What Marshall Goldsmith Taught Me About Finding the Right Executive Coach

In brief: In spring 2025, I attended a small group coaching session with Marshall Goldsmith — one of the world’s most recognized executive coaches. Six of us were in the room. One of them is now a partner coach at Enable Leaders. What Marshall demonstrated that day — generosity, directness, and the judgment to push someone exactly as far as they need to go — is the same standard we hold every coach in our network to. Photo credit Wikipedia

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.

In the spring of 2025, I received an invitation to a small group Marshall Goldsmith executive coaching session after completing a generous offer I saw in a LinkedIn Post from Marshall.

The request from him was to ask MarshallGoldsmith.ai at least 50 questions, and he would personally invite you to a small group coaching session. No charge. No catch. Just Marshall, a handful of people, and a few hours of his time.

I took him up on it.

There were six of us in that session. One of them — a former Marine Corps officer and publicly traded company  executive named Matt Eichmann — is now a partner coach at Enable Leaders. That alone tells you something about the kind of people Marshall attracts.

“My name is Marshall Goldsmith and I…”

Marshall opened the session with a prompt that sounds simple and isn’t.

“My name is _____________ and I am the world’s best at _____________.”

He went around the virtual table. For some people, he listened and nodded. For others, he asked questions. For a few, he pushed.

When he got to me, I didn’t have a good answer. I could feel it. Marshall could see it. He pushed — gently but firmly — and when it became clear I wasn’t going to find the answer in that moment, he moved on. No unnecessary lingering. No forcing. Just the right amount of pressure, then release.

That’s coaching. Not the technique — the judgment. Knowing when to push, how far, and when to let go.

I’ve thought about that moment many times since. It wasn’t comfortable, but it was certainly useful.

What he shared that stayed with me

Marshall has slept in airports. He has ground it out. When I told him I was just starting Enable Leaders and focused on building a product, he didn’t sugarcoat it: I was going to have to work like hell over the next year to get things moving.

He was right. The product itself didn’t become what I hoped it would. But understanding how much work it takes to build something real — and hearing that from someone who has done it himself — is a different kind of lesson than reading it in a book.

He also talked about his books. He’s written 35 of them. Thirty-four were written with other people. His advice: “Find a writer.” Know what you’re good at. Find people who are good at what you’re not.

The MG100 and What Marshall Goldsmith Executive Coaching Looks Like in Practice

The Marshall Goldsmith 100 Coaches — the MG100 — started from a simple idea: pay forward what you’ve been given. Marshall had benefited from the generosity of people like Peter Drucker and Frances Hesselbein. He decided to do the same. He adopted 100 coaches, taught them everything he knew, and asked only that they pay it forward when their time came.

The coaches he selected — people like Keith Ferrazzi, Herminia Ibarra, and others across academia, military, industry, and human behavior — were chosen because, as Marshall put it, “they are very intelligent, very motivated, and they have good hearts.”

I’ve had the privilege of connecting with others in that orbit. Mark C. Crowley, Tasha Eurich, Sanyin Siang — each of them has been generous and gracious in their own way. That’s not a coincidence. It reflects something Marshall models: that the best people in this field give more than they take.

What this means when you’re looking for a coach

Marshall’s only ask of the six of us in that session was this: if you become rich and famous, help five other people.

That spirit — generosity, directness, genuine investment in someone else’s growth — is exactly what you should be looking for in a coach.

Credentials matter. Experience matters. But the qualities that make a coaching relationship actually work are harder to put on a resume: the willingness to tell you the truth, the judgment to know when to push and when to let go, and the genuine desire to see you succeed rather than simply complete an engagement.

At Enable Leaders, every coach in our network has been personally vetted — not just for credentials, but for character. These are people I know, or people who have come through trusted referrals from people I know. Given our model — we make the match, we stand behind it — they have to be. Trustworthy isn’t a nice-to-have. It’s the whole thing.

When you’re evaluating a coach, watch for the same things Marshall demonstrated in that room: Are they listening or performing? Do they ask better questions than you expected? Are they willing to push you somewhere uncomfortable — and do they know when to stop?

A good coach makes you more honest with yourself. That’s the whole job.

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Woman looking over a scenic fjord with a cruise ship below and green mountains

What got you here won’t get you there.  – Marshall Goldsmith (source)

A picture of Jonathan Dunnett, CEO of Enable Leaders, smiling
Jonathan Dunnett, CEO, Enable Leaders

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