How to choose an executive coach.

Why this is hard to shop for

Anyone can call themselves an executive coach. There is no license, no board, no malpractice standard. The industry has responded with certifications, which mostly tell you someone paid for a training program and finished it. So the usual proxies for quality don't work here, and the price range is so wide it carries almost no information on its own.

What you are actually buying is pattern recognition. A coach who has sat with hundreds of people under the kind of load you're under can hear things in your third sentence that you haven't said yet. A coach who hasn't will hand you a framework. Both will sound confident in a sales call. This guide is about telling them apart.

Start with the job you're hiring for

Coaching is one word covering at least three different jobs, and the first mistake most buyers make is not knowing which one they're hiring for.

There is accountability coaching, which is structure: someone who keeps you pointed at your own stated priorities. There is skills coaching, which is targeted: presentations, media, running a board meeting, managing a specific executive. And there is depth work, which is about the patterns underneath all of it: why you delay the same conversation every time, why a certain kind of person on your team gets under your skin, why the thing that made you successful is now the thing in the way.

All three are legitimate. They cost different amounts, take different lengths of time, and are done well by different people. Ask yourself what would need to be true in eighteen months for the engagement to have been worth it. If the answer is "I ship the reorg," you may want the second kind. If the answer is "I stop doing the thing I've been doing since my first company," you want the third.

What credentials do and don't tell you

Treat certifications as a floor. They screen out the wholly untrained, and that is all they do. Nothing about a credential tells you whether the person can hold their nerve when you push back, or whether they'll notice the moment in a session where you changed the subject because you were close to something.

Better signals, roughly in order: how many hours they have spent with clients at your level, not in total. Whether they have real training in interpersonal and group dynamics, the kind where they were the one being observed rather than the one reading about it. Whether they have clinical literacy, because the line between a performance pattern and a mental health condition is not one you want your coach to miss. And whether, in the first conversation, they ask you a question you have to actually stop and think about. That last one is the least fakeable.

Questions worth asking in the chemistry call

Most coaches offer an introductory call. Use it to interview, not to be sold to. Some questions that produce informative answers:

• What kind of client do you do your best work with, and who should not hire you?
• Tell me about an engagement that failed. What happened?
• What would make you end an engagement from your side?
• When a client wants reassurance and you think they need the opposite, what do you do?
• Who supervises your work, or where do you take the cases you're stuck on?

The content of the answers matters less than their texture. A coach who can name who they're wrong for has a real practice. A coach who has never had an engagement fail is either new or not being straight with you. A coach with no supervision or peer review has no one checking their blind spots, and they will be working on yours.

Red flags

Some things that should end the conversation. Guaranteed outcomes, because nobody who does this work honestly can promise them. A trademarked framework presented as the answer to your situation before they've understood your situation. More talking than listening in the intro call. Client logos offered in the first ten minutes, which tells you how they treat confidentiality. And total agreement with everything you say, which is the most expensive thing a coach can give you, because you can get it free from almost everyone else in your life.

How pricing works

The market has three broad tiers. Coaches building a practice charge by the session, usually a few hundred dollars. The middle of the market works in monthly retainers. At the senior end, where coaches work with founders and executives on longer arcs, engagements are typically annual, and annual commitments run well into five figures and past six at the top of the market.

The annual structure isn't a pricing trick. The patterns that matter take months to show themselves under real conditions. You cannot see how someone handles a board crisis, a down quarter, and a co-founder rupture inside a six-session package, and it is exactly in those moments that the work happens. Serious coaches price for the year because that is the honest unit of the work.

The way through the sticker shock is to price the alternative. A wrong executive hire costs a year and seven figures. A co-founder rupture can cost the company. A decade-old pattern quietly steering your biggest decisions has a compounding cost that never shows up on any invoice. Against those numbers, the fee question mostly answers itself, in one direction or the other.

Coaching and therapy

The industry draws a clean line between them. The work itself doesn't. The pattern that shows up in your exec team showed up somewhere first, and pretending the history is out of scope makes the work slower, not more professional. Our view is that the line exists mostly to protect the professions rather than the client.

What you should actually verify: does this coach have enough clinical grounding to recognize when what looks like a performance issue is depression, anxiety, or burnout that needs a different kind of care? And will they say so instead of keeping the engagement? If you want a quick, private read on that question for yourself, the Founder Well-being Check takes two minutes and stays in your browser.

Deciding

Do two or three chemistry calls, not eight. Then notice which conversation is still working on you a week later. The coach whose question you kept arguing with in the shower is usually the one. Comfort is the wrong selection criterion. You are choosing the person who will tell you the thing nobody else in your professional life is positioned to say.

If you want to run this evaluation on us, that is what the discovery call is for. Bring the hard questions. We'd rather lose the engagement in the first call than in the sixth month.

Related reading

• The post-fundraise dip. Why founders feel worse after the round closes, and the ninety days after the wire.
• After the exit. Founder identity after the sale, and how to take a fallow period seriously.
• The reading list. The books and papers we hand to clients, organized by question.