What Are Good Questions to Ask a CEO
70 questions to ask a CEO during a meeting, whether that is an all hands, a final round interview, a lunch, a minute at a conference or a rare one to one. They include the ones to put to the CEO or owner of your own company about pay, promotion and how to raise a problem. The business questions come first, on strategy, customers and money, followed by decisions and candor, your own company, the job itself and how they lead. Each notes what a real answer contains and what the standard evasion sounds like.
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The questions
Each question, and why to ask it
Strategy
What are the two or three things you're personally spending most of your time on this quarter?
Why ask it
Where a chief executive spends their week is the clearest statement of company priorities available, and it often differs from the published strategy. If the answer is a list of six areas, you have learned that attention is spread thin.
What did we decide not to do this year that was hard to pass up?
Why ask it
Strategy is mostly subtraction, and this asks for the subtraction rather than the ambition. An executive who cannot name anything declined is describing a wish list rather than a plan.
What has to go right in the next twelve months for this to count as a good year?
Why ask it
Forces a small number of conditions instead of a vision statement, and gives you something you can check later. Vague answers about momentum usually mean the targets are not settled internally.
Which assumption in the current plan worries you most?
Why ask it
Every plan rests on something untested, and naming it takes more candor than listing risks in general. This is a good early question because it invites honesty without asking anyone to admit a mistake.
How will we know in six months whether the new strategy is working?
Why ask it
Asks for the leading indicator rather than the goal, which is the part most strategies never specify. If nobody can answer this, the plan cannot be evaluated until it is too late to change.
What's the tradeoff in the current plan you're least comfortable with?
Why ask it
Every plan sacrifices something, usually quality, speed, or a team that gets less investment. Naming it publicly is a good sign, and claiming there are no tradeoffs is the least credible answer available.
Of everything we're doing this quarter, what would you protect if we had to drop half of it?
Why ask it
Priorities only become real when something has to go, and this is the phrasing that gets a ranked answer rather than a list. Whatever they name is where your own work is safest.
Which parts of the plan are already funded, and which still depend on how the year goes?
Why ask it
Announced initiatives and funded initiatives are not the same list. Knowing which side your project sits on tells you whether to plan for hiring or to plan for doing it with the people you have, and it is information your manager may not have either.
What is stopping you growing faster: people, cash, demand or regulation?
Why ask it
Forces a single constraint instead of a list of opportunities. It is also the most useful answer for you personally, because work that relieves the constraint gets noticed and work that does not gets absorbed.
What are you spending on now that won't pay back for two or three years?
Why ask it
This is where the actual strategy sits, since it is the spending nobody has to do. If nothing comes to mind, the company is being run quarter to quarter whatever the strategy deck says.
Where do you expect us to look different in a year: product, customers, size?
Why ask it
Concrete and near enough to be checkable, which makes it harder to answer with ambition alone. Compare the answer with what you hear next quarter, and you will know how much weight to give the one after that.
How do you decide what to stop doing?
Why ask it
Most organizations only add. A chief executive with a real answer here has killed a product or a project recently, so ask which one and what it cost.
Which part of the business would you not start again if you had the choice?
Why ask it
An honest look at legacy products, acquisitions or lines that persist out of habit. It is a safer version of asking what is failing, and it still gets you a name.
What would you not trade for growth?
Why ask it
Values questions usually get slogans; this framing gets a boundary. The useful follow up is whether that boundary has ever actually been tested.
What are you doing about AI in the business, and what have you dropped?
Why ask it
The abandoned experiments are more informative than the announced ones, because dropping one means somebody measured the result. If nothing has been dropped, ask how they would tell a pilot that worked from one that did not.
Customers and money
When we lose to a competitor, why do we usually lose?
Why ask it
Executives who talk to the sales team have a crisp answer here: price, a missing feature, a slow process. A reply about how nobody really competes with us tells you the loss reasons are not reaching the top.
Who do you consider the real competition?
Why ask it
Whoever they name tells you how they define the market, and it is often not the company the sales team worries about. If the answer is the status quo or customers doing nothing, ask what finally moves a customer to buy.
Which customers would be most upset if we disappeared tomorrow, and which would barely notice?
Why ask it
Reframes market position in terms of dependence rather than revenue, and the second half is where the uncomfortable insight is. Executives close to customers answer with names, while others answer with segments.
How exposed are we to the largest customers?
Why ask it
Concentration is often the quietest risk in a business, since losing one large account can undo a good year. Expect a rough share rather than names, and ask what the plan is if the biggest one leaves.
How do you spend time with customers?
Why ask it
Listen for a habit with a frequency: calls they sit in on, visits, complaints they read themselves. A chief executive who hears about customers only through reports is working from a summary, so ask when they last spoke to one who was unhappy.
What do customers complain about that you haven't fixed?
Why ask it
Any chief executive who reads support tickets can answer this immediately. Hesitation suggests customer feedback reaches them only after it has been through several layers of summarising.
How much of our roadmap comes from customers versus our own view?
Why ask it
Both extremes cause trouble: purely customer-led work produces an incoherent product, purely internal vision misses the market. Where a leader places the company is worth knowing.
How is the company making money now compared to two years ago?
Why ask it
Shifts in revenue mix explain reorganizations, hiring freezes and product bets better than any statement of strategy does. Listen for which line is growing and which is being quietly run down, then ask where the new hires are going.
Which metric do you look at first on a Monday morning?
Why ask it
Small and specific, so it is hard to answer with a speech, and it tells everyone in the room what actually gets watched. If the metric named is not one the company reports on, that gap is worth understanding.
What did the board or your investors push you on most recently?
Why ask it
Reframes the chief executive as someone who is also accountable, and the pressure they are under explains targets that otherwise look arbitrary. Expect a general answer, since some of it will be confidential.
How is the company positioned if the market turns down?
Why ask it
A real answer mentions costs that can flex, how long the cash lasts and which customers would cut back first. Confidence without any of those specifics is not an answer to the question.
What would make you decide to slow hiring or cut back?
Why ask it
Lets an executive describe their thresholds without being asked to predict layoffs, which is the question everyone actually wants answered. A refusal to describe any trigger is itself informative for anyone weighing an offer.
If we miss this year's targets, what happens first?
Why ask it
The natural follow up to any answer about thresholds, because it asks for the order of the levers. Whether the first to go is hiring, marketing spend, contractors or jobs tells you what kind of company you are working for.
Decisions and candor
How does a decision get made here when two leaders disagree?
Why ask it
Candidates and new employees need this more than any values statement, since it describes how the company really works. Watch whether they can describe the mechanism or only the aspiration that people work it out.
How do you want decisions made when you're not in the room?
Why ask it
Practical, and rarely asked. The answer, written proposals, a named owner, a threshold for escalation, is directly usable by anyone who leads a piece of work.
What did you change your mind about in the past year?
Why ask it
Asks for a specific reversal and what caused it, which is a better test of judgment than any question about vision. Answers about growing as a leader are a dodge, so ask what happened in the business as a result.
What did the company get wrong in the last year?
Why ask it
A chief executive who names something concrete usually runs an organization where problems travel upward. A non-answer tells you how mistakes are handled several levels down.
What decision from the last six months do people here still not understand?
Why ask it
Gives them an opening to re-explain something without anyone having to accuse them of a bad decision. If they cannot name one, it usually means the internal grumbling is not reaching them.
Was there something you couldn't tell us at the time that you can talk about now?
Why ask it
Acknowledges that some silences were necessary, which makes it easier to answer honestly. A chief executive who takes this up builds more trust than one who insists nothing was ever held back.
How do you make sure bad news reaches you early?
Why ask it
Every chief executive says they want candor, and the useful part is the mechanism: skip level meetings, an inbox they read themselves, a named person who tells them the truth. No mechanism usually means the news arrives late.
What's a piece of employee feedback you've heard repeatedly and not acted on?
Why ask it
Harder to dodge than asking what feedback they have received, because it presumes something is outstanding. A real answer usually comes with a reason and a tradeoff, and a denial tells you how much survey results actually travel.
What is the company bad at that you have stopped trying to fix?
Why ask it
Mature answers exist: slow hiring, thin documentation, a market the company never learned to sell into. Naming one tells you what to stop waiting for, and insisting there is nothing tells you the weak spots are not discussed at the top.
Which team do you worry about most at the moment?
Why ask it
Riskier to answer than it looks, so expect a careful reply about a function rather than a person. Even a hedged answer tells you where attention and headcount are about to go.
Where do you think our culture is drifting away from what you intended?
Why ask it
Presumes drift, which is normal in a growing company, so it is easier to answer than a question implying failure. Compare their answer against what people in the room complain about privately.
What do you wish more people here understood about the business?
Why ask it
Invites the explanation they keep having to repeat. It usually concerns money: margins, cash, or how long a sale genuinely takes from first contact.
Your own company
What behavior gets someone promoted here that isn't written down anywhere?
Why ask it
There is always an unwritten answer, and hearing whether the chief executive knows it is as useful as the answer itself. If they insist the written criteria are the whole story, ask who was promoted most recently and why.
What does progression look like for people who don't want to manage?
Why ask it
Tests whether there is a real individual contributor track or only a title. The answer decides whether staying hands-on here is viable for years or only for now.
What work here is undervalued?
Why ask it
Shows whether leadership sees the unglamorous parts: support, documentation, maintenance, internal tools. If only revenue-facing work gets named, that is what will be rewarded.
How is pay decided here, and when does it get reviewed?
Why ask it
Ask about the mechanism, not your own salary, and you will get an answer in a public setting. Bands, review timing and who signs off are the things that let you have a useful conversation with your manager later.
How are decisions about headcount made, and where are we adding next?
Why ask it
The process matters as much as the answer, because it tells you whether your manager's request for another person ever had a chance. Watch for whether hiring follows revenue, a plan, or whoever asks loudest.
What would make you change the policy on office and remote working?
Why ask it
Asking what would change it gets you the criteria rather than the current line. If there are no criteria, the policy will move with the mood of whoever is loudest, and you can plan accordingly.
If I think something is going badly and my own chain isn't moving on it, how should I get it to you?
Why ask it
You want a named route: a skip-level, an email, a specific forum. Asking in public also makes the route harder to close later, and the reply tells you whether escalation here is normal or career-limiting.
What is something people here wait for permission to do that they should just do?
Why ask it
Useful in two directions: it may hand you real latitude, and the answer reveals whether they understand why people hesitate. Leaders who blame timidity while running a culture of reversed decisions are describing a problem they created.
Which internal process do you know is broken that we're living with?
Why ask it
Shared frustration, safely expressed, and it invites a genuine answer about approvals, tooling or a legacy system. If they name something, ask who owns fixing it, because the answer may be nobody.
What do you wish people brought to you, and what do they actually bring?
Why ask it
Gives you a practical instruction for your own next conversation with them. Most answers come down to wanting problems earlier and with a recommendation attached.
What do you want new employees to push back on?
Why ask it
Gets a real answer about where they know the company is weak, since nobody invites challenge on the parts that work. If they cannot name anything, disagreement from newcomers is probably tolerated more than it is wanted.
If I were starting here tomorrow, what would you want me to spend my first month on?
Why ask it
Turns the conversation into something you can act on, and candidates who ask it get a much clearer picture of the role than the advert gave. Note whether the answer is about learning or about output.
What should someone in my position be building towards to still be useful here in three years?
Why ask it
Better than asking about promotion, because it invites a view of where the work itself is heading. Vagueness usually means nobody has thought about your function's future, which is worth knowing now.
What's one thing you'd like me to take back to my team?
Why ask it
Ends the conversation with something usable and respects that the time was limited. Whatever message gets chosen also shows what leadership thinks is not landing.
The job itself
What surprised you most about this job?
Why ask it
Softer, but it tends to get a candid answer about pace, isolation, or how little direct control the role carries. It suits a one to one or a fireside chat better than a crowded all hands.
What do you want to be different about how you lead a year from now?
Why ask it
A personal question that stays professional, and the answers are often surprisingly specific about delegation or communication. Watch whether it names a habit or restates a strength.
What's the question you wish people would ask you at these meetings?
Why ask it
Gives them a chance to open a topic that nobody raises, which is often the one that matters most to them. It also breaks the pattern of the same three safe questions at every all hands.
If you left tomorrow, what unfinished work would bother you most?
Why ask it
Gets at what they genuinely care about rather than what is on the slide, and the answer is usually one project or one team. Best asked one to one or at the end of a long session, since it needs a moment of reflection.
What did you do before this that turned out to be better preparation than it looked?
Why ask it
An easy one for a lunch, because it lets them tell a story instead of defending a plan. The jobs people name are often unglamorous ones, and that tells you which kinds of experience they rate when they hire.
What do you read or listen to that changes how you run the company?
Why ask it
Works across a table or in a corridor at a conference, since it takes thirty seconds to answer and gives you a reason to write afterwards. A named book or person is worth more than a general claim to read widely.
Which part of the job would you hand to someone else tomorrow if you could?
Why ask it
Lighter than asking what they dislike, and it tends to get a laugh first and a real answer second. What they would give away shows which duties came with the title and which ones they chose.
Who outside the company do you call when you are stuck?
Why ask it
Chief executives have few peers inside the building, so many keep a former boss, a board member or another founder to ring. You are asking how they get advice and not for names, and over a meal the story of one such call can carry the conversation.
If you joined this company today as a new hire, what would you notice first?
Why ask it
A creative way to ask what is wrong without using the word. It makes them look with a stranger's eyes, and the first thing they mention is often something they have stopped seeing from the top.
What did you hear at this event that you expect to act on?
Why ask it
Made for the minute you get after a keynote or in the coffee queue, because it is about today and needs no background. If they name something, you can follow up in a month and ask how it went.
Leadership
How would the people who report to you describe the way you lead?
Why ask it
Asking for the team's description and not their own makes a flattering self-portrait harder to give. Notice whether a complaint is included, since a description with no rough edge in it is the public version.
What do you look for when you choose someone for your leadership team?
Why ask it
The qualities they list are the ones that get people to the top here, whatever the values page says. Ask who joined that team most recently and what that person had, and the answer stops being abstract.
What did you have to stop doing yourself as the company grew?
Why ask it
Running a bigger company means giving up work you were good at, and most chief executives remember which task was hardest to hand over. It suits the CEO of a large company especially, where the distance from the daily work is widest.
Who taught you the most about leading people, and what did they do?
Why ask it
Requests a person and a behavior, which keeps the answer away from quotations and book titles. Whatever they admired in someone else is a fair standard to hold them to.
When did you last have to lead through something you did not have the answer to?
Why ask it
Any chief executive can describe leading when the plan is clear. This is about the other case, and a good reply covers what they told people while they still did not know.
How do you decide when to step in and when to leave a team alone?
Why ask it
The honest answer names a signal: a missed date, a customer complaint, a leader who has gone quiet. If the rule is simply that they step in when they are worried, the teams below them will have noticed already.
Asking Well in the Room You Are Actually In
Practical guidance for the conversation itself
How to Ask
Ask Something They Can Answer in Public
At an all hands, questions touching unannounced deals, individual performance or specific numbers will get a deflection that wastes everyone's time. Choose the version of your question that can be answered honestly with the whole company listening.
One Question, Not Three
Stacked questions get answered at the easiest part. Ask the single sentence you care about most and let the follow up come from their answer.
Ask for the Mechanism
How do you know, who decides, what would change your mind. These turn abstract commitments into something checkable, and they are the difference between a good question and a compliment shaped like one.
Have the Follow Up Ready
The first answer from a chief executive is often one they have given before, and the second rarely is. Decide in advance what you will ask if the reply stays general: which one, since when, who owns it.
Write Down the Answer
Note what they said would be true in six months, then look at it in six months. That habit is what turns a Q and A into something useful rather than theater.
Skip the Homework Questions
Anything answered by the last earnings call, the strategy deck or the careers page makes you look unprepared. Read those first, then ask about what they left out.
Which to Ask Where
- All hands with the whole company: 1, 3, 33, 39 and 57 are answerable in public and useful to everyone listening.
- Town hall at your own company: 41 to 54, the group headed Your own company, ask how pay, promotion, headcount and escalation work rather than about any one person's case.
- Final round interview: 16, 29, 41 and 52 tell you how the company works, and asking them signals you are evaluating the role seriously.
- First one to one as a new employee: 24, 31 and 51 are small enough to ask without taking much of their time.
- Skip level or fireside format: 35, 36, 39 and 55 fit a setting where slightly harder questions are expected.
- Board or investor conversation: 2, 5, 10 and 13 focus on execution rather than narrative.
- Networking or a conference, where you may get ninety seconds: 17, 31, 60 and 64 ask about a view or a decision of theirs and can be answered briefly.
- Press or podcast interview: 18, 31 and 58 give you something quotable that is not a press release.
- Lunch with the CEO: 55 and 59 to 62 can be answered between courses and leave room for them to ask about you, so keep the strategy questions for a meeting with a table and no plates.
- A meeting where leadership is the subject, such as a mentoring hour or a class visit: 56 and 65 to 70, the group headed Leadership.
- The CEO of a large company, who sits furthest from the daily work: 30, 35 and 67 ask how decisions and bad news cross the layers in between.
- When you want a creative question in place of a safe one: 13, 18, 57 and 63 come at a familiar subject from the side.
Common Pitfalls
Don't Ambush at an All Hands
A question designed to corner someone in front of five hundred people gets a polished non answer and costs you the relationship. If the topic is genuinely sensitive, ask it in a smaller room.
Don't Accept the Reframe Silently
A common move is to answer a narrow question with a broad one. It is fine to say that you were asking about the specific case, once, politely.
Don't Use the Slot to Perform
A long preamble establishing your own expertise costs the room the answer. State the question in one sentence.
Don't Push Into Legal Territory
Questions about pending litigation, undisclosed results or personnel decisions cannot be answered even when the executive wants to. Ask about the framework rather than the case.
Don't Ask About Your Own Case
Your own pay, your team's request for another person or one manager's decision belong with your manager or a recruiter. Ask how pay or headcount is decided instead, which a chief executive can answer in front of anyone.
Ready Made Sequences
Ten Minutes at an All Hands
- 1Open with: "What are the two or three things you're personally spending most of your time on this quarter?"
- 2Follow with: "What has to go right in the next twelve months for this to count as a good year?"
- 3Then: "Which assumption in the current plan worries you most?"
- 4Close with: "What's the question you wish people would ask you at these meetings?"
Evaluating an Offer
- 1Start with: "How does a decision get made here when two leaders disagree?"
- 2Ask: "What behavior gets someone promoted here that isn't written down anywhere?"
- 3Then: "What would make you decide to slow hiring or cut back?"
- 4End with: "Where do you think our culture is drifting away from what you intended?"