120 Leadership Conversation Starters

Leadership is one of those topics that everyone’s curious about, but not everyone knows how to talk about. You don’t need a fancy title to join the conversation—you just need the right question to get things going.

In this list, I’ve put together a bunch of easy-to-use leadership conversation starters—whether you’re new to leading or have years of experience behind you. They’re perfect for workshops, team check-ins, personal reflection, or just casual chats with people who love talking leadership as much as you do.

Questions to Ask a Leader or Mentor

1. What’s something you wish more people understood about leadership?
2. When did you first realize you had leadership potential?
3. How do you stay grounded when things get hectic at work?
4. What’s one leadership mistake that taught you a lot?
5. How do you balance confidence with humility in your role?
6. Who’s been a big influence on your leadership style?
7. What’s a common leadership myth you totally disagree with?
8. How do you handle decisions when there’s no clear right answer?
9. What’s the hardest part of leading people that nobody talks about?
10. How do you encourage creativity and innovation in your team?
11. What’s your go-to strategy for building trust with new team members?
12. What do you do when someone on your team is struggling?
13. How do you measure your success as a leader?
14. Have your leadership values changed over time? If so, how?
15. What’s a recent leadership challenge that stretched you?

Self-Reflection Prompts for Aspiring or Current Leaders

1. What type of leader do I naturally gravitate toward becoming?
2. How do I respond when I’m faced with pressure or uncertainty?
3. What leadership strengths do I feel proud of right now?
4. In what situations do I feel the most confident leading others?
5. What kind of impact do I want to have on the people I lead?
6. How do I typically handle feedback, and what does that say about me?
7. What does leadership success actually look like for me?
8. How do I want people to describe me as a leader?
9. What leadership habits do I want to work on this year?
10. Do I lead by example, or do I sometimes lead by instruction only?
11. How do I make sure I’m listening more than I’m talking?
12. Am I creating space for others to grow, or just getting tasks done?
13. What emotions do I experience most often when I’m leading?
14. What’s one fear that’s been holding me back as a leader?
15. How do I define leadership in my own words?

Leadership Icebreakers for Group Settings

1. What’s one word you associate with great leadership?
2. Share a leadership quality you admire in someone you know.
3. Who was your first example of a leader growing up?
4. What’s one leadership trait you think is underrated?
5. If you could learn one leadership skill overnight, what would it be?
6. What’s a leadership quote or saying you actually like?
7. Have you ever been surprised by someone’s leadership potential?
8. What’s your biggest pet peeve in a leader?
9. Would you rather lead a team or work behind the scenes?
10. What does a supportive leader look like to you?
11. What’s your leadership superpower—real or imagined?
12. What’s one mistake leaders often make, in your opinion?
13. Have you ever had to step up as a leader unexpectedly?
14. Who’s a famous leader you actually find relatable?
15. What’s something you’ve learned about leadership just by observing others?

Conversation Starters for Leadership Training

1. What’s the biggest shift you’ve made in your leadership style recently?
2. How do you handle resistance when leading change?
3. What’s one thing you’d like to do better as a leader?
4. What leadership model or framework do you find helpful?
5. What role does empathy play in your day-to-day leadership?
6. How do you create psychological safety in your team?
7. How do you balance structure with flexibility when leading?
8. What’s one leadership decision you’re proud of and why?
9. What’s something you’ve unlearned about leadership?
10. How do you help others take ownership of their growth?
11. What’s a leadership tool or method you rely on often?
12. What does accountability look like in your team?
13. How do you adapt your leadership approach to different people?
14. What’s one question you often ask yourself as a leader?
15. How do you build leadership capacity in others?

Team-Based Leadership Questions

1. How do you motivate a team when morale is low?
2. What’s your approach to handling team disagreements?
3. How do you make sure everyone feels included and valued?
4. What’s your process for setting team goals?
5. How do you know when to step in and when to step back?
6. What’s one way you keep strong communication within your team?
7. How do you give credit and celebrate team wins?
8. What do you do when someone on the team feels unheard?
9. How do you help teammates build trust with each other?
10. What’s your take on team diversity and leadership?
11. How do you handle underperformance without hurting the team’s vibe?
12. What kind of leader do your teammates need you to be?
13. How do you resolve tension without taking sides?
14. What’s one team dynamic you always try to encourage?
15. How do you align personal goals with team success?

Challenges and Lessons in Leadership

1. What’s one tough leadership moment that shaped you?
2. How do you bounce back from leadership failures?
3. What’s a lesson you learned the hard way?
4. How do you stay resilient when things don’t go your way?
5. What’s the most uncomfortable feedback you’ve ever received?
6. How do you deal with imposter syndrome as a leader?
7. What’s one challenge you didn’t expect to face in leadership?
8. How do you keep growing when you feel stuck?
9. What’s the best advice you’ve ever received as a leader?
10. How do you handle it when your team doesn’t agree with you?
11. What’s one habit that helped you overcome a leadership struggle?
12. How do you manage emotions when making tough calls?
13. Have you ever had to lead through burnout?
14. What helped you most during your first big leadership role?
15. What’s something you would’ve done differently as a new leader?

Vision and Future-Focused Leadership

1. What’s a big-picture change you’d love to lead?
2. Where do you see your leadership journey heading next?
3. How do you keep your vision clear when things feel chaotic?
4. What does long-term impact look like for you?
5. How do you stay future-focused without losing sight of today?
6. What leadership trends are you keeping an eye on?
7. How do you encourage forward thinking in your team?
8. What’s something you’re building that you’re excited about?
9. How do you align your daily actions with your big goals?
10. What’s a future skill every leader should work on?
11. How do you help others stay motivated for the long haul?
12. What legacy do you want to leave behind?
13. How do you stay open to change while staying grounded?
14. What’s your strategy for evolving as a leader?
15. What does leadership look like 10 years from now, in your opinion?

Decision-Making and Problem-Solving in Leadership

1. What’s your go-to process when you need to make a tough call?
2. How do you weigh people vs. results in your decisions?
3. What’s a decision you made under pressure that taught you something?
4. How do you avoid overthinking when time is short?
5. How do you involve others in big decisions?
6. What role does intuition play in your leadership choices?
7. How do you handle conflicting opinions on your team?
8. How do you know when it’s time to pivot?
9. What’s one lesson you’ve learned about making quick decisions?
10. How do you recover from a decision that didn’t go as planned?
11. Do you follow a decision-making framework or go with your gut feeling?
12. What’s a time when a mistake led to a breakthrough?
13. How do you stay calm during high-stakes problem-solving?
14. How do you balance logic with emotion in decision-making?
15. What’s a question you always ask yourself before making a big move?

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