16 Leadership Questions

  1. What does confidence mean to you?

  2. How would you define it?

  3. When was a time in your life you were confident? What did that feel like?

  4. When was a time in your life you were NOT confident? What caused that to happen?

  5. Who is someone who has contributed to your confidence?

  6. What did that person do or say to build up your self-esteem and feeling of self-worth?

  7. Who is someone who has compromised your confidence? What did that person do or say to bring you down and cause you to doubt yourself?

  8. Would you call yourself a confident person? Why or why not? Is it situational?

  9. What is one specific thing you do that helps you like yourself and your life?

  10. What is one specific thing you do that undermines your self-worth and causes you to not like yourself or your life?

  11. Do you compare yourself to others?

  12. How does that impact your confidence?

  13. Are you good at something? Does that make you feel confident? Explain.

  14. Do you think you can “give” someone (i.e., a child, friend or employee) confidence?

  15. What’s the best advice someone gave you about how to feel and act more confident?

  16. What’s your advice to someone who wants to boost their self-esteem?

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