150 Questions to Ask Women Leaders

It’s not every day we get the chance to learn from women who are making big moves in the world. It’s a golden opportunity to ask questions and understand her journey. So, when we do, we’ve got to make the most of it. 

But, what do you ask? Well, worry not! We’ve put together a list of engaging questions to help you have that rich, insightful conversation—whether for a formal interview, a casual chat, or just to satisfy your curiosity. Let’s dive in!

Questions About Leadership Skills And Styles

  1. What skills do you think are most important for a leader to have?
  2. How do you motivate your team?
  3. How do you handle disagreements in the workplace?
  4. How do you encourage creativity in your team?
  5. How do you adapt your leadership style to different people or situations?
  6. What core values guide your leadership style?
  7. How do you decide which tasks to delegate and which to handle yourself?
  8. How do you help new members integrate into your team culture?
  9. What role does transparency play in your leadership style?
  10. How do you deal with team members who resist change?
  11. What is one leadership skill you’re currently working on improving?
  12. What’s an unconventional leadership lesson you’ve learned over your career?
  13. How do you lead a team during a crisis or difficult times?
  14. What’s your favorite part about being a leader?
  15. How important do you feel empathy is in your leadership role?
  16. Can you share a difficult leadership challenge and how you overcame it?
  17. How do you ensure you continue developing as a leader?
  18. How has your leadership style evolved over time?
  19. What is one leadership practice you believe is underused or underrated?

Questions About Strategy And Decision-Making

  1. Can you talk about a time when you had to make a difficult decision?
  2. What steps do you take to foster innovation in your field?
  3. Can you share a key strategy that has helped your organization succeed?
  4. How do you handle unexpected hurdles or roadblocks?
  5. How do you maintain a positive mindset during challenging times?
  6. What practices do you follow to make difficult decisions less stressful?
  7. How do you foster strategic thinking within your team?
  8. Can you share a significant setback in your career and how you bounced back?
  9. How do you balance staying true to your vision and adapting to new circumstances?
  10. How do you measure the success of your strategic initiatives?
  11. How do you approach risk-taking in business decisions?
  12. What challenges are you currently facing in your role, and how are you approaching them?
  13. How do you approach risk management when making strategic decisions?
  14. How do you ensure your decision-making processes are ethical and transparent?
  15. What role does data play in your decision-making processes?
  16. Can you describe a decision you made that was a turning point in your career?
  17. How do you involve your team in the decision-making process?

Questions About Personal And Career Journey

  1. Can you tell me about your journey to becoming a leader?
  2. Who inspired you along your path to leadership?
  3. What were some challenges you faced as a female leader?
  4. Can you share a time you made a mistake and what you learned from it?
  5. What was your first job, and what did you learn from that experience?
  6. Can you tell me about a book, person, or event that significantly influenced your career?
  7. Can you share a time when you felt underestimated and how you handled it?
  8. What was a defining moment in your career, and why was it significant?
  9. How have you navigated the issue of gender bias in your leadership journey?
  10. Can you share a time when you took on a challenge outside your comfort zone?
  11. How have your experiences as a woman shaped the way you lead today?
  12. What’s a project or initiative you’re really excited about right now?
  13. Who have been your biggest supporters throughout your career?
  14. How do you nurture relationships in your professional network?
  15. How did you decide to pursue the career path you’re on now?
  16. Can you share how you’ve managed career transitions or changes?

Questions About Team Management And Communication

  1. How do you set goals for your team and track progress?
  2. How do you foster a positive work environment?
  3. How do you ensure you’re effectively communicating with your team?
  4. What’s your approach to giving feedback to your team members?
  5. How do you celebrate achievements or success with your team?
  6. How do you handle a situation where a team member isn’t meeting expectations?
  7. How do you foster a sense of unity and collaboration within a diverse team?
  8. How do you ensure your team members feel valued and heard?
  9. How do you help your team members develop their own leadership skills?
  10. Can you share an example of a team dynamic challenge and how you handled it?
  11. How do you handle situations where you need to motivate a disengaged team member?
  12. How do you ensure you’re approachable to your team and promote open communication?
  13. How do you show appreciation to your team after a job well done?
  14. How do you ensure the wellness of your team?
  15. Can you share an example where effective communication significantly impacted a project or outcome?
  16. How do you inspire trust within your team?
  17. How do you delegate tasks within your team to ensure efficiency and balance?
  18. How do you encourage different viewpoints and ideas in your team?

Questions About Impact And Legacy

  1. Can you share a success story that you’re particularly proud of?
  2. Can you share an experience where you had to stand your ground for something you believe in?
  3. Can you share a proud moment where your leadership made a positive impact?
  4. What kind of legacy do you hope to leave in your role or industry?
  5. How have you influenced organizational culture during your time as a leader?
  6. What are some strategies you use to manage your time effectively?
  7. How important has mentorship been in your career, and do you serve as a mentor now?
  8. Can you share an experience where you effectively handled office politics?
  9. How do you handle the pressure and high expectations that come with your role?
  10. How important is emotional intelligence in your position, and how do you cultivate it?

Questions About Advice And Recommendations

  1. What’s the best advice you’ve ever received?
  2. What’s the most helpful feedback you’ve ever received?
  3. What resources (books, podcasts, courses, etc.) would you recommend for aspiring leaders?
  4. What advice would you give your younger self at the start of your career?
  5. What do you wish more people knew about your job or industry?
  6. What are some misconceptions about leadership roles that you would like to clarify?
  7. What kind of advice would you give someone aiming to climb the corporate ladder in your industry?
  8. What’s the most common piece of career advice that you disagree with?
  9. What advice would you give to other leaders striving to build a more diverse and inclusive culture?
  10. Can you share one of your most impactful leadership lessons?
  11. What would you advise someone taking on a leadership role for the first time?
  12. How do you define and measure success in your current role?

Questions About Industry Insights And Future Vision

  1. What’s your secret to achieving success in your industry?
  2. What future trends or changes are you anticipating in your industry?
  3. How important is networking in your industry, and how do you go about it?
  4. How has the industry changed since you first started your career?
  5. What are the key changes you would like to see in your industry?
  6. How do you ensure you’re always learning and growing in your field?
  7. What’s your vision for the future of your team or organization?
  8. How do you incorporate sustainability and social responsibility into your work?
  9. Can you talk about a time when you had to adjust your strategy because of changes in the industry?
  10. How do you keep up with new trends and changes in your field?
  11. How are you guiding your team or organization to be future-ready in your industry?
  12. Can you predict any game-changing trends or technologies that will impact your industry in the future?
  13. How does your organization stay competitive in a constantly evolving market?
  14. How have digital transformation and technological advancements changed the way your organization operates?

Questions About Diversity And Inclusion

  1. How do you ensure that diversity and inclusion are prioritized within your organization?
  2. Can you share a specific initiative or program you’ve implemented to foster diversity and inclusion in your workplace?
  3. How do you address unconscious bias within your team or organization?
  4. Can you describe how diversity within your team has positively impacted your work?
  5. How do you create a safe space for different perspectives and backgrounds within your team?
  6. What resources or training do you provide to promote diversity and inclusion in your organization?
  7. What challenges have you faced in creating an inclusive environment, and how have you overcome them?
  8. How do you measure the success of your diversity and inclusion efforts?

Questions About Work-Life Balance And Self-care

  1. How do you balance work and personal life?
  2. How do you handle stress and pressure?
  3. What role does self-care play in your success?
  4. How important is work-life balance to you, and how do you achieve it?
  5. How do you deal with burnout or periods of high stress?
  6. What practices have helped you maintain a healthy work-life balance?
  7. How do you set boundaries between your work and personal life?
  8. How do you handle the guilt that sometimes comes with being unable to meet every demand at home and work?
  9. How do you make time for your hobbies or interests outside of work?
  10. What advice would you give other leaders struggling to find a healthy work-life balance?
  11. How important is vacation or downtime for you as a leader?

Fun Questions To Ask Female Leaders

  1. What’s the funniest or most unusual thing that has happened to you at work?
  2. If you could have dinner with anyone, alive or dead, who would it be and why?
  3. If you could be an expert in anything else for a day, what would it be?
  4. What’s your favorite way to relax after a busy week at work?
  5. If you could only eat one food for the rest of your life, what would it be?
  6. What book, movie, or TV show are you loving right now?
  7. What hobby or activity do you enjoy doing in your free time?
  8. Do you have a “happy place” you like to visit or imagine when you need to unwind?
  9. If you could live anywhere in the world, where would you choose and why?
  10. If you could have a superpower, what would it be?
  11. What’s something you’ve always wanted to try but haven’t gotten around to yet?
  12. Do you have a favorite quote or saying that you live by?
  13. If your life was a movie, who would you want to play you?
  14. What was your dream job when you were a child?
  15. What’s a skill or talent you have that people might be surprised to know about?
  16. If you could time travel, would you go to the past or future, and why?
  17. What’s something that never fails to make you laugh?
  18. If you were on a deserted island and could only bring three items, what would they be?
  19. If you could learn any language fluently, which one would it be?
  20. What’s the most adventurous thing you’ve ever done?
  21. What song always gets you up and dancing?
  22. What’s your guilty pleasure TV show or movie?
  23. What’s your go-to karaoke song?
  24. If you could be any animal, which one would you be and why?
  25. What’s the most interesting place you’ve ever visited?

Frequently Asked Questions

What should I keep in mind when asking these questions?

There are several key things to keep in mind:

Respect: Treat every question as an opportunity to learn from the woman leader. Avoid any kind of judgment or bias. Remember that you’re there to understand her perspective and experience.

Preparation: Research the leader’s career, field, and current role before you ask your questions. This will show that you respect her time and are interested in her work.

Listen: Active listening is just as critical as asking the right questions. Show that you’re engaged with the conversation by maintaining eye contact, nodding when appropriate, and providing feedback.

Flexibility: Be prepared to adapt your questions based on the conversation. You may need to ask follow-up questions or change your approach based on her responses.

How should I prepare before asking these questions?

Preparation is vital when you’re asking questions about women leaders. Here’s how you can prepare:

– Learn about her career, leadership style, company, and industry.
– Choose the most relevant questions from the article or think of new ones based on your research.
– Say your questions out loud to build confidence.
– Think about the time you have and decide which questions are most crucial.
– Plan how you’ll remember her answers, like taking notes or recording the talk (with her permission).

Are there any questions I should avoid?

Yes, there are certain types of questions that you should generally avoid when interviewing women leaders:

Personal questions: Avoid questions that pry into their personal life unless they directly relate to her leadership experience or she has openly discussed these topics before.

Stereotype-based questions: Avoid questions based on gender stereotypes. For example, don’t assume she leads a certain way because she is a woman.

Negative questions: Avoid questions that focus excessively on negatives or failures. It’s okay to ask about challenges and how she overcame them, but don’t dwell solely on the tough times.

Irrelevant questions: Stay focused on the topic at hand, which is her leadership experience and insights. Don’t ask questions that aren’t relevant to her career, her industry, or your overall purpose.

What if a question makes the leader uncomfortable?

If a question makes a leader uncomfortable, look out for signs such as pausing, evading the question, or stating discomfort. If you see these signs, quickly apologize and move to a different, less sensitive question. 

Remember this moment for future interactions to help ensure your questions remain respectful and professional. Always prioritize the leader’s comfort and privacy in the conversation.

How can we support women in the workplace?

Supporting women in the workplace is essential to gender equality and diversity. Here are some ways to accomplish this:

Equal opportunities: Ensure women have the same opportunities as their male colleagues for jobs, promotions, and important projects.

Workplace policies: Implement family-friendly policies, including maternity leave and flexible work hours, to support women who balance work and family responsibilities.

Promote inclusivity: Create an inclusive work environment where everyone feels respected and valued. This includes a zero-tolerance policy towards harassment and discrimination.

Mentorship and training: Provide mentorship programs and training opportunities specifically designed for women. This can help them develop the skills needed for career advancement.

Recognition: Acknowledge and reward the contributions of women in the workplace. This validation can boost confidence and motivation.

Encourage diversity: Make diversity a key aspect of your company culture. This includes diverse leadership and decision-making teams.


Remember, every question we ask brings us closer to understanding the steps women leaders have taken to achieve their goals. Their answers can inspire, teach, and show us that we, too, can conquer our dreams. 

These are more than just questions—they’re keys to lessons that could change our lives. So, the next time you meet a woman leader, don’t hold back. Ask, listen, and learn. Keep the conversation going, and happy learning!

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Robby is a multimedia editor at UpJourney with a journalism and communications background.

When she's not working, Robby transforms into an introverted art lover who indulges in her love for sports, learning new things, and sipping her favorite soda. She also enjoys unwinding with feel-good movies, books, and video games. She's also a proud pet parent to her beloved dog, Dustin.