Power Questions to Connect Personally

  1. What would you like to be remembered for?
  2. What has been your greatest accomplishment?
  3. What has brought you the most fulfillment in your life?
  4. What was the happiest day of your life?
  5. What do you wish your younger self had known about (success, relationships, being a parent, etc. that you know today?
  6. Can you tell me something about your own career and how you got to your current position?
  7. What do you like best about working for your organization?
  8. In terms of your own effectiveness and how you spend your time, what would you like to do less of, and on which activities do you want to spend more time?
  9. Tell me about your family. How old are your children?
  10. When you’re not shaking things up here at work, how do you spend your free time?
  11. What do you think about (a current event, election results, or something else in news)?
  12. Who have been influential role models or mentors to you?
  13. Where did you grow up? What was that like?
  14. What were your parents like? What did you learn from them?
  15. If you hadn’t gone into (whatever field they are in), what do you think you would have done instead?
  16. If you had to write your obituary today, what would it say?
  17. What’s the most memorable book (movie, concert, etc.) you’ve ever read (seen, been to)?
  18. Do you think you are an introvert or extravert? Why do you say that?
  19. In thinking about e-mail, the phone, writing, face-to-face meetings, social media – how would you describe your communication style and preferences?
  20. Tell me about your early career – what did you do the first five or ten years?
  21. How did you get your start?

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