Most executives looking for a coach want the same thing: someone with meaningful operating experience, who has been through significant company growth and can be a practical, candid thought partner on executive leadership, organizational effectiveness, stakeholder management, executive presence, and strategic product and business challenges. The hard part is telling that person apart from a confident one before you have paid for six months. It is the difference between an operator who coaches and a career coach who has read about operating, and it is not visible on a website. Six questions make it visible. If you are the executive, ask them. If you are the assistant, chief of staff or head of people assembling a shortlist for someone else, ask them and you will be able to compare the answers side by side. Here is what each question is really testing, and what my own answers are.
Question one: what is your coaching approach and what do you specialize in?
What the question tests: whether the coach has a method, or just a personality.
A good answer names the work and how it gets done. Mine: I coach senior operators through the problems that do not fit on a slide. Leading through a transition into a bigger seat. The team that worked at the last size and does not at this one. Stakeholder management and executive presence with a board, investors, and the peers who wanted your job. Accountability that does not backfire. Alignment across a leadership team. The human side of change.
The method is the same one I used running transformations for twenty-five years, which I call the Three Rs: the right formula, meaning the thing that actually needs to change, named precisely; the right tactics, meaning how it gets done in this company with these people; and repeatable actions, the rhythm that keeps the change alive after I am gone. Most coaching produces insight. Insight does not survive contact with a real quarter. The Three Rs are how it does.
If a coach cannot describe their approach in a paragraph a stranger could repeat, they do not have one.
Question two: what is your operating experience, and who are your typical clients?
What the question tests: has this person done the job, or studied it?
This is the filter that matters most for a senior operator, and it is the one most coaching websites are vaguest about. Ask for specifics: which seat, which company, what happened. My answer is specific because it can be. I founded Interland, grew it to $200M in revenue and 650 people, and took it public on Nasdaq. I was EVP at New Relic while it grew from $300M to $500M, leading 450 people across four countries. I ran a $250M budget at Cox Automotive through a cloud and DevOps transformation. As COO at a venture-backed company I cut burn in half while revenue grew 40 percent and took it to a merger with FireHydrant. Across my career I have worked through 35 mergers and acquisitions and 18 exits, on both sides of the table.
I am also a certified coach, ICF and CEC since 2019, with a psychology degree and CMHC graduate work underway at Mercer. The combination is the point. We can talk about the board meeting and the person walking into it in the same hour.
Typical clients: CEOs, COOs, CPOs, CTOs and general managers at companies in significant growth, and the leaders one level below being built for those seats. Founders scaling past the team they started with. Executives at companies backed by private equity where the sponsor has a playbook and a clock.
Question three: how is an engagement structured, and how long does it run?
What the question tests: whether you will know what you are buying.
Ask for the steps. Mine are four, and there is no mystery in them. First, a discovery call: a straight conversation about what is actually going on and whether I am the right person for it. Second, calibration: we agree what success looks like and how we will both know, before the work starts, not after, and we check the work against that measure at set points along the way, not only at the end. Third, standing coaching calls, weekly, every other week, or monthly, on video or in person, with the cadence set in calibration. Fourth, ad hoc access, because the hard things do not wait for the calendar.
Duration: long enough for the change to hold. Engagements run in months, not weeks, and they are built around repeatable actions you keep after we finish. Be wary of anything sold in a fixed number of sessions with no measure attached, and of anything open-ended with no calibration at the start.
Question four: are you available in person, in my city?
What the question tests: logistics, and honesty about them.
Many executives prefer in person, and many are not in Georgia. It is a fair ask and it deserves a straight answer, not a brochure. Mine: I am based in Alpharetta, Georgia. Standing calls run on video with leaders everywhere, and I work on-site when the engagement calls for it. Atlanta metro in person is easy. For New York, San Francisco and elsewhere, sessions mix and match: video for the standing cadence, and I fly in when the engagement books time for it, with travel scoped into the engagement up front.
Ask any coach the same: where are you, how do you work day to day, and what happens when the work needs a room, such as an offsite or a leadership team working session.
Question five: what does individual executive coaching cost?
What the question tests: whether the coach will be straight with you about money.
You will notice I do not publish a figure. Here is what I will tell you instead, because it is what the quote will contain. Five things set the price of an executive coaching engagement. Who is being coached, one executive or a leadership team. The cadence of standing calls and what access sits between them. The length of the engagement. Whether the work is remote, in person, or a blend that includes travel. And who is paying: most of my clients are funded by their organization, because companies invest in the leaders they intend to keep, and coaching at this level is normally a line item rather than a personal expense. That is not a quirk of my practice. The International Coaching Federation's own survey of the profession finds that coaches who mainly serve executives charge the most, and that fees rise with the share of clients whose company pays. If you need to make that case internally, I will help you build it. I have approved those requests as the executive on the other side.
By the end of the discovery call you will have a scope and a number for it. If you have a budget in mind, say so on the call. It shortens the conversation, and I would rather shape the engagement to it than guess.
Question six: do you offer an introductory chemistry or discovery session?
What the question tests: whether you can find out before you commit.
Yes. Forty-five minutes on video, no pitch. We work out whether there is something here worth doing, and if there is not, I will tell you. Use that conversation well: bring a real problem, not a hypothetical, and notice whether you leave with a sharper version of it than you arrived with. If you hear one true thing you had not said out loud yet, you have your answer about the person. The rest is scope.
When coaching is not worth it
Ask the six questions and you will find out whether the coach is worth it. Whether coaching is worth it is a different question, and sometimes the honest answer is no.
It is not worth it if you want someone to hand you the answer. That is consulting. I do that work too, and it is a different engagement with a different shape.
It is not worth it if you are not willing to change how you operate. Coaching produces a sharper view of your own patterns; if you will not act on it, you have paid for an interesting conversation.
It is not worth it if the gap is a technical skill. A course or a specialist will close that faster and for less.
It is not worth it if what you need is therapy. A good coach will say so and help you find the right person. My psychology degree and CMHC training are part of why I can tell the difference, and why I will tell you.
And it is not worth it if your company is using coaching to avoid a decision about you. If that is the situation, ask the question out loud before anyone signs anything.
If none of those describe you, coaching is likely worth it, and the six questions will tell you whether the person in front of you is.
The three-proof test, for any coach
If you want a shorter version of all six questions, it is this. Has this person operated at the level you are playing at? Are they trained and certified, not just experienced? Most clients now expect it; in the ICF's 2023 survey, eight in ten coaches said so. And after one real conversation, did you hear something true you had not said out loud yet? Chemistry matters. Proof matters more. One more piece of fine print: if a coach leads with a return-on-investment percentage, ask which study. The figures that circulate come from one 2001 case study of thirty mostly mid-level managers estimating their own results, and from a 2009 survey in which fewer than one in ten respondents could supply the numbers. A coach who quotes them as an industry average has told you how they handle evidence.
The order matters: operating experience first, method second, logistics and money third, and a way to test the fit before committing. If you are choosing an executive coach, ask those six questions of everyone on your list, including me, and choose the one whose answers were the most specific. Specific is what candid sounds like in writing.