20 Questions to Ask Other Leaders

As a leader, how do you become a better leader? If you’re like me, you probably read a lot of books, listen to podcasts, and attend a few conferences. But one of the best ways to grow is to ask other leaders questions.

Photo courtesy of ©iStockphoto.com/JLGutierrez, Image #3401233

A few weeks ago, Michael Smith called and asked if he could interview me. Michael is 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 the 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 has 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.

Question: What do you like to ask other leaders when you get the chance?
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Posted on 19 June 2009

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33 Comments so far

  1. okjedi says:

    A great set of questions. Thank you!

  2. Michael – I would be very interested in reading your answers to each of these questions. Maybe as a blog entry per answer and then encourage others to give their own responses. Can you imagine the collective resource that could become for organizational leadership? Pretty powerful potential – thank you Michael Smith for your excellent thought-provoking questions and your exemplary stewardship of your sabbatical – your congregation is blessed to have you as a leader!

  3. MonikaM says:

    These are super. My questions:
    1. Can you recall a time when you were at the end of your rope when faced with solving a problem? If yes, what role, if any, did the supernatural play in how the resolution came about?
    2. Has the weight of responsibility in your leadership ever have any negative effects on other areas of your life? If yes, how long did it take from when you realized what was happening to when you made some changes? How were you able to act so quickly or why was it a lengthy process?
    I like this question:) I could go on…I think I'll find someone to interview too! Another great motivational/informational blog:) I nearly always DO something or start working on something after I read them:)

  4. JimMartin says:

    These are wonderful questions! Very thoughtful and are the kind of questions that invite reflection. I will use these. Thanks for posting these.

  5. MonikaM says:

    Yes. Yes. Would love that!

  6. Bre says:

    Mr. Hyatt – These are great, thought-provoking questions, and I'm very interested to read your answers. Please let us know when Michael Smith posts them! I'm excited to read the answers from other leaders he's interviewed as well.

    And on a general note, thank you for having the courage to blog. I've been reading (lurking) for a while now, and you continue to quietly inspire me.

  7. I’d like to echo the request to see your answers. :)

  8. Here's another question: Which book or books have influenced you the most?

  9. JoBrunette says:

    Excellent! Thanks for sharing, and I too, await your answers with bated breath! Be blessed.

  10. Cal says:

    Michael, I love this but you could make it better.
    Video yourself answering the questions and post one answer each day to your blog.

    • That's a very interesting idea. Hmmm.

      • Joel Ceballos says:

        Michael,
        How about a 20 minute podcast for each of your 20 questions… call this series 20 on 20… LOL.
        I enjoy your blogs and believe many more will enjoy your answers on podcast format – whether video or voice. Make the link available on your blog site and I think you'll be pleasantly surpised at how many of us will download your material in our IPods and listen during our morning workouts… Of course the 20 blog entries would be cool too for feedback…
        Michael Smith did a great job asking thought provoking questions. Would love to hear about his sabatical project when it's completed.

  11. Phil Bandy says:

    Mike, Years ago when I ran a Salem station in Chicago our afternoon talk show host had numerous business, government and church leaders in the studio. As many times as I could I would engage them in conversation hopefully discerning some key nuggets from their knowledge. One stuck in my mind. It was Herb Kelleher, the founder of Southwest Airlines. I was having to make a decision about hiring another talk show host and I asked him what he looked at when he was hiring a key person. He was a bit earthy in his reply, but it sticks with me to this day. He said:
    "I hire attitude. I can teach any @#$%& to fly an airplane. But if someone has a bad attitude I can never change it and they can kill the organization."

  12. yes, what are your answers!

  13. patriciazell says:

    Although I am not in the corporate world, I have had leadership positions both in parenting seven children and teaching high school students. I think every leader needs to be as patient as possible because the world is throwing so many obstacles and challenges at all of us right now. Also, the biggest mistake any leader can make is hypocrisy. I sincerely hope the days of "Do as I say and not as I do" are over–leaders need to lead by example.

    And, for leaders who love God, their most important task is to ask Him for knowledge, understanding, and wisdom.

  14. Allen Resha says:

    As an entrepreneur who is in the planning of a business this article inspired me. I am going to take this and use to learn about other leaders and how they are not only leaders in their company, but but innovators. Thanks for the great post!

  15. Forrest Long says:

    These questions are great, and with a little fine-tuning can be applied to pastoral leadership as well. Coming out of a position of pastoral leadership I found them very thought-provoking and challenging. I too would like to hear your response to these Michael. Thanks for sharing them.

  16. I think you all have convinced me to try and answer each question in a separate blog post. I think this will be fun!

  17. When I have the chance to be influenced by a leader I admire, I get quiet and listen. :-) It's so natural for a leader to pour wisdom into others if we are willing to listen. A quality I admire in any leader is the willingness to remain teachable. A quality that will kill leadership is knee-jerk assumptions.

  18. Good questions Michael. I really like the questions focused on values and culture. I would also ask: How do you manage your time and priorities? What does your strategic planning process look like? How do you balance pursuing opportunities and maintaining focus? What does your process look like for developing leaders? Good post!

  19. J.R. Briggs says:

    Questions I ask leaders:
    [1] What are you reading? How much time do you devote to reading every day? week?
    [2] When are you most tempted to give in to the pressures of pleasing others rather than making tough decisions?
    [3] How would your three closest friends describe your leadership?
    [4] They say "its lonely at the top." What does friendship look like when you are a leader?
    [5] What are your rhythms? When do you rest? How do you recover and get re-energized?
    [6] What other leaders do you recommend that I talk to?

  20. Wally Bock says:

    These are great questions. The only problem I have is that a list like this may make it seem like you run down the list and then move on to something else. In real life and in the apprentice trade that is leadership, questioning, trying, and getting feedback are never-ending.

  21. Ed Hart says:

    What would the world be like if your organisation did not exist?

  22. PaulWallis says:

    Just got to this post 3 weeks after everyone else! Can I add that along with hearing the leader's verbal account of him/herself I have found it tremendously valuable to actually tag along with another leader for a day and simply watch. Sometimes actions speak louder than words. I'm a very verbal learner but actually seeing another leader's attitude and approach in action – I have found that invaluable.

  23. What a fantastic post! I really appreciated it…


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