Funny Questions to Ask CEO
Break the ice with your CEO using these humorous questions that show personality, create memorable interactions, and reveal the lighter side of leadership.
1If you could have any superpower for a day in the office, what would it be?
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If you could have any superpower for a day in the office, what would it be?
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Why this works
Reveals what they find most challenging or wish they could change about their role in a lighthearted way.
2What's the funniest thing that's ever happened in a board meeting?
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What's the funniest thing that's ever happened in a board meeting?
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Why this works
Opens up about unexpected moments and shows they can laugh at themselves and the serious nature of leadership.
3If you could swap jobs with anyone in the company for a day, who would it be?
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If you could swap jobs with anyone in the company for a day, who would it be?
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Why this works
Reveals what other roles they're curious about and shows their understanding (or lack thereof) of different departments.
4What's the most ridiculous business trend you've ever encountered?
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What's the most ridiculous business trend you've ever encountered?
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Why this works
Shows their business acumen while adding humor about industry fads and their perspective on what actually matters.
5If our company was a movie, what genre would it be?
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If our company was a movie, what genre would it be?
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Why this works
Reveals how they view the company culture and whether they see it as a comedy, drama, action film, or something else.
6What's your go-to karaoke song?
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What's your go-to karaoke song?
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Why this works
Shows their fun side and reveals something personal that humanizes them beyond their CEO role.
7If you could uninvent one piece of technology, what would it be?
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If you could uninvent one piece of technology, what would it be?
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Why this works
Opens up about pet peeves and what aspects of modern work life they find frustrating or unnecessary.
8What's the worst business advice you've ever received?
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What's the worst business advice you've ever received?
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Why this works
Reveals their business wisdom through the lens of what NOT to do, making it both funny and educational.
9If you had to describe your leadership style as a food, what would it be?
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If you had to describe your leadership style as a food, what would it be?
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Why this works
Encourages creative self-reflection and reveals how they think about their approach in a non-traditional way.
10What's your secret talent that has nothing to do with business?
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What's your secret talent that has nothing to do with business?
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Why this works
Shows their human side and reveals interests outside of work, making them more relatable.
11If you could make one company policy disappear, what would it be?
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If you could make one company policy disappear, what would it be?
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Why this works
Opens up about frustrations with corporate bureaucracy and what they'd change if they could wave a magic wand.
12What's the most embarrassing thing that's ever happened to you in a professional setting?
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What's the most embarrassing thing that's ever happened to you in a professional setting?
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Why this works
Shows vulnerability and willingness to laugh at themselves, making them more approachable.
13If you could have dinner with any business leader, living or dead, who would it be and why?
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If you could have dinner with any business leader, living or dead, who would it be and why?
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Why this works
Reveals who they admire and what qualities they value in leaders, with room for humorous choices.
14What's your favorite way to procrastinate?
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What's your favorite way to procrastinate?
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Why this works
Humanizes them by showing they struggle with the same challenges as everyone else.
15If you could rename our company, what would you call it?
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If you could rename our company, what would you call it?
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Why this works
Opens up creative and potentially funny alternatives that reveal how they think about the brand.
16What's the weirdest thing you've ever done to close a deal?
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What's the weirdest thing you've ever done to close a deal?
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Why this works
Reveals creative problem-solving and willingness to go the extra mile, often with funny stories attached.
17If you had to work in a completely different industry, what would you choose?
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If you had to work in a completely different industry, what would you choose?
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Why this works
Shows their alternative interests and what they might do if they weren't in their current role.
18What's your favorite excuse for being late to a meeting?
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What's your favorite excuse for being late to a meeting?
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Why this works
Acknowledges that even CEOs are human and sometimes struggle with punctuality, adding humor to a relatable situation.
19If you could add any perk to the company, no matter how ridiculous, what would it be?
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If you could add any perk to the company, no matter how ridiculous, what would it be?
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Why this works
Opens up their imagination and reveals what they think would make work more fun or enjoyable.
20What's the most unusual question you've ever been asked in an interview?
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What's the most unusual question you've ever been asked in an interview?
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Why this works
Opens up about their own interview experiences and often leads to funny stories about awkward or bizarre questions.
Best Practices for Humorous CEO Conversations
Expert tips and techniques for getting the most out of these questions.
Best Practices
Read the Room
Make sure the setting is appropriate for humor. A company happy hour is different from a formal business meeting. Gauge their mood first.
Be Respectful
Funny doesn't mean disrespectful. Keep questions lighthearted and avoid anything that could be seen as offensive or too personal.
Be Ready to Laugh at Yourself
If you're going to ask funny questions, be prepared to answer them yourself and share in the humor.
Question Sequences
The Hypothetical Fun Sequence
The Personal Side Sequence
Common Pitfalls
Don't Force It
If the CEO isn't in a playful mood or the moment isn't right, don't push humor. It can backfire and make things awkward.
Don't Make Fun of Them
The goal is to laugh with them, not at them. Avoid questions that could be seen as mocking their position or decisions.
Don't Overstep Boundaries
Remember they're still the CEO. Maintain appropriate professional boundaries even while being funny.