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Work deck · 30 cards

Leadership questions for teams

Discuss leadership styles and lessons.

How to play

Every card in the pile

  1. 01What does a leader do that makes people want to share ideas?
  2. 02What's the difference between a boss and a leader?
  3. 03What quality do you admire most in a leader?
  4. 04What's a leadership challenge you've faced, with or without the title?
  5. 05If you led this team for a month, what would you change first?
  6. 06What's the hardest thing for you to delegate or hand off?
  7. 07What makes you trust a leader?
  8. 08Who's the best boss you've ever had, and what did they do differently?
  9. 09How has your idea of a good leader changed over time?
  10. 10What book, podcast, or person shaped how you think about leadership?
  11. 11What makes it safe for you to speak up in a meeting?
  12. 12How do you give constructive criticism without crushing someone?
  13. 13What's the hardest call you've had to make at work?
  14. 14What's the best thing a mentor ever did for you?
  15. 15What's the worst leadership habit you've seen?
  16. 16When did you lead without having the title?
  17. 17Can you be friends with the people you manage?
  18. 18When did you have to make or defend an unpopular decision?
  19. 19When has someone at work stood up for you, or you for them?
  20. 20What's a sign that someone has let power go to their head?
  21. 21What's one piece of advice you'd give to someone stepping into a leadership role?
  22. 22How can you tell when a teammate needs support but won't ask?
  23. 23What's something a leader did that made you feel trusted?
  24. 24What do you need from a leader during uncertain times?
  25. 25Who took a chance on you early in your career?
  26. 26Which leader from history do you admire, and why?
  27. 27What's a leadership mistake you've witnessed that taught you something?
  28. 28How should a leader own a failure in front of their team?
  29. 29What one word describes how you lead?
  30. 30Should a leader always have the answer, or is "I don't know" okay?

How to use them

Read one out loud and let everyone answer before the next. Or start a game: Candor deals the pile at random, and a room code puts the same card on every phone.