Leadership Questions to Ask
Powerful questions to ask leaders that reveal their leadership philosophy, decision-making process, and approach to building and managing teams.
1What's your leadership philosophy and how has it evolved?
Click to see why this works
What's your leadership philosophy and how has it evolved?
Click to see why this works
Why this works
Understanding their leadership approach helps you learn from their experience and develop your own leadership style.
2How do you make difficult decisions when you don't have all the information?
Click to see why this works
How do you make difficult decisions when you don't have all the information?
Click to see why this works
Why this works
Learning about decision-making under uncertainty helps you develop skills for handling complex situations.
3What's the most important lesson you've learned about leading people?
Click to see why this works
What's the most important lesson you've learned about leading people?
Click to see why this works
Why this works
Getting insights about people management helps you understand the human side of leadership and develop your interpersonal skills.
4How do you handle conflict within your team?
Click to see why this works
How do you handle conflict within your team?
Click to see why this works
Why this works
Understanding conflict resolution helps you develop skills for managing difficult situations and maintaining team harmony.
5What's your approach to building trust with your team?
Click to see why this works
What's your approach to building trust with your team?
Click to see why this works
Why this works
Learning about trust-building helps you understand the foundation of effective leadership and develop your relationship skills.
6How do you balance being supportive with holding people accountable?
Click to see why this works
How do you balance being supportive with holding people accountable?
Click to see why this works
Why this works
Understanding this balance helps you develop skills for managing performance while maintaining positive relationships.
7What's the biggest mistake you've made as a leader and what did you learn?
Click to see why this works
What's the biggest mistake you've made as a leader and what did you learn?
Click to see why this works
Why this works
Learning from their mistakes helps you avoid common pitfalls and develop resilience in your own leadership journey.
8How do you develop and mentor other leaders?
Click to see why this works
How do you develop and mentor other leaders?
Click to see why this works
Why this works
Understanding leadership development helps you learn how to grow others and build a strong leadership pipeline.
9What's your approach to giving feedback, both positive and negative?
Click to see why this works
What's your approach to giving feedback, both positive and negative?
Click to see why this works
Why this works
Learning about feedback delivery helps you develop skills for effective communication and performance management.
10How do you handle stress and pressure while leading others?
Click to see why this works
How do you handle stress and pressure while leading others?
Click to see why this works
Why this works
Understanding stress management helps you develop resilience and maintain effectiveness under pressure.
11What's your approach to building a diverse and inclusive team?
Click to see why this works
What's your approach to building a diverse and inclusive team?
Click to see why this works
Why this works
Learning about diversity and inclusion helps you understand how to create equitable and effective teams.
12How do you communicate your vision and get buy-in from your team?
Click to see why this works
How do you communicate your vision and get buy-in from your team?
Click to see why this works
Why this works
Understanding vision communication helps you develop skills for inspiring others and driving organizational change.
13What's your approach to handling failure and setbacks?
Click to see why this works
What's your approach to handling failure and setbacks?
Click to see why this works
Why this works
Learning about resilience helps you develop skills for bouncing back from challenges and maintaining team morale.
14How do you balance short-term results with long-term strategy?
Click to see why this works
How do you balance short-term results with long-term strategy?
Click to see why this works
Why this works
Understanding strategic thinking helps you develop skills for balancing immediate needs with future goals.
15What's your approach to building psychological safety in your team?
Click to see why this works
What's your approach to building psychological safety in your team?
Click to see why this works
Why this works
Learning about psychological safety helps you understand how to create an environment where people can thrive and innovate.
16How do you handle difficult conversations with team members?
Click to see why this works
How do you handle difficult conversations with team members?
Click to see why this works
Why this works
Understanding difficult conversations helps you develop skills for addressing challenging situations with empathy and effectiveness.
17What's your approach to delegation and empowerment?
Click to see why this works
What's your approach to delegation and empowerment?
Click to see why this works
Why this works
Learning about delegation helps you develop skills for building capability and creating autonomous teams.
18How do you stay current with leadership best practices?
Click to see why this works
How do you stay current with leadership best practices?
Click to see why this works
Why this works
Understanding continuous learning helps you develop strategies for ongoing leadership development and improvement.
19What's your approach to building resilience in your team?
Click to see why this works
What's your approach to building resilience in your team?
Click to see why this works
Why this works
Learning about team resilience helps you understand how to create strong, adaptable teams that can handle challenges.
20What's the most important quality you look for in potential leaders?
Click to see why this works
What's the most important quality you look for in potential leaders?
Click to see why this works
Why this works
Understanding leadership qualities helps you develop the characteristics that make effective leaders and identify them in others.
Learning from Effective Leaders
Expert tips and techniques for getting the most out of these questions.
Preparing for Your Conversation
Research Their Background
Learn about their leadership experience, challenges they've faced, and successes they've achieved.
Prepare Thoughtful Questions
Write down questions that will help you understand their leadership approach and learn from their experience.
Be Open to Learning
Approach the conversation with curiosity and a willingness to learn from their insights and experience.
Essential Areas to Explore
Leadership Philosophy
People Management
Decision Making
Common Pitfalls to Avoid
Don't Ask Generic Questions
Avoid questions they've heard many times. Focus on specific, thoughtful questions that reveal deeper insights.
Avoid Being Overly Critical
Don't use the conversation to challenge their leadership style. Focus on learning and understanding their approach.
Don't Ignore Their Advice
Listen to their guidance and take their advice seriously. They have valuable experience to share.