1. How do you demonstrate leadership?

2. How do you invest in developing your leadership skills?

3. What leaders inspire you, and why?

4. What are your primary leadership strengths?

5. Who are your leadership mentors?

6. What are your metrics for determining your effectiveness?

7. Who is someone you can enlist to help enact needed change?

8. Are you guiding/coaching your people? (Bill Campbell)

9. Who is counting on you to lead?

10. What tone does your presence establish in the organization, and how does it change while you’re away?

11. What will result from you succeeding and failing as a leader?

12. How have you abdicated leadership responsibilities?

13. How do you address your leadership gap?

14. How are you able to get your people to do heroic things? (Bill Campbell)

15. What mentee will carry on your legacy?

16. How are you leaving your mark on the organization?

17. How do you surprise and delight your working relationships?

18. Who are the primary voices that influence your leadership?

19. How do you celebrate the successes and wins of your people? (Frank Blake)

20. What is your theory of change?

21. What is your favorite leadership win?

22. Who do you depend upon to tell you the unvarnished truth?

23. What does it take to do the impossible? (Steven Kotler)

24. What is the one thing I can do, such that by doing it, everything else is either easier or unnecessary? (Gary Keller)

25. What do people experience when you lead them? (Michael Crawford)

26. What can we do today that we couldn’t do yesterday? (Henry Kissinger)

27. How long are you going to wait before you demand the best for yourself? (Epicurus)

28. How do you know?

29. Are you being a good ancestor?

30. How do you identify your blindspots?

31. What was the best mistake you’ve ever made, and how did it lead to something better? (Tim Ferriss)

32. What would have to be true for the option under consideration to work out fantastically? (Roger Martin)

33. How can I make a living without losing my soul? (Yvon Chouinard)