Do Successful Leaders Need an Executive Coach?

Sometimes a leader will look at me and ask, a little sheepishly, "If things are going well, do I actually need a coach?"

I love that question. It's honest. Revenue is steady, the team is growing, and most of the big calls have turned out right. So why add something to the calendar when nothing's broken?

Here's my answer. Yes. And I'd go a step further. Success is usually when coaching matters the most.

In the early stages of leadership, coaching helps you figure things out. You're learning how to delegate, how to run a meeting, how to have a hard conversation without losing the relationship. But as you grow, coaching becomes something different. It becomes about precision. You're making bigger decisions. You're hiring more and more talent. You're carrying more complexity than any one person can fully see. And the cost of a mistake at that level is far more expensive than the cost of coaching.

That's the whole argument in one paragraph. The rest of this post is about why it's true, what the research says, and what you can do this week if you're a leader who's doing well and wondering what's next.

Why Does Success Make Leadership Harder to See Clearly?

The tension is this. The better you get, the fewer people tell you the truth.

When you're new, feedback comes from everywhere. Your boss corrects you. Your peers push back. Your mistakes are small and visible, so you learn fast.

Then something shifts. You become the boss. People start agreeing with you a little faster than they used to. Meetings go the way you expected them to go. And slowly, without anyone meaning to, the honest feedback dries up.

I've watched this happen with leaders I coach, and honestly, I've felt it myself. Nobody sets out to build an echo chamber. It just forms around success the way moss grows on the north side of a tree. Quietly. Gradually. And you don't notice until something goes wrong.

Here's what makes it tricky. At this level, your decisions don't stay small. You hire a senior leader, and that person shapes a whole department. You set a direction, and dozens of people spend a year running toward it. You misread a situation, and the ripple can take months to undo.

So you end up in a strange spot. Your decisions are carrying more weight than ever, and the inputs you get on those decisions are getting thinner.

That's not a character flaw. It's what success does to almost every leader. Which is exactly why it's worth naming.

What Does the Research Say About Coaching for Senior Leaders?

I don't want you to take my word for this, so let me show you what the research says.

Most top leaders are going it alone. A 2013 survey from Stanford Graduate School of Business and The Miles Group polled more than 200 CEOs, board directors, and senior executives. Nearly two-thirds of CEOs said they don't receive any outside coaching or leadership advice, and almost half of senior executives said the same. Here's the part I find most telling. Nearly all of those CEOs said they enjoy receiving coaching, and among the ones who had a coach, most said it was their own idea. In other words, the leaders who get coached aren't being sent to the principal's office. They're choosing it.

Power and experience make blind spots bigger, not smaller. Organizational psychologist Tasha Eurich led a research program with nearly 5,000 participants, published in Harvard Business Review in 2018. Her team estimated that only 10 to 15 percent of the people they studied actually met the criteria for self-awareness, even though most people believe they're self-aware. And it gets more pointed for senior leaders. Eurich found that the more power a leader holds, the more likely they are to overestimate their skills. She cites one study of more than 3,600 leaders in which higher-level leaders overvalued their abilities more than lower-level leaders did, compared to how others saw them. That's the echo chamber, measured.

Coaching works. A 2016 meta-analysis by Rebecca Jones, Stephen Woods, and Yves Guillaume, published in the Journal of Occupational and Organizational Psychology, pulled together 17 studies of workplace coaching. They found that coaching had positive effects across the board, with the strongest effects showing up in individual-level results. Coaching isn't a feel-good extra. It moves real outcomes.

Leadership mistakes are expensive. Gallup estimates that replacing a leader or manager can cost around 200 percent of that person's annual salary. Think about that the next time a senior hire doesn't work out. One misjudged decision about one person can cost more than years of coaching.

Even the best in the world benefit from a second set of eyes. In a 2011 New Yorker essay called "Personal Best," surgeon and writer Atul Gawande described inviting a retired surgeon he'd trained under, Robert Osteen, to watch him operate. Gawande was already an accomplished surgeon. Osteen still came away with a notebook full of observations, down to how Gawande positioned his elbow and where he stood so the light hit the surgical site best. Gawande's point was simple. In sports, having a coach was once unthinkable, and now not having one is. He wondered why we don't apply the same logic to other high-stakes work.

Put all of that together and the conventional wisdom starts to look incomplete. We tend to think coaching is for people who are stuck. The research suggests the opposite. The higher you go, the more you need someone who can see what you can't.

Is Coaching a Sign Something Is Wrong?

Here's the reframe I keep coming back to.

I talk a lot about the difference between an amateur leader and a pro leader. It's not about talent. It's not about title. It's about how you relate to your own growth.

Amateur leaders get help when something breaks. They wait for the crisis. The key person quits, the board gets frustrated, the culture starts to sour, and then they go looking for someone to help them fix it.

Pro leaders build help into their rhythm before they need it. They treat outside perspective as part of the job, the same way a surgeon treats preparation or an athlete treats practice. They're not asking, "What's wrong with me?" They're asking, "What can't I see from here?"

That's why I think of coaching in two seasons.

The first season is figuring it out. You're building basic skills. You're learning what good leadership even looks like in your context. Coaching here is about foundations.

The second season is precision. You already know how to lead. Now the question is whether you can make the next decision a little clearer, the next hire a little sharper, the next hard conversation a little healthier. The gains in this season look small on paper. A slightly better question. A slower response. A challenged assumption. But at your level, small adjustments carry big consequences.

So no, coaching isn't a sign that something is wrong. Most of the time, it's a sign that someone is serious about not staying where they are.

What Does an Executive Coach Actually Give a Successful Leader?

When I think about why I value coaching so much, both as a coach and as someone who's been coached, it comes down to three things.

An outside perspective you can't find inside yourself. You can't read the label from inside the jar. No matter how smart or self-aware you are, you're looking at your leadership from the inside. A good coach stands outside the jar. They notice the pattern in how you talk about a certain team member. They catch the decision you keep circling but haven't made. They ask about the thing you mentioned once and moved past quickly.

A space to think strategically instead of reactively. Most senior leaders I know spend the bulk of their week responding. Emails, meetings, fires, requests. There's very little room to step back and ask, "Where are we actually going, and is this the best way to get there?" Coaching protects that space. For an hour, you're not putting out fires. You're thinking about the fire code.

Someone to challenge your assumptions before they turn into expensive mistakes. This is the big one. Every leader carries assumptions about their people, their market, and themselves. Most of those assumptions are probably right. That's partly why you're successful. But the ones that are wrong are dangerous precisely because they feel like facts. A coach's job is to gently ask, "How do you know that?" before you build a year of strategy on top of it.

I think of a leader who's growing fast and about to make a key hire. Everything in them says this person is the one. The resume is great, the interviews went well, the gut feeling is strong. A good coach doesn't say, "Don't hire them." A good coach asks, "What would have to be true for this to go badly?" Sometimes the answer changes nothing. Sometimes it changes everything. Either way, the leader walks into that decision with clearer eyes.

That's what precision looks like in real life. It's not dramatic. It's just better thinking at the moment it matters most.

How Can You Tell If It's Time for an Executive Coach?

If you're doing well and wondering whether coaching makes sense, here are some practical steps you can take this week. You don't need to hire anyone to start.

1. Name your biggest decision of the next 90 days. Write it down in one sentence. A hire, a restructure, a new market, a hard conversation. Getting it on paper is the first step toward thinking about it instead of just carrying it.
2. List the assumptions underneath it. Under that decision, write three things you're assuming are true. About the people involved, the timing, or yourself. Then circle the one you'd be most embarrassed to be wrong about. That's where your attention belongs.
3. Ask who has challenged your thinking lately. Not who agreed with you. Who pushed back? If you can't name anyone from the last month, that's not a judgment on you. It's a signal that your feedback loop has gotten quiet.
4. Audit one week of your calendar. Count how many hours went to responding and how many went to thinking ahead. Most leaders are surprised by how lopsided it is. If strategic thinking time is close to zero, you've found your first problem to solve.
5. Ask three people one honest question. Pick a direct report, a peer, and someone outside your organization. Ask them, "What's one thing I do that makes your job harder?" Then just listen. Don't defend, don't explain. Write down what you hear.
6. Have one exploratory conversation with a coach. Most credentialed coaches offer an initial conversation. Bring your 90-day decision and see what questions they ask. Pay attention to whether the conversation makes your thinking clearer or just makes you feel good. You want the first one.
7. Decide on a rhythm, not a rescue. If you move forward with coaching, set a regular cadence and keep it, even when things are going well. Especially when things are going well. The value isn't in one breakthrough session. It's in having a place where your thinking gets sharpened on a schedule.

Why the Best Leaders Refuse to Plateau

Let's go back to that question one more time. "If things are going well, do I actually need a coach?"

Here's what I've noticed. The leaders who ask that question are usually the ones who would benefit most. They're paying attention. They care about getting it right. And somewhere underneath the question is a quiet sense that "going well" might not be the same thing as "going as far as it could."

Even the top CEOs and founders I know have coaches. Not because they're struggling. Not because someone made them. They have coaches because they've learned that the view from the top is impressive, but it isn't complete.

So maybe that's you. Maybe things are working, and you're starting to wonder what's next. You don't need a crisis to justify getting better. You just need to decide that where you are isn't where you're stopping.

You don't hire a coach because you're stuck. You hire one because you refuse to stay where you are.