130+ Questions to Ask Women Leaders

Being a woman in leadership can feel like stepping onto a stage that’s been set by others, with rules you didn’t write and expectations you never agreed to.

Yet countless women are stepping up, breaking down barriers, and showing us that leadership is about vision, integrity, and grit—not about fitting into some old, outdated mold.

If you’ve ever wanted to know how they do it—or maybe even get a few tips for your own path—this list of questions is a great starting point.

Leadership Philosophy and Style

  1. How would you describe your approach to leadership?
  2. What are the core values that guide your leadership decisions?
  3. How do you adapt your leadership style to different team members or situations?
  4. What is one leadership trait you consider essential for success?
  5. How do you handle decision-making under pressure?
  6. How has your leadership style evolved over the years?
  7. What leadership practices have you adopted from other leaders you admire?
  8. How do you foster an environment of accountability within your team?
  9. How do you handle feedback and criticism as a leader?
  10. How do you define success for yourself and your team?
  11. What’s the biggest leadership challenge you’ve faced, and how did you overcome it?
  12. How do you motivate and inspire your team, especially during tough times?
  13. How do you balance being approachable with setting boundaries?
  14. How do you ensure that your leadership aligns with your personal values?
  15. What advice would you give to those trying to develop their own leadership style?

Gender-Specific Challenges and Bias

  1. What are some gender-specific challenges you’ve encountered in your career?
  2. How have you handled instances of gender bias in the workplace?
  3. What advice would you give to women dealing with bias in their roles?
  4. Have you ever felt pressure to conform to traditional gender roles as a leader?
  5. How do you navigate situations where your authority is questioned because of your gender?
  6. What strategies do you use to advocate for yourself in male-dominated environments?
  7. How do you respond to stereotypes or assumptions about women in leadership?
  8. What changes do you think are still needed to reduce gender bias in your field?
  9. How can men in the workplace support women leaders more effectively?
  10. What initiatives have you implemented to support other women in your organization?
  11. How do you balance assertiveness with perceptions of likability?
  12. Do you believe being a woman has influenced your leadership style? If so, how?
  13. How do you approach conversations about gender equity with colleagues or superiors?
  14. What advice would you give to men looking to understand gender bias better?
  15. What do you consider the biggest challenge women in leadership face today?

Career Path

  1. What was your first job, and how did it shape your career?
  2. What inspired you to pursue your current field?
  3. Were there any key turning points that helped you advance in your career?
  4. How do you set and pursue long-term career goals?
  5. What’s one skill you developed that was essential to your growth?
  6. How did you handle career setbacks or disappointments?
  7. How have mentors or role models influenced your career path?
  8. What’s the best career advice you received early on?
  9. How do you decide when it’s time to move on to a new role?
  10. What is one thing you wish you’d done differently in your career?
  11. How do you measure personal success in your career?
  12. What is the biggest risk you’ve taken in your career?
  13. What are your career goals moving forward?
  14. How do you keep learning and improving as a leader?
  15. What advice would you give to those at the start of their career?

Career Advice and Professional Development

  1. What’s the most valuable lesson you’ve learned in your career?
  2. How do you prioritize your own professional development?
  3. What advice would you give to someone aiming for a leadership role?
  4. How do you approach learning new skills or knowledge?
  5. How important is networking in your career, and how do you do it effectively?
  6. How do you handle constructive criticism in the workplace?
  7. What’s one habit you’ve developed that contributes to your success?
  8. How do you stay organized and manage your time?
  9. What role has mentorship played in your career?
  10. What advice would you give to someone facing career burnout?
  11. How do you balance ambition with realistic expectations?
  12. How do you approach setting and reaching professional goals?
  13. What’s the best way to handle setbacks professionally?
  14. How important is emotional intelligence in the workplace?
  15. What advice would you give to those considering a career change?

Building and Leading Effective Teams

  1. What do you look for when hiring team members?
  2. How do you create a collaborative team environment?
  3. What’s your approach to handling team conflicts?
  4. How do you ensure everyone on the team feels valued?
  5. How do you set and communicate team goals effectively?
  6. How do you balance individual strengths within a team?
  7. What’s your approach to giving feedback to team members?
  8. How do you handle a situation where a team member is underperforming?
  9. What’s the most rewarding part of leading a team for you?
  10. How do you maintain team morale during challenging times?
  11. How do you celebrate team successes?
  12. How do you encourage open communication among team members?
  13. What’s one challenge you faced in team leadership, and how did you address it?
  14. How do you manage a diverse team with different work styles?
  15. How do you foster trust and transparency within your team?

Diversity, Equity, and Inclusion (DEI) Initiatives

  1. What DEI initiatives are you most passionate about?
  2. How do you advocate for underrepresented groups in your organization?
  3. How do you foster a culture of inclusivity within your team?
  4. How do you address resistance to DEI initiatives?
  5. What role do you believe leaders play in promoting diversity?
  6. How do you approach recruitment with diversity in mind?
  7. What is one DEI achievement you’re proud of in your career?
  8. How do you ensure that DEI principles are integrated into daily work culture?
  9. What’s the biggest challenge you’ve faced in advancing DEI?
  10. How do you create safe spaces for employees to discuss DEI topics?
  11. What’s one thing everyone can do to support diversity and inclusion?
  12. How do you measure the success of DEI initiatives?
  13. How do you encourage team members to embrace diversity?
  14. What is your approach to handling unconscious bias within the team?
  15. What changes would you like to see in DEI efforts across industries?

Work-Life Balance

  1. How do you manage your work-life balance?
  2. What’s one strategy that helps you unwind after a long day?
  3. How do you set boundaries between work and personal life?
  4. How do you avoid burnout in your career?
  5. How do you prioritize personal relationships alongside work?
  6. How do you handle work during particularly busy personal times?
  7. What advice would you give to others struggling with work-life balance?
  8. How has your approach to work-life balance evolved over time?
  9. What’s one non-negotiable part of your routine for maintaining balance?
  10. How do you communicate your boundaries to your team?
  11. How do you disconnect from work on weekends or vacations?
  12. What role does self-care play in your career?
  13. How do you manage your time when work demands are high?
  14. How do you support your team’s work-life balance?
  15. What’s one activity you enjoy outside of work?

Lessons Learned and Regrets

  1. What’s one mistake that taught you a valuable lesson?
  2. If you could change one decision in your career, what would it be?
  3. What is the biggest lesson you’ve learned as a leader?
  4. How do you approach learning from past experiences?
  5. What’s one thing you wish you’d known earlier in your career?
  6. What was your biggest professional regret, and what did it teach you?
  7. How do you handle failures in your professional life?
  8. How has your perspective on success changed over time?
  9. What’s one thing you’re proud of overcoming in your career?
  10. How do you approach taking risks in your career?
  11. What’s the most important advice you’d give to your younger self?
  12. How do you view setbacks and challenges now compared to earlier in your career?
  13. What’s one leadership lesson you learned the hard way?
  14. How do you find meaning in difficult career moments?
  15. What’s one thing you hope future leaders learn from your experiences?

Advice for Aspiring Leaders

  1. What qualities do you believe are essential for a successful leader?
  2. How can aspiring leaders develop their own leadership style?
  3. What’s the first step someone should take if they want to become a leader?
  4. How important is self-awareness in leadership, and how can one develop it?
  5. What role does resilience play in leadership, and how can it be strengthened?
  6. What advice do you have for handling criticism and feedback as a new leader?
  7. How should aspiring leaders approach building trust with their team?
  8. What are common mistakes you see new leaders make, and how can they be avoided?
  9. How can aspiring leaders learn to make tough decisions confidently?
  10. What’s one leadership lesson you wish you’d learned sooner?
  11. How can emerging leaders improve their communication skills?
  12. How important is empathy in leadership, and how can it be cultivated?
  13. What’s your advice for balancing assertiveness with approachability?
  14. How can aspiring leaders practice accountability in their roles?
  15. What’s the most effective way to inspire and motivate others as a leader?

Final Thoughts

Women leaders show us what it really takes to lead with strength, honesty, and courage. Their stories teach us that leadership isn’t about following a set path—it’s about finding your own way, staying true to what matters, and making a difference, even when things get tough.

In the end, these women remind us that anyone with passion and purpose can create change. Let’s keep learning, stay curious, and support leaders who inspire us to reach higher and lead with heart.

How useful was this post?

Click on a star to rate it!

As you found this post useful...

Share it on social media!

We are sorry that this post was not useful for you!

Let us improve this post!

Tell us how we can improve this post?

Photo of author

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.