A plain guide for founders, CEOs and the boards and investors who back them.
Executive coaching works when the fit is right and the terms are clear. Most disappointing engagements fail on the basics: no clear goals, confusion about who the client is, or a coach who was never the right match. This guide covers what to check before you sign, and ends with ten questions to ask any coach.
Coaching helps when the job has outgrown the way you do it: a new or bigger seat, a company scaling past the stage it was built for, a new owner after a deal, or the move to what comes next after an exit.
It is not the right help for every problem. If you need someone to do the work, hire a consultant. If you want advice from someone who has done your exact job, find a mentor. If something calls for clinical support, see a licensed therapist. A good coach will tell you which one you need, even when the answer is not coaching.
If you pay for coaching yourself, you are the client. If a board, investor or counsel pays, there are two parties: the sponsor, who helps set the goals, and the leader, who does the work.
Before anything starts, agree in writing what the sponsor will hear, usually goals, attendance and progress, and what stays between the leader and the coach, usually the content of the sessions. Confusion here is the most common reason engagements go wrong.
Look for formal coach training from a recognized program, and a credential or membership with the International Coaching Federation (ICF). The ICF awards credentials at three levels: ACC, PCC and MCC.
Ask which code of ethics the coach follows and whether they work under supervision or keep up ongoing training. If they use a 360 or other diagnostic, ask whether they are certified in it. Credentials alone do not make a great coach, but missing ones are a warning sign.
Ask what kinds of leaders and situations the coach works with most. A coach who has operated, carrying a P&L, hiring and replacing leaders, answering to a board, knows the pressure firsthand. A career coach may bring deeper technique. Neither is wrong, but you should know which one you are buying.
Ask to speak with two leaders the coach has worked with in situations like yours, with their permission.
Good engagements share a shape: goals agreed at the start, with the sponsor if there is one; a clear picture of where you stand, often from a 360 diagnostic or interviews with the people around you; regular sessions; progress measured against the goals; and a defined length with a point to review whether it is working.
Be careful with open-ended engagements that have no stated goals or end point.
Some coaches, or the firms they work for, also assess or evaluate leaders for boards and investors. If so, ask directly whether they would ever evaluate you. Ask whether the coach has any financial stake in your company, and whether they coach anyone who reports to you or could compete with you for your seat.
The answers should be clear, and in writing. A coach you cannot be candid with is not much use.
Chemistry matters, but it is not enough. In the first conversation, notice whether the coach asks more than they tell, whether they push back on you, whether they can explain how they work in plain words, and whether you would tell them the truth about what is hard.
Executive coaching is usually priced as a monthly retainer or a fixed-fee engagement, and less often by the hour. Ask what is included between sessions, how cancellations work, who pays, and what happens if the engagement is not working.
A fixed scope and fee agreed in writing prevents surprises. Do not choose on price alone; the cost of the wrong coach is mostly time.
About Gannett.Partners. Gannett.Partners offers executive coaching for founders and CEOs, led by Chris Gannett as head coach, under the ICF Code of Ethics. Most leaders start with the Baseline: three weeks with Chris, a 360 and a one-page plan they own. Leaders can also go straight to a monthly retainer. We also run Founder & CEO Diligence for boards and investors, and we never evaluate a leader we have coached.
For general information only. Not legal, financial, medical or employment advice. © 2026 Gannett Partners, LLC