Chief executive officer interview questions

What this hire must get done

Write the scorecard before you interview, then hire against it. Set the bracketed targets from your own numbers.

What to tell candidates before the interview

Say the hard parts plainly. People who wouldn't stay drop out early, and the ones who stay knew what they signed up for.

• Say plainly who decides what: the calls you keep as owner, the CEO's spending and hiring limits, and how often you'll meet. Put it in the offer letter.
• Share the hard facts with finalists once they sign a confidentiality agreement: the debt, the margin, the open problems and any leader they'll inherit who isn't working out.
• Explain the process at the start: a long career interview, a timed business case, and reference calls with former bosses that the candidate will set up. Knowing the calls are coming tends to make answers more candid.
• Name any background check and when it happens. If a screening company runs it, federal law requires a separate written notice and the candidate's written permission first. Many states and cities also limit when you can ask about criminal records.

How to run the interview

1. Same questions, same order. Ask every candidate the questions below and the same follow-ups. It is the only way to compare people fairly.
2. Two interviewers. An owner or manager and someone who does the work. Take notes on what the candidate says, not on how you feel about them.
3. Score right after each answer. 5 sounds like the strong answer, 3 like the mixed one, 1 like the weak one. Use 2 and 4 for answers in between.
4. Rate alone, then compare. Compare candidates question by question, and talk only after everyone has scored. Big gaps are worth a conversation.

1. Behavioral · Track record

   Starting with your first management job and moving forward to today, walk me through each role. For each one, what were you hired to do?

   Walking every job in order shows patterns that one polished story hides: how fast they deliver, how they treat bosses and why they leave.

   Follow-ups

   • What did you get done, and which numbers show it, from your first month to your last?
   • What was the low point in that job, and how did you handle it?
   • Why did you leave, and how will your boss there describe your work when we speak?

   5Strong

   Each job has a clear mandate and a result with before-and-after numbers. Names mistakes without being pushed. Reasons for leaving fit together and mostly point toward something new. Gives bosses' names readily and expects you to call them.

   3Mixed

   Results are real but told as team wins with few numbers, or one or two exits are explained loosely and change a little when you ask again.

   1Weak

   Can't say what they were hired to do, numbers shift when probed, or every exit was someone else's fault.

2. Technical · Pricing and margin

   Over [two] years revenue grew [25] percent, but net profit stayed flat. Walk me through how you find where the margin went and what you change.

   Margin leaks quietly through stale prices, discounts, slower crews and overhead added ahead of sales. A CEO who can trace it raises profit without selling more.

   Follow-ups

   • What goes into the true cost of one billable hour?
   • How would you tell a pricing problem from a productivity problem?
   • Who in the company may approve a price change or a discount?

   5Strong

   Splits it into gross margin by service line and overhead as a share of revenue. Checks whether prices kept up with fully loaded labor cost, how much is discounted and by whom, any shift to lower-margin work, and billable against paid hours. Reprices from cost and sets who may discount.

   3Mixed

   Finds the right area, such as overhead creep or discounting, but fixes it with an across-the-board price rise or cost cut without tracing which service lines lost margin.

   1Weak

   Blames the market or wages, or plans to grow out of it with more sales.

3. Situational · Capital and growth

   You can fund one move next year: open a branch [an hour] away, buy a smaller competitor that's for sale, or add a service line for current customers. How do you decide?

   It shows whether they compare return, risk and the people needed to run each option, or chase the most exciting one.

   Follow-ups

   • What would you need to know about each option before choosing?
   • How would you pay for it, and what would you refuse to risk?
   • What result, by when, would tell you it was a mistake?

   5Strong

   Compares payback and risk for each, asks who would run it, checks the seller's real earnings and customer overlap, keeps a cash cushion and room under the loan covenants, and sets in advance the result that would make them stop.

   3Mixed

   Weighs the money well but assumes today's managers can absorb a new branch or company, or leaves out how it gets funded.

   1Weak

   Picks the biggest or most exciting option with no numbers, or would borrow to the limit to do it.

4. Behavioral · Capital and growth

   Tell me about the largest acquisition, new location or major investment you led. How did the results two years later compare with the plan?

   Closing a deal is the easy part. The answer shows whether they track results against the case and own the gap.

   Follow-ups

   • What did you find after closing that your review missed?
   • Who ran it day to day, and how did you choose them?
   • What would you do differently?

   5Strong

   States the plan and the actual results side by side, owns the gap, describes the hard parts of joining the two businesses (systems, pay plans, people, customers) and names a lesson they've used since.

   3Mixed

   The deal turned out fine, but they can't compare it with the original case, or credit and blame stay vague.

   1Weak

   Talks only about winning the deal, has no numbers for what happened after, or blames the seller for everything.

5. Behavioral · Building the leadership team

   Think of the senior hire you most regret. What did you miss when you hired them, and how many months passed before you acted?

   Every CEO makes some wrong hires. What matters is how fast they see it, how they handle it and what they learn.

   Follow-ups

   • When did you first see the problem, and what did you do then?
   • How did you handle the exit and the team left behind?
   • Who did you hire next, and how did that go?

   5Strong

   Saw the gap against written goals within months, coached with a clear deadline, then acted with respect and told the team plainly. Changed how they hire, such as writing a scorecard or calling more references, and the next hire worked.

   3Mixed

   Made the right call but waited [a year or more] hoping it would fix itself, and can say now that it was too long.

   1Weak

   Says they've never made a bad hire, or blames the person entirely and changed nothing.

6. Situational · Building the leadership team

   You inherit an operations leader who has worked for the owner for [15] years. Everyone likes them, and they've missed plan [three] quarters in a row. What do you do in your first [90] days?

   New CEOs often inherit the owner's most loyal leader. The answer shows whether they act on facts while keeping the owner's trust.

   Follow-ups

   • What would you talk through with the owner first?
   • What would you need to see to keep this person in the seat?
   • If they move on, how do you keep the field steady?

   5Strong

   Agrees with the owner up front on who makes the call. Sets written goals and a deadline with real support, judges against them, and moves the person if needed, possibly into a role that fits. Plans coverage and tells the team what's changing.

   3Mixed

   Sets clear goals and a deadline but would act without first agreeing with the owner, or plans to wait out the year before deciding.

   1Weak

   Replaces the leader in week one without facts, or won't touch the owner's longtime person at all.

7. Situational · Owner and board partnership

   Six months in, the founder, now board chair, keeps calling your managers directly and overriding your decisions on pricing and hiring. What do you do?

   A founder who can't let go can sink a CEO hire in an owner-led company. You want someone who fixes it privately and in writing.

   Follow-ups

   • What would you say to the founder, and where?
   • What would you put in writing?
   • What do you tell the managers in the meantime?

   5Strong

   Talks with the founder privately, never in front of the team. Looks for what's driving it, such as worry about results or missing information. Proposes a written list of who decides what and better reporting. Asks managers to bring owner requests to them without undercutting the founder.

   3Mixed

   Raises it with the founder but only in general terms, with no agreed rules, or puts up with it to keep the peace.

   1Weak

   Confronts the founder in front of managers, tells managers to ignore the founder, or lets it go on.

8. Behavioral · Owner and board partnership

   Tell me about a time you brought bad news to your owners, board or bank before they heard it anywhere else.

   Owners forgive a bad quarter. They don't forgive finding out late, and lenders treat surprises the same way.

   Follow-ups

   • When did you first know, and how long until you told them?
   • What did you bring along with the bad news?
   • How did the relationship look a year later?

   5Strong

   Told them as soon as the trend was clear, with the cause, the size of the problem, options and a recommendation. If a covenant was at risk, went to the bank early to ask for a waiver or new terms. Trust held or grew.

   3Mixed

   Told them, but only once the result was certain, or brought the problem without a plan.

   1Weak

   Hoped it would turn around, and the owners or bank found out from someone else.

9. Situational · Crisis and safety leadership

   Your slow season starts early, a large commercial customer stops paying, and your CFO says the credit line's covenant test will fail at quarter-end, [ten] weeks out. What do you do in the first [two] weeks?

   Cash crises are where CEOs earn their pay. The answer shows what they protect, what they cut and who they tell.

   Follow-ups

   • Which call do you make first, and what do you bring to it?
   • What do you cut, and what do you protect?
   • What do you tell employees?

   5Strong

   Asks the CFO for a weekly [13]-week cash forecast, calls the bank early with a plan, chases the unpaid account with counsel, pauses capital spending and hiring. Protects payroll, payroll tax deposits and safety, and tells employees the truth at the right level.

   3Mixed

   Cuts costs quickly and sensibly but waits to tell the bank until the covenant breaks, or cuts across the board, including the people who bring in cash.

   1Weak

   Waits for sales to catch up, or would hold back payroll tax deposits to get through.

10. Behavioral · Crisis and safety leadership

    Walk me through the worst injury or near miss on your watch as a leader, from the first phone call to the changes that followed.

    Crews watch what the top person does after an incident. That, more than any poster, decides whether safety beats the schedule.

    Follow-ups

    • What did you look at before that day to know whether the company was safe?
    • How did you hold managers to safety, not just output?
    • How do you know the change lasted?

    5Strong

    Made sure the worker got care and the incident was reported as required, then led a review that looked at the system (schedule pressure, training, equipment), not only the worker. Changed something measurable and now reviews near-miss reports and site audits along with injury counts.

    3Mixed

    Handled the incident well, but safety otherwise belongs to a safety manager, and they track only injury counts.

    1Weak

    Blames the worker, wasn't involved, or talks about safety only as an insurance cost.

Work exercise: grow-or-buy business case

Send finalists a short packet the day before, shaped like a decision you really face but with made-up numbers: two years of results and the balance sheet for a [three]-branch company, a bank term sheet and a one-page summary of a smaller competitor that's for sale. Ask them to spend no more than [two] hours preparing. In the meeting they take [20] minutes to present their first-year plan, including whether to buy and how to pay for it, then answer questions for [25] minutes.

Use made-up materials, never real customer work, and keep it to the time shown. Follow your own safety rules for anything hands-on.

Reference check questions

Tell finalists you'll call a former manager, and get their permission first. Ask about what they did, not whether they were nice.

• What was the business like when they arrived and when they left, in revenue, margin and leadership team? How much of that change was their doing?
• How did they keep you informed? Tell me about a time they brought you bad news.
• In our interview they described [a low point from the career interview] in that job. How did you see it at the time?
• On a scale of [one to ten], how would you rate their work as your CEO, and what would have made it a ten?

Questions to skip, and what to ask instead

Ask only what the job needs. Questions that touch age, health, family or pay history can break federal, state or local law, even when you mean well.

• SkipWhat are you making in your current job?

  AskThis role pays [base range], plus [bonus plan and any equity]. What range would you need to make a move? Don't ask former employers what they paid either; New York, for one, bans that too.

• SkipHow many more years do you plan to work?

  AskThe plan we're hiring for runs [five] years. What would you want to have built by the end of it?

• SkipWill your spouse be willing to move here?

  AskThe job is based in [city], with [how much] travel. When could you start working from here?

Common mistakes when hiring a chief executive officer

• Hiring a CEO before deciding what you'll give up

  If the founder still wants the final say on prices, hires and big purchases, the new CEO becomes an expensive advisor. Write down the decisions that move to the CEO before you post the job, and test that list against your own habits.

• Hiring for the size you hope to be

  A leader from a large company may be used to a full finance team, a marketing department and a deep bench. Ask what they built themselves with a small staff, and weigh that against your own size today.

• Going easy on references because they're senior

  Owners often skip deep references for executives out of courtesy. Calls with former bosses, peers and people who reported to them are where patterns from the career interview get confirmed or fall apart.

Chief executive officer interview FAQ