Leader Prompts and Discussion Questions

As you think about posting on REV, here are some questions you can ask yourself. You can also use these ideas to create discussions.

1. What keeps you up at night?
2. Talk about the one person who has been the most influential in your life?
3. What lessons did that person teach you?
4. What do you feel most grateful for in your life?
5. What are some of the most important lessons you’ve learned so far?
6. What encouraging things do you remember about your very first job?
7. What are you proudest of in your life?
8. Was there ever a time when you felt most alone? Describe it and talk about how you came out the other side of that loneliness.
9. How has your career been different than what you’d imagined?
10. How would you like to be remembered long after you’re gone?
11. Do you have any regrets?
12. Is there anything you want people to know about you that they likely don’t know? 
13. What traits do you admire in other people?
14. Talk about the hardest thing you’ve ever done.
15. What invention would you like to see in your lifetime?
16. Besides your mom, who knows you best and why?
17. Who is the nicest person at work, and why do you think so?
18. What does a typical Monday morning look like in your house?
19. What was your worst vacation?
20. What made you laugh today?
21. What’s something you changed your mind about recently?
22. What do you have in your bag or pocket or your car that describes your personality?
23. What is the scariest thing you’ve ever done for fun?
24. If you could re-live just one year of your life, which one would it be and what would you do differently?
25. What are you pretending not to know?
26. How do you make a positive impact in your organization?
27. What would you put on a billboard?
28. Talk about the best project you ever worked on. 
29. Why do you work? And don’t just say because you need the money.
30. What is one of your happiest memories?
31. What do you know now that you wish you’d known before you started your first job?
32. If someone were to guess your personality based on your handwriting, what would they say?
33. If you could invent anything to make your life easier, what would it be?
34. Do you prefer to donate time or money to those in need? Why?
35. What is the best day of the year for you?
36. What does your dream house look like?
37. What is the greatest gift you have ever gotten, and what made it so great?
38. What is the greatest mistake you’ve ever made?
39. When did you first know what it was you wanted to do with your life?
40. What is your greatest fear and why?
41. What is your most deeply held belief?
42. If someone could answer one question for you, what would that question be and why?
43. What small bit of advice would you give to someone just beginning their career?
44. What are you interested in that probably no one else is?
45. What did you Google last?
46. What do you look for in an employee?
47. What are you absolutely determined to accomplish in your organization?
48. Who has impressed you most with what they’ve accomplished?
49. How do you relax after a hard day of work? 
50. Where do you usually go when you have time off?
51. What risks have you taken that were worth it?
52. Who inspires you to be better?
53. What do you have doubts about?
54. What’s the hardest lesson you’ve learned? 
55. What’s the best thing about getting older? The worst?
56. What challenging thing are you working through these days?
57. Which of your scars has the best story behind it?
58. What were some of the turning points in your life? 
59. What are some personal rules you never break? 
60. What is one professional rule you never break?
61. What’s the worst advice you’ve ever received? 
62. When was the last time you changed your opinion or belief about something major? 
63. What are some events in your life that made you who you are today?
64. In your opinion, what characteristics make a good leader?
65. Tell us a story of a leader who has impacted your life.
66. Tell us about your hometown.
67. What drew you to your current position?
68. Why is it important for leaders to be good listeners? 
69. In what ways have you grown as a person this year? What/who has influenced you? And what have you learned?
70. What can you do or change in your life to focus more on your health and wellbeing? Be honest.
71. What do you think is the most unique thing about you? Do you keep it hidden or let it show? 
72. What encouraging things do you remember about your very first job?
73. How has your career been different than what you’d imagined?
74. How would you like to be remembered long after you’ve retired?
75. Do you have any regrets?
76. Is there anything you want people to know about you that they likely don’t know? 
77. What traits do you admire in other people?
78. Talk about the hardest thing you’ve ever done.
79. How do you relax after a hard day of work?
80. Talk about the best project you ever worked on. 
81. What small gesture from a stranger had the biggest impact on you?
82. Why is it important for leaders to be good listeners? 
83. What do you think is your biggest personal success? What about your biggest professional success?