10.

The difference? Nathan learned that proposals are not about showcasing your expertise. They are about making it easy for buyers to say yes.

What a proposal actually does

Most coaches treat proposals like marketing brochures for themselves. They load them up with credentials, methodology explanations, and coaching philosophy. This misses the point entirely. A proposal is a tool your buyer uses to get internal approval. It needs to answer the questions that finance, legal, and other stakeholders will ask. It needs to remove objections and uncertainty. Write for your buyer’s internal process, not for your ego.

The approval journey

Most coaches think the process is simple: write a proposal, they approve it, you start. Reality depends on the size of the engagement.

For small engagements under $25K, your contact and maybe their boss read it and approve. That can happen in days. For medium engagements ($25K-$100K), your HR contact shares it with their VP, finance reviews it for budget approval, procurement may review vendor terms, and legal might get involved. Expect 2-6 weeks. For large engagements over $100K, add executive sponsor approval (CHRO, VP, sometimes CEO or CFO), possible formal presentations to leadership, and competitive bids or RFP processes. That takes 2-6 months.

Your proposal needs to serve all these readers. The executive summary exists for the senior leader who will never read the full document. The business case section is for finance and executives. The methodology section is for your main contact and HR. Logistics and pricing are for procurement and legal. If you have an appendix, it catches everyone who wants more detail.

Proposal structure

Here is a structure that works across different engagement types and sizes.

Page 1: executive summary

This is often the only page senior executives read. It should include a one-sentence headline, 2-3 sentences on the challenge you are solving, 3-4 sentences on your approach, 3-5 bullet points on expected outcomes, the total cost and timeline, and what happens next if approved. All on one page.

Here is an example:

EXECUTIVE SUMMARY

Proposal: Leadership Team Coaching to Improve Executive Alignment and Decision-Making

The Challenge [Company]’s executive team is facing delays in decision-making and misalignment on strategic priorities, resulting in slower execution and confusion across the organization. Recent feedback indicates that the team needs to improve trust, communication, and collaborative decision-making to lead the company effectively through its next phase of growth.

Our Approach We propose a 9-month leadership team coaching engagement focused on building trust, improving decision-making processes, and creating stronger strategic alignment. Through monthly half-day sessions, team assessments, and leadership stakeholder interviews, we will help the executive team operate as a high-performing, cohesive unit.

Expected Outcomes - Faster, higher-quality decision-making (target: reduce decision cycle from 6 weeks to 2 weeks) - Improved alignment on strategic priorities (measured by leadership alignment survey) - Increased trust and psychological safety within the team (measured by team assessment) - Better organizational clarity driven by unified executive communication - Sustainable practices for ongoing team effectiveness

Investment - Duration: 9 months (January-September 2026) - Fee: $120,000 - Includes: Monthly team coaching sessions, team assessment, stakeholder interviews, progress reviews with CEO/CHRO

Next Steps Upon approval, we will conduct stakeholder interviews and team assessment in January, with first coaching session in February 2026.

Notice the business language (decision-making, alignment, execution), not coaching jargon. Specific outcomes with measures. Clear timeline and investment. Someone can read this single page and understand the whole proposal.

Section 2: context and opportunity (1-2 pages)

This section establishes why coaching is needed now. Cover the current situation, what happens if nothing changes, and why coaching is the right intervention at this moment. This helps internal sponsors sell the proposal upward.

Example:

CONTEXT AND OPPORTUNITY

Current Situation [Company] is at an inflection point. After rapid growth over the past 3 years (50% headcount growth, expansion into 4 new markets, Series C funding), the executive team is facing new challenges that require a different level of collaboration and strategic clarity.

Recent feedback from the organization and board has highlighted:

- Slow decision-making: Critical decisions taking 4-8 weeks when market conditions require 2-3 weeks

- Misalignment: Different executives communicating conflicting priorities, creating confusion

- Silos: Functions operating independently rather than collaboratively

- Trust gaps: Team members hesitant to challenge each other or surface difficult issues

Impact of Status Quo Without addressing these dynamics:

- Strategic execution will continue to be slower than market demands

- Talented employees will become frustrated with lack of clarity and may leave

- The organization will struggle to compete against more agile competitors

- Board confidence in the executive team may erode

Why Coaching, Why Now The executive team has the right people with the right capabilities. This is not a skills gap, it is a team effectiveness gap. What is needed is improved ways of working together, stronger trust and communication, better decision-making processes, and aligned strategic direction.

Leadership team coaching is designed for exactly this situation: helping capable executives operate as a high-performing team. With the company’s growth trajectory and competitive landscape, addressing this now is critical to sustaining momentum.

Section 3: approach and methodology (2-3 pages)

This section explains how you will deliver value. Cover your overall approach, specific activities (session structure, frequency, assessments, between-session support), timeline and milestones, and a brief note on your qualifications. Do not make the qualifications section all about you. Keep it short.

Example:

APPROACH AND METHODOLOGY

Overall Approach Our leadership team coaching follows a proven three-phase model:

1. Foundation (Months 1-3): Build trust, establish ways of working, surface key issues

2. Development (Months 4-7): Address specific team challenges, develop new practices, measure progress

3. Sustainment (Months 8-9): Solidify new behaviors, create ongoing practices, evaluate impact

Specific Activities

Team Coaching Sessions (9 sessions, monthly) - Half-day sessions with full executive team - Structured agenda with experiential activities - Focus alternates between trust-building, strategic alignment, and decision-making - CEO actively participates as team member

Team Assessment (Month 1 and Month 9) - Research-backed team effectiveness assessment - Provides baseline and post-coaching measures - Identifies specific dynamics to address

Stakeholder Interviews (Month 1) - Confidential 1-hour interviews with each executive team member - Interviews with 5-8 leaders reporting to executive team - Synthesized themes shared with team

Progress Reviews (Quarterly) - Brief review sessions with CEO and CHRO - Track progress against success metrics - Adjust approach as needed

Timeline and Milestones

Month

Activity

Milestone

Jan

Stakeholder interviews, team assessment

Diagnostic complete

Feb-Apr

Foundation phase coaching sessions

Trust baseline established

May

Mid-point review

50% toward outcomes

May-Jul

Development phase coaching sessions

New practices adopted

Aug-Sep

Sustainment phase coaching sessions

Impact demonstrated

Sep

Final assessment and review

Engagement complete

Why We Are Suited for This Work [Your firm/you] has worked with 15+ leadership teams in high-growth technology companies, specifically helping teams navigate the transition from startup to scale-up. Our approach is grounded in organizational psychology research and adapted to the realities of fast-paced business environments. [Include 1-2 relevant client examples, with permission.]

This section gives confidence that you know what you are doing and have a plan. But notice it is not overly detailed or jargon-heavy. Clear and practical.

Section 4: expected outcomes and success metrics (1 page)

This section defines success. Include 3-5 key outcomes, how you will measure each one, and what “good” looks like.

Example:

EXPECTED OUTCOMES AND SUCCESS METRICS

Primary Outcomes

1. Faster, Higher-Quality Decision-Making

- Metric: Decision cycle time (tracked through leadership survey)

- Target: Reduce from 6 weeks to 2-3 weeks for strategic decisions

- Measurement: Monthly tracking, review at months 5 and 9

2. Improved Strategic Alignment

- Metric: Leadership alignment survey (custom survey of direct reports)

- Target: 80%+ of leaders report clear, consistent strategic direction

- Measurement: Baseline in month 1, repeat in month 9

3. Increased Trust and Psychological Safety

- Metric: Team effectiveness assessment scores

- Target: Improve trust scores from 3.2 to 4.0+ (out of 5)

- Measurement: Assessment in month 1 and month 9

4. Better Organizational Clarity

- Metric: Organizational clarity survey (pulse survey to broader organization)

- Target: 75%+ of employees report clarity on company priorities

- Measurement: Baseline in month 2, repeat in month 9

5. Sustainable Team Practices

- Metric: Team adoption of new practices (observed and self-reported)

- Target: 5 new team practices established and maintained

- Measurement: Documented and reviewed monthly

Success Criteria We will consider this engagement successful if:

- At least 4 of 5 outcomes show meaningful improvement

- Executive team members report high value from coaching

- CEO and CHRO assess team effectiveness as significantly improved

- Organizational stakeholders observe positive changes in executive team

This section removes ambiguity. Everyone knows what you are aiming for and how you will know if you got there.

Section 5: investment and logistics (1 page)

Cover fees, payment terms, timeline, logistics, and agreement terms.

Example:

INVESTMENT AND LOGISTICS

Professional Fees - Total Investment: $120,000 - Includes: - 9 monthly half-day team coaching sessions - Team effectiveness assessment (administered twice) - Stakeholder interviews (12-15 interviews) - Quarterly progress reviews with CEO/CHRO - Session preparation and follow-up - Email/phone support between sessions - All assessment tools and materials

Payment Terms - 50% upon contract signing - 25% at month 5 - 25% upon completion

Timeline - Start: January 2026 (stakeholder interviews and assessment) - First coaching session: February 2026 - Completion: September 2026

Logistics - Sessions held on-site at [Company] headquarters - Half-day sessions (typically 9am-1pm or 1pm-5pm) - Full executive team participation required - Video conferencing available for remote participants

Agreement Terms - 30-day cancellation notice required - All coaching conversations confidential - Summary themes shared with CEO/CHRO (no individual attributions) - Standard professional services agreement

Next Steps Upon approval:

1. Execute service agreement

2. Schedule stakeholder interviews

3. Distribute team assessment

4. Confirm coaching session dates

5. Begin engagement in February 2026

Optional appendix

For people who want more detail, include an appendix with detailed coach bios, sample assessment questions, client testimonials or case studies (with permission), research or framework details, and FAQs. Do not put this in the main proposal. It makes it too long. But having it available shows depth.

What not to include

Leave out long explanations of general coaching theory, extensive credential listings in the main body, jargon-heavy coaching language, multiple options (propose one approach), overly detailed session-by-session breakdowns, and excessive self-promotion. All of these make the proposal longer, harder to read, and signal that you care more about showcasing yourself than solving their problem. Multiple options create decision fatigue and complicate approval. Keep it tight.

Pricing strategy

Fixed fee

This is the right choice for most engagements. One total fee for the whole engagement, like “$120,000 for 9-month leadership team coaching.” It is simple, easy for buyers to budget, and aligns incentives because you are paid for value rather than hours. The only real risk is unexpected scope expansion, which you can manage with clear boundaries in your agreement. If you are not sure which pricing model to use, use this one.

Per-person fee

Works well for cohort-based coaching and HiPo programs where participant numbers might shift. Something like “$15,000 per executive for 6-month coaching” scales naturally. It can feel transactional, so frame it around outcomes per person rather than just a unit price.

Retainer

A monthly or quarterly retainer ($10,000/month, say) works for ongoing executive coaching relationships and long-term partnerships. Buyers sometimes find open-ended arrangements harder to approve, so define what is included each month.

Hourly or day rate

Avoid this unless scope is genuinely unclear and you need a short-term arrangement. Hourly pricing focuses the conversation on time rather than value, invites scope creep and billing disputes, and feels transactional. If you must, $5,000/day is a common rate for team coaching sessions.

Pricing mistakes

The most common mistake is underpricing to win work. It signals low value, attracts price-sensitive clients, and is not sustainable. Close behind is defaulting to hourly pricing for everything, which turns you into a commodity. Offering too many pricing options creates decision fatigue and makes you seem uncertain. Make sure you account for prep and follow-up in your fees, not just session time. And if a client pushes back on price, defend the value before you even think about discounting. Cutting your price quickly signals your initial number was inflated.

What to charge: benchmarks

For individual executive coaching, $10K-$25K per executive for 6-9 months is typical. CEO coaching or very senior executives run $25K-$50K+. If you bill hourly (and again, try not to), $500-$1,500 per hour.

For leadership team coaching, $80K-$200K for 6-12 months. Half-day sessions typically run $5K-$10K per session, and that should include assessment, prep, and follow-up.

For program-based coaching (HiPo programs and the like), $10K-$20K per person for 9-12 months, often including cohort sessions, individual coaching, and assessment.

Your specific rates will depend on your experience, client size and industry, engagement complexity, geography, and the value you are creating.

Common objections and how to address them

Even good proposals face pushback. Here is how to handle the ones that come up most.

“This is too expensive” usually means one of two things: they do not see the value relative to cost, or it genuinely exceeds their budget. Before you touch the price, reinforce outcomes. What is the cost of slow decision-making? Of losing key executives? Compare your fee to the cost of the problem. If budget is the real issue, ask what they had in mind and see if you can restructure scope to fit. Offer payment terms. But do not immediately discount. If someone wants 50% off with no rationale, they do not value coaching, and you should walk away.

“We’re not sure coaching is the right approach” is actually a useful objection because it means you need to go back to diagnosis. Step back and ask what they are trying to achieve. If coaching genuinely fits, explain why. If it does not, say so and recommend what would work better. Pushing coaching on a situation that calls for something else will damage your credibility. But often this objection means the buyer just needs help connecting the dots between coaching and their business problem. A concrete example from similar work you have done can go a long way.

“Can we start with a smaller pilot?” is reasonable and you should usually say yes. Propose something like a 3-month pilot with 3 executives, same approach but shorter duration, with clear success criteria that trigger expansion to the full cohort. Make sure the pilot is a fair test, and price it to be profitable for you.

“We need to compare you to other coaches” is normal due diligence. Support the process, ask what criteria they are evaluating on, and differentiate your approach. Do not get defensive or pressure them to decide.

“Can you coach more people for the same fee?” is a request to maximize value. Explain the trade-off: adding more people means less time and attention per person. You can offer group coaching for additional participants at a lower cost, or selectively add 2-3 more people with an adjusted fee. Do not agree to double the participants for the same price.

“Our budget cycle doesn’t align with your timeline” usually means they cannot access budget right now. Adjust timing, ask about project budget or discretionary funds, offer a smaller scoping phase now with full work when budget opens, or plan to reconnect during their next budget cycle.

Following up after you send the proposal

Sending the proposal is the beginning of the approval process, not the end. In the first day or two, send a quick email confirming they received it and offer to walk through it together. During the first week, ask about the timeline for review, who else needs to see it, and whether they need anything else from you. Over weeks two and three, offer to meet with other stakeholders and answer questions promptly. If you are heading into week four with no decision, check in on where things stand and ask if something is blocking approval that you can help address. If it hits two months with no movement, be direct: either set a specific time to revisit, or acknowledge that timing is not right and stay in touch.

Staying organized

Track proposals in a simple system:

- Company name

- Contact person

- Date sent

- Amount

- Status (Sent / Under Review / Approved / Declined / Dead)

- Next follow-up date

Do not let proposals languish without follow-up. But also do not be annoying. Find the balance.

Delivering excellence

Carlos was three months into a coaching engagement with a major financial services company when he got an unexpected call from the VP of Talent Development. “We need to talk about one of your coaching clients.”

Carlos’s heart sank. He’d been coaching the Head of Operations, and the sessions were going well. Or so he thought. Deep conversations, meaningful insights, clear progress on the leader’s goals.

The VP continued: “Her team says she’s been more withdrawn lately. She missed two important deadlines. And when her boss asked how coaching was going, she said ‘fine’ but couldn’t articulate any specific changes. We’re wondering if coaching is the right intervention.”

Carlos was blindsided. From inside the coaching relationship, everything seemed great. But from the organization’s perspective, coaching was making things worse.

This chapter is about the gap between “good coaching” and “good coaching in an organizational context.” They’re not the same thing.

The core tension

In private practice, the arrangement is clean. A client hires you, you coach them, they decide if it’s valuable, and confidentiality is absolute. One relationship, two people, simple.

In organizations, everything gets layered. The organization is paying the bill. You’re coaching an individual who may or may not have chosen to be there. Multiple stakeholders care about outcomes, and confidentiality has limits you need to negotiate before the first session even starts.

This is where Carlos went wrong. He was coaching as if it were private practice: deep one-on-one work, absolute confidentiality, the client as the sole judge of value. Meanwhile, the organization was watching from the outside, seeing no visible change, and drawing its own conclusions. Most coaches are trained for the private practice arrangement. They struggle in the organizational one.

The three-party relationship

Organizational coaching is a triangle, and the tension lives in the space between the three sides. You, the coach, want to serve your client well, maintain your professional integrity, and (let’s be honest) get hired again. The coachee wants personal growth, psychological safety, and confidentiality. They may have their own agenda that doesn’t quite line up with what the organization wants. And then there’s the sponsor, the person or function paying for coaching, who cares about business outcomes: performance improvement, retention, leadership capability. They need some level of accountability and visibility into what their money is buying.

These interests genuinely conflict sometimes. The coachee might want to explore whether they should leave the company. The sponsor is paying for coaching specifically to retain them. You’re sitting in the middle, holding both truths, trying to serve both parties honestly. Or the coachee might be working through a difficult relationship with their boss, who happens to be the sponsor. Now the person you’re reporting progress to is part of the problem your client is trying to solve.

There’s no formula that resolves these tensions cleanly. Your job is to serve all three parties while maintaining appropriate boundaries. That means you can’t simply default to “everything is confidential” the way you might in private practice. But you also can’t become a reporting mechanism for the organization. You have to find the middle, and you have to negotiate it explicitly before coaching begins. The coaches who do this well are the ones who name the tension openly in the contracting conversation rather than pretending it doesn’t exist.

What organizations expect

Companies expect certain things from coaches, even when they don’t spell them out. Part of the reason coaches stumble in organizational settings is that these expectations feel obvious to the people inside the organization, so nobody thinks to state them explicitly. Then the coach violates an unspoken norm and everyone acts surprised.

Business-relevant outcomes

Organizations don’t hire coaches for personal growth. They hire coaches to improve business performance. That sounds obvious, but many coaches miss the translation step. They do good work on self-awareness, emotional regulation, communication patterns, and then write a progress report that reads like a therapy summary. Your coachee may be developing real self-awareness about their communication patterns. That’s great. But what the organization wants to hear is that stakeholder relationships have improved and the product roadmap is moving faster as a result.

The things that matter to sponsors are leadership effectiveness, team performance, reduced turnover risk, smoother change management, and stronger cross-functional relationships. Self-awareness, emotional intelligence, and personal fulfillment matter only to the extent that they produce visible behavior change. If you can’t connect your coaching work to business outcomes the organization cares about, you’ll be seen as a nice-to-have that gets cut in the next budget cycle.

When you write progress updates, resist the urge to describe the inner journey. Instead of “Sarah has become much more self-aware about her communication style,” write “Sarah has improved her stakeholder relationships, which is helping accelerate the product roadmap.” Same underlying work. Different language. The second one gets your contract renewed.

This isn’t about being cynical or reducing coaching to a corporate exercise. The inner work matters. It’s what makes the outer change possible. But the organization is paying for the outer change, and if you can’t articulate it in terms they understand, they’ll question the investment. Learn to speak both languages fluently.

Appropriate transparency

Confidentiality is critical, but in organizational contexts it’s not absolute. This is where many coaches get uncomfortable, and where getting it wrong costs you.

Organizations reasonably expect high-level progress updates, engagement and participation data, flagging of serious concerns (safety risks, ethical violations), and some indication of outcomes and impact. They do not expect verbatim session content, personal issues unrelated to work, private reflections, or anything shared in confidence that doesn’t affect the organization.

The key is to clarify all of this before you start coaching. What gets reported, and to whom? Under what circumstances would you break confidentiality? How will progress be measured and communicated? Who “owns” the coaching relationship?

Different coaches draw these lines in different places, and that’s fine. Some maintain that nothing beyond session attendance can be shared. Others believe that outcome-focused progress (behavior change, skill development, goal achievement) can be reported while keeping personal content private. What matters is that you know where your lines are and that you make them explicit in the contracting conversation. If you don’t negotiate these boundaries upfront, you’ll end up improvising when it matters most. That never goes well.

Professional standards

Organizations assume all coaches operate with similar professional standards. They’re often wrong about this, but the expectation is there. Show up on time. Don’t cancel sessions. Have a structured approach with clear goals. Maintain documentation. Respect ethical boundaries. Avoid conflicts of interest. None of this is remarkable, but coaches who slip on the basics, rescheduling frequently, coaching without clear goals, getting drawn into organizational politics, find that their reputation erodes quickly and quietly.

Organizational savvy

Good coaches understand people. The coaches who become trusted advisors understand systems. This means recognizing when an issue is systemic rather than individual, knowing when to escalate appropriately, and seeing patterns across multiple coaching engagements.

Here’s the difference. A coach without organizational savvy says, “I’m coaching the VP and we meet weekly.” A coach with it says, “Based on my work here, I’m seeing that better clarity around decision rights could accelerate leadership effectiveness across the team. This isn’t specific to any individual. It’s an organizational pattern worth addressing.” The second coach becomes a strategic resource. The first is just executing a contract.

The quality bar

Intake and contracting

Good intake means a three-way conversation between you, the coachee, and the sponsor (typically the coachee’s manager or HR). You want goals aligned across all parties, success criteria defined upfront, confidentiality boundaries clarified, logistics agreed upon, and a timeline with check-in points established.

The three-way conversation matters more than you might think. When you contract with just the coachee, you often end up with goals that make sense to the individual but don’t connect to what the organization is trying to achieve. When you contract with just the sponsor, the coachee may feel like coaching is being done to them rather than for them. The three-way meeting surfaces misalignments early, when they’re easy to resolve, rather than six sessions in when everyone is frustrated.

Sample intake questions:

- To the sponsor: “What would success look like for this coaching engagement?”

- To the coachee: “What are your goals, and how do they align with what the sponsor shared?”

- To both: “How will we know if coaching is working?”

- To both: “What should I share with the sponsor about our coaching work, and what stays confidential?”

Documentation

Documentation sits at the intersection of practical necessity and confidentiality. You need enough to track progress, maintain continuity between sessions, and demonstrate value. But you also need to protect the coachee’s privacy and the trust that makes coaching work.

Track session dates and attendance, goals and success criteria, high-level progress notes, action commitments, and any concerns or red flags. Store everything securely.

A good session note looks like this: “Session focused on stakeholder management. Client identified three key relationships to develop. Committed to weekly check-ins with each.”

A bad one looks like this: “Client shared that they hate their boss and are considering leaving. They talked about personal financial stress and marriage problems.” The test is simple: if this ended up in a legal discovery process, would you be comfortable with what you wrote? If the coachee read your notes, would they still trust you? Write accordingly.

Outcome reporting

Provide regular high-level updates to the sponsor, monthly or quarterly depending on the engagement. Focus on outcomes and behavior change, not process. “We had six sessions” tells the sponsor nothing. Observable behavior change tells them everything.

The best progress reports tie coaching outcomes back to the goals established in the intake conversation. This closes the loop for the sponsor and reinforces that coaching is a disciplined process, not just open-ended conversations.

Sample progress report:

To: VP of Talent Development Re: Coaching Progress Update, Q2

Coaching engagement with [Name] continues to progress well. We’ve completed 6 sessions focused on leadership presence and strategic communication.

Progress highlights: - Improved executive presence in leadership team meetings (feedback from peers) - More proactive in strategic planning conversations - Developing stronger relationships with cross-functional stakeholders

Current focus areas: - Delegation and team development - Managing up more effectively

Engagement is strong. Client is actively applying insights between sessions. No concerns to flag.

Next check-in: End of Q3

Handling difficult situations

The disengaged coachee

When someone keeps cancelling, doesn’t follow through on commitments, and sessions feel like they’re going through the motions, name it directly. “I’m noticing we’ve rescheduled three times. What’s getting in the way?” Sometimes the answer is simple: they’re drowning in work and genuinely can’t carve out the time. Sometimes the answer is more revealing: they didn’t choose to be coached and they’re passively resisting. Either way, explore whether coaching is the right fit right now. Sometimes pausing and revisiting in a few months is the honest answer. If engagement doesn’t improve after you’ve named the pattern, loop in the sponsor. Continuing to bill for sessions that aren’t going anywhere helps nobody.

Coaching as complaint session

Some coachees want to use every session to vent about organizational dysfunction, bad leadership, and political games. Acknowledge their frustration, then redirect: “What’s in your control here?” Name the pattern if it persists: “I notice we spend a lot of time on what others are doing wrong. What if we focused on what you can influence?” If they can’t make that shift, coaching may not be what they need.

Coaching surfaces performance issues

This is one of the trickiest situations you’ll face. Through coaching, your coachee reveals significant performance problems, ethical concerns, or interpersonal issues that the organization probably needs to know about.

The worst responses are at opposite extremes: maintaining absolute confidentiality when the organization needs to act, or immediately reporting everything to HR without talking to the coachee first. Both destroy trust. Both are wrong.

The better path starts long before the situation arises. In your contracting conversation, be explicit: “If we uncover serious performance or ethical issues, I may need to bring those to the sponsor’s attention. I’ll always discuss this with you first.” This isn’t just covering yourself. It gives the coachee fair warning and actually makes the coaching safer, because everyone knows the rules.

Then when something surfaces, go to the coachee first. “What we’ve discussed raises concerns I think your manager needs to be aware of. How do you want to handle this?” Give them the chance to self-report. Most people, when given the opportunity and some coaching support, will choose to raise the issue themselves. That’s the best outcome for everyone.

If the issue is developmental, coach them to address it on their own. If it’s serious (safety, ethics, legal), you have an obligation to escalate regardless of what the coachee wants, and you should document carefully what was discussed and why escalation was necessary. These situations are uncomfortable, but handling them well is part of what separates a professional organizational coach from someone who just does coaching inside organizations.

You realize coaching isn’t the right intervention

Sometimes, a few sessions in, you realize the problem isn’t the individual. It’s a toxic culture, impossible expectations, a terrible manager, or a structural issue that no amount of coaching will fix. The temptation is to keep going because you’re getting paid.

Don’t. This is a moment that defines what kind of coach you are.

Be honest with the coachee: “I’m wondering if coaching is the right tool here. The challenges you’re facing seem more organizational than individual.” Then have a candid conversation with the sponsor: “I want to be transparent. I’m seeing systemic issues that individual coaching can’t solve. What might help more is team coaching for the leadership group, or an organizational effectiveness assessment.”

You might worry that this conversation will cost you the engagement. It will. But consider the alternative: you keep coaching someone through a problem that coaching can’t fix. Six months later, nothing has changed, and the organization concludes that coaching doesn’t work. Now you’ve lost not just this engagement but every future one with that company.

This kind of honesty is rare, and it’s exactly what builds the reputation that brings you more work. Organizations remember the coach who told them the truth, even when it meant giving up revenue. They don’t remember the one who quietly billed through a doomed engagement.

It also helps to have specific alternatives ready when you make this call. “Coaching isn’t working” is a dead end. “Coaching isn’t the right tool, but here’s what I think would help” positions you as a thoughtful advisor, even as you’re winding down the engagement. Some of the strongest organizational relationships I’ve seen coaches build started with exactly this kind of honest redirect.

Common mistakes

The fastest way to damage your reputation in organizational coaching is to go dark on the sponsor. You finish the contracting conversation, start coaching, and then the sponsor hears nothing for months. They have no idea if coaching is working. They start to wonder if it’s worth the money. By the time they reach out to ask, they’ve already half-decided to cut the program. I’ve seen coaches lose renewals not because the coaching was bad, but because nobody on the organization side could tell whether it was good. Set a regular check-in cadence with the sponsor from the start and stick to it. Proactively share wins and flag concerns. Silence creates doubt, and doubt kills contracts.

Closely related: failing to flag concerns. If you see serious performance issues, if the coachee has disengaged, if coaching clearly isn’t working, say something. Organizations hire you as a professional and expect you to exercise professional judgment. They don’t expect you to have all the answers, but they do expect you to raise your hand when something isn’t right. Waiting until it’s a crisis helps no one and makes you look either oblivious or complicit. Neither is a reputation you want.

Beyond those two, watch for overstepping your role (you’re a coach, not a therapist or consultant or friend), failing to adapt to organizational culture (being too “new age” in a conservative firm or too rigid in a startup), and poor session management (frequent rescheduling, showing up unprepared, not tracking engagement). None of these are dramatic failures. They’re quiet erosions that close doors without anyone telling you why.

Building long-term relationships

Excellence compounds. When you coach someone well and they get promoted, they hire you again in their new role and refer you to peers. When a sponsor sees real results from one engagement, they buy more and you become their go-to coach for key leaders. When HR sees you navigate complexity with professionalism, they bring you in for the high-stakes situations and invite you to support initiatives beyond individual coaching.

Over time, multiple successful engagements create a track record. Renewals happen without competitive bids. You’re seen as safe, reliable, and worth the investment. In organizational coaching, reputation is everything. One excellent engagement leads to three more. One poor engagement closes doors across an entire company, or across an industry if it’s a small world. The quality of your delivery today is the pipeline for your business tomorrow.

The invisible coach problem

Elena had been an internal coach at a healthcare company for two years. She coached 15 leaders per year, maintained a waitlist of people wanting to work with her, and consistently received glowing feedback. Leaders she coached got promoted. Teams she worked with improved their performance metrics. She was doing exceptional work.

Then the company announced budget cuts. Her role was eliminated.

Elena was stunned. “But everyone loves the coaching! My clients are some of the company’s top performers!”

Her manager was sympathetic but direct: “The executive team doesn’t really know what you do. When we had to make cuts, they saw your role as ‘nice to have’ because they didn’t understand the business impact. I fought for you, but I couldn’t make the case strong enough.”

Elena had fallen into the trap that catches many excellent coaches: doing great work invisibly.

I’ve seen versions of Elena’s story play out more times than I can count. The coach who transforms a struggling team, the coach who saves the company from losing a critical executive, the coach who quietly builds the next generation of leaders. And then someone in finance looks at a spreadsheet and asks, “What does this person actually do?” If nobody can answer that question with specifics, the coaching is gone.

In organizations, doing good work isn’t enough. If leadership doesn’t see your impact, you’re vulnerable. This chapter is about making your coaching work visible without being salesy, self-promoting, or violating confidentiality.

Why coaching stays invisible

Coaching is invisible by design. Confidentiality is the foundation of the work, and the most powerful moments (breakthroughs, vulnerable conversations, hard realizations) happen behind closed doors. The people who control budgets rarely see any of it.

They see line items and vague descriptions like “executive coaching services.” Maybe they see some aggregate satisfaction scores. They don’t see the leader who was about to quit but stayed, or the executive who stopped micromanaging and finally developed their team, or the team that resolved a conflict that had been dragging down project delivery for months.

Here’s the painful paradox: the better you are at creating safe, confidential coaching spaces, the less visible your impact becomes. You’re rewarded for discretion with obscurity.

The problem goes deeper than confidentiality, though. Coaching impact is indirect. You don’t “increase sales by 15%.” You help a leader make better decisions, which leads to better outcomes, which eventually shows up in the numbers.

Organizations struggle to connect dots that aren’t directly connected. When a leader improves, the credit gets spread across a dozen possible causes. Was it the coaching? Their own growth? A new manager? Market conditions? Probably all of the above. But coaching rarely gets the credit because the causal chain isn’t clean.

And most coaches make this worse by refusing to self-advocate. We’re trained to be humble, serve the client, stay in the background. Those are good coaching values. But in organizations, if you don’t advocate for the value of your work, no one else will. Humility becomes invisibility.

What’s at stake

The consequences are real and they hit from every direction.

External coaches don’t get renewed. They don’t get referred to other companies. They end up competing on price instead of value, which is a race to the bottom.

Internal coaches get their roles eliminated during budget cuts. They get left out of strategic conversations. Their teams stagnate without new headcount or budget because nobody upstairs sees the point.

In both cases, coaching gets labeled “nice to have” instead of strategic. And when budget pressure comes (it always does), “nice to have” is the first thing cut. Organizations make decisions based on perceived value, not actual value. If they can’t see your impact, it doesn’t exist for decision-making purposes.

Translate impact into business language

The core move is translation. You’re not lying or exaggerating. You’re describing the same outcomes in language that resonates with business stakeholders.

Coaches tend to talk about “increased self-awareness” and “deeper reflection” and “authentic leadership.” Those words mean something to us. They mean nothing to a CFO.

Decision-makers respond to “improved decision-making speed” and “reduced turnover risk” and “accelerated time-to-impact for new leaders.” Same work. Different framing.

Here’s what that translation looks like in practice:

What you do in coaching

Coaching language

Business language

Help leader explore their communication style

Increased self-awareness about communication patterns

Improved cross-functional collaboration and stakeholder management

Support leader through difficult team conversations

Developed capacity for difficult conversations

Resolved long-standing team conflicts affecting project delivery

Work on delegation and empowerment

Enhanced ability to let go and trust others

Developed high-performing team, freeing leader for strategic work

Coach on work-life balance and boundaries

Greater clarity on personal values and priorities

Improved sustainability and reduced burnout risk for key leader

Explore emotional reactions to feedback

Deepened emotional intelligence and self-regulation

More effective at receiving and acting on feedback from leadership

Aggregate and anonymize

This is the single most important visibility strategy because it solves the core tension between confidentiality and demonstrating value. You can’t share individual coaching details, but you can share patterns.

Too many coaches stay completely silent about their work to protect confidentiality, and that’s a mistake. You can say plenty without revealing anything sensitive.

Something like: “Over the past quarter, I coached 12 leaders across three departments. Common themes included stakeholder management, delegation, and navigating organizational change. All 12 leaders reported improved confidence and capability in their roles.”

No individual details. No broken trust. But now someone in leadership knows what you’re actually doing all day.

Even better, share the patterns that demonstrate value beyond individual coaching. “I’m seeing a pattern across multiple coaching engagements: new VPs struggle to transition from tactical to strategic thinking. This suggests an opportunity for onboarding support specifically focused on this transition.”

That kind of insight positions you as someone who sees across the organization, not just someone who has private conversations. It also shows strategic thinking, which is exactly the kind of value that makes leadership pay attention.

You can also report outcomes in aggregate: “Three of the leaders I coached this year received promotions, and two were identified as high-potential in the talent review process.” That connects coaching to talent pipeline results without naming anyone.

Notice how this framing ties coaching to things the organization already tracks and cares about. You’re not asking them to adopt new metrics. You’re showing up in the metrics they already use.

Client testimonials

Ask for them. Coaches are often squeamish about this, but it’s straightforward and most clients are happy to help.

When you’re wrapping up an engagement, ask your client if they’d be comfortable sharing feedback you could use with internal stakeholders. Give them control over it. Let them write it themselves or offer to draft something for their approval. The worst that happens is they say no, and in my experience that’s rare when the coaching has gone well.

Here’s a simple request that works:

“Hi [Name], as we’re wrapping up our coaching engagement, I’m gathering feedback to share with [HR/my manager] about the impact of coaching work. Would you be willing to share a few sentences about what changed for you as a result of our coaching? I’d be happy to draft something for your review if that’s easier. Thanks for considering!”

The key is steering them toward business impact rather than process.

A weak testimonial sounds like: “Coaching with [Coach] was great. I really enjoyed our conversations and learned a lot about myself.”

A strong one sounds like: “Coaching helped me navigate a difficult reorganization and build stronger relationships with my new team. I’m now much more effective in my role, and my team’s engagement scores improved by 15 points this quarter.”

The second one gives a decision-maker something to work with. The first one sounds like a spa review. If your client drafts something vague, it’s okay to gently ask: “Would you be comfortable adding something about what changed in your work or on your team?”

Quarterly impact reports

Don’t wait for annual reviews to share your impact. Create a rhythm of regular reporting so that your stakeholders never have to wonder what coaching is accomplishing. A quarterly report doesn’t need to be elaborate. One page is fine. The point is consistency, not length. Here’s a sample:

Q2 2025 Coaching Impact Report

Engagements - 8 active coaching engagements (6 leaders, 2 teams) - 48 total coaching sessions delivered - 100% session completion rate

Focus areas - Leadership transitions (3 engagements) - Team effectiveness (2 engagements) - Strategic thinking and influence (3 engagements)

Outcomes - 2 coached leaders successfully navigated into new VP roles - 1 team resolved long-standing conflict affecting project delivery - Average satisfaction score: 4.8/5.0

Themes and insights - Leaders transitioning to VP level need support with “managing up” and executive presence - Teams struggle most with decision-making clarity and role boundaries - Coaching is most effective when paired with 360 feedback or assessment data

Next quarter focus - Scaling team coaching to two additional departments - Piloting group coaching for high-potential leaders - Developing resources for managers to support their coachees

This works because it combines quantitative data with qualitative outcomes, shows pattern recognition beyond individual cases, and demonstrates forward-looking strategic thinking. Send it to your manager, your HR sponsor, and anyone else who has influence over your budget or role. If it feels uncomfortable to send, that’s normal. Send it anyway. Elena’s coaching was excellent, and she still lost her job because nobody with budget authority knew what she was doing.

Connect coaching to strategic priorities

Every organization has priorities it talks about constantly: growth, culture transformation, digital transformation, retention, leadership pipeline. Your job is to draw explicit lines between coaching and those priorities.

Don’t say “I provide executive coaching.” Say “I support leaders navigating our digital transformation by helping them develop new leadership capabilities and manage change effectively.”

The difference matters. The first version describes what you do. The second describes why it matters to the organization. Decision-makers care about the second one.

Company priority

How coaching connects

Culture transformation

Coaching leaders to embody and model new cultural values

Retention of top talent

Coaching addresses development needs that keep high-performers engaged

Leadership pipeline

Coaching accelerates readiness for senior roles

M&A integration

Coaching supports leaders navigating post-merger complexity

Find out what the strategic priorities are. Read annual reports. Listen to earnings calls and CEO communications. Attend all-hands meetings. Ask your HR sponsor: “What are the top three strategic priorities this year?”

Then explicitly connect your coaching work to those priorities in every update you send. This isn’t spin. It’s context. You’re helping stakeholders understand where coaching fits in the bigger picture.

Other approaches worth using

Anonymized before-and-after stories stick in people’s minds better than statistics. A one-paragraph narrative about a newly promoted Director who went from working 70-hour weeks to 50, while their team’s delivery speed increased by 30%, says more than any metric alone. Keep these short and focused on the outcome, not the coaching process.

When you do have access to measurable data, use it. Promotion rates for coached versus non-coached leaders, retention rates, engagement score changes, 360 feedback improvements.

Something like: “Of the 12 leaders who received coaching, 3 were promoted to VP level versus a historical average of 1 per cohort. All 12 remained with the company versus 15% attrition in prior cohorts. Average engagement scores improved from 68 to 78.”

Just be honest about causality. These leaders also received other support, so don’t claim coaching did it all. But you can say coaching was a key component, because it was.

Visibility also comes from presence. Show up to talent review meetings, strategic planning sessions, and culture task forces. Offer pattern insights proactively: “Based on my coaching work, I’m seeing a pattern of new managers struggling with delegation. Thought you’d want to know.”

Run workshops on topics you see coming up repeatedly in coaching. Write internal articles on leadership challenges. Facilitate lunch-and-learns on leadership topics. The goal is to be seen as a contributor to organizational thinking, not just someone who sits in a room with people one-on-one.

And cultivate champions. These are the people who will advocate for you in rooms you’re not in: leaders you’ve coached successfully, your HR sponsor, senior leaders who understand coaching’s value. Ask them directly for support: “I’d love your help making the case for coaching internally. Would you be willing to share your experience in the next talent review meeting?”

Give them language they can use. Don’t assume they know how to advocate for coaching on their own. Provide talking points. Make it easy for them. You can’t be in every room, but your champions can.

Visibility mistakes to avoid

The most important warning: never violate confidentiality for visibility. Not even a little. Not even when you think it would really demonstrate value. One breach destroys trust permanently, and no amount of visibility is worth that. Don’t share coaching conversation details publicly, don’t name coachees without explicit permission, don’t reveal sensitive information in presentations or case studies without consent.

Beyond that, don’t oversell or exaggerate. Credibility is your currency, and once people think you inflate results, they discount everything you say. Don’t claim coaching created outcomes that were influenced by many factors. Don’t use words like “transformational” or “game-changing” without evidence. Present data honestly.

Don’t be constantly self-promotional, because people tune out obvious self-promotion faster than anything. Quiet confidence and letting results speak is more effective.

Don’t report only on quantity (“I coached 50 people”) without saying whether those 50 people got any value. And don’t position your work against other coaches or interventions. You’re trying to build coaching’s reputation, not just your own.

The long game

Making impact visible isn’t a one-time effort. It’s a practice you build into your regular workflow.

Monthly, send brief updates to key stakeholders and collect feedback from clients. Quarterly, produce an impact report and share insights at relevant meetings. Annually, put together a comprehensive review with data and stories, and use it to plan strategically for the year ahead.

In between, stay visible in organizational conversations, contribute thought leadership, and maintain your champion relationships. None of this takes enormous time. A monthly update is a few bullet points. A quarterly report is one page. The effort is small compared to the alternative, which is having your program cut because nobody could articulate what it accomplished.

The coaches who survive budget cuts are the ones who made their impact impossible to ignore long before the cuts were announced. Don’t wait until your position is threatened to start making the case. By then it’s too late.

Internal versus external coaches

Internal and external coaches face different versions of the visibility problem.

Internal coaches compete with dozens of other priorities for attention and need to justify their headcount annually. They’re especially vulnerable during reorgs and budget cuts. The most important moves for internal coaches are reporting beyond just HR (get in front of executive leadership directly), connecting explicitly to strategic priorities, building champions at multiple levels of the organization, and participating in strategic initiatives beyond coaching itself.

External coaches face the “out of sight, out of mind” problem since they’re not there day-to-day. They need to over-communicate with sponsors (err on the side of more updates, not fewer), create tangible deliverables between sessions, build multiple relationships so they’re not dependent on a single champion, and stay connected between engagements by sharing relevant articles and insights.

Both need to make advocacy a habit, not an afterthought.

From project to program

Rashid had just completed a successful pilot coaching program with a Fortune 500 manufacturing company. He’d coached 8 high-potential leaders over six months. The results were excellent: every participant gave him 5-star ratings, three had been promoted, and the VP of Talent Development was thrilled.

Then the VP said, “This was great! We’ll definitely keep you in mind for future projects.”

Rashid’s heart sank. He’d been hoping to hear “Let’s scale this to 50 leaders” or “Can you become our ongoing coaching partner?”

Instead, he’d gotten the kiss of death: “We’ll keep you in mind.”

Two years later, the company hadn’t called him back. The pilot was successful, but it died there. Rashid never understood why.

Most coaches don’t understand why. They assume good work sells itself. It doesn’t. The transition from successful pilot to embedded program is where the majority of coaching engagements go to die, not because the coaching failed, but because no one designed for what comes next.

Why pilots die (even successful ones)

A rough rule of thumb: maybe 20-30% of successful coaching pilots lead to larger programs. The rest end after the pilot. If you want to beat those odds, you need to understand what kills the other 70%.

The two most common killers are definitional. The first is that “success” was never defined clearly enough to trigger a scale decision. The pilot “went well” in the sense that people liked it, but there were no specific criteria agreed upon in advance that would make scaling the obvious next step. Without those criteria, scaling becomes a brand new decision requiring a brand new business case. Your sponsor has to go back to their leadership and argue for budget all over again, this time without the novelty factor that got the pilot approved. The conversation after the pilot sounds like “Yes, it was great, let’s see what budget looks like next year,” and then nothing happens. You can prevent this entirely by defining scale triggers before the pilot begins. Get your sponsor to agree to something concrete: “If we see 20% improvement in engagement scores and 90% satisfaction, we’ll expand to 30 leaders next year.” That agreement changes the post-pilot conversation from “should we?” to “we said we would.”

The second killer is closely related: the pilot didn’t generate visible business impact. Participants enjoyed coaching, but when the CFO asked what the company got for that $50K investment, nobody could point to anything beyond “people felt they grew.” Satisfaction is not a business case. Organizations scale based on retention numbers, promotion rates, performance improvements, and revenue impact. If you can’t connect coaching to outcomes the finance team cares about, you won’t get funding at scale. This means designing measurement into the pilot from day one, not scrambling to find data after the fact.

The other reasons pilots die are more situational, but equally deadly if you’re not prepared. Champions leave. The VP who sponsored your pilot gets promoted or moves to a different company, and the replacement has their own priorities. This is why you should never build your entire relationship through a single person. Budget reality sets in when organizations realize that scaling from 8 people to 50 costs real money that has to come from somewhere in the annual plan, not from a discretionary innovation fund. Organizational priorities shift between pilot start and scale decision (new strategy, restructuring, market disruption), and coaching gets classified as discretionary. And sometimes scaling just feels too hard operationally, because nobody has thought through how to handle intake, matching, and quality management for a program five times the size of the pilot.

Every one of these is preventable, but only if you plan for them before the pilot starts. By the time you’re presenting final results, it’s too late.

Before the pilot

The most important work happens before anyone gets coached.

Start by understanding whether there’s real intent to scale. Ask your sponsor directly: “If the pilot goes well, what would scaling look like? Is there budget allocated, or would that be a separate decision? What would need to happen for you to want to scale?” The answers tell you a lot. If you hear “Let’s just see how it goes” or “We’ll figure that out later,” you’re looking at a one-off project, not a pilot. That doesn’t mean you shouldn’t do it, but you should go in with clear eyes. What you want to hear is something like “I’ve already discussed this with my VP, and they’re supportive if the pilot works” or “We’ve allocated budget for a potential expansion in next year’s plan.”

Once you’ve established scale intent, define success criteria with your sponsor. Work together to agree on what success looks like, both for coaching quality and for business impact.

Category

Metric

Target

Measurement

Engagement

Session completion rate

>90%

Attendance tracking

Satisfaction

Participant satisfaction

>4.5/5.0

Post-coaching survey

Behavior Change

360 feedback improvement

>15% increase

Pre/post 360 assessments

Business Impact

Retention

100% retention vs. 85% baseline

HR data

Scale Trigger

All of the above met

Meets all targets

Summary report

The critical piece is getting agreement that if these targets are met, scaling will be seriously pursued. Without that agreement, the table is just decoration.

Build measurement into the pilot design from the start. Collect pre-coaching baseline data (360s, engagement scores, performance ratings), run mid-pilot check-ins, and plan for post-coaching measurement using the same metrics. Don’t wait until the pilot ends to think about what you’ll measure.

Finally, build relationships with multiple stakeholders. Meet your sponsor’s boss, the finance partner who allocates budget, and other VPs whose teams might benefit from coaching. Offer periodic updates to a small steering committee rather than funneling everything through one person. When your champion leaves (and they might), you want other people in the organization who already understand and value what you’re doing.

During the pilot

Deliver quality coaching. That’s obvious, but it’s worth saying: no amount of smart positioning overcomes mediocre coaching. The pilot has to actually work.

Beyond quality, your job during the pilot is to create visible wins along the way. Don’t save everything for the final report. In the first couple of months, share that all participants have completed intake and early feedback is positive. By mid-pilot, report on completion rates, participant progress, and any early outcomes like promotions or visible behavior changes. In the final months, signal that the comprehensive impact report is coming and share any unsolicited feedback from participants’ managers. These regular micro-updates keep the program top-of-mind for your sponsor and build confidence that the investment is paying off.

Collect testimonials during the pilot, not after. Ask participants what specifically changed as a result of coaching, how it impacted their team or work, and what they’d want leadership to know if the company were deciding whether to scale. Get these in writing with permission to share. Your pilot participants are your best advocates, so look for opportunities to connect them with decision-makers, whether through a brief showcase session, one-on-one conversations with executives, or quotes in your impact report.

Build the business case in real time. Track cost per participant, time investment, business outcomes, and operational learnings throughout the pilot. Develop a scaling model: what it would cost to expand to 50 leaders, what the ROI looks like based on retention impact alone, what infrastructure you’d need. Share a draft business case with your sponsor mid-pilot. By the time the pilot ends, the case for scaling should already be familiar to everyone who matters.

After the pilot

At pilot completion, deliver an impact report that makes it easy to say yes. Structure it simply: an executive summary with key outcomes and your scaling recommendation, participation and engagement data, outcome evidence (satisfaction, behavior change, business impact), learnings and what you’d adjust for scaling, and a concrete scaling proposal with costs, timeline, and success metrics for the larger program.

Don’t just email the report. Present it to the people who control the scale decision. A 30-minute session works well: ten minutes of your overview, ten minutes of participant testimony (have one or two coached leaders share their experience directly), and ten minutes for discussion. Anticipate the questions you’ll get: How much would it cost? Do we have budget? What’s the operational model? How do we know this works at scale? What if we start smaller? Have answers ready.

Rarely will you get “yes, scale exactly as proposed.” Be ready to negotiate on scope (30 leaders instead of 50), timeline (phased over 18 months), cost (volume pricing), or structure (blending group and individual coaching). Know your flexibility in advance, including the minimum viable scale below which it’s not worth doing.

If the answer is “not yet” rather than “no,” don’t just accept it. Get specific about what’s holding them back. Is it budget, timing, competing priorities, or unconvincing results? Then create a path forward: a smaller continuation with 5 leaders while building the larger case, a pilot with a different population, embedding coaching into an existing program, or simply staying connected through budget planning season. The goal is to keep a thread alive. Programs that die completely are almost impossible to resurrect. Programs that stay small can always grow.

What makes programs stick

If you do get to scale, understand that running a program is fundamentally different from running a pilot. A pilot can survive on your personal attention and your sponsor’s enthusiasm. A program needs infrastructure.

The most important piece is a clear program owner inside the organization. Someone has to manage intake, track participation, communicate with stakeholders, handle quality issues, and report on impact. This might be an internal OD or L&D leader, a dedicated program manager, or you if you’re an embedded external partner. Programs without clear ownership drift, lose quality, and eventually die. This is not optional.

You also need standardized processes that work at scale. How do people enter the program: nomination, application, or referral? How are coachees matched to coaches? How are goals set and progress tracked? How do engagements end and transition? Ad hoc approaches that worked for 8 people will break at 50. Think through intake, matching, contracting, tracking, feedback, and closure. Write them down. Make them repeatable.

The third requirement is a sustainable budget model. Programs funded from unclear or unstable sources are vulnerable every budget cycle. Work with your sponsor to establish whether coaching will be funded centrally by HR, charged to department budgets, or run as a hybrid. Whichever model you choose, get it formalized so the program doesn’t have to re-justify its existence every year. Quality management and communication matter too. As you scale, quality variance increases, so you need selection criteria for coaches, onboarding processes, and performance management for underperformers. And if people in the organization don’t know the program exists or understand its value, participation drops and renewal gets harder.

From program to institution

The final level is when coaching becomes part of how the organization operates, not a program someone runs but infrastructure everyone assumes is there. You know you’ve arrived when coaching is integrated into talent processes (standard for VP onboarding, expected support during transitions), when the budget is locked in annually without debate, when leaders proactively request coaching rather than HR having to sell it, when “have you talked to your coach about this?” is a normal thing people say, and when the program survives leadership changes because new executives inherit it as infrastructure rather than questioning it.

Getting there requires consistent quality over years, integration with other talent processes rather than operating as a standalone offering, champions at multiple levels, repeatedly demonstrated business value, and operational excellence. This typically takes 3-5 years minimum. There are no shortcuts, but the coaches who get there build something that generates its own demand, where coached leaders become advocates who create organic growth without anyone having to make a sales pitch.

Surviving reorgs, budget cuts, and leadership changes

On a Tuesday morning, Lauren logged into the company portal and saw the announcement: “Organizational Restructure Effective Immediately.” Her stomach dropped.

Lauren had been an internal coach for three years, building a thriving coaching practice inside a tech company. She reported to the VP of Organizational Development, who reported to the CHRO. Her work was valued, her calendar was full, and her impact was visible.

The restructure announcement continued: “OD will be consolidated under HR Operations. Several roles will be eliminated to reduce redundancy.”

Within two weeks, Lauren’s position was gone. Not because her work was poor. It was excellent. But when organizations restructure, coaching roles are often seen as “nice to have” rather than “must have.”

Lauren wasn’t prepared. She should have been.

Organizations are always changing

Here is what most coaches don’t internalize: the average CHRO stays about three to four years. Significant reorganizations happen every two to three years. In any given downturn, 70 to 80 percent of companies face budget cuts. And over a three-year period, there is roughly a coin-flip chance that your champion will change roles or leave entirely.

If you work with an organization for three or more years, you will almost certainly face at least one major disruption. That is not pessimism. That is base-rate math.

The specific form of disruption varies. Leadership changes, reorganizations, budget cuts, strategic pivots, full-blown crises. But the effect on coaching is remarkably consistent across all of them. New leaders bring new priorities. Cost pressure makes coaching look discretionary. Restructures eliminate the functions that house coaching. Strategic shifts can make your current work irrelevant overnight.

The common thread is that coaching, no matter how good, is vulnerable whenever an organization is in flux. Excellent work is not protection. Lauren proved that.

Reading the signals

Smart coaches don’t get blindsided. They pay attention to organizational tea leaves, and they start preparing before the announcement drops.

The most reliable warning signs are financial. When a company starts missing revenue or profit targets, everything downstream gets squeezed. Watch for “efficiency” language in all-hands meetings, hiring freezes, travel budget cuts, or the CFO talking about “cost discipline.” If you hear “every department needs to find 10 percent savings,” coaching is about to be in the conversation. These are early indicators that coaching budgets will face scrutiny, and they usually show up months before anyone cuts your program.

Leadership changes are the other major trigger. A new CEO or CHRO in their first year will almost always restructure. That is just what new executives do. They want to put their stamp on the organization, and reshaping the org chart is how they do it. If consulting firms are running organizational assessments or “strategic reviews,” a reorg is coming. The consultants are building the blueprint.

Pay attention to whether your champion seems restless, too. If they have been in role for three-plus years, mention being “ready for new challenges,” or start delegating everything to their team, they may be on the way out. Executive departures rarely come out of nowhere if you are paying attention.

The response to all of these signals is essentially the same: diversify your relationships so you are not dependent on one person, document your impact so you can make the case quickly, and start thinking through scenarios so you are not caught flat-footed. You do not need to panic. You need to prepare.

Be valuable during the transition

This is the single most important piece of advice in this chapter. When change hits, most people hunker down and wait it out. They go quiet, keep their heads low, and hope to survive. Smart coaches do the opposite. They lean in.

Think about what a new leader needs in their first 90 days. They are trying to understand an organization they did not build. They are making judgments about who is valuable and who is not. They are looking for people who can help them get oriented. A coach who reaches out proactively, who offers to brief them on coaching work, who shares what they are seeing across the organization (the patterns, the themes, the places where leaders are struggling) becomes a source of insight. That is an incredibly valuable position to be in during a transition.

This is not about self-promotion. It is about genuine usefulness. New leaders are overwhelmed and looking for people who can make their lives easier. If you are one of those people, you become hard to cut.

The same principle applies during reorganizations, budget cuts, and strategic pivots. Understand the new structure or strategy quickly. Reposition your work to support it. Offer options rather than waiting to be told what happens to you.

If there are budget cuts, come to the table with a scaled-down version before anyone asks. Show what coaching looks like at 75 percent of the current budget, and at 50 percent. Demonstrate that you are a partner who understands business constraints, not a vendor who just wants to protect their contract.

If there is a strategic pivot, reframe your coaching to support the new priorities. If the company is shifting from growth to profitability, talk about how coaching supports operational discipline and retention of key talent. If there is a merger, talk about how coaching helps leaders navigate integration.

The coaches who survive disruptions are the ones who make themselves useful during the disruption itself, not just before or after.

Diversify your stakeholder relationships

If your entire coaching practice depends on one champion, you are one departure away from losing everything. This is worth repeating because it is the most common way coaches get blindsided.

Build relationships at multiple levels and across functions. Your direct sponsor matters, but so does their boss, their peers, the business unit leaders who benefit from coaching, and the finance partners who control budget. When your champion leaves (and eventually they will), these other relationships are what keep you anchored.

Consider two versions of the same role. One coach reports to the Director of L&D. That is her only significant relationship. When that director leaves, she has no one advocating for her.

A different coach holds the same role, reports to the same director, but has also been providing quarterly updates to the VP of Talent and the CHRO. She coaches executives who become advocates. She supports three different business units. She collaborates with OD and Change Management teams. When that same director leaves, this coach has ten relationships anchoring her value instead of one.

Chapters 13 and 14 covered the mechanics of building stakeholder relationships in depth, so I will not repeat them here. But in the context of surviving disruption, the principle is simple: never let one person be the single point of failure for your work.

Know when to hold on and when to let go

Not every organizational change can be survived, and not every one should be. If new leadership is genuinely hostile to coaching, if budget cuts are deep and sustained, if your champions have all left and their replacements do not value your work, the writing may be on the wall. In those cases, the best move is a strategic exit while you still have relationships to leverage, referrals to request, and goodwill to spend. Clinging to a situation that has fundamentally turned against coaching costs you time and energy that would be better invested elsewhere. Leave while you can leave well.

Four coaches, four disruptions

At a financial services company, an internal coach lost her CHRO champion after three years. But she had spent those years building relationships with multiple VPs, documenting her impact extensively, and coaching executives who became advocates for her work. Within the first week of the new CHRO’s arrival, she reached out proactively with a brief overview of the coaching program and an offer to adapt to new priorities. The new CHRO kept her on and eventually expanded her role. Multiple champions and documented impact saved her.

An external coach with a three-year contract at another company faced a 15 percent budget cut across all departments. He proposed a scaled-down version of the program at half the cost, showed ROI data proving coaching paid for itself in retention, and got three coached executives to advocate to the CFO. His one mistake was waiting for his sponsor to raise the issue instead of getting ahead of it. The contract was cut by 40 percent but not eliminated. He kept the relationship and rebuilt the engagement over the next two years.

Then there is the cautionary tale. An internal coach at a tech company lost her role when the company eliminated the OD function and consolidated everything under “People Operations.” Her only relationship was with the Head of OD. She had no documented business impact beyond satisfaction scores. She was not visible to executives. She did not see the reorg coming. Her role was eliminated. She found a new job, but she lost a good situation that better preparation could have protected. Single-champion dependency and lack of visibility made her expendable.

The most instructive case is the external coach working with a manufacturing company on leadership development when a new CEO announced a hard pivot to “operational excellence and efficiency.” Instead of treating this as a threat, she treated it as information. She spent the first two weeks researching operational excellence frameworks, reading what the CEO had published, and understanding what the shift actually meant for the business. Then she reframed her coaching as “leadership capability for operational transformation” and reached out to the new CEO’s office offering to support leaders through the transition.

She started coaching plant managers, people she had never worked with before, who were now critical to the company’s new direction. Previously she had worked only with corporate leaders. Now she was on the factory floor, helping operational managers develop the leadership skills that the new strategy demanded. She became known as the coach who “gets the business.”

Her work did not just survive. It expanded. She became a trusted partner to operations leaders who had never used coaching before. The disruption became her biggest growth opportunity because she moved toward it instead of away from it.

From stability to adaptability

The mindset that protects you through organizational turbulence is simple, even if it is uncomfortable. Stop assuming stability.

The belief that good work will keep you safe, that your champion will protect you, that the organization will recognize the value of coaching on its own: all of that is wishful thinking. Organizations are always changing. Good work is necessary but not sufficient. You need multiple champions, visible value, documented impact, and the willingness to adapt when the ground shifts.

The coaches who last are not the ones who avoid disruption. They are the ones who expected it and built accordingly.

Expanding your scope

Michael had been coaching executives at a pharmaceutical company for two years. His work was excellent. Clients loved him, results were strong, and his contract was renewed annually. He was making good money and the work was meaningful.

But Michael felt stuck. He was executing the same playbook over and over: 1:1 executive coaching, six-month engagements, individual development goals. He wanted to influence organizational strategy, not just support individual leaders. He wanted to be in the room where strategic decisions were made.

His sponsor, the VP of Leadership Development, kept telling him he was “doing great work” and should “keep doing what you’re doing.”

Michael was trapped in tactical excellence.

This chapter is about breaking out of that trap. How to expand your scope and influence within organizations, moving from tactical delivery to strategic partnership.

The altitude ladder

Think of organizational influence as a ladder with four levels. At the bottom is tactical execution, where you deliver coaching services as specified. Someone hands you eight executives and says “please coach them.” You’re measured on delivery quality and satisfaction, and you have little input into strategy or design. You’re useful, but you’re also replaceable.

One step up is trusted delivery partner. You’re still executing, but people ask your opinion on implementation. “We’re planning a new leadership program. How should we structure the coaching component?” You’re consulted, but you’re consulted about how to do things, not about what to do or why. The next level, strategic advisor, is where the questions change. Instead of “how should we structure the coaching component,” you hear “we’re seeing leadership challenges in our digital transformation. What’s your take on what’s happening and what we should do?” You’re influencing which problems get solved and how. You have relationships with senior leadership. Your input shapes organizational decisions, and you’re genuinely hard to replace because of the strategic value you provide.

The highest level is strategic partner, where you’re essentially an extension of the leadership team. You’re part of strategic planning and decision-making. You’re involved in business strategy, not just people strategy. “We’re considering a major acquisition. How should we think about the leadership and cultural integration implications?” Most coaches operate at levels one and two. Very few reach three or four. But those who do have fundamentally different careers, with more influence, more interesting work, more security, and often more income.

Why coaches get stuck

The most counterintuitive reason coaches stay at tactical altitude is that they’re too good at execution. When you’re excellent at delivering coaching, organizations want you to keep delivering coaching. Your sponsor thinks, “why would I change what’s working? They’re amazing at coaching executives. Let’s just have them coach more executives.” Your excellence at the tactical level actively prevents you from being invited to the strategic level.

The second reason is that most coaches never demonstrate strategic thinking. We’re trained to be neutral, process-focused, and non-directive. Those are good coaching skills, but they’re terrible strategic positioning skills. Organizations elevate people who have strong points of view, see patterns and connections, and think about business outcomes rather than coaching outcomes. If you only talk about coaching methodology and individual development, you’ll stay tactical. Related to this, many coaches simply lack business acumen. Strategic conversations require business fluency. You need to understand how the organization makes money, what the competitive landscape looks like, what keeps executives up at night. If you only understand coaching and psychology, you can’t participate in business strategy conversations.

The remaining reasons are more straightforward. Some coaches never build relationships above director level, which puts a hard ceiling on their influence. Others wait passively for an invitation to strategic conversations, and that invitation rarely comes. Organizations are busy. If you’re doing great tactical work, they’ll keep you in that box unless you actively push beyond it.

Developing pattern recognition and business acumen

The foundation of strategic altitude is the ability to see beyond individual coaching engagements to organizational patterns. This is the difference between tactical thinking (“I’m coaching three VPs on stakeholder management”) and strategic thinking (“I’m seeing a pattern across three VPs that suggests our matrix structure is creating confusion about decision rights”). The first is a workload description. The second is an organizational insight that matters to senior leaders.

Start asking yourself what themes you’re seeing across multiple clients. What systemic issues keep coming up? What problems can’t be solved by individual coaching alone? Document these patterns. When you share them with your sponsor, you’re testing whether they value strategic input. If they respond positively, do more. If they seem uninterested, either refine your approach or recognize they may not be the right sponsor for strategic partnership.

You also need business fluency, and there’s no shortcut here. Read annual reports and earnings calls for public companies. Ask your sponsor for access to internal strategy documents. Read industry publications. Ask direct questions: “Can you help me understand the business strategy?” and “What are the biggest business challenges right now?” Attend all-hands meetings and town halls when possible. Build relationships with P&L owners, not just HR. If you’re serious about the strategic path, consider business courses or executive education. You don’t necessarily need an MBA, but you need to be able to hold your own in a conversation about margins, competitive positioning, and market dynamics.

Building strategic relationships and offering insights

Once you’re seeing patterns, share them proactively. Don’t just report “I coached six leaders this quarter, satisfaction is high.” Add something like, “I’m noticing a pattern across the leaders I coach: struggles with managing up to new executives hired from outside. This suggests onboarding support for new executives might prevent downstream issues.” In casual conversations, connect your coaching observations to strategic initiatives. Send occasional written observations to your sponsor or other stakeholders. Start small and see what lands.

As your insights gain traction, expand your relationship portfolio. Your sponsor is the best path: “Would it be valuable for me to brief the CHRO on patterns I’m seeing?” or “I’d love to understand the business units better. Could you introduce me to the VP of Sales?” Senior coached executives can also make introductions. The goal is to build relationships at the level where you want to operate. You can’t influence strategy without knowing the people making strategic decisions.

Asking for and delivering at bigger scope

At some point you need to directly ask for expanded scope. The timing matters. Do it after you’ve demonstrated strategic thinking for six to twelve months, when you have strong relationships with decision-makers, and when there’s a clear opportunity like a new initiative or strategic challenge. Don’t say “I’d like to do more strategic work.” Instead, identify a specific strategic problem, develop a point of view on it, connect it to your coaching work, and propose how you could help.

For example: “I know the integration of the acquired company is a major priority. In my coaching work, I’ve supported several post-merger integrations, and I’m seeing some patterns in your current situation that suggest cultural alignment will be a key risk. I’d like to propose a leadership coaching approach for the integration team that could accelerate alignment. Would it be valuable to discuss this?” If you get the opportunity, deliver real strategic value. The most common failure mode is a coach who gets invited to a strategic conversation and then only offers coaching methodology input. Strategic advisors diagnose broadly. Sometimes coaching is the answer. Sometimes it’s org design, team restructuring, process changes, or different leadership. Be willing to recommend non-coaching solutions.

Common mistakes

The most important mistake to avoid: offering coaching when strategy is needed. When you’re in a strategic conversation and default to “have you considered coaching for this?” when broader interventions are needed, you’re demonstrating limited thinking and confirming you belong at tactical altitude. Beyond that, don’t move too fast (master your current level before reaching for the next one), don’t neglect your core coaching delivery while chasing strategic positioning, don’t wait passively for strategic invitations, and make sure you can speak the language of business rather than only the language of coaching and psychology.

How long this takes

In year one, your job is to master tactical delivery, build a strong foundation, and begin developing strategic insights. Year two is about demonstrating strategic thinking consistently, expanding relationships, and building business acumen. By year three, you should start getting invited to strategic conversations and taking on some strategic projects. Years four and five are when you establish a reputation as a strategic advisor and operate regularly at higher altitude.

This takes years, not months. Anyone promising a shortcut is selling you something. Some things accelerate the timeline: previous business experience, an executive coaching background with higher-altitude clients, strong business education, natural networking ability, or simply being in the right place when a strategic need emerges that you can fill.

Not every coach wants or needs to reach strategic altitude. Tactical excellence is valuable and can be a great career. But if you want strategic influence, understand it’s a multi-year journey that requires intentional effort the whole way through.

Internal versus external coaches

The key difference comes down to access versus positioning. Internal coaches have the advantage of already being inside the organization, with easier relationship-building, more visibility into strategic discussions, and the ability to participate in internal initiatives. The risk is being pigeonholed in your current role, where internal politics and org hierarchy constrain your upward movement. External coaches have more positioning freedom (you can present yourself as a strategic partner from the first engagement) and bring inherently valuable outside perspective, but you have less access. It’s harder to build deep relationships as an outsider, you may not be invited to strategic forums, and it’s easy to be seen as just a vendor. Either path can work, but the obstacles are different.

The business cycle and your coaching practice

In early 2020, Patricia had her best year ever as an executive coach. She had five major corporate clients, a waiting list of individual executives wanting to work with her, and had just signed two new retainer agreements. Her revenue was up 40% from the prior year.

By June 2020, three of her five clients had paused or canceled coaching. New inquiries dried up. Her pipeline, so robust in February, was empty by summer.

Patricia had run into a brutal reality: coaching demand is deeply tied to economic conditions, and when the economy shifts, coaching budgets shift fast. By late 2021, as the economy reopened, demand surged again. Companies that had cut coaching were now desperate to retain and develop leaders. Patricia’s calendar was full again, though she had lost two years of momentum and had to rebuild.

Coaching is pro-cyclical

This is the thing most coaches don’t understand until they live through it. Coaching is not recession-proof. It is not counter-cyclical. It tracks the economy almost exactly, and in some ways it amplifies it. When things are good, companies are growing, hiring, investing in leadership development, and coaching demand runs high. When the economy contracts, coaching is one of the first things cut, often sharply and without much warning.

The pattern plays out predictably. During expansions, organizations pour money into developing leaders, onboarding new executives, and building out high-potential programs. As growth slows and conversations start to include words like “efficiency,” spending gets scrutinized more carefully. Once a real downturn hits, coaching budgets get slashed or eliminated outright. And during recovery, coaching comes back gradually, usually focused on a few critical roles before broadening out again. If you have been doing this long enough, you have seen this cycle repeat at least twice.

Why coaching gets cut early

Coaching gets cut before most other things for straightforward reasons. It looks discretionary. Nobody’s production line stops because they canceled a coaching engagement. The benefits of coaching play out over six to twelve months, and in a crisis, nobody is thinking six months ahead. And coaching tends to show up as a visible, separate line item in the budget, often tagged to an external vendor. When someone needs to find cuts fast, a $150,000 coaching contract is a lot easier to eliminate than laying off two employees, even if the coaching was generating more value.

Reading the signals

You don’t need to become an amateur economist, but you should pay enough attention to avoid getting blindsided. On the macro side, watch interest rate decisions, stock market trends, and layoff announcements in your key industries. If venture capital funding is drying up and tech companies are announcing hiring freezes, that’s going to hit your pipeline within a quarter or two.

The more useful signals come from your own client conversations. Listen for the language. When clients start saying things like “we’re being more careful with spending” or “let’s hold off on expanding that program,” that’s an early warning. When hiring freezes get announced and travel budgets get cut, the concern is real. When your invoices start getting delayed or questioned, when contracts aren’t renewed, when multiple clients pull back at the same time, you’re already in it. Most coaches I know who got through 2008 and 2020 in decent shape say the same thing: they saw it in client conversations weeks or months before the headlines confirmed it.

Diversify your client base

The single most important thing you can do to recession-proof your practice is diversify. If one client represents more than 30% of your revenue, you are exposed. If all your clients are in the same industry, you are exposed. If they are all the same size (all startups, or all Fortune 500), you are exposed.

A good rule of thumb: no single client should account for more than 30% of your revenue, and no single industry should account for more than half. Mix large enterprises (they are slower to cut but also slower to decide) with mid-size companies. Spread across three or four industries. If you can, include some counter-cyclical sectors like healthcare, education, or government, where funding follows different rhythms. Individual executive clients are worth cultivating too, since they often continue paying for coaching out of pocket even when their company’s budget disappears.

Position for essentials, not discretionary

How you describe your work determines how fast it gets cut. “General executive development” sounds like a nice-to-have. “Onboarding coaching for critical revenue roles” sounds like something you can’t skip. “Leadership coaching for personal growth” is easy to defer. “Performance coaching for underperforming high-value employees” is harder to justify cutting. The principle is simple: connect coaching directly to business outcomes that organizations cannot defer, even in a downturn. This is partly about the work you do and partly about how you frame it.

Build financial reserves

Even with good positioning and a diversified client base, your revenue will drop in a serious downturn. The coaches who get through it without panic are the ones who saved money during the good years. Build an emergency fund covering six to twelve months of living expenses, separate from your business operating funds. Save 20 to 30 percent of your revenue during good years. Keep your fixed costs low and avoid taking on debt that requires consistent revenue to service. Financial reserves don’t just protect your bank account. They protect your judgment. When you are not desperate, you make better decisions about which work to take and which clients to keep.

Long-term contracts can provide some buffer too. Annual retainers and multi-year agreements are harder to cancel than project-based work, though in severe downturns companies will sometimes pay termination penalties just to cut costs. They buy you time, not immunity.

Positioning across the cycle

The short version: in boom times, expand aggressively, raise your rates, take on bigger work, invest in your practice, and save money because the downturn is always coming. In downturns, protect your core client relationships, emphasize ROI in every conversation, be flexible on pricing and terms, and reduce your overhead. Do not panic-slash your rates or disappear from the market. In recovery, move fast. Reconnect with past clients, pursue new opportunities aggressively, and raise your rates back. The coaches who stay in survival mode too long miss the growth window, and that is an expensive mistake.

Coaches through economic cycles

One coach I know specialized in CFO and finance leadership coaching when the 2008 financial crisis hit. While most coaches lost 50 to 70 percent of their business, she actually grew. Finance leaders were the critical function during the crisis. Companies needed their CFOs to navigate the downturn, and CFO transitions increased as many were fired or moved on. She repositioned around crisis leadership for finance executives, and the specialization that some people had told her was too narrow turned out to be her greatest protection.

A generalist executive coach with diverse corporate clients and no particular specialization lost four of six major clients within three months during the 2020 pandemic. General executive development was the first thing cut, and it took eighteen months to rebuild.

An internal coach at a large retail company during the 2008 recession faced a 30% HR budget cut that put her role on the chopping block. She pivoted to supporting store managers through the crisis, positioning coaching as a retention tool that was cheaper than replacing managers, and focused on change leadership as stores restructured. She documented the cost savings from improved retention and presented them to senior leadership. Not only did she survive the cuts, she expanded her role. The speed of her repositioning made the difference.

Another coach had spent years saving 30% of her revenue during good years. When the pandemic hit and her revenue dropped 60% for eight months, she was able to maintain her business without panic, stay selective about work, and recover strong in 2022.

The quarterly organizational calendar

Beyond multi-year economic cycles, there is an annual rhythm to organizational life that affects when coaching gets bought and sold. Understanding it gives you a practical edge.

Q4, from October through December, is budget planning season. This is when organizations decide what they will spend on next year, when L&D and OD leaders make their budget requests, and when strategic priorities get set. If you want to be in next year’s budget, you need to be in conversations with budget owners during Q3 and Q4. If you are not in the conversation by then, you are late.

Q1, from January through March, is when budgets get executed. New fiscal years start, programs launch, and the work that was budgeted actually begins. This is an energized, optimistic time in most organizations. If you are not already in the budget, you are playing catch-up for the first half of the year.

Q2 is execution. Programs are in full swing, and there is some flexibility for mid-year adjustments. Focus on delivering excellent work and building the case for expansion.

Q3, from July through September, is where it gets interesting. Organizations start planning next year while also trying to spend their remaining current-year budget. This creates two opportunities at once: next-year budget conversations and year-end surplus spending that can fund pilot programs or quick-start projects. Position for the future while capitalizing on what is left in this year’s budget.

Building a sustainable practice

David left his corporate HR role after 15 years to become an independent executive coach. He had coaching training, a strong network, and several potential clients who said they’d hire him.

Within three months, he was panicking. The clients who “definitely wanted to work with him” were taking forever to actually sign contracts. His savings were depleting faster than expected. He was learning that running a coaching business was completely different from being a coach.

Five years later, David has a thriving practice, but it took him three years to build sustainable, predictable revenue. He wishes someone had told him what he was really signing up for.

The reality of what you’re building

Here is the thing nobody tells you when you leave corporate: you are not becoming a coach. You are becoming a small business owner who happens to deliver coaching. Sales calls, invoicing, proposal writing, contract negotiations, marketing, bookkeeping. Early on, 30 to 50 percent of your time goes to business development and operations, not coaching. If that ratio surprises you, recalibrate now. The people who flame out in year one are almost always the ones who thought the coaching would sell itself.

The financial trajectory is predictable enough that you can plan around it. In year one, most coaches make less than they did in their corporate roles, sometimes significantly less, because so much time goes to building the business rather than billing. By years two and three, revenue starts to stabilize as repeat clients and referrals generate more consistent work and you figure out your pricing and delivery model. By years four and five, you can reach a sustainable practice with predictable revenue, a strong reputation, and the ability to be selective about clients.

Plan for two to three years of building before you have a stable, full practice, and make sure you have the financial runway to cover that period.

Business models

Most readers will start as solo practitioners, and that is a perfectly good place to be. You are the business, you deliver all the coaching, you keep all the revenue, and you have full control. The ceiling is your own capacity, typically six to twelve clients at a time, with revenue potential in the $100K to $300K range depending on your rates and utilization. The downside is that the business stops when you stop, and every role (sales, delivery, administration) falls on you.

If you want to scale beyond your personal capacity, you can build a coaching firm with multiple coaches. You sell and manage client relationships while other coaches deliver. This gets you into the $500K to $5M range but fundamentally changes your job from coaching to running a company. You need to be comfortable managing people and maintaining quality across a team.

A third option is partnering with established coaching or consulting firms as a contractor. They provide clients and handle administration, you deliver coaching. Revenue potential is lower ($75K to $200K) because the firm takes 30 to 50 percent, but you avoid the business development burden entirely.

Many coaches start with firm partnerships while building their own client base on the side, which is essentially the hybrid model: mixing direct clients, firm work, and possibly part-time corporate roles to diversify your income while you build.

The build phases

The first year is about getting paying clients and learning the business. Leverage your existing network aggressively. Former colleagues, warm introductions, alumni connections. Offer pilot pricing to get in the door, say yes to most reasonable opportunities, and focus on collecting testimonials and case studies you can use later. This is not the time to be picky about clients or to spend heavily on branding. Figure out your delivery model, test your pricing, and understand your actual costs.

Expect to make 30 to 50 percent of your prior corporate salary, maybe less. The common mistakes at this stage are spending too much on infrastructure, not networking enough, and underpricing so dramatically that you cannot sustain the business.

During years one and two, the goal shifts to building repeatable systems. You need a standard coaching process, clear engagement models, and a pipeline that does not depend entirely on ad-hoc networking. This is when you refine your positioning and start to figure out who you actually serve best. Revenue is growing but still variable. You will have good months and lean months. By the end of this phase, you should be approaching your prior corporate salary equivalent.

By years three through five, you are optimizing rather than building. You have a reputation, a referral engine, and enough experience to be selective. You can charge premium rates and focus on the clients and problems you find most compelling. The question at this stage is whether you want to stay solo or build something larger.

Getting and keeping clients

Most sustainable coaching practices run on referrals, not marketing. The coaches who struggle are the ones constantly chasing new leads through cold outreach. The coaches who thrive are the ones whose past clients and professional contacts send them a steady stream of introductions. This means your network is your most valuable business asset.

Stay in regular contact with past colleagues, other coaches, HR leaders, consulting firms, and executive search firms. Be generous with your own referrals. Over three to five years, a well-maintained network becomes largely self-sustaining.

Specialization makes the referral engine work. The more specific your focus, the easier it is to get clients. This feels counterintuitive, but “I know the perfect coach for CFOs navigating their first two years in the role” is a referral that actually happens. “I know a good coach” is not. Specialists become memorable, referable, and able to charge premium rates. You can specialize by role, by industry, by challenge type, or by methodology.

The fear is always that you will miss out on clients outside your niche. The reality is that you attract more clients inside your niche than you would ever get as a generalist, and you can still take outside work selectively.

On pricing, the most common mistake is underpricing. Market rates for organizational coaching engagements generally fall in these ranges: $25K to $50K or more for Fortune 500 C-suite work, $15K to $25K for mid-size company VPs, and $8K to $15K for startups or nonprofits. Hourly rates for experienced coaches typically run $200 to $500 per hour, though engagement-based pricing (a flat fee for a six-month coaching engagement, for example) tends to work better for both coach and client.

When you are at 80 percent or more of your capacity, raise your rates. If demand does not drop, you were underpriced. Increase rates 10 to 20 percent annually as your expertise and reputation grow.

One financial principle worth stating directly: no single client should represent more than 30 to 40 percent of your revenue. If that client leaves, you are in crisis. Worse, it is hard to be fully objective with a client when you desperately need their fees to make payroll.

Operations basics

You do not need a section of this book to tell you which scheduling tool to use. But a few operational items are non-negotiable. Get professional liability insurance, typically $1M minimum coverage, because many organizational clients require it. Have a lawyer draft or review your master services agreement before you sign your first client. Set up a separate business bank account and proper accounting from day one. And set aside 30 to 40 percent of your income for taxes, because nothing derails a new practice faster than a surprise tax bill in April.

Common pitfalls

The biggest trap is the feast-famine cycle. You get booked solid, stop doing business development because you are too busy coaching, then your engagements end and your pipeline is empty. You panic, network aggressively, land new clients, get busy again, and stop marketing again. The only way to break this cycle is to treat business development as a permanent, non-negotiable part of your calendar, even when you are fully booked. Ten to twenty percent of your time should always go to pipeline building.

Beyond the feast-famine cycle, watch for a few other patterns. Saying yes to every client regardless of fit will burn you out and dilute your reputation. Working alone without peer support leads to professional isolation and stagnation, so join a mastermind group or peer coaching circle. Stop investing in your own development and your coaching gets stale. And do not assume that because referrals are flowing today, they will flow forever. Maintain at least a minimal, consistent presence through writing, speaking, or sharing your work.

Expanding coaching inside your organization

Keisha was hired as the first dedicated internal coach at a tech company with 3,000 employees. She was excited: a full-time role doing what she loved, with steady income and benefits. Her manager told her, “We want to build a coaching culture here.”

Two years in, Keisha was frustrated. She had a waitlist of people wanting coaching, but her capacity was maxed at 15-20 people per year. She kept seeing organizational problems that coaching could address, but she had no authority to expand programs or hire additional coaches. She was executing what others designed, not shaping coaching strategy.

Meanwhile, at another company, Marcus started in a similar internal coach role. Five years later, he’s now Director of Leadership and Coaching, manages a team of four internal coaches, oversees a $2M budget for external coaching, and sits in strategic planning meetings with the executive team.

What was the difference? Marcus understood how to navigate internal politics, demonstrate value strategically, and expand his influence over time. Keisha, despite being an excellent coach, didn’t.

The challenges of being internal

The central tension of internal coaching is what you might call the access-objectivity paradox. You need to be inside enough to access information and build relationships, but outside enough to maintain objectivity and safety for clients. You work for the organization, not the coachee. Your manager has opinions about who should be coached and why. You sit in meetings where your coaching clients are discussed. Being too embedded compromises coaching integrity, but being too detached limits your influence and career prospects. There is no clean resolution to this tension, only ongoing navigation.

Beyond that paradox, internal coaches face a cluster of related frustrations. You typically don’t control the coaching budget, don’t decide who gets coached, and can’t expand without approval from above. You see opportunities everywhere but need permission and resources you don’t have. There’s also a “just a coach” ceiling that many hit: you’re valued but not seen as strategic, not invited to the bigger conversations. Organizational politics compound things further, because you’re embedded in a system you’re trying to help, which makes both objectivity and self-preservation harder. And perhaps most discouraging, the career path for internal coaches is genuinely unclear. Where do you go from here? Senior coach? Manager of coaches? Something else entirely? Many internal coaches feel stuck after three to five years because no one has mapped the progression for them.

The growth path

The good news is that a career progression does exist, even if most organizations haven’t formalized it. It typically runs from individual contributor coach through program manager, senior coach, director, and eventually into executive leadership roles.

The first transition, from individual contributor to program manager, is the most important one to get right because it’s where most internal coaches either break through or plateau. In your first two years, your job is simply to be an exceptional coach. Build strong relationships with clients, document your impact rigorously, and develop a reputation for reliability and results. But don’t stop there. Start noticing organizational patterns that cut across your individual coaching conversations.

Around years two through four, you want to start taking on program management responsibilities. Volunteer for intake coordination, coach matching, quality tracking, and reporting. If your organization uses external coaches, offer to manage those relationships. The goal is to demonstrate that you can think beyond individual sessions. Build systems and processes. Make your manager’s life easier by owning complexity they don’t want to deal with. This is the phase where you prove you’re operationally capable, not just interpersonally skilled.

From there, the senior coach level (roughly years three through six) involves coaching more senior leaders, providing thought leadership internally, and mentoring other coaches. You become the person people call for the complex situations. The director level (years five through eight or beyond) means managing a team of coaches, setting coaching strategy, managing external vendors, and reporting to senior HR or OD leadership. At the furthest end, some coaches move into VP-level roles leading entire leadership development or organizational development functions, where coaching becomes one tool among many. That transition typically takes eight to twelve years and requires expanding well beyond pure coaching into broader business partnership.

Strategies for expanding influence

Much of what helps internal coaches expand their influence is covered in earlier chapters. Making your impact visible through data, testimonials, and business outcomes is essential (see chapter 13). Building strategic relationships across the organization, not just with your direct manager, determines your ceiling (chapters 13 and 15). Demonstrating strategic thinking by connecting coaching to business priorities and speaking in business language moves you from tactical to strategic (chapter 16). And piloting new approaches before asking for big budgets is always smarter than pitching unproven ideas (chapter 14). Building the formal business case for growth, with clear ROI and strategic rationale, is covered in chapter 14 as well.

Two strategies deserve more attention here because they’re specific to the internal coach’s situation.

The first is creating a vision for expanded coaching. Don’t wait for someone else to envision what coaching could become in your organization. Draft it yourself. What would it look like to scale from 20 coached leaders per year to 100? What if you added team coaching, group coaching, or a manager-as-coach development track? What if coaching were integrated into standard talent processes: onboarding for new VPs, high-potential programs, succession planning, transition support for internal moves? Create a “future state” document, share it informally with your boss and other stakeholders, and build support before you formally propose anything. People rally around a vision more easily than they approve a budget line.

The second is considering strategic career moves. Sometimes expanding coaching’s reach requires changing your own role. Moving from a pure coaching position into a broader OD or L&D role gives you budget and strategic scope, with coaching as one capability you bring. Embedding in a business unit HR role (supporting sales, engineering, or operations directly) puts you closer to real business problems and increases your strategic influence. Change management and transformation roles leverage coaching skills in higher-visibility contexts. Talent management roles, covering succession planning and leadership pipeline, let you integrate coaching into broader talent strategy. The honest question is whether you want to be “a coach” forever or whether you want strategic scope. If the latter, you may need to expand beyond a pure coaching title.

When it comes to owning problems and bringing solutions, this is the pattern that gets internal coaches promoted faster than anything else. When you spot an organizational challenge, like poor retention of mid-level leaders or a struggling change initiative, develop a coaching-based solution and pitch it. Don’t just identify the problem; offer to pilot or lead the fix. People who solve organizational problems get more responsibility. Do this repeatedly and your scope expands naturally.

Common pitfalls

Internal coaches tend to fall into a few predictable traps. Staying too small, content to coach fifteen people a year indefinitely without pushing for expansion, leaves you vulnerable in reorgs and limits your impact. Losing boundaries and objectivity by getting too embedded in organizational politics compromises the integrity that makes coaching work. Failing to document and communicate impact means that even great coaching stays invisible to the people who control budgets and headcount. Not building relationships beyond your direct manager means you have no champions when leadership changes. And thinking too tactically, focusing on individual sessions rather than systemic patterns and business outcomes, keeps you in a box that’s hard to escape.

Special situations

If you’re the only coach in the organization, your most important move is documenting the unmet demand. Track your waitlist, the requests you can’t fulfill, and the cost of leaders going undeveloped. Then propose a small pilot with one or two external coaches or part-time internal coaches. Even modest expansion, if well-documented, builds the case for permanent growth.

If your manager doesn’t value coaching expansion, you have a harder road. Try educating them on the opportunity first. If that doesn’t work, carefully cultivate an executive champion who does see the value. Sometimes the honest answer is that expansion isn’t possible under your current manager, and you need to either move internally to a different team or move externally to an organization that takes coaching more seriously.

Budget cuts and leadership changes that threaten coaching are covered in chapter 15. The short version: when budgets tighten, position coaching aggressively as a retention tool with clear ROI. When new leadership arrives skeptical of coaching, get in front of them early, reframe coaching around their priorities, and deliver quick wins that matter to them.

Career progression examples

One internal coach spent her first two years delivering excellent one-on-one coaching, then took on program management and external coach oversight in years two through four. By year six, she was coaching executives and had built a strong reputation as the go-to person for complex leadership situations. She proposed and built a full leadership development function that included coaching, was promoted to Director, and now leads a team of six with a $3M budget.

Another coach started at a mid-size company, but around year three made a deliberate move into change management, using coaching skills in transformation work. By year five he was leading org effectiveness initiatives where coaching was one tool among several. He was promoted to Director of OD by year seven and VP by year ten, with coaching embedded throughout his broader portfolio. The key was expanding beyond coaching early and demonstrating business acumen.

A third coach spent four years at a large tech company building an internal coaching community, managing external coaches, and becoming highly visible to senior leaders. At year six, she left to start an external practice, taking several executives as clients. The company remained a major client. Her internal reputation and relationships became the foundation for a thriving independent business.

When organizations get coaching wrong

Tom was excited when a rapidly growing startup reached out about building a coaching program. The CEO had just raised $50M and wanted to “invest in leadership development.” They offered him a generous contract to coach 20 leaders over the next year.

Three months in, Tom realized something was wrong. Leaders were being “nominated” for coaching as a remedial intervention, a nicer way of saying “your performance is concerning.” The CEO expected Tom to “fix” struggling leaders and report back on their progress. Confidentiality was unclear. Leaders felt coaching was punitive, not developmental.

Tom tried to course-correct, but the organizational mindset was already set. By month six, he realized he was participating in something that wasn’t really coaching. It was performance management disguised as development. He had a choice: continue taking the money and compromising his integrity, or walk away from a lucrative contract.

He walked away.

This chapter is about recognizing when organizations are setting up coaching to fail, how to help them get it right, and when to walk away because the situation is unsalvageable.

How organizations get coaching wrong

The single most damaging mistake organizations make is treating coaching as punishment or remediation. When coaching is something you “get” because your performance is slipping, when it happens alongside or just before a performance improvement plan, the whole endeavor is poisoned from the start. Coachees show up defensive and ashamed instead of open and motivated. Confidentiality evaporates because the sponsor needs to know if “it’s working.” And the coach is set up to fail, because you cannot coach someone through systemic performance problems that the organization created or tolerated for years. This is exactly what happened to Tom, and it happens in organizations every day.

The second most common failure is coaching without clear confidentiality boundaries. When a manager expects detailed reports on coaching conversations, or HR wants to know “what’s really going on” with a coachee, the psychological safety that coaching depends on disappears completely. Coaching becomes performance theater. The coachee says what sounds good, the coach writes up something diplomatic, and nobody actually develops. This is not just ineffective. It violates professional coaching ethics, and it corrodes trust in ways that make future coaching work harder across the entire organization.

The third mistake is using coaching when other interventions are needed. A dysfunctional team does not need individual coaching; it needs team facilitation or restructuring. A toxic culture does not get fixed by coaching people to “navigate” it; it needs culture change at the leadership level. A person in the wrong role does not need coaching to succeed in that role; they need a talent decision. If you have read chapter 10’s diagnostic framework, you already know that coaching is one intervention among many, and that choosing the wrong intervention wastes everyone’s time. Organizations that reach for coaching as a universal band-aid waste money and delay solving their real problems.

Beyond these three, organizations make a cluster of related structural mistakes that are worth naming even if they do not each need their own section. They launch coaching with no clear purpose or goals, so nobody knows what success looks like and coaching is the first thing cut when budgets tighten. They select the wrong people, offering coaching only to executives when mid-level leaders need it more, or only to struggling performers while missing high-potential development entirely. They make random coach-client pairings with no attention to chemistry or fit. They provide no support structure to reinforce what happens in coaching sessions, so insights from coaching run directly into organizational systems that reward the opposite behavior. They treat coaching as a short-term transaction (three sessions and done) rather than a sustained developmental relationship. And they expect coaches to be therapists, consultants, or miracle workers who can “fix this person’s personality” or “coach them to want to stay at the company.” All of these share a common root: the organization has not thought seriously about what coaching is, who it is for, or how to set it up to succeed.

How to course-correct

When the problem is naivety rather than bad intent, education is your best tool. Many organizations genuinely want coaching to work but have never thought through the mechanics. They need someone to explain why confidentiality matters, how behavior change actually works (it takes months, not three sessions), and what coaching can and cannot accomplish. Three-way contracting between coach, coachee, and sponsor solves many problems before they start. You define what gets reported and what stays confidential. You clarify roles. You set success criteria upfront so that six months later nobody is arguing about whether coaching “worked.” If you encounter an organization that is open to learning, this is relatively straightforward work, and it often turns skeptics into advocates.

When the organization is asking you to violate professional ethics, education is not enough. You need firm boundaries. “I cannot share confidential coaching conversations. That is an ethical boundary, not a preference.” “I will not coach someone who is being forced into coaching against their will.” These are not negotiating positions. They are the floor beneath which you cannot go. If an organization insists on violating confidentiality, or insists that coaching must function as a form of surveillance, you are not the right coach for that situation, and you should say so directly. Paradoxically, setting firm boundaries often builds more respect than accommodation does. The VP of HR who initially wanted detailed session reports may become your biggest champion once you explain why that request would destroy the very thing they are paying for.

When coaching is being used as a band-aid for systemic issues, the most useful thing you can do is name the real problem. “You are asking me to coach leaders through a toxic culture. What if we addressed the culture itself?” “It sounds like the issue is unclear decision rights, not individual leadership capability. Have you considered organizational design work?” Be honest about coaching’s limits. Recommend what would actually work, even if it means referring the organization to someone else. Some organizations will hear you and redirect their resources toward the real problem. Others are committed to avoiding the harder interventions (firing, restructuring, culture change) and will keep reaching for coaching because it feels less confrontational. You cannot save those organizations from themselves, and you should not pretend otherwise.

When to walk away

Walk away when the organization insists on violating confidentiality or other coaching ethics. Walk away when coaching is purely punitive, with no developmental intent whatsoever. Walk away when the organizational dysfunction runs so deep that coaching individuals is like bailing water from a sinking ship, everyone can see what is happening, and leadership refuses to address the hull. Walk away when your gut tells you the engagement will damage your reputation or compromise your integrity.

This applies whether you are external and considering a new contract, or internal and watching your role get co-opted for organizational politics. The calculus is slightly different. An internal coach may need to find another role before leaving, while an external coach can simply decline the work. But the principle is the same: your professional integrity is worth more than any single engagement or paycheck.

Be honest but diplomatic when you decline. “I don’t think coaching is the right intervention for this situation.” “Based on what we have discussed, I am concerned that the setup will not allow coaching to be effective.” Do not burn bridges. People move between organizations, and the company that misuses coaching today might fix its approach next year with different leadership.

Coaches navigating dysfunction

An external coach hired by a manufacturing company discovered early that the VP of HR expected detailed reports on every coaching conversation. Rather than quietly complying or walking away immediately, she explained coaching confidentiality clearly and proposed an alternative: high-level quarterly updates on progress and themes, with a commitment to flag any serious concerns. She was direct about her boundary. “If we cannot agree on confidentiality, I cannot do this work.” The VP pushed back initially but ultimately agreed. The coaching was successful, and over time the VP became a genuine champion for coaching across the organization, bringing her back for expanded work with additional leadership teams.

A startup board wanted to hire a coach for their struggling founder, but what they actually wanted was someone to assess whether the founder should be removed. The coach they approached recognized this immediately. He explained that this was not coaching but assessment consulting, and that he could not coach someone while simultaneously evaluating whether they should be fired. The dual role would make honest coaching impossible. He declined the work and referred them to organizational consultants who could do the assessment properly. He lost that contract, but months later a board member referred him to a different company for legitimate coaching work. Walking away cost him money in the short term and earned him trust in the long term.

The most instructive case is the internal coach at a financial services firm who inherited a coaching program used exclusively as a last-ditch effort before firing people. She could have accepted this as immovable reality. Most people would have. Instead, she documented the poor outcomes from remedial-only coaching, tracked the completion rates and satisfaction scores, and built a case that the current model was wasting money. Then she proposed a pilot: coaching for high-potentials and new leaders, framed as investment rather than intervention. The pilot showed dramatically better engagement, satisfaction, and behavioral outcomes. She educated leadership on coaching best practices, connected the developmental model to the company’s talent strategy, and over two years shifted the entire program from remedial to developmental. She expanded the program significantly and got promoted. Internal change like this requires patience, data, and a willingness to play a long game, but it demonstrates that one person with a clear vision can reform a broken system from inside.

An internal coach at a tech startup spent eighteen months trying to do meaningful coaching work inside a company with toxic culture and dysfunctional leadership. Coaching was being used to help people “cope” with the dysfunction rather than to develop them. He advocated repeatedly for cultural and leadership changes, but the leadership team was not interested in addressing root causes. Eventually he accepted what was in front of him. The organization would not change. He left for an external coaching practice and took several of his coached leaders as clients when they also left the company. Sometimes the most professional thing you can do is recognize that an organization will not change and stop exhausting yourself pretending it will.

Conclusion

This book has covered a lot of ground: organizational literacy, finding buyers, speaking the language of business, navigating budget cycles, surviving restructures, working alongside HR and talent management, and now, recognizing when the whole setup is wrong. If you have read this far, you have a map of organizational terrain that most coaches never develop.

The core argument across all twenty chapters comes down to this. Succeeding in organizational coaching is not just about being a good coach. You can be brilliant in the room and still fail in organizations if you do not understand how they work, where money flows, who makes decisions, and how to position your work so it survives contact with organizational reality. The coaches who build sustainable practices, whether internal or external, are the ones who combine coaching craft with genuine organizational savvy.

The work is complex. It is sometimes frustrating, occasionally political, and there will be moments when budgets get cut, programs get canceled, or you walk away from money because the situation compromised your values. None of that means you are failing. It means you are doing real work inside imperfect systems with competing priorities and limited resources. The organizations you serve need what coaching offers. Helping them access it well, and knowing when to step back, is the work of an entire career.