What Are Good Questions to Ask a CEO
Twenty questions for an all hands, a final round interview, or a rare one to one with a chief executive. Each notes what a real answer contains and what the standard evasion sounds like.
The questions
Open any question for the note
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 unproven, 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.
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.
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.
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.
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'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 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.
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.
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.
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.
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.
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 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.
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.
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.
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.
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, 15 and 19 are answerable in public and useful to everyone listening.
- Final round interview: 5, 7 and 8 tell you how the company works, and asking them signals you are evaluating the role seriously.
- First one to one as a new employee: 6 and 10 are small enough to ask without taking much of their time.
- Skip level or fireside format: 9, 11 and 15 fit a setting where slightly harder questions are expected.
- Board or investor conversation: 2, 12 and 13 focus on execution rather than narrative.
- Press or podcast interview: 10, 14 and 20 give you something quotable that is not a press release.
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.
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?"