Jonathan Dunnett is the CEO of Enable Leaders, a curated executive coach matching service. With decades of experience in leadership and leadership development, he’s passionate about helping emerging and senior leaders find the right executive coach for them, all at no cost for the match.
Why Would I Get an Executive Coach? Triggers, Warning Signs, and Myths
Why Executive Coaching Might Be Right for You
Executive coaching is right for you when your current level of performance, clarity, or leadership effectiveness is being limited by something you can’t fully see or solve on your own — a blind spot, a pattern, a transition, or simply the isolation that comes with senior leadership. The trigger moments and warning signs below will help you decide.
Most leaders who ask themselves why hire an executive coach say the same thing afterward: I wish I’d done this sooner.
Not because they were struggling. Not because someone told them they had to. But because once they experienced what a great coaching relationship actually felt like — the clarity, the accountability, the shift in how they saw their own leadership — they couldn’t believe they’d been navigating without it.
So why do so many leaders wait? Usually, it comes down to one of three things:
- They’re waiting for the right trigger moment
- They’re not recognizing the warning signs in front of them, or
- They’re held back by a myth about what coaching actually is.
This post addresses all three, so you can make a clear-eyed decision about whether now is the right time for you.
Part 1: Trigger Moments — Situations Where Executive Coaching Delivers the Most Value
The best time to work with a coach isn’t necessarily when things are falling apart. Some of the highest-value coaching engagements happen when a leader is on the verge of something significant: a transition, an opportunity, a stretch.
Here are the situations where leaders consistently get the most from coaching:
You’ve just stepped into a new leadership role
The first 90 days of a new role are critical and sometimes lonely. You’re expected to lead with confidence while learning the landscape, the politics, the team dynamics, and the unwritten rules all at once. A coach gives you a confidential space to process what you’re seeing, stress-test your instincts, and make strategic decisions before they become costly mistakes.
This is one of the most common triggers for coaching engagements, and for good reason: the stakes are high, the learning curve is steep, and the cost of getting it wrong compounds quickly. Coaches like Jill Carroll and Tracy Wilk specialize in exactly this kind of leadership transition support.
Your scope has significantly expanded
A promotion isn’t just a title change: it’s a fundamentally different job. What made you effective as a manager often doesn’t scale to director, VP, or C-suite level. The shift from doing to leading, from leading teams to leading leaders, from functional expert to enterprise executive — each of these transitions requires a genuine identity shift, not just new skills.
Coaching accelerates that shift. Rather than figuring it out through trial and error over two or three years, a good coach helps you develop the mindset, presence, and strategic perspective your new scope demands. Dr. Kimberly Harden works specifically with mid-level managers and rising leaders preparing for exactly this kind of expanded responsibility.
You’re leading through significant organizational change
Restructuring. Mergers. Layoffs. Rapid growth. A shift in strategy. These are the moments when leadership is tested most visibly — and when leaders most need a trusted, objective thought partner who has no stake in the organizational outcome.
A coach isn’t a consultant who tells you what to do. They help you think more clearly, decide more confidently, and lead more steadily when the pressure is highest. Kelly Landes works with executives leading through high-stakes transitions including the AI revolution now reshaping organizations.
Your team performance isn’t where it needs to be
Sometimes the issue isn’t the team: it’s the leader. Not through incompetence, but through blind spots, communication patterns, or management habits that are subtly undermining trust, engagement, or performance. A coach helps you see what you can’t see yourself, and gives you practical tools to shift the dynamic.
Matt Eichmann works with leaders specifically on team transitions and building high-performing teams, while Dr. Sheila Rioux helps analytical and technical leaders develop the emotional intelligence and people leadership skills that drive genuine team performance.
You’re at a career inflection point
Considering a pivot. Deciding whether to stay or go. Navigating a difficult relationship with a board, a boss, or a key stakeholder. These moments call for someone who can hold the bigger picture with you — someone who isn’t your spouse, your friend, or your colleague, but a skilled professional with no agenda other than your clarity and growth.
Devin Keane brings over 20 years in global financial services talent and leadership strategy to help professionals navigate exactly these kinds of career crossroads.
You’re a high performer who wants to go further
This one is underrated. Executive coaching isn’t remedial. Some of the most productive coaching relationships involve leaders who are already performing at a high level but who also know there’s another level available to them — if they can remove the friction, the self-doubt, or the habits that are creating a ceiling.
Gaye Kuelsen works specifically with high-achieving leaders who appear confident externally but struggle with perfectionism internally — helping them break the high-achievement paradox and lead with both confidence and calm. Babette Bensoussan, known as The Decision-Making Maverick™, helps executives who are already strong make even sharper, more confident decisions under pressure.
Part 2: Warning Signs — When Your Leadership Is Telling You Something
Trigger moments are clear and situational. Warning signs are subtler — they show up in patterns of thought, behaviour, and feeling that are easy to rationalize or ignore. If several of these resonate, it’s worth paying attention.
You’re the smartest person in every room — and it’s starting to feel like a problem. If you find it hard to delegate because no one does it quite right, or you’re regularly frustrated by the gap between your thinking and your team’s, a coach can help you identify whether this is a hiring issue, a communication issue, or a leadership issue.
You’re exhausted in a way that sleep doesn’t fix. Leadership fatigue that persists regardless of rest is often a signal that something structural is wrong — with your role, your boundaries, your team, or your relationship to the work itself. This is different from burnout, and a coach can help you diagnose it clearly.
You know what you should do, but you’re not doing it. This gap between insight and action is one of the most common reasons leaders seek coaching. You’ve read the books, attended the programs, know the frameworks — but something isn’t translating into behaviour change. A coach provides the structure, accountability, and safe challenge that closes that gap.
Your feedback has flatlined. If the people around you have stopped giving you honest feedback — or if you’ve stopped truly hearing it — you’ve likely developed a blind spot that’s costing you more than you realize. A coach is one of the few relationships where you reliably get truth.
You’re making decisions more slowly than you used to. Decision paralysis in senior leaders often signals one of several things: cognitive overload, misaligned values, unclear strategy, or eroded confidence. None of these fix themselves. A coach helps you identify the root cause and address it directly.
You feel isolated at the top. The higher you go, the fewer people you can talk to honestly about what you’re actually experiencing. This isolation — common among senior leaders — erodes judgment, creativity, and resilience over time. Coaching provides a confidential relationship specifically designed to address this.
You’re succeeding by the metrics but not feeling it. Achieving goals that no longer feel meaningful is one of the clearest signals that something in your leadership direction needs to be examined. A coach helps you reconnect with what matters — or recalibrate toward something that does.
Part 3: Myths That Keep Leaders from Getting Started
Even when the triggers are clear and the warning signs are present, certain beliefs get in the way. These are the most common ones — and why they don’t hold up.
“Coaching is for leaders who are struggling”
This is probably the most persistent myth, and it’s simply wrong. Some of the world’s highest-performing executives have ongoing coaching relationships not because something is broken, but because they understand that sustained performance at a high level requires investment in self-awareness, thinking quality, and leadership development. The analogy to professional athletes is overused but accurate: elite performers don’t stop working with coaches when they become elite. That’s often when the coaching relationship becomes most valuable.
“I don’t have time for coaching right now”
This usually means: I’m too busy being reactive to invest in becoming more strategic. Which is, of course, precisely the problem coaching solves. Most executive coaching engagements run 60–90 minutes every two to three weeks — a small investment relative to the compounding return on better decisions, clearer thinking, and stronger leadership.
“I should be able to figure this out myself”
Leadership isn’t a solo endeavour, but most leaders treat their own development as if it is. The expectation that you should be able to diagnose your own blind spots, hold yourself accountable, and generate breakthroughs in isolation is one that we wouldn’t apply to any other domain of high performance. A coach doesn’t have the answers — but they help you find yours, faster.
“Coaching is expensive”
Relative to what? According to the International Coaching Federation, executive coaching consistently delivers measurable ROI for both individuals and organizations. One poor hiring decision. One failed team. One year of underperformance. One missed opportunity for a promotion or a client. Executive coaching, properly scoped, is one of the highest-ROI investments a leader or organization can make. At Enable Leaders, coaching engagements start from $250 for a single session and range to comprehensive programs — so there are options at different investment levels depending on where you are and what you need.
“I don’t know how to find the right coach”
This is the most legitimate of the myths — not because it’s true, but because the process of finding a coach has historically been genuinely difficult. Searching directories, reviewing credentials, scheduling multiple exploratory calls only to discover a poor fit — it’s a real friction. It’s the exact problem Enable Leaders was built to solve.
So — Is Now the Right Time?
If you’ve recognized yourself in any of the trigger moments above, or felt the pull of any of the warning signs, or found yourself nodding at the myths — then yes, the answer is probably now.
The leaders who get the most from coaching aren’t the ones who waited until conditions were perfect. They’re the ones who recognized a moment of readiness — a transition, a frustration, a feeling that there was more available — and acted on it.
At Enable Leaders, we make the next step straightforward. Tell us about your goals and challenges, and within 24 hours we’ll introduce you to 2–3 pre-vetted coaches whose expertise matches your specific situation. No directories to scroll, no credentials to decode, no awkward cold calls. No cost to you for the match. You pay when you find a coach that works for you.
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Frequently Asked Questions About Hiring an Executive Coach
Why hire an executive coach if things are going well?
Because the best time to work with a coach isn’t when things are falling apart — it’s when you’re on the verge of something significant. The leaders who get the most from coaching are often already performing well but know there’s another level available to them. A coach helps you remove the friction, blind spots, and habits that are creating a ceiling before they become a problem.
Why hire an executive coach instead of a mentor or consultant?
A mentor gives advice based on their own experience. A consultant tells you what to do. A coach helps you develop your own clarity, judgment, and capability — so the growth sticks. For senior leaders, coaching is often more valuable than mentorship because the challenges you face are specific to your organization and context. A mentor’s experience may not map directly. A coach helps you build your own answers, faster.
What are the most common reasons leaders get an executive coach?
Leaders who ask why hire an executive coach most commonly point to these triggers:: stepping into a new leadership role, a significant scope expansion or promotion, leading through organizational change, team performance challenges, and career inflection points. Beyond trigger moments, many leaders also seek coaching when they notice warning signs — decision paralysis, feedback flatline, leadership isolation, or the gap between knowing what to do and actually doing it.
How do I know if executive coaching is right for me right now?
If you’re still asking why hire an executive coach, and you’ve recognized yourself in any of the trigger moments, you probably would benefit from an executive coach. The leaders who benefit most from coaching aren’t waiting for conditions to be perfect — they’re recognizing a moment of readiness and acting on it. If you’re unsure, request a match and we’ll help you think it through at no cost.
What does executive coaching actually cost?
At Enable Leaders, coaching engagements start from $250 for a single focused session and range to comprehensive 3–6 month transformation programs from $2,500. The matching service itself is always free — you only pay when you find a coach that works for you. For context on ROI, the International Coaching Federation consistently finds that executive coaching delivers measurable returns for both individuals and organizations.
How does Enable Leaders match me with the right executive coach?
You tell us what you’re navigating — your role, your challenge, your goals. We review your situation personally and identify 2–3 vetted coaches whose expertise, style, and experience match your specific needs. Most leaders have a shortlist within 24 hours. No directories to scroll, no credentials to decode, no awkward cold outreach. Learn more about how the matching process works.