Funny Questions to Ask CEO
Twenty light questions for a CEO when the setting allows for it: an all-hands with an open mic, an offsite, a hallway on a slow afternoon. Includes notes on reading the room and telling a real answer from the rehearsed version.
The questions
Open any question for the note
If you could have one superpower for a day in this office, what would it be?
Why ask it
A soft opener that still gives something away, because most people name the thing that eats their week. Answers about being in two places at once or reading a room mean scheduling and politics, in that order.
What's your go-to karaoke song?
Why ask it
Low risk and hard to fake, since the answer is either instant or invented on the spot. A pause before naming something safe and popular usually means they have thought about how the answer will travel.
Which of our internal acronyms do you still not know the meaning of?
Why ask it
The safe answer is a laugh with no acronym attached. Naming a real one is a small admission that the company has outgrown its own vocabulary, and the room tends to remember it fondly.
If this company were a movie, what genre would it be?
Why ask it
Genre is a shortcut for how much chaos they think we are in. Heist or disaster movie is candid, inspirational drama is a press release, and comedy is the most honest answer most staff will recognize.
If you could swap jobs with anyone here for a day, whose job would you take?
Why ask it
Watch whether they name a specific person or a department. A named individual means they know what that person actually does; a vague answer about the front line means they have not been near it lately.
What's a talent of yours that has nothing to do with work?
Why ask it
The point is whether the answer is genuinely unrelated. Anyone whose secret talent turns out to be a leadership metaphor has answered a different question, and everyone in the room hears it.
What's your favorite way to procrastinate?
Why ask it
Useful because the honest answer is small and specific, like reorganizing a spreadsheet or reading support tickets. Claiming not to procrastinate is a worse answer than any real one.
What meeting on your calendar would you cancel forever if nobody would notice?
Why ask it
Funny on the surface and a live question underneath, because whatever they name is probably wasting other people's time too. A dodge here is normal, since the meeting has an owner sitting in the room.
If you could add one absurd perk, what would it be?
Why ask it
Reveals what they think is missing from the day. Answers about naps, food and quiet space point at a tired company; answers about parties point at one that thinks it has a morale problem instead.
If you could rename the company, what would you call it?
Why ask it
Founders usually cannot resist explaining the name they nearly chose, which is a better story than the one you asked for. Anyone who defends the current name at length is being careful, not sentimental.
What piece of technology would you uninvent?
Why ask it
The specific answer, a particular tool or notification, is funnier and more revealing than a broad complaint about phones. It also tells you which channel not to use to reach them.
What's the most ridiculous trend you've watched this industry chase?
Why ask it
Good because it invites them to name something they were probably part of. Watch whether the example is safely historical or from the last two years, which is where the actual opinion lives.
If your leadership style were a food, what would it be?
Why ask it
A silly frame that produces an unusually candid answer, since food has texture and temperature and nobody has media-trained for it. Compare their answer with what their direct reports would pick.
What's the worst business advice you were ever given by someone confident?
Why ask it
The confidence clause is what makes this land, because it turns the story into a character sketch rather than a lesson. Answers with no attribution and a tidy moral are the rehearsed kind.
What's the funniest thing that's ever happened in a board meeting?
Why ask it
Board rooms are the one part of the company most staff never see, so almost any story is interesting. Expect the details to be sanded down; the audio failure and the wrong slide deck are the usual survivors.
What's the weirdest thing you've done to close a deal?
Why ask it
Sales stories are where executives relax, and the good ones involve airports, borrowed clothes or a whiteboard in a hotel lobby. If the answer sounds like a case study, ask what went wrong in it.
What's the most unusual question you've been asked in an interview?
Why ask it
Reverses the usual power flow for a moment, which is why it works in a Q and A. Their reaction to a strange question then often predicts how they will handle yours now.
What's the most embarrassing thing that's happened to you at work?
Why ask it
Only ask it if the room is warm, because a bad answer here is worse than no answer. Anyone who tells a story where they end up looking humble and wise has picked their least embarrassing option.
If you could delete one company policy tonight, which one goes?
Why ask it
Half joke, half agenda-setting, and people will hold them to it. A specific policy is a small commitment in front of witnesses, which is why most answers stay abstract.
What's something everyone here believes about you that isn't true?
Why ask it
Save it for last. It works because they have almost certainly heard the rumor and never had a place to address it, and a straight answer buys more goodwill than any of the earlier questions.
Asking a CEO a light question without it going wrong
Practical guidance for the conversation itself
Reading the room first
Check what week it is
Humor lands badly in the days around layoffs, a missed quarter, a funding announcement or an acquisition rumor. If people are refreshing their inboxes, this is not the moment for a karaoke question.
Company size changes everything
At forty people the CEO knows your name and a joke reads as friendly. At four thousand you are a stranger with a microphone, so pick a question that works without shared history.
One question, not three
In an open Q and A you get one. Ask it, take the answer, and sit down. Stacking follow-ups turns a light moment into your segment.
Telling a real answer from a prepared one
- Real answers have proper nouns in them: a person, a city, a product that failed, a specific meeting.
- Prepared answers arrive with a moral attached and end on a value the company already lists on a wall.
- A joke told at their own expense with a real detail in it is usually genuine. A joke about how busy they are is filler.
- If they turn the question back on the room, they liked it and want the pressure off. That is a fine outcome.
What not to do
- Do not smuggle a real grievance inside a funny question. Everyone hears it, including your manager, and you get neither the laugh nor the answer.
- Do not ask about anyone's compensation, anyone's departure or anything a lawyer would need to review, however lightly you phrase it.
- Do not ask a question that requires them to criticize a named colleague to be funny.
- Do not keep going if the first answer is short. A CEO giving you two words is telling you something.
If you are the one running the session
- Send one or two of the lighter questions in advance. Warmth is easier when nobody is ambushed.
- Open with something low stakes, put the sharper question in the middle, and close on something the whole room can answer too.
- Keep a spare question ready for the moment nobody raises a hand.
- Let the answers end the item. Summarizing the CEO back to the room kills the tone you just built.