Questions to Ask a CEO Candidate
These questions to ask a CEO candidate are written for the people doing the choosing: a board, a search committee, a founder handing over the job, or an investor with a seat at the table. They suit a company or a nonprofit and run in the order a search tends to take: what the candidate has already done, how they see your organization, the team they would build, how they would work with the board, money, and then pressure and integrity. No one meeting covers all 57, so split the groups among your interviewers and hold the last for finalists.
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The questions
Each question, and why to ask it
Track record
What state was the last organization you led in when you took over, and what state did you leave it in?
Why ask it
Start here, because every later answer gets weighed against this one. A full reply has a before and an after that someone else could check: revenue or budget, headcount, cash, customers or people served. A candidate who describes only the after may have inherited more than they built.
What did the board that last hired you ask you to do, and did you do it?
Why ask it
A turnaround, a sale, growth, a steady hand after a founder: each mandate suits a different person. Hold the answer against what you are hiring for, since a strong record on a different mandate tells you less than it seems to.
Which of your results came from a good market, and which did you have to fight for?
Why ask it
Every record has some of both, and a candidate who can tell them apart is likely to be straight with you about results here too. Follow up on the one they fought for by asking who opposed it at the time.
Tell me about a strategy you set that did not work. When did you know, and how long before you said so out loud?
Why ask it
The gap between knowing and saying is the thing to measure. A few weeks is ordinary, and a year means that board was told late. If they cannot name a failed strategy of their own, ask about one they inherited and kept too long.
How did each of your last two jobs end, and who decided it was time?
Why ask it
You will hear the other side of this from references, so write down the account you are given now. A departure the board decided is not a disqualification on its own. An account that changes between this round and the next one is a bigger worry.
What were revenue, margin and cash on your first day and on your last?
Why ask it
Ask for the figures themselves, then ask where you could confirm them: audited financial statements, a public filing, a former director. For a nonprofit, swap in annual budget, reserves and the split between restricted and unrestricted income. Rounded numbers are fine, but a candidate who cannot recall them at all was probably not the one watching them.
What is the largest organization you have run with nobody above you to appeal to, by people and by budget?
Why ask it
Set the scale beside yours in both directions: a leader from a far larger place may expect staff and systems you do not have, and one from a much smaller place will be learning as they go. If the answer is a division, with a chief executive above to break ties, you are looking at a first-timer. That can be the right hire, so ask which part of the top job they expect to find hardest.
What did your successor change in their first year, and were they right to?
Why ask it
What the next person undid is a fair measure of what was left behind: a team rebuilt, a strategy dropped, costs taken out. A candidate who has not kept track is telling you something as well. If they are still in the role, ask what they would expect a successor to change first.
How did your time split between the inside of the organization and the outside: customers, funders, regulators, the press?
Why ask it
Some leaders run the place and some represent it, and few are equally good at both. Work out which one your organization needs for the next few years before you hear the answer, then ask who covered the half they spent less time on.
This organization
Why do you want to be chief executive here, and what else are you considering?
Why ask it
A convincing reason could not be said about the other organizations this person is talking to. On a nonprofit search, this is also where a connection to the mission shows up or fails to. Whatever else is in play tells you how fast you need to move and how a counteroffer might land.
From what you have seen so far, where does this organization's money come from, and what puts that at risk?
Why ask it
A serious candidate has read whatever is public and formed a view. It does not have to be right, since they have not seen the inside. It has to be specific enough that you could argue with it.
Who have you spoken to about us before today, and what did they tell you?
Why ask it
Customers, former staff, funders, a competitor: the list shows how this person goes about learning a new subject. What they were told is also free information about how you look from outside.
What do you suspect we are getting wrong that is hard to see from the inside?
Why ask it
Two things are being tested: whether they have an independent read, and whether they will say it to the people deciding their future. Do not argue the point in the room. Write it down and see whether another finalist says the same thing.
Who is our real competition, and what do they do better than we do?
Why ask it
For a nonprofit, competition means whoever else your funders could give to and whoever else serves the same people. A name you had not considered is the valuable answer, and it tends to come from a candidate outside your sector.
Walk us through your first 90 days. What would you decide early, and what would you refuse to decide until later?
Why ask it
Nearly everyone says they would listen first, so push on the second half. A good answer names the calls that cannot wait, such as a cash problem or a vacancy at the top, and the ones that need a few months of knowledge, such as a restructuring or a change of direction.
Where should this organization be in three years, and what would have to be true for it to get there?
Why ask it
The first half gets you ambition and the second gets you the plan. Count the conditions that sit outside anyone's control, like a funding market or a regulator, and ask what the fallback is if one of them does not hold.
Which of our products, programs or markets would you look hardest at closing?
Why ask it
Saying what to stop is harder than saying what to start, and it is usually where a new chief executive first meets resistance. 'I would need to see the numbers' is a fair reply once. Then ask how they made that call the last time they faced it.
Which part of what we do have you never run, and how would you learn it without the organization paying for the lesson?
Why ask it
Nobody arrives knowing every part. What you want is a named gap and a method: a strong deputy in that area, time spent on the front line, an adviser. Be wary of a candidate who says the gap does not matter at this level.
At the end of your first year, what should we be able to point to as evidence we chose well?
Why ask it
Whatever they offer can go straight into the goals you set after the offer. If the measures are all activity, such as a plan written or a team hired, ask for one result that a customer, a funder or a member of staff would notice.
What would you need to see in our financials and board minutes before you could say yes?
Why ask it
An experienced leader's request list is short and pointed: cash, debt and its conditions, the biggest customers or funders, any dispute or claim, the last few sets of board minutes. Decide beforehand what you can share at each stage and under what confidentiality terms.
What would make you turn this job down if we offered it tomorrow?
Why ask it
Better to hear the obstacle now than after an offer: the location, the terms, the makeup of the board, a predecessor who has not really left. If the answer is 'nothing', ask which of those they have already looked into.
Team
How has the way you lead changed since your first senior role, and what forced the change?
Why ask it
This is the leadership style question with a story attached, which is harder to answer with adjectives. The event that forced the change, such as a team that pushed back, a bad year or blunt feedback, is usually the most revealing part.
In your first months, how do you decide which members of an inherited leadership team stay?
Why ask it
A sound answer has a method and a timetable. Deciding in the first week is as worrying as still deciding after a year. Ask how it went the last time, and how many of the team they inherited were still there two years on.
Who was the last member of your top team you let go, and what did the delay cost?
Why ask it
Almost every chief executive says they waited too long, so the admission alone means little. The useful parts are what they saw first, who they consulted, and how the person was treated on the way out.
Which executive hire of yours failed, and what did you miss when you interviewed them?
Why ask it
A leader who has hired a dozen executives has at least one miss. If the blame goes entirely to the person hired, note it. If they can name what they overlooked, ask what they changed about how they hire.
Who would you want to bring with you, and what would that mean for the people already here?
Why ask it
Followers are a good sign: people have chosen to work for this person twice. Three or four arrivals in the first six months can also empty your existing team. Whether an agreement with a former employer limits who the candidate may recruit depends on the contract and the place, so ask your search firm or counsel how that works for you.
Who on your past teams disagreed with you most usefully, and where are they now?
Why ask it
If that person was promoted or is still close to the candidate, dissent was safe on their team. If nobody comes to mind, or the dissenter left soon after, ask a reference from the team how disagreement went in practice.
How does bad news reach you, and when did you last hear something from the front line that your executives had not told you?
Why ask it
People at the top hear filtered information unless they build ways around the filter: site visits, conversations that skip a level, reading the complaints themselves. A specific recent example is the only convincing answer.
How did people who never sat in a meeting with you know what mattered most that year?
Why ask it
Staff meetings, a regular written note, days spent on site: the channel matters less than whether the message arrived. Ask what a front-line employee would have named as last year's top priority. A candidate who answers in one plain sentence has probably said it many times.
If we asked people two levels below you what it was like to work there, what would they say?
Why ask it
Here is the culture question in a form you can check. Take the answer and put the same question to a reference who sat at that level. The distance between the two accounts is what you are measuring.
Have you had to cut jobs as chief executive? How did you choose how deep to go, and what did you say on the day?
Why ask it
Two details matter: whether they cut once or kept coming back for more, and whether they delivered the news in person. If your organization may face this, say so now. A candidate who has never done it should hear that before accepting.
Who could have stepped into your job when you left, and what had you done to get them ready?
Why ask it
Succession is the chief executive's work as much as the board's. No internal successor may mean the organization was small or the exit sudden, so ask which. A leader who left nobody ready in two or three roles running tends to build teams that depend on them.
The board
Where do you draw the line between what belongs to the board and what belongs to the chief executive?
Why ask it
There is no single correct line, and it moves with the size of the organization and with whatever your bylaws or shareholder agreements say. What you need is a line close to your own. Describe a decision your board made recently and ask who they think should have made it.
Tell me about a time your board said no to something you wanted. What did you do in the month after?
Why ask it
Three things can follow a no: the leader accepts it, comes back with a better case, or does it anyway by another route. The third is the one that should worry you, and a director from that board can tell you which it was.
What is the worst news you have had to take to a board, and how did the directors first hear it?
Why ask it
Directors can live with bad news and cannot live with surprises. A good account has a call to the chair before the meeting and the whole picture in writing, not a line slipped into the last five minutes. Ask what the board did with the news, since that shows whether its members were treated as a help or as an audience.
How did you and your board chair work together between meetings?
Why ask it
Some pairs speak every week and some only when there is trouble. Tell the candidate how your chair likes to work and watch the reaction. At an investor-backed company, ask the same about the lead investor.
What went into your board packets, and what did you include that you would rather have left out?
Why ask it
A chief executive controls most of what a board sees. One who can name the uncomfortable page they kept in, such as a missed target or a staff survey, is showing you how they would report to you. Have them describe a typical packet page by page. The document itself belongs to their former employer, so do not ask for a copy.
What would you do if a director, an investor or a major donor went around you to your staff?
Why ask it
It happens on most boards sooner or later. An answer that bans all contact is brittle, and a shrug suggests they have not lived it. The workable answer is a direct conversation with the person and a word with the chair.
If the founder or the outgoing chief executive stays on the board, or in the building, how would you handle it?
Why ask it
Skip this if the predecessor is leaving completely. If not, settle the arrangement among yourselves before any offer, because the candidate will ask what authority the former leader keeps, and 'we will see how it goes' is the reply that loses good candidates.
How do you want us to assess you, on what, and how often?
Why ask it
A candidate who welcomes a yearly review against agreed goals is easier to govern than one who reads assessment as mistrust. Be ready to say how you assessed the last chief executive. If the honest answer is that you did not, this search is the moment to change that.
What has a board done that made your job harder, and what would you need from this one?
Why ask it
Common answers are directors who reopen settled decisions, a split board, and slow replies between meetings. Take it as feedback on your own board as much as information about the candidate, and check that what they need is something you can give.
Money
How much capital have you raised, from whom, and what was your own part in getting it?
Why ask it
The question separates a leader who led the pitch and negotiated the terms from one who was present while a finance chief or a chair did it. For a nonprofit, ask about the largest gift or grant they asked for in person.
Which investors, lenders or funders came in because of you, and which walked away while you were in charge?
Why ask it
Relationships that followed the candidate from one role to the next are an asset you may be hiring. The ones who left deserve a follow-up on why, and they are good people to hear from at the reference stage if the candidate agrees.
What is the closest you have come to running out of cash, and what did you pay first?
Why ask it
A leader who has been through a cash squeeze can tell you which obligations they protected and who they told. One who has not is untested on the point, which matters a great deal if your reserves are thin and hardly at all if they are deep.
What did you forecast for your last full year, and where did you finish against it?
Why ask it
Missing a forecast is ordinary. Find out whether they miss in the same direction every year, and when the board learned the number would be missed. Check the answer with the finance chief or treasurer if one is among the references.
What is the largest spending decision you took to a board, and did it pay back?
Why ask it
A new site, a system, a senior hire, a program expansion: the example they choose shows what this person thinks money is for. Ask what return they promised, when they went back to measure it, and whether the board ever saw that comparison.
Have you bought, sold or merged an organization, and would you do that deal again?
Why ask it
This one is essential only if a deal is likely in your next few years, in which case ask what had happened to the people and the numbers two years afterward. If they have never done one, ask who they would lean on, since boards often carry that experience themselves.
What would you want your own pay tied to, and over what period?
Why ask it
The measures a candidate proposes show what they think the job is for. Leave the amounts to the committee and its advisers. What is usual or allowed in executive pay depends on the kind of organization and where it is, so ask how it works for yours before anyone makes a promise.
Pressure and integrity
What is the hardest decision you have made that you could not hand up to anyone?
Why ask it
How they decided matters as much as what they decided: who they consulted, how long they took, what they did the next morning. A candidate whose hardest call sounds easy has either been lucky or is choosing a safe story, so ask for a second one.
Tell me about a crisis that became public. What did you say in the first day, and who wrote it?
Why ask it
Three things count: speed, plain words and whether they stood in front of it themselves. If they have never had a public crisis, describe one your organization could plausibly face and ask what they would do in the first 24 hours.
What do you do when you do not know what to do, and who do you call?
Why ask it
The top job has no peers inside the building. A candidate with two or three people to call, such as a former chair, a mentor or another chief executive, will make fewer lonely mistakes than one who says they trust their gut.
When has doing the right thing cost your organization money, and how did you explain it to the board?
Why ask it
A real example usually involves a customer refunded, a deal declined or a problem reported before anyone asked. If the story has no cost in it, it does not answer the question, and it is fair to say so and ask again.
What did you do the last time a senior, high-performing person was found to have behaved badly?
Why ask it
This shows whether results buy exemptions on their watch. Ask what the rest of the staff were told afterward. The details may be confidential, and a candidate who protects them while still describing their own actions is handling it correctly.
Have you had a conflict of interest in a past role, and how was it declared and managed?
Why ask it
Outside board seats, relatives on the payroll, a stake in a supplier: most senior people have had one, and the test is whether they raised it first. Ask what they hold now that your board would need to know about.
Is there anything in your past, such as a lawsuit, an investigation or a dismissal, that we should hear from you before we hear it elsewhere?
Why ask it
Ask it in the same words of every finalist so nobody is singled out. What you may ask about, and which checks need the candidate's written consent, varies by place, so have your search firm or counsel confirm the rules where you are before this round.
When we speak to your last board chair, what will they say you were slow to do?
Why ask it
Because the candidate knows the call is coming, the answer tends to be accurate. Put the same wording to the chair. Agreement between the two is a good sign even when the criticism itself is serious.
Who should we call who is not on your reference list: someone you dismissed, a director who voted against you, a funder or customer who left?
Why ask it
A confident candidate offers names. Get their agreement before you call anyone, and never approach a current employer without it, since a leak can cost the candidate their job and cost you the candidate.
Interviewing chief executive candidates from the board's side
Practical guidance for the conversation itself
Before the first candidate
Agree on the mandate before you agree on a person
A committee that has not decided whether it wants a turnaround, growth, a sale or a steady hand will score every candidate differently, and will argue about people when the disagreement is really about the job. Write the mandate in a few sentences, with the two or three results that would make the first two years a success, and have the full board approve it before the search begins.
Give each group to one interviewer
Give Track record and Money to the directors who read financial statements for a living, The board to the chair, and Team to someone who has managed executives. This organization suits a founder or a long-serving director, who can tell an informed view of the place from a flattering one. Pressure and integrity is best asked by two people together in a late round, one asking and one taking notes. Each interviewer can then go deep on one area, and the candidate is not asked for their first 90 days four times.
Decide what you will disclose, and when
Finalists for the top job will ask for financial statements, board minutes and the truth about why the seat is open. Settle in advance what is shared at each round and under what confidentiality agreement. Holding back a known problem until after the offer starts the relationship with a grievance.
Keep a common core
Choose eight to ten questions that every finalist will be asked in the same words, with some from each group. Internal candidates get the same core as external ones, even when the committee thinks it knows them already. Without that, the comparison at the end is between different conversations.
When one candidate already works for you
An internal candidate is known on the things an interview struggles to test and unknown in the top seat. Put them through the same rounds as everyone else, and press the Track record question about the largest thing they have run with nobody above them. Decide before the final round who will tell them the result, and what you would do to keep them if the answer is no.
Across the rounds
Evidence first, plans second
Start with Track record, because everything a candidate says about your organization should be weighed against what they have done before. Plans for a first year sound alike from one candidate to the next, and records do not.
Ask for the figure, then for its source
When a candidate gives a result, ask what the number was, over what period, and who else could confirm it. Experienced leaders expect this from a board and do not take it as an accusation. Note each figure so that the reference calls can test it.
Set a working session for finalists
Give the last two or three candidates a real problem, such as last year's results and a decision the board is facing, with a few days to prepare and the confidentiality terms in place. An hour of working through it with the committee shows how they think and how they take a challenge, which a prepared interview answer hides.
Leave time for their questions
A strong candidate is assessing you: the unity of the board, the money, the reason the last leader left. What they ask is evidence of what they would pay attention to in the job. A finalist with no questions has either not prepared or has already decided.
Stay off personal ground
Age, health, family plans, religion and similar subjects have no place in the interview, and many places restrict asking about them. If relocation or travel matters, describe what the job requires and ask whether the candidate can meet it. Check with your HR adviser or counsel what applies where you are.
Checking what you were told
Make the calls yourselves
A search firm can arrange references, but at this level at least two directors should speak to the most important ones directly: a former board chair, a peer, someone who reported to the candidate. Put the same short list of questions on each call, including what the person would tell a friend about working with them.
Go beyond the list, with consent
The names a candidate supplies are the ones they expect to speak well. Ask permission to add others, such as a director from an earlier board or an executive who left their team. Never contact a current employer or colleague without the candidate's agreement.
Match the numbers to documents
Where financial statements are public, read them for the years the candidate was in charge and compare them with what you were told. Where they are not, ask a reference who saw the figures. Small differences of memory are normal, and a different story is not.
Leave the formal checks to people who do them
Verification of degrees, past employment, directorships and any legal history is usually handled by the search firm or a specialist provider. What can be checked, and what consent it needs, differs by country and state, so ask them what is covered and get the candidate's consent in writing before anything starts.
Where chief executive searches go wrong
Hiring the opposite of the last one
After a leader who disappointed, committees often choose whoever least resembles them: a cautious operator after a visionary, an outsider after an insider. Hire for the mandate you wrote down, which may need some of what the last person was good at.
Mistaking presence for record
Chief executive candidates are good in a room, or they would not have reached your shortlist. If the committee is leaning toward the best presenter, go back to the Track record notes and the reference calls and see whether they agree.
A divided committee, papered over
A split vote hidden behind a unanimous announcement leaves the new leader with directors who never wanted them. If the committee cannot agree, interview again or reopen the search. The delay costs less than a first year spent managing the board.
The outgoing leader choosing the successor
A departing chief executive or founder knows the job better than anyone and should be heard on what it needs. The choice belongs to the board, and the predecessor should not sit in on interviews or see the scores.
Letting the deadline do the choosing
An interim arrangement feels uncomfortable, and that pressure makes the last candidate standing look better than they are. An acting leader for a few more months is a smaller risk than the wrong appointment.