Fun Questions to Ask Female Leaders
Engaging and insightful questions to ask female leaders that spark meaningful conversations while keeping things light and enjoyable.
1What's the best piece of advice you've ever received that you initially thought was crazy?
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What's the best piece of advice you've ever received that you initially thought was crazy?
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Why this works
Reveals unconventional wisdom and shows how they've evolved their thinking over time, making for engaging storytelling.
2If you could have coffee with any woman from history, who would it be and what would you ask her?
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If you could have coffee with any woman from history, who would it be and what would you ask her?
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Why this works
Uncovers their inspirations and values while allowing them to share their perspective on historical achievements.
3What's one skill you wish you had learned earlier in your career?
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What's one skill you wish you had learned earlier in your career?
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Why this works
Provides practical insights while showing vulnerability and creating a relatable learning moment.
4What's the most ridiculous thing you've done in the name of productivity or success?
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What's the most ridiculous thing you've done in the name of productivity or success?
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Why this works
Humanizes their journey with humor while revealing their dedication and the lengths they've gone to achieve their goals.
5If you could swap jobs with anyone for a day, who would it be?
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If you could swap jobs with anyone for a day, who would it be?
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Why this works
Shows their curiosity and interests outside their current role, revealing hidden passions or career paths not taken.
6What's your go-to strategy for dealing with imposter syndrome?
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What's your go-to strategy for dealing with imposter syndrome?
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Why this works
Addresses a common challenge that creates connection while providing actionable advice for others facing similar feelings.
7What's the funniest or most unexpected thing that's happened during an important meeting?
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What's the funniest or most unexpected thing that's happened during an important meeting?
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Why this works
Invites storytelling and humor while showing how they handle unexpected situations with grace and poise.
8If you could go back and give your younger self one career tip, what would it be?
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If you could go back and give your younger self one career tip, what would it be?
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Why this works
Provides mentorship wisdom while revealing key turning points and lessons learned from their journey.
9What's your secret talent that has nothing to do with your work?
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What's your secret talent that has nothing to do with your work?
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Why this works
Shows their multidimensional personality and creates a fun, humanizing moment in the conversation.
10What book or podcast has recently changed the way you think about leadership?
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What book or podcast has recently changed the way you think about leadership?
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Why this works
Reveals their commitment to continuous learning while providing valuable recommendations for others.
11What's the most valuable thing you learned from a failure?
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What's the most valuable thing you learned from a failure?
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Why this works
Demonstrates resilience and growth mindset while normalizing failure as part of the success journey.
12If you could create a new national holiday, what would it celebrate?
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If you could create a new national holiday, what would it celebrate?
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Why this works
Shows their values and priorities in a playful way while revealing what matters most to them.
13What's your favorite way to unwind after a challenging day?
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What's your favorite way to unwind after a challenging day?
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Why this works
Highlights the importance of work-life balance and self-care while providing relatable stress management strategies.
14What's one leadership myth you'd like to bust?
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What's one leadership myth you'd like to bust?
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Why this works
Invites them to challenge conventional wisdom and share their unique perspective on effective leadership.
15If you could have dinner with any three women (living or dead), who would you choose?
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If you could have dinner with any three women (living or dead), who would you choose?
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Why this works
Reveals their role models and inspirations while creating opportunities for engaging follow-up questions.
16What's the best purchase you've made for under $100 that improved your work life?
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What's the best purchase you've made for under $100 that improved your work life?
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Why this works
Provides practical recommendations while showing attention to detail and resourcefulness in small ways.
17What's your guilty pleasure TV show or music genre?
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What's your guilty pleasure TV show or music genre?
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Why this works
Creates a fun, relatable moment that shows their human side and breaks down professional barriers.
18If you could instantly master any skill, what would it be and why?
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If you could instantly master any skill, what would it be and why?
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Why this works
Shows aspirations and areas of interest while revealing what they perceive as valuable for future growth.
19What's the most important thing you've learned about building and leading diverse teams?
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What's the most important thing you've learned about building and leading diverse teams?
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Why this works
Addresses crucial leadership competencies while demonstrating their commitment to inclusion and equity.
20What's your favorite way to celebrate wins with your team?
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What's your favorite way to celebrate wins with your team?
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Why this works
Shows their leadership style and how they recognize achievements, revealing their approach to team culture and motivation.
Engaging Female Leaders in Conversation
Expert tips and techniques for getting the most out of these questions.
Best Practices
Balance Professional and Personal
Mix questions about their career with lighter, more personal topics to create a well-rounded conversation that feels authentic rather than like an interview.
Listen Actively and Follow Up
Pay close attention to their answers and ask follow-up questions based on what they share - this shows genuine interest and creates deeper dialogue.
Be Respectful of Time
Female leaders often have packed schedules, so be mindful of their time while making the most of your conversation opportunity.
Avoid Gender-Specific Clichés
Focus on their expertise and experiences rather than asking questions you wouldn't ask male leaders - treat them as leaders first.
Conversation Sequences
The Inspiration Discovery
The Challenge Navigator
Common Pitfalls
Don't Ask Gender-Focused Questions Only
While it's okay to acknowledge their experience as a woman in leadership, don't make every question about gender - focus on their expertise and insights.
Avoid Asking About 'Having It All'
This tired question puts pressure on women to justify their choices and doesn't contribute to meaningful dialogue about leadership.
Don't Interrupt or Over-Explain
Give them space to fully answer and resist the urge to fill silences too quickly - their thoughtful responses are valuable.