20 Questions to Ask Other Leaders

As a leader, how do you become a better leader? If you’re like me, probably by reading a lot of books, listening to podcasts, and attending a few conferences. Those are excellent growth strategies, but there’s one missing.  

According to Stanford psychologist Carol Dweck, people who have a growth mindset  believe they can improve themselves by their own efforts and strategies, plus input from others.

That means one of the best ways to grow as a leader is to ask questions of other leaders. 

Some time ago, Michael Smith called and asked if he could interview me. At the time, Michael was on the staff of ClearView Baptist Church in Franklin, Tennessee. We follow each other on Twitter, but we have only met one time previously. He said that he wanted to interview me on the topic of leadership. I happily agreed.

Michael began our meeting by sharing with me that he is on a sabbatical. One of his goals is to grow as a leader and one of his sabbatical projects is to interview leaders in various professions. I was honored that he choose me as someone worth interviewing.

What really impressed me was how thoroughly prepared he was. Michael asked great, thoughtful questions. In fact, the questions were so good that I asked him for permission to post them here. I have printed this list out and put it in my Moleskine notebook. The next time I am with a leader I respect, I can pop out this list and start interviewing.

  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?
  8. How do you encourage others in your organization to communicate the “core values”?
  9. Do you set aside specific times to cast vision to your employees and other leaders?
  10. How do you ensure your organization and its activities are aligned with your core values?
  11. How do you help a new employee understand the culture of your organization?
  12. When faced with two equally-qualified candidates, how do you determine whom to hire?
  13. What is one characteristic that you believe every leader should possess?
  14. What is the biggest challenge facing leaders today?
  15. What is one mistake you witness leaders making more frequently than others?
  16. What is the one behavior or trait that you have seen derail more leaders’ careers?
  17. Can you explain the impact, if any, that social networking and Web 2.0 have made on your organization or you personally?
  18. What are a few resources you would recommend to someone looking to gain insight into becoming a better leader?
  19. What advice would you give someone going into a leadership position for the first time?
  20. What are you doing to ensure you continue to grow and develop as a leader?

You might start by asking yourself these questions. Better yet, ask them and then blog about them. This will give you some basis of comparison as you begin to learn from the leaders around you.

I have a few questions about your leadership.

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