Leaders and the Questions They Ask

question-mark9 As I mentioned before, I’m leading a few breakout sessions at the National Student Leadership Conference at Taylor University on The Leader as Question-Asker. The art of asking significant questions is a topic I’ve been studying rigorously for the past several years. In fact, I have been writing the material for this breakout session in my head for the past several years (I just hope it comes out coherently).

One of the things I love doing is getting around good leaders and asking them thoughtful questions. It’s one of the best ways to learn as a leader.

A few years ago, thanks to Michael Hyatt, I began to gather thoughtful questions to ask leaders. Then I cut out the list and taped it into my Moleskine notebook. When I am grabbing coffee with a leader I pull the list out and ask a handful of them.

1. Can you name a person who has had a tremendous impact on you as a leader? Maybe some one who has been a mentor to you? Why and how did this person impact your life?

2. What are the most important decisions you make as a leader of your organization?

3. As an organization gets larger there can be a tendency for the “institution” to dampen the “inspiration.” How do you keep this from happening?

4. How do you encourage creative thinking within your organization?

5. Where do the great ideas come from in your organization?

6. Which is most important to your organization—mission, core values or vision?

7. How do you or other leaders in your organization communicate the “core values”? How do you encourage others in your organization to communicate the “core values”?

8. Do you set aside specific times to cast vision to your employees and other leaders?

9. How do you ensure the your organization and its activities are aligned with what you care about?

10. How do you help a new employee understand the culture of your organization?

11. When faced with two equally-qualified candidates, how do you determine whom to hire?

12. What is one characteristic that you believe every leader should possess?

13. What is the biggest challenge facing leaders today?

14. What is the biggest challenge you are facing as a leader today?

15. What is one mistake you observe leaders making more frequently than others?

16. What is the one behavior or trait that you have seen derail more leaders’ careers?

17. What are a few resources you would recommend to someone looking to gain insight into becoming a better leader?

18. What advice would you give someone going into a leadership position for the first time?

19. What are you doing to ensure you continue to grow and develop as a leader?

A few additions from blog reader Alex Barker:

  1. What is the greatest idea you’ve ever learned that’s shaped your life?
  2. How has failure shaped your life?
  3. What holds you back from success – and how do you define it?

What other questions would you want to add to the list?