Questions to Ask an Executive Coach
Questions to ask an executive coach on the chemistry call, while the terms are being settled, and in the sessions once the work has begun. The early groups cover method, training, fees and what your employer is told if it is paying. The later ones are for the coach you already have: delegation, pressure, peers, the board, and whether the coaching is working.
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The questions
Each question, and why to ask it
Before hiring
How would you describe the way you work with a client?
Why ask it
Coaches vary more than their websites suggest: some run structured curricula, others follow whatever the client brings that week. Listen for whether they describe a method or just describe being supportive.
What kind of leaders do you usually work with?
Why ask it
A coach whose practice is mostly first-time managers will handle a board-level problem differently from one who works with founders. If they claim every level and every sector equally, they are probably describing an ambition rather than a client list.
What training or certification do you have, and who accredits it?
Why ask it
Coaching is largely unregulated, and in most places anyone can use the title. A credential from a body such as the ICF or EMCC means logged client hours and an assessment, which a short course certificate does not. Plenty of capable coaches are former operators with neither, but you should know which one you are hiring.
How will we know in six months whether this worked?
Why ask it
Coaching outcomes are hard to measure, so the answer shows whether they have a workable proxy such as specific behavior changes or feedback from your team. Answers built entirely on how you feel are hard to hold anyone to.
How many sessions does a typical engagement run, and over how many months?
Why ask it
Six months of sessions every two weeks and a rolling monthly retainer are different purchases, so get the numbers before price comes up. If the answer is open-ended, ask where the review point falls, because without one an engagement can run on habit.
Walk me through a first session: what do we actually do?
Why ask it
The description tells you how much of the early work is assessment, goal setting, or simply talking. If they cannot describe session one concretely, session ten is unlikely to be any more structured.
Have you held a senior operating role yourself, and how does that show up in your coaching?
Why ask it
Time spent running a function helps a coach follow a story about a board or a budget without a glossary. It also tempts them to tell you what they did in your place. Ask about a client whose situation was unlike anything in their own career, and how that went.
How much do you need to know about my industry to be useful to me?
Why ask it
Sector experience saves you explaining what a regulator or a sales cycle is, and it can also mean sharing the industry's blind spots. For trouble with a peer or a team that will not disagree with you it matters little; for a first board seat in a regulated business it may matter more. Notice whether the answer fits your case or is the pitch everyone gets.
When I ask what you would do in my position, will you tell me?
Why ask it
Some coaches hold strictly to questions and never offer a view; others drift into consulting. If you want a sparring partner and get a mirror, you will be restless by the third session, so hear their answer before you sign.
Do you use a 360 or other assessments, and what do you do with what comes back?
Why ask it
Collecting a 360 is easy; using it well is not. Ask what they do when the feedback contradicts how you see yourself, because that moment is where most of the value or most of the damage happens.
What do people at my level most often get wrong?
Why ask it
A coach with real mileage near your level names patterns quickly: holding on to the old job, managing peers like direct reports, going quiet with the board. Generalities about communication suggest most of their clients sit further down the organization.
From what I have told you so far, where would you want to start?
Why ask it
This turns the chemistry call from a pitch into a sample of the work. A tentative read they are ready to revise, or a sharp question back, shows you how they think. A confident diagnosis after twenty minutes shows you something else.
Have you coached someone through a situation like mine, and what was different by the end?
Why ask it
Expect the details to be disguised, and be wary if they are not: a coach who names clients to you will name you to others. Listen for the outline: where the person started, what the two of them did, what colleagues could see afterwards. A promotion on its own proves little, since plenty of things produce one.
Who is the wrong client for you?
Why ask it
The useful answer is specific: someone sent against their will, someone who really wants a consultant, a sector they do not understand. Claiming to work well with anyone usually means the calendar has gaps.
Tell me about a client you could not help. What went wrong?
Why ask it
Anyone who has coached for long has a failure to describe. If they cannot name one, they are either new or not being straight with you. The story itself shows which conditions make their approach fall apart: a skeptical client, a hostile boss, a goal set by someone else.
How do you give feedback a client does not want to hear?
Why ask it
Executives are surrounded by people who soften things, and a coach can become one more of them. Ask for the last time they told a client something that was pushed back on, and what happened to the engagement afterwards.
Where does coaching end for you, and when do you refer someone elsewhere?
Why ask it
Career pressure, grief, burnout, and clinical depression can look similar in a session. A coach who has clear referral limits is safer than one who believes coaching covers all of it.
Who do you talk to about your own work?
Why ask it
Supervision, peer groups, or their own coach all suggest someone still examining their practice. No answer at all suggests a practitioner working entirely from instinct.
Is coaching your main work, and how many clients do you carry at a time?
Why ask it
Full-time coaches with a dozen clients and consultants who coach on the side give different kinds of attention. Neither is disqualifying. The practical test is how quickly they answer a message in the week everything goes wrong for you.
Can I speak to two former clients in a role similar to mine?
Why ask it
Client confidentiality limits what they can offer, but a coach with an established practice can usually arrange a call or two. Ask the reference what they do differently now and what the coach was not good at, which tells you more than whether they liked the sessions.
Confidentiality
If my employer is paying, who sees what I say in our sessions?
Why ask it
The person paying is often not the person being coached, so pin the boundary down before you say anything difficult. Ask for the list of what goes back: attendance, themes, progress against agreed goals, or what was actually said. A promise that HR can see everything makes the room a poor place to be candid, and whatever is agreed belongs in the contract.
Who do you see as your client: me, or the company paying you?
Why ask it
Coaches differ: some say the person in the room, some say both, and some are tied to a contract that names the company. Test it with a case, such as your manager wanting you smoother with peers while you think the role is scoped wrong. What they would do then tells you how much to bring into the sessions.
Will I see anything you write for my employer before they do?
Why ask it
Sponsors often expect a midpoint and a final summary. In many arrangements you read it first or draft it with the coach, so that nothing in it is news to you. If reports go out unseen, you will start editing what you say in sessions, and that is worth raising before you sign.
Will there be a three-way meeting with my manager, and who sets its agenda?
Why ask it
Sponsored engagements often open and close with you, the coach and your manager in one room. Ask whether you see the proposed goals before your manager does. Run well, it is the one meeting where your boss has to say plainly what they want from you.
Do you coach anyone else at my company, and how do you keep those conversations apart?
Why ask it
Someone who also works with your peers or your boss hears about you from other chairs. That can be managed, but only with a stated rule they can repeat to you. If they coach the person you report to, think hard about how candid you would really be.
Is there anything I could tell you that you would have to pass on?
Why ask it
Coaching agreements usually carve out exceptions, typically a serious risk of harm or illegal conduct, and sometimes breaches of company policy. The limits depend on the country and on the contract with your employer, so ask what they are in this one before you find out by accident.
Do you take notes or record our sessions, and where are they kept?
Why ask it
Your doubts about your chief executive end up somewhere: a notebook, a cloud folder, an AI transcription tool. Ask who else can open them, how long they are held, and whether the company's contract gives it any claim on them.
If I start thinking about leaving the company, can I say that to you?
Why ask it
Company-paid coaching gets awkward at exactly this point. Many coaches treat it as confidential and will help you think it through; some feel they must pause or end a sponsored engagement. Find out which before you say it, not after.
Terms
What is your fee, what does it include, and how is it billed?
Why ask it
Find out whether calls between sessions, assessments, travel and preparation time sit inside the fee or are invoiced on top. Some coaches bill per session, some per month and some for the whole engagement up front, and each changes what stopping early would cost you.
Do we meet in person or by video, and how long and how far apart are the sessions?
Why ask it
Ninety minutes every two weeks and an hour a month are different engagements, even at the same total. Too close together and you have had no time to try anything; too far apart and each session opens with a recap. Ask what they recommend for your goal and why.
Can I reach you between sessions when something blows up?
Why ask it
The hard moments (a resignation on your desk, a board meeting that went badly) rarely fall on a session day. Ask whether a short call or message is part of the arrangement, how quickly they usually reply, and whether it is billed separately.
What is your policy on cancellations and rescheduling?
Why ask it
Senior calendars break constantly, so this clause gets used. Find out now whether a same-day cancellation costs a full session and how much notice they need.
Will every session be with you personally?
Why ask it
Larger coaching firms sometimes sell with a senior name and deliver with an associate. If you are being matched through a firm or a platform, also ask whether you can change coach without starting the paperwork again.
Is there a written agreement, and can I read it before we start?
Why ask it
It should state the fee, the number of sessions, what is confidential, and how either side can end things. When your employer holds the contract, ask to see the parts that concern you. That is a reasonable request, and how it is received shows who the coach thinks the client is.
If we are three months in and it is not working, how do we end it?
Why ask it
Asking about the exit while you are still being courted gets you a straight answer about notice periods and unused fees. It also shows whether they treat the possibility as normal or as a threat.
Once the engagement is over, can I come back for a single session?
Why ask it
The real test of coaching often arrives months later, with a new boss or a reorganization. Some coaches offer occasional sessions to past clients and some only sell full programs. Ask about the rate and whether the confidentiality terms carry over.
First sessions
What should I send you before we start?
Why ask it
Usually whatever already exists: your last review, any 360 report, the org chart, the goals your manager has set. Sent a few days ahead, it keeps the first hour from going on background the coach could have read.
How do we decide what we are working on, and how often do we revisit it?
Why ask it
Reveals whether goals are set once and forgotten or reviewed as circumstances change. Watch for coaches who let the agenda become whatever crisis you walked in with.
What do you expect me to do between sessions?
Why ask it
The between-session work is where change either happens or does not. A coach with no expectations there is selling you an hour of conversation.
If I turn up three times running without having done what I said I would, what will you do?
Why ask it
Most engagements reach this point. You want someone who names it in the room and asks whether the goal is still one you want, not someone who moves quietly to a new topic for another quarter. The answer also shows how blunt they are prepared to be with a senior client.
Will you watch me work, in a meeting or on a recording?
Why ask it
Everything a coach knows about you otherwise comes from your own account, which is the least neutral source available. Sitting in on a team meeting or watching a recorded presentation gives them something to check your story against. Agree what your team is told about why they are there.
Should I tell my team I am working with a coach?
Why ask it
Telling people makes it easier to ask them what they notice, and it raises the stakes on changing. Keeping it private is safer where coaching is read as a sign of trouble. Your coach will have seen both, and can help you work out which kind of company you are in.
What separates your clients who change from the ones who just enjoy the sessions?
Why ask it
Most coaches can answer this without pausing. A common version: the clients who change try something uncomfortable between sessions and report back honestly, including when it failed. Treat the answer as instructions, and ask to be told if you start drifting into the second group.
How should I tell you when a session has not been useful?
Why ask it
You will have a flat session at some point. Agreeing in advance how to say so, at the end of the hour or in a note the next day, makes it ordinary instead of awkward. A coach who asks for this themselves at the close of every session is ahead of you.
In sessions
What is the gap between how I think I come across and what my feedback says?
Why ask it
Ask this with the 360 or the interview notes on the table. The useful part is the specific mismatch, such as believing you are decisive while your team experiences you as closed. Expect to argue with it for a session before you can use it.
What pattern do you keep hearing in the situations I describe?
Why ask it
After a few sessions a coach has heard you tell a dozen stories, and the common element in all of them is you. They may have been waiting for permission to say it. Brace for something like: you always describe the meeting, never what you asked for in it.
What am I still doing that someone at my level should have handed off?
Why ask it
Bring a list of what you did last week instead of a general wish to delegate more. The items you defend hardest are usually the ones to look at: the work you were promoted for and still do because you are quicker at it than anyone you manage.
If you looked at my calendar for the past month, what would you question?
Why ask it
Put the real calendar on the screen. An outsider spots in minutes what you have stopped noticing: the standing meeting with no decision in it, no unbroken hour before six, time with every direct report except the one you find difficult.
Can we rehearse the conversation I have been putting off?
Why ask it
Most leaders arrive with one: a performance talk, a disagreement with a peer, asking the chief executive for something. Saying the first two sentences aloud to someone playing the other part shows where you hedge. Have the coach answer the way that person really would, not politely.
How do I come across when I am under pressure?
Why ask it
You are the worst-placed person to know, because under pressure you are attending to the problem. A coach who has collected feedback or watched you in a meeting can describe it: the clipped answers, the interrupting, the silence that others read as anger. Then ask what the earliest sign is, so you can catch it.
What do I do that makes people stop bringing me bad news?
Why ask it
The more senior you get, the more news tends to be filtered before it reaches you, and some of that filtering is a response to how you reacted last time. Find out what your team told the coach about this, and work on the first ten seconds of your reaction, which is the part people remember.
Which of my strengths has turned into a problem at this level?
Why ask it
The trait that earned the promotion is often the one that causes trouble after it: attention to detail becomes interference, speed becomes not listening. The work is in keeping the strength while changing when you use it.
What should I do about someone on my team I have lost confidence in?
Why ask it
Leaders tend to sit on this one for months. A coach has only your account of the person, so expect questions back: what have you told them directly, and what did they say? If the answer is 'not much', that conversation comes before any decision, and the formal steps depend on your country and employer, so take those to HR.
How do I get my peers to back something when I have no authority over them?
Why ask it
Senior roles run sideways as much as down, and peers are the people a coach hears least about until asked. Go through one actual proposal: who gains, who loses budget or attention, who has not been consulted. The answer is rarely a better slide.
How do I handle a boss or a board that wants something I think is wrong?
Why ask it
No coach can tell you who is right, but one can help you separate three things that blur together: what you were asked for, what you believe, and what you have said out loud so far. Often the third is much less than you think. Work out the sentence you have not yet said to them.
How do I bring my team through a change I did not choose?
Why ask it
The honest difficulty is that you may be carrying a decision you argued against. Use the session to work out what you can say truthfully, what you cannot say yet, and what your team will ask first. Rehearsed reassurance is spotted at once; a plain account of what is known usually holds.
What happens in the room when I present, and what would you change first?
Why ask it
Executive presence is too vague to work on, so get it down to one observable thing: pace, where you look, how long you take to reach the point, what you do when challenged. A recording helps. Change a single habit before the next big meeting instead of five.
What would I need to change to be credible for the next role?
Why ask it
Worth raising if promotion is part of why you sought coaching, and worth saying so plainly. The obstacle is often one perception (too operational, not known outside your function) more than a missing skill. Check the coach's read against someone who sits in those discussions.
How do I recover after a decision of mine has gone wrong in public?
Why ask it
Bring it while it still stings; a tidy retelling three months later teaches less. The session is for sorting what was bad judgment from what was bad luck, and deciding what you say to your team about it. Leaders who say nothing leave everyone else to write the story.
How do I keep this job from taking over everything else?
Why ask it
This sits at the edge of what coaching covers, and a careful coach will tell you when exhaustion needs a doctor more than a session. Inside that limit they can help with the practical part: what you agree to, what you never hand off, and which limits you announce and then break.
Reviews
Are we still working on the right thing, or has the real issue moved?
Why ask it
The midpoint is the time for this one. The goal written in the first month was a guess made before either of you knew much, and a sponsored goal may have been your manager's guess. Changing it is normal; if your employer is paying, agree who needs to hear about the change.
What have you seen change in me since we started, and what has not moved?
Why ask it
You are asking for both halves on purpose. Press for an example of each, with a date if they can give one. If the coach can only describe how the sessions feel, neither of you has been watching the thing you set out to change.
What have you been holding back because you were not sure I would take it well?
Why ask it
Coaches pace their honesty to what they think a client can hear, and that judgment can be too cautious. Asking directly gives permission. Take the answer quietly, say thank you, and bring your objections to the next session instead of this one.
How do I find out whether the people around me have noticed a difference?
Why ask it
Your own sense of progress and your team's can be far apart. Options range from the coach interviewing a few colleagues again to you asking two people one specific question. Pick whichever you will actually do, and ask about a behavior, not about whether you have improved.
When do you tell a client they no longer need you?
Why ask it
A coach's income depends on clients continuing, so it is worth hearing how they think about finishing. The good ones describe signs: you arrive with decisions already made, or you start predicting their questions. Raise it at the start and again at each review.
What should I keep doing after we finish, and who will hold me to it?
Why ask it
Habits built with a coach tend to fade once the regular appointment is gone. Leave with something small and scheduled: a monthly hour to review the same questions, a peer you report to, a check-in booked six months out. Decide it in the last session, not afterwards.
Choosing and Using an Executive Coach
Practical guidance for the conversation itself
Before You Commit
Take More Than One Chemistry Call
Many coaches offer a free introductory call. Taking two or three lets you compare how differently they read the same problem, which tells you more than any single conversation. Bring the same real issue to each one.
Settle Who the Client Is
When the company pays, there are three parties: you, the coach, and the sponsor. Agree in writing what the sponsor receives, who sets the goals, and what happens if your interests and theirs diverge. Do this before the first working session, not after something sensitive comes up.
Define One Concrete Change
Vague aims such as being a better leader give you nothing to measure. Pick something observable, such as delegating a specific area, running shorter decision meetings, or having a conversation you have been avoiding for a year.
Book a Review Point
Set a date, usually after three or four sessions, where you both decide whether to continue. Without it, engagements often continue on momentum long after the useful part has finished.
Once the Work Starts
Bring One Live Situation
The questions under In sessions work best attached to something happening this month: a meeting on Thursday, a person you owe an answer, a decision on your desk. General questions about leadership get general answers, and you can get those from a book.
Bring Evidence, Not Only Your Account
Your calendar, a recording of a presentation, the email you are about to send, the feedback report. Without it, the only version of events in the room is yours and nobody can test it. Material from outside your head is what lets the coach disagree with you.
Ask for the Read, Then Sit With It
Several of these questions invite the coach to say something unwelcome. If you ask and then spend the rest of the hour explaining why they are wrong, they will learn to stop. Write it down, and argue next time if you still want to.
Use the Reviews
The Reviews questions belong at the midpoint and in the last session. They are the main protection against an engagement that is pleasant, well attended and changing nothing.
Common Pitfalls
Hiring for Impressive Biography Alone
A former chief executive is not automatically a good coach. Operating success and the ability to help someone else think are separate skills, and the strongest operators sometimes just tell you what they would have done.
Letting Sessions Become a Vent
An hour of sympathetic listening feels productive and changes nothing. If three sessions in a row have been about how difficult other people are, say so and ask the coach to redirect.
Skipping the Confidentiality Detail
General reassurance is not a boundary. Ask specifically what your sponsor hears about themes, attendance, and progress, and get the answer written down.
Treating Coaching as Treatment
Coaching is not treatment. If what sits underneath is depression, drinking or exhaustion that rest does not fix, that is for a doctor or a therapist, and leaning on a coach can put off seeing one. A careful coach will say so early.