What makes a good CEO coach?

A good CEO coach has enough operating history to understand what you are describing, no stake in which way you decide, and the willingness to be unpopular with you. The craft matters too, but those three are the filter. Credentials, frameworks and a polished website tell you almost nothing.

Here is how to judge the three, and what to ignore.

They understand the weight without needing it explained

You should not have to teach your coach what a down round is, why a co-founder split is different from a normal falling out, or what it does to a person to make payroll from their own savings.

This is not about them having run a company identical to yours. It is about whether they have carried consequence. Someone who has held responsibility for other people's income, at real scale, hears your situation differently from someone who has read about it. My own version of that history is on the 1-on-1 coaching page.

The tell is speed of comprehension. Describe something genuinely complicated from your last quarter. A coach with the right background will ask their second question quickly and it will be a good one. Someone without it will ask you to explain the setup for ten minutes.

That said, I have met certified coaches with no founder background who are better at this than plenty of ex-CEOs. Operating history is a strong signal, not a guarantee. Craft still decides the outcome.

They have nothing to gain from your answer

This is the structural thing that makes the relationship work, and it is easy to compromise without noticing.

A coach who takes equity now has a preference about whether you sell. A coach placed and paid by your board has an interest in you staying in the role. A coach who has become a friend has an interest in you liking them.

The last one is the common failure and it happens slowly. Month four is warm, month nine is comfortable, month fourteen is a pleasant fortnightly conversation where nothing is at stake. Both people enjoy it and nothing changes.

A good coach notices the drift and names it, which is also the argument in why not every CEO needs one. Mine is a paid relationship with a job to do, and when it stops doing the job it should end.

They will be unpopular with you

The whole value is somebody who does not need you to like them. Most people in the market cannot do this, because their income depends on you renewing.

Watch for it in the first conversation. A coach who spends the intro call agreeing with you has shown you the next six months. A good one will disagree with something before you have paid them anything, and they will do it without being rude about it.

You will not enjoy every session with a good coach. If you enjoy all of them, something has gone soft.

The three questions that do the work

Most vetting advice is vague. These three separate the field fast.

"Describe a client you failed."
Everyone who has done this seriously has one. A coach who cannot name a failure is either new or managing you, and both should cost them the job. Listen for whether they take responsibility or blame the client's lack of commitment. The second answer tells you what they will say about you.

Mine, since I am asking you to ask it. Two engagements ended badly and they were the same failure twice.

The first was an executive who had just left a company after thirteen years and wanted to work out what came next. The second was a first-time CEO trying to manage upward to a board and sideways across an executive team he had inherited. In both cases I did what I always do: I asked questions, because my whole premise is that clients already hold the answer and simply do not trust it, and that handing someone my answer overwrites theirs.

Both of them wanted answers. Both said they were not getting enough value. Both ended it.

The honest reading is not that they lacked commitment. It is that a single method has a limit, and I had found mine. Someone standing in an empty diary after thirteen years, or three weeks into a job they have never done, may not yet have an answer inside them to be drawn out. What they have is a blank, and asking a good question into a blank is not craft, it is stubbornness. I told both of them at the start that I do not give answers, which made me consistent rather than useful. The mismatch was visible in the first conversation to anyone willing to see it, and I was not.

"What happens between sessions?"
If the answer is nothing, you are buying a fortnightly conversation. Pleasant, occasionally useful, rarely enough to change how you operate. In my practice you write between sessions, and most of the value shows up there rather than during the hour.

"Who is this not for?"
A coach with a real practice has turned people away and can describe who. Someone who says everyone can benefit is selling. I do not work with idea-stage founders or people looking for general life advice, because the work assumes a company with real weight in it.

What to ignore

Certifications. They demonstrate someone completed a programme. My view is that lived experience beats credentials for this audience, and I will push back on anyone treating a certificate as the bar.

Named frameworks. Most are repackaged versions of the same handful of models. A framework with no scar behind it is decoration.

Client logos. Big names on a website tell you a big name once bought a session. It says nothing about whether anything changed.

Confidence. The most confident person in the market is usually the one with the least to be confident about. Certainty is cheap in this field.

The practical checks

Beyond conversation, three things worth doing.

Ask for a paid trial. Three sessions with a clean exit. A good coach will offer it before you ask. Anyone making the exit difficult is telling you something.

Speak to a current or former client. Not a testimonial on the site, an actual conversation. Ask what changed in how they operate, not whether they enjoyed it.

Check the logistics match the price. Availability, cadence, what happens if you need them in a crisis, how the engagement ends. Vagueness here usually predicts vagueness later.

What good looks like six months in

You are saying things in sessions you have not said anywhere else. You have made at least one decision you had been carrying for months. Somebody has told you something uncomfortable and been right. You have occasionally left a session annoyed.

If none of that has happened by month six, the relationship is not working, and the honest move is to say so rather than let it run out of politeness.

Common questions

Does a good coach need to have been a CEO?
It helps a great deal and it is not required. What is required is that they have carried real consequence and can keep up with your situation without a tutorial.

How much should a good CEO coach cost?
Rates run from a few hundred to several thousand per session. Mine are on the services page. Price sorts poorly for quality in this market. Use the three questions instead.

Should my company pay or should I?
If you pay, the conversation has no ceiling. If the company pays, there is usually a quiet limit on what can be discussed, particularly about whether you want to keep doing this.

How do I end it if it is not working?
Directly, and sooner than feels comfortable. A good coach will take that conversation well, and how they take it is the last piece of evidence about whether they were any good.

The short version

Operating history, no stake in your answer, and the willingness to be disliked. Ask about a failure, ask what happens between sessions, and notice whether they disagree with you before you have paid.

More on the role in what is a founder coach, and on running the search itself in how do I choose a CEO coach. If you want to test whether we would work well, start with the services page.