25 Great Questions for Leaders

“Leaders who don’t listen will eventually be surrounded by people who have nothing to say.”
Andy Stanley

One of the greatest skills leaders can cultivate is the art of great question-asking. Jesus was the Master of great questions: “What do you want me to do for you?” (Mark 10:51). “Who do people say that I am?” (Matthew 16:13) “But what about you? …Who do you say I am?” (Matthew 16:15). 

Leaders who ask great questions draw others out, and in turn enjoy deeper loyalty. Here are 25 questions to get you started in cultivating a deeper connection with those you lead.

  1. What part of your life fuels your energy most effectively?
  2. Are you more of an extrovert or an introvert? How does that influence your marriage, your parenting, your ministry, or your career?
  3. If you weren’t in your current job, what would you like to be doing?
  4. Where would you like to see yourself in five years? Follow up questions: 
  • List specific goals for yourself in 5 years.
  • What steps do you need to take now in order to achieve those goals then?
  • What step do you need to take immediately in order to begin moving in that direction?
  1. If money weren’t an issue, what dream would you pursue? 
  2. Tell me about the current project you’re working on.
  3. Tell me your thoughts about church.
  4. Tell me about your relationships. Which of those relationships are the most fulfilling? What makes them fulfilling? 
  5. Tell me about the most annoying person in your life and what they do that annoys you. What do you see as the underlying cause of tension in that relationship?
  6. Who is your favorite world leader at this moment? What do you admire about them?
  7. What would make your marriage more enjoyable for you?
  8. When do you feel most loved by your spouse?
  9. How do you best experience God’s presence? 
  10. What specific choices do you make daily to spend time with God?
  11. If you could do the last five years over, what would you do differently?
  12. What causes stress or anxiety in your life?
  13. What techniques do you use to cope with stress in your life?
  14. How does your childhood influence your relationship with God, your spouse, or your children?
  15. Where do you see yourself lacking faith?
  16. What do you think you’ll do to move forward?
  17. What would you like to do?
  18. How might that choice impact your relationship? (Or team dynamics, job performance, etc.)
  19. If you were to change the culture of your organization, what would you like to see change? Are there steps you can take to help facilitate those changes?
  20. What do you like best about your job?
  21. How can I pray for you?