Fun Questions to Ask Senior Leaders
Engaging and lighthearted questions to ask senior leaders that help build relationships while learning about their experiences and perspectives.
1What's the most interesting mistake you've made in your career?
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What's the most interesting mistake you've made in your career?
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Why this works
Learning about mistakes helps you understand that failure is part of growth and see how leaders handle setbacks.
2If you could have dinner with any historical figure, who would it be and why?
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If you could have dinner with any historical figure, who would it be and why?
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Why this works
Understanding their historical interests reveals their values and what they find inspiring or admirable.
3What's the best piece of advice you've ever received?
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What's the best piece of advice you've ever received?
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Why this works
Learning about their favorite advice helps you understand their values and potentially apply wisdom to your own career.
4What's something you're surprisingly bad at?
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What's something you're surprisingly bad at?
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Why this works
Understanding their weaknesses humanizes them and shows that even leaders have areas for improvement.
5If you weren't in your current role, what would you be doing?
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If you weren't in your current role, what would you be doing?
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Why this works
Learning about their alternative interests helps you understand their passions and what drives them beyond work.
6What's the funniest thing that's happened to you at work?
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What's the funniest thing that's happened to you at work?
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Why this works
Sharing humor helps build rapport and shows that leaders can be approachable and human.
7What's your go-to stress relief activity?
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What's your go-to stress relief activity?
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Why this works
Understanding their stress management helps you learn healthy coping strategies and see their human side.
8If you could have a superpower, what would it be and why?
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If you could have a superpower, what would it be and why?
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Why this works
Exploring hypothetical scenarios helps you understand their priorities and what they value most.
9What's the most unexpected skill you've had to develop in your career?
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What's the most unexpected skill you've had to develop in your career?
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Why this works
Learning about unexpected skills helps you understand that career paths aren't always linear and that adaptability is key.
10What's your favorite way to celebrate a big win?
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What's your favorite way to celebrate a big win?
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Why this works
Understanding their celebration style helps you learn about their values and how they recognize success.
11If you could travel back in time to your first day on the job, what would you tell yourself?
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If you could travel back in time to your first day on the job, what would you tell yourself?
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Why this works
Learning about their hindsight helps you understand their growth and get advice for your own career journey.
12What's something you're really excited about outside of work?
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What's something you're really excited about outside of work?
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Why this works
Understanding their personal interests helps you connect on a human level and see them as whole people.
13What's the most creative solution you've ever come up with?
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What's the most creative solution you've ever come up with?
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Why this works
Learning about their creativity helps you understand their problem-solving approach and innovative thinking.
14If you could have lunch with any fictional character, who would it be?
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If you could have lunch with any fictional character, who would it be?
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Why this works
Exploring fictional interests helps you understand their personality and what they find entertaining or inspiring.
15What's something you wish you'd known when you were starting your career?
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What's something you wish you'd known when you were starting your career?
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Why this works
Getting career wisdom helps you avoid common pitfalls and accelerate your professional development.
16What's your favorite way to recharge on weekends?
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What's your favorite way to recharge on weekends?
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Why this works
Understanding their relaxation preferences helps you see their human side and learn about work-life balance.
17If you could learn any new skill instantly, what would it be?
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If you could learn any new skill instantly, what would it be?
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Why this works
Learning about their learning interests helps you understand their curiosity and what they find valuable.
18What's the most interesting place you've traveled for work?
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What's the most interesting place you've traveled for work?
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Why this works
Sharing travel experiences helps build connection and might inspire your own career exploration.
19What's something that always makes you laugh?
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What's something that always makes you laugh?
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Why this works
Understanding their sense of humor helps you build rapport and see their lighter side.
20If you could give your younger self one piece of career advice, what would it be?
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If you could give your younger self one piece of career advice, what would it be?
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Why this works
Getting career guidance helps you learn from their experience and avoid mistakes they might have made.
Building Relationships with Senior Leaders
Expert tips and techniques for getting the most out of these questions.
Creating Meaningful Connections
Be Genuinely Curious
Ask questions you're genuinely interested in rather than trying to impress or get something specific.
Listen Actively
Show genuine interest in their responses and ask follow-up questions to deepen the conversation.
Share Your Own Experiences
When appropriate, share your own related experiences to create a two-way conversation and build rapport.