There are two CEO interviews. In the first, you are the candidate for the CEO seat and the board is deciding. In the second, you are interviewing with the CEO for a senior role, and the CEO is deciding whether to trust you with part of the company. Lists of CEO interview questions run to 70 or 125 items, almost all written for boards and search firms. The sharpest of them come back to one thing: how you make decisions when the information is incomplete and the stakes are high.
I have sat on both sides. I founded Interland and took it from a startup to a Nasdaq IPO in three years as its CEO, on its way to $200M in revenue and 650 people, and I spent a decade as a managing partner at a venture firm and a board member across 35 deals. The method behind every answer below (find the question under the question, ask one back, answer with one story, close with "did I answer your question?") is in how to prepare for an executive interview.
Key takeaways
- Boards hiring a CEO test decision quality: limited information, a conflict in the executive team, a risk you took.
- Bring a first 100 days that is a way of diagnosing, not a fixed plan.
- Expect the board to ask what your own executive team would say is your biggest flaw. Know the answer.
- Interviewing with a CEO for another senior role, work out the CEO's problems before the meeting and answer to them.
- Ask the board what it would hold you accountable for in the first year.
The questions at a glance
| They ask | What they are really asking |
|---|---|
| Tell us about a decision you made with limited information. | How do you decide when you cannot know? |
| Tell us about a conflict in your executive team, and how you resolved it. | Can you lead strong people who disagree? |
| What is the biggest risk you have taken, and how did it turn out? | Do you take risks deliberately, and own the result? |
| What would your first 100 days look like? | Will you diagnose before you act? |
| How do you define and measure success? | Will you hold yourself to numbers we can check? |
| What would your executive team say is your biggest flaw? | Do you know yourself, and will you tell us? |
| When you took your last CEO role, what was your vision, and what happened? | Do you deliver what you set out to do? |
| How do you work with a board and with investors? | Will you bring us bad news early? |
| What mandate would you want from us, and what is non-negotiable? | Do you know what you need to succeed, and will you say it? |
| Who in the top team would you keep? | Can you judge talent, and keep the people who matter? |
| How would your peers react if you got this job? | Can you lead the people who wanted it too? |
| What are the biggest risks you see in this company? | Have you studied us, and will you say what you found? |
| What would your plan for the first year be, and how does it create value for the owners? | Do you think like the people who own the company? |
| Why you, and why now? | Do you want this company, or a CEO title? |
Interviewing for the CEO seat
Tell us about a decision you made with limited information.
What they are really asking: how do you decide when you cannot know?
How to answer: the decision, what you knew and did not know, the options, how you weighed them (data, people, instinct), who you consulted, what you decided and when, and what happened. Then what you would do differently. This is the question boards care about most and candidates prepare least.
Tell us about a conflict in your executive team, and how you resolved it.
What they are really asking: can you lead strong people who disagree, without losing them or the decision?
How to answer: what each leader wanted and why each had a case, how you got the disagreement into the room, how you decided, and what you did with the leader who lost. Name the result for the company, not just the peace.
What is the biggest risk you have taken, and how did it turn out?
What they are really asking: do you take risks deliberately, and do you own the result?
How to answer: a real bet with a number on it: what you risked, why, how you limited the downside, and what happened. If it failed, say so plainly and say what you learned. Boards trust the CEO who can describe a loss.
What would your first 100 days look like?
What they are really asking: will you diagnose before you act, or arrive with the last company's plan?
Ask back first: "What would the board want to see at day 100?"
How to answer: who you would listen to first (the board, the executive team, customers, the people closest to the work), what you would measure, the decisions you would not make until you knew more, and the one visible problem you would fix early. More in the first 90 days as a new executive.
How do you define and measure success?
What they are really asking: will you hold yourself to numbers we can check?
How to answer: the three or four measures you ran your last company on, why those, and one time a measure told you something you did not want to hear, and what you did.
What would your executive team say is your biggest flaw?
What they are really asking: do you know yourself, and will you tell us?
How to answer: a real one, the cost of it, how you compensate (the people around you, the habits), and evidence it is improving. Every strength has a shadow; a CEO who knows theirs is easier to back.
When you took your last CEO role, what was your vision, and what happened?
What they are really asking: do you deliver what you set out to do?
How to answer: the vision in one sentence, the two or three moves you made, the results against it, and what you changed when it was not working.
How do you work with a board and with investors?
What they are really asking: will you bring us bad news early, and use us well?
How to answer: how you set the agenda and the reporting, one time you brought bad news early and what the board did with it, and one time board advice changed your decision.
What mandate would you want from us, and what is non-negotiable?
What they are really asking: do you know what you need to succeed, and will you say it to the people hiring you?
How to answer: name the two or three things you would need (the authority over the team, the budget, the scope of change, how often you meet the board), say which one is non-negotiable and why, and connect each to the plan you just described. A candidate who wants the job too much to name conditions worries a board more than one who names them.
Who in the top team would you keep?
What they are really asking: can you judge talent from the outside, and keep the people who matter?
How to answer: explain how you would assess the top team in your first weeks, what you would look for, and how you would hold on to the strongest while you decide. Then a time you assessed a leadership team you inherited: who stayed, who left, and what happened to the results. Do not name people in this company you have only met in the process.
How would your peers react if you got this job?
What they are really asking: if you are an internal candidate, or one of several finalists, can you lead the people who wanted the job too?
How to answer: be honest that some may be disappointed, say what you would do in the first weeks with each of them, and give one example of leading former peers or a passed-over rival. Boards worry about losing good people after a CEO decision.
What are the biggest risks you see in this company?
What they are really asking: have you studied us, and will you say what you found?
How to answer: name one or two risks you found in the filings, the press and the conversations so far, say what each could cost the plan, and say what you would want to learn in your first month to know if you are right. A board that hears only opportunities wonders what you missed.
What would your plan for the first year be, and how does it create value for the owners?
What they are really asking: do you think like the people who own the company? In companies owned by a private equity firm or another sponsor, the CEO is expected to arrive with an operating plan, and the few CEO roles posted publicly say so: build the operating plan, sometimes before the deal closes, and lead with an institutional board and operating partners in place.
Ask back first: "What does the investment case assume this business will do over the next few years?"
How to answer: the two or three value drivers you see (growth, margin, acquisitions, cash), what you would do first on each, what you would measure monthly with the board, and one time you built and delivered a plan like this, with the numbers.
Why you, and why now?
What they are really asking: do you want this company, or a CEO title?
How to answer: the problem in this company you want to own, why your record fits it, and why now. Make it about them.
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How boards organize the CEO interview
McKinsey's guide for prospective CEOs, built from debriefs with CEO candidates and conversations with board members, groups the board's questions into seven areas. Prepare a view on each before you walk in:
| Area | What the board is testing | What to bring |
|---|---|---|
| Strategy and vision | Do you have a view of where this company should go? | your vision, what you would stop, and a first-year and a three-year plan |
| Where the company stands today | Have you diagnosed the business honestly? | strengths, weaknesses, the biggest wins and misses, the competitors that matter |
| Culture and organization | Can you shape the culture and the team? | your read of the culture and the top team, and what you would change |
| CEO requirements | Do you know what the next CEO needs, and do you have it? | the profile the job needs, measured honestly against yours |
| Experience and motivation | Why you, and why do you want it? | your record, your failures and what you learned, your motivation |
| Governance and processes | How would you run the company and work with the board? | the mandate you need, the executive committee, the key processes |
| Stakeholders | Can you hold the people around the company? | how peers, employees, investors and regulators would react, and what changes in year one |
What boards and owners put in writing
Most CEO searches are confidential and run by retained search firms, so few CEO roles are posted. The ones that are, and the search firms' own guidance to boards, show what the board decides before it meets you: the leadership the company needs next, the mandate for the new CEO, and the team the CEO will inherit. Prepare for all three:
| What the board defines | The question under it | What to bring |
|---|---|---|
| The leadership the company needs in the next phase | Are you the leader for this phase, not the last one? | a phase you led that looks like theirs |
| The mandate for the new CEO | Do you understand what we are hiring you to do? | your read of the mandate, and a question to confirm it |
| The team the CEO will inherit | Will you build the team, or replace it all? | how you assessed and changed a leadership team, with the results |
| The plan and the owners' expectations (sponsor-owned companies) | Do you think like an owner? | an operating plan you built and delivered |
Interviewing with the CEO
When you are interviewing for a senior role and the CEO is in the loop, the CEO is often the last and most important conversation. CEOs who talk about how they hire describe the same things: they will meet you more than once, the resume matters less than the conversation, they want the why behind each career move, and late in the process they are testing whether you really want this job.
Prepare for it the same way:
- Work out the CEO's problems before you go. Read what the company has said publicly, listen to what the other interviewers kept coming back to, and arrive with your view of the two or three problems the CEO most needs solved.
- Answer at the CEO's altitude. Strategy and results first, the detail when asked.
- Know the why behind every move on your resume, and say it in one honest sentence each.
- Ask questions only the CEO can answer. What would you want to stop doing yourself once this role is filled? What does this role have to deliver for the company to hit its plan?
Questions to ask the board
- What would you hold me accountable for in the first year?
- What team will I inherit, and what do you expect me to change in it?
- Where does the board see the company differently from the executive team?
- What did the last CEO get right that you want kept?
- How does the board want to work with the CEO: how often, and on what?
- What is the decision you most need the next CEO to make?
Questions people ask
What questions does a board ask a CEO candidate?
Decisions made with limited information, conflict in an executive team, the biggest risk taken, the first 100 days, how you measure success, your biggest flaw, how you work with a board, the risks in the company, and why you and why now.
How do I prepare for a CEO interview?
Study the company like an owner, prepare three or four stories with numbers that show decisions under uncertainty, bring a way of diagnosing the first 100 days rather than a fixed plan, and prepare questions about what the board will hold you accountable for.
What should I expect when interviewing with the CEO for another role?
More than one conversation, questions about the why behind your career moves, a test of whether you really want the role, and a focus on strategy and results more than detail.
What questions should I ask a CEO in an interview?
What the CEO wants to stop doing once the role is filled, what the role must deliver for the plan, where the leadership team disagrees, and what would make hiring you the right call a year from now.
What questions should a CEO candidate ask the board?
What the board will hold you accountable for in year one, where it sees the company differently from the executive team, and the decision it most needs the next CEO to make.
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