I’ve sat in both chairs. The one where you’re being coached, and the one where you’re doing the coaching. For most of my career, I was the one being developed—workshops, seminars, retreats. I’d come home from a weekend energized, convinced something had changed. Monday went great, then Tuesday happened, and the next budget crisis, the next personnel problem, the next 11:00 P.M. board meeting. Whatever had shifted quietly shifted back.

I don’t regret any of it. That work made me better. But it took years of leading organizations, including ten and a half as a town manager, before I hit the limits of how I’d been developing and understood there was something different. What I finally had to learn was what each of those experiences was actually good for—and what I’d been asking them to do that they were never built to do.

Three Ways We Develop

After many years of leading and coaching, I’ve come to recognize a pattern—in myself, in colleagues, and in the executives I work with now. There are three basic approaches to growth, and I spent a long time treating them as a ladder. I don’t anymore. They’re more like three tools that do different jobs.

The first phase/approach is building skills and situations. Setting goals with tangible qualities. The promotion. The larger community. The larger department. I’m at Place A, I believe Place B will be better for me, and getting there gives me something I want or need. Skills are real. A manager who can’t navigate a negotiation or build a budget has a skills gap, not a mindset problem, and the fastest fix is training. I built my early career this way.

After a while, one of three things happens. Sometimes it keeps working, and you’re satisfied. Sometimes you reach Place B and something’s still missing—you’re achieving and it feels hollow. And sometimes the skill gap compresses. Early on, the growth curve is steep; sit in the seat long enough and it flattens. The ways you get better stop being obvious, and you feel a pull toward a new perspective. How do I focus on the culture when the day-to-day is eating the work I’m actually here to do?

The second phase/approach is working on perspective and mindset. At some point you figure out that changed circumstances don’t fix everything, and you start working on how you see things. Where your time goes. The story you tell yourself about the pressure you’re under. You read the books. You reframe. This is where most leadership development lives, and it earns its place.

This approach has its own ceiling, and you find it in two ways. The first is the most frustrating. You have the insight. You have the knowledge. You can articulate exactly what you should be doing, and you still can’t do it. The second is the compression factor again, but tighter this time. It’s not as much about adding to your toolbox as it is learning to employ the tools you have differently.

The third phase/approach is harder to describe. If I had to name it, I’d call it full awareness. It came to me last, and it works from a different direction. Instead of striving toward Place B, you look at all the sides of Place A. You slow down. You notice what you weren’t aware of before. You learn that things can get better not by adding or changing skills and frameworks, but by subtracting some of the thoughts and beliefs you carry or changing your perspective around them. To see it clearly enough that it loses its grip.

For years, I asked the first two approaches to do the third one’s job. I’d build a skill or adopt a mindset and expect it to dissolve a negative pattern neither could touch because the pattern lived underneath both. That’s why the weekend seminar never survived Tuesday. It wasn’t a bad experience. It was the right tool for a different job.

A special few leaders intuitively use all three and have gotten good at diagnosing which one a given moment calls for. That diagnosis, it turns out, is half of what coaching helps with.

The Thing Nobody Tells You About Knowledge

Let me expand on the gap between the second and third approaches because it’s the part most leaders find uncomfortable.

The executives I coach almost always know what they need to do. They know they need to have the difficult conversation they’ve been avoiding. They know they don’t need to attend every meeting on their schedule. They know they need to delegate more, react less, slow down before they respond, take action instead of thinking about the issue. They know and they still can’t do it.

This is where the three approaches sort themselves out. If the gap is knowledge or skill, training closes it. If it’s perspective, a reframe closes it. But for most experienced executives, the gap is neither. It’s what’s underneath. The internal block that makes the difficult conversation feel impossible in the moment. The identity you’ve developed that keeps you from delegating. The old pattern that kicks in under pressure no matter how often you’ve promised yourself you’d respond differently.

A good coach doesn’t tell you what you already know. A good coach helps you identify what you already have that’s getting in the way.

Finding the Right Coach Doesn’t Have a Clear Road Map

When municipal leaders hear coaching, they usually picture one of three things: a sports metaphor, a performance improvement plan, or someone who might not know the difference between an open public meeting and an initial public offering. None of that is wrong, exactly. But coaching runs a spectrum that maps onto those same three approaches: skills work that’s really mentoring, performance coaching in the middle, and the slower, messier transformative work I’m most often called on for. The point isn’t which is best. It’s which gap you need to close.

The Weight of Having No Choice

The third approach can be thought of like this: we do a lot automatically without noticing. Eventually we stop seeing things objectively, and we lose sight of the choices we have to see things from different angles and act differently. What good coaching helped me see (slowly, not in a weekend) is that “That’s just who I am” is almost never literally true. Maybe what you’re doing is actually providing you something you didn’t realize before. Maybe you’ve locked onto one way of seeing it and narrowed it, without realizing, to the only way.

When you see there are other parts of the same issue that you were missing, something changes. The straitjacket you’ve been wearing turns out to have buckles. You were never stuck. You were choosing without knowing you were choosing. That doesn’t make the job easier, but it gives you more freedom inside it.

That’s not semantics. For leaders who have been in their roles a while, it can be the difference between growth that’s fulfilling and moves the needle...and development that feels like repetitions.

What to Look For

I know a lot of town managers and other leaders curious about what a coach could do for them. Part of why I’m writing this is to hand you a rough map so you can find yourself on it. So start with the honest question: is one approach resonating with you more than the others right now?

It’s not black and white. Early on, elements of all three serve you; so do they 15 years in. But the longer I served as town manager, the more of the technical and mindset work I’d worked through. Then I was stuck. I was fortunate to find a coach who showed me the third approach, and that’s what got me into this work. Start there, and the question of who to work with gets a lot easier.

Understand what credentials do and don’t tell you. An ICF certification means a coach has been trained, supervised, and held to a consistent standard, both ethically and competently. That’s worth something; it tells you what you’re getting. It doesn’t tell you whether this coach will be good for you, and its absence doesn’t mean you won’t get something helpful. Some of the most useful developmental conversations of my career came from people with no credential at all. Treat certification as information, not a verdict.

Then there’s our world specifically. You don’t have to have served as a town manager to be a good coach, but a coach who hasn’t served in that capacity will never fully understand what that weight feels like. You can’t teach someone what it is to be the chief executive of an organization. So if you need someone who has shouldered that weight, find that person. If you’d rather have someone from outside it, that can serve you, too. They’ll see what a peer would miss. Just know which you’re choosing and why.

Ask about their approach. A coach who can’t explain how they work, not just what outcomes they produce, is worth questioning. And notice how you feel after a sample conversation. Not inspired in a motivational-speaker way. Seen. Challenged without being judged. More clear about something you walked in confused about. That’s the signal.

Its Own Craft

City/county manager roles share a lot in common with CEOs in the private and nonprofit sectors, but local government leadership is its own craft, its own discipline. Some pressures are unique, and the public nature of the work is relentless.

The experienced leaders I’ve watched struggle, including myself, aren’t the ones who lacked skill. They’re the ones who stopped developing and stopped becoming aware of the real issue. I’ve been that person—several times. The role has a way of doing that if you’re not paying attention.

Coaching isn’t a cure for that. But chosen well, a coach can help you name what you’re actually working toward and speed up progress in ways you wouldn’t reach alone. The leaders who make it, really make it and not just survive, are the ones who never stop asking harder questions about themselves. They’ve found a way to be okay with who they are as a leader while staying humble about how much they still have to grow. That’s not a personality trait. It’s a practice. And in this job, it might be the most important one you develop.

MICHAEL HERBERT served as town manager for Ashland, Massachusetts for 10 years, and is the founder of C5 Executive Strategies.