200 Questions to Ask Women Leaders

Women leaders have broken barriers, shattered glass ceilings, and paved the way for future generations. Their journeys are filled with valuable lessons, unique challenges, and incredible triumphs, all of which we can learn from their experiences.

In this article, I’ve compiled a list of thought-provoking questions to ask designed to help you engage in meaningful conversations with women leaders.

Are you ready to learn from the best and discover what it truly means to lead as a woman? Let’s dive in and explore the wisdom of these remarkable leaders.

Leadership Philosophy and Style

  1. How do you define your leadership style?
  2. What principles guide your decision-making process as a leader?
  3. Can you share a time when your leadership philosophy was put to the test?
  4. How do you inspire and motivate your team?
  5. What do you believe is the most challenging aspect of being a leader today?
  6. How do you stay adaptable as a leader in a constantly changing environment?
  7. What role does emotional intelligence play in your leadership?
  8. How do you balance being assertive with being approachable in your leadership role?
  9. Can you share an example of how you’ve empowered someone on your team?
  10. How do you foster innovation within your team or organization?
  11. In what ways do you encourage creative thinking in your leadership practices?
  12. How do you handle dissent or disagreement within your team?
  13. What techniques do you use to build trust with your team?
  14. How do you approach making difficult decisions?
  15. What’s your take on failure, and how do you handle it as a leader?
  16. How do you measure success as a leader?
  17. In your view, what is the biggest misconception about leadership?
  18. How do you ensure your team stays aligned with the organization’s goals?
  19. How do you maintain your authenticity in a position of power?
  20. What advice would you give to leaders on embracing vulnerability?
  21. How do you manage your time and priorities as a leader?
  22. What’s the best leadership advice you have ever received?
  23. How do you see the future of leadership, especially for women?
  24. What steps do you take to continue growing as a leader?
  25. How do you balance tradition with innovation in your leadership approach?

Career Path and Milestones

  1. What sparked your interest in pursuing leadership roles?
  2. Can you share a pivotal moment in your career that shaped your leadership journey?
  3. How did you navigate the transition from team member to leader?
  4. What were some of the initial challenges you faced in leadership positions?
  5. How have mentors influenced your career path?
  6. Looking back, what would you do differently in your career?
  7. What achievement in your career are you most proud of?
  8. How do you stay motivated during difficult times in your career?
  9. What has been the most unconventional step you’ve taken in your career?
  10. How did you prepare for your first leadership role?
  11. Can you share a career decision that took you out of your comfort zone?
  12. What role has networking played in your career development?
  13. How do you approach goal setting in your career?
  14. In what ways have you had to advocate for yourself in your career?
  15. What’s the best career advice you’ve ever been given?
  16. How do you approach learning and development in your career?
  17. Can you share a time when you had to make a significant career shift?
  18. What strategies have you used to overcome imposter syndrome?
  19. How do you celebrate your career achievements?
  20. How do you approach risk-taking in your career decisions?
  21. What’s one leadership role you aspire to in the future?
  22. How do you balance your career ambitions with personal development?
  23. What legacy do you hope to leave in your professional field?
  24. How do you deal with burnout and maintain resilience in your career?
  25. What’s the most important lesson you’ve learned in your professional journey?

Challenges and Obstacles

  1. What was the biggest challenge you faced as a woman in leadership?
  2. How do you handle gender bias in the workplace?
  3. Can you share a time when you were underestimated because of your gender and how you addressed it?
  4. What strategies have you employed to overcome barriers in your career?
  5. How do you handle the pressure of being a role model for other women?
  6. In what ways have you had to prove yourself more than your male counterparts?
  7. How do you address work-life balance challenges, especially related to leadership roles?
  8. Can you share an instance where you had to navigate through a failure or setback?
  9. What advice do you have for dealing with workplace discrimination?
  10. How do you maintain confidence in environments that are not inclusive?
  11. What has been your strategy for handling microaggressions in the workplace?
  12. How do you fight against stereotype threats in your career?
  13. In what ways do you think being a woman has impacted your leadership style?
  14. How do you ensure your voice is heard in male-dominated spaces?
  15. What measures do you take to support other women facing obstacles in their careers?
  16. How have societal expectations of women affected your career path?
  17. What challenges have you faced in achieving work-life integration?
  18. How do you navigate the challenges of being a mother and a leader?
  19. Can you discuss a time when you had to stand up for what you believe in at work?
  20. How do you protect your mental health amidst professional pressures?
  21. What obstacles have you faced in accessing leadership opportunities?
  22. How do you stay resilient in the face of persistent challenges?
  23. Can you share ways you’ve had to adapt your leadership approach to overcome barriers?
  24. What’s the hardest decision you’ve had to make as a leader?
  25. How do you balance assertiveness with empathy in challenging situations?

Advice for Aspiring Leaders

  1. What advice would you give to young women aspiring to leadership roles?
  2. How can aspiring leaders develop their own leadership style?
  3. What are some essential skills you believe every leader should have?
  4. How important is mentorship in building a leadership career, and how can one find a mentor?
  5. What common pitfalls should aspiring leaders avoid?
  6. Can you share a piece of advice you wish you had known at the start of your leadership journey?
  7. How do you suggest handling the fear of failure in leadership?
  8. In what ways can aspiring leaders build resilience?
  9. How should someone approach leadership opportunities, even if they feel unprepared?
  10. What strategies would you recommend for effective communication as a leader?
  11. How can aspiring leaders foster a supportive and inclusive team environment?
  12. What can women do to support and uplift each other in leadership roles?
  13. How can someone stay authentic while adapting to a leadership role?
  14. What steps can young leaders take to advocate for gender equality in their organizations?
  15. How important is personal branding for a leader, and how can one develop it?
  16. What role does self-awareness play in leadership, and how can one enhance it?
  17. How can aspiring leaders manage and utilize feedback effectively?
  18. What’s your advice for balancing ambition with humility?
  19. How can one maintain motivation and passion in their leadership journey?
  20. What guidance would you give for making difficult decisions?
  21. How can aspiring leaders ensure they remain approachable and relatable?
  22. What advice would you offer for developing strategic thinking skills?
  23. How can someone prepare for the unexpected challenges of leadership?
  24. In what ways can aspiring leaders contribute to diversity and inclusion efforts?
  25. What final piece of advice would you give to someone stepping into their first leadership role?

Mentorship and Growth

  1. How has mentorship shaped your career and leadership style?
  2. Can you share an impactful mentoring experience you’ve had?
  3. What qualities do you think make a good mentor?
  4. How do you approach being a mentor to others in your field?
  5. What’s the best way to seek out mentorship opportunities?
  6. How can mentorship benefit women in leadership positions?
  7. Can you discuss a time your advice as a mentor significantly impacted someone’s career?
  8. What challenges have you faced in mentoring relationships, and how did you overcome them?
  9. How do you structure a mentoring relationship for success?
  10. In what way has being a mentor also contributed to your own growth?
  11. How do you balance providing support with encouraging independence in your mentees?
  12. What’s the most rewarding aspect of being a mentor?
  13. How do you keep mentoring relationships productive and beneficial for both parties?
  14. What advice would you give to someone looking to become a mentor?
  15. How important do you think diversity is in mentor-mentee relationships?
  16. Can you share strategies for providing constructive feedback as a mentor?
  17. How do you measure the success of a mentoring relationship?
  18. What role does empathy play in your mentorship approach?
  19. How do you encourage your mentees to take on leadership roles?
  20. How do you stay engaged and committed as a mentor?
  21. What’s one key lesson you always share with your mentees?
  22. How do you approach challenging conversations with mentees?
  23. Can you share an example of how a mentoring relationship helped you see things from a different perspective?
  24. How do you adapt your mentoring style to fit the needs of different mentees?
  25. What’s your advice for establishing trust in a mentoring relationship?

Diversity and Inclusion

  1. How do you define diversity and inclusion in a leadership context?
  2. What strategies have you implemented to promote diversity and inclusion within your team or organization?
  3. Can you share a challenge you’ve faced in creating a diverse and inclusive environment and how you addressed it?
  4. How do you measure the impact of your diversity and inclusion efforts?
  5. What role does leadership play in advancing diversity and inclusion initiatives?
  6. How do you foster open dialogue around diversity and inclusion in your workplace?
  7. What advice would you give leaders struggling to create a diverse and inclusive culture?
  8. How do you ensure all voices are heard and valued within your team?
  9. What’s the biggest misconception you’ve encountered about diversity and inclusion efforts?
  10. How do you deal with resistance to diversity and inclusion initiatives?
  11. What impact has focusing on diversity and inclusion had on your leadership and your organization?
  12. How do you stay informed about best practices for diversity and inclusion?
  13. In what ways do you support underrepresented groups in leadership positions?
  14. How do you approach mentoring and supporting diverse talent?
  15. What steps can organizations take to make their recruiting processes more inclusive?
  16. How do you address unconscious bias within your team or organization?
  17. Can you share an example of a diversity and inclusion initiative that had a significant impact?
  18. How do you balance the need for diversity with the need for inclusion?
  19. What resources would you recommend for someone learning more about effective diversity and inclusion practices?
  20. How do you integrate diversity and inclusion into your leadership development programs?
  21. What challenges do you foresee in the future of diversity and inclusion efforts?
  22. How do you encourage individuals to take personal responsibility for promoting diversity and inclusion?
  23. What role does empathy play in fostering a culture of diversity and inclusion?
  24. How can leaders better support employees from diverse cultural backgrounds?
  25. What advice would you give to leaders looking to make their workplace more inclusive?

Innovation and Change

  1. How do you foster a culture of innovation within your organization?
  2. Can you share an example of a significant change you initiated in your organization and the outcome?
  3. What strategies do you use to encourage innovative thinking in your team?
  4. How do you manage resistance to change within your organization?
  5. In what ways do you ensure your organization stays ahead of industry trends?
  6. How do you balance innovation with risk management?
  7. What role does diversity play in fostering innovation in your organization?
  8. How do you approach making bold decisions that may disrupt the status quo?
  9. What challenges have you faced in implementing new ideas, and how did you overcome them?
  10. How do you measure the success of an innovation or change initiative?
  11. What’s the biggest risk you’ve taken as a leader to drive innovation?
  12. How do you keep your team motivated during periods of significant change?
  13. Can you discuss a time when an innovative approach failed and what you learned from it?
  14. How do you encourage collaboration and cross-functional teaming for innovation?
  15. What tools or methods do you use to generate new ideas?
  16. How do you involve your team in the decision-making process for change initiatives?
  17. How do you maintain organizational culture while implementing significant changes?
  18. What advice would you give to leaders who are hesitant to embrace change?
  19. How do you ensure that innovations align with your organization’s overall goals and values?
  20. What’s your process for evaluating which innovations to pursue?
  21. How do you deal with the uncertainty that comes with driving change?
  22. How do you support your team through the challenges of adapting to new innovations?
  23. How do you prioritize which changes to implement first?
  24. What role does customer feedback play in your innovation process?
  25. How do you balance focusing on current operations and exploring new innovations?

Work-Life Balance

  1. How do you manage to maintain work-life balance in a leadership role?
  2. What strategies have you found effective for disconnecting from work and focusing on personal time?
  3. Can you share a personal habit that helps you decompress from the stresses of leadership?
  4. What advice would you give leaders struggling to balance their professional and personal lives?
  5. How do you prioritize your health and well-being while fulfilling your leadership responsibilities?
  6. How important do you believe work-life balance is for maintaining effective leadership?
  7. What challenges have you faced in trying to achieve work-life balance, and how have you addressed them?
  8. How do you set boundaries between work and personal life?
  9. What role does your organization play in supporting work-life balance for its leaders?
  10. How do you encourage your team to maintain a healthy work-life balance?
  11. Can you share a time when you had to make a difficult decision to maintain your work-life balance?
  12. How do you handle the guilt of taking time for yourself?
  13. What impact has prioritizing work-life balance had on your leadership effectiveness?
  14. How do you manage expectations (both yours and others) regarding availability and work hours?
  15. What tools or techniques do you use to efficiently manage your time?
  16. How do you delegate responsibilities to ensure you’re not overwhelmed?
  17. How has your approach to work-life balance evolved over your career?
  18. What advice would you give to women leaders who feel overwhelmed by the pressure to excel in every area of their lives?
  19. How do you cope with the days when work-life balance seems impossible?
  20. What’s one change you’ve made that significantly improved your work-life balance?
  21. How do you ensure you’re present in both your personal and professional life?
  22. Can you share how you’ve overcome a work-life conflict?
  23. What’s your advice for managing work-life balance with unexpected work demands?
  24. How do you keep your personal relationships healthy while managing a demanding career?
  25. What’s the biggest misconception about work-life balance you’d like to address?

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.


Final Thoughts

Remember, every leader’s journey is unique, and there is no one-size-fits-all approach to success. However, by learning from the wisdom and experiences of those who have come before us, we can better navigate our own paths and make a positive impact in our careers and communities.

So don’t hesitate to reach out, ask questions, and learn from the incredible women leaders around you.

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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.