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

Photo courtesy of ©iStockphoto.com/JLGutierrez

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 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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  • Michael


    thanks Michael for valuable questions.

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  • http://www.faithfulchoices.com Paula

    Hi Michael,
      I love the guidance you give on helping us to become better leaders.  A while back to offered your readers an opportunity to receive free leadership training from an organization you trust.  Is that offer still available?  If so, what is your code for the discount?

  • http://www.facebook.com/people/Tiffany-Harris/100002104788202 Tiffany Harris

    Absolutely a great list of questions. Thank you! I just finished a book called “That’s a Great Question” by management consultant Greg Bustin. In it, he poses more than 500 questions that top business leaders use to help drive results and impact change at their organizations. It’s been a huge help to me as I’ve advanced at my company. Check it out at Bustin’s site http://www.bustin.com

    • http://michaelhyatt.com Michael Hyatt

      Thanks for the suggestion of that book. I just bought it.

    • Greg Bustin

      Thanks Tiffany and Mike, for mentioning my new book, “That’s A Great Question.” Through my years of consulting with leaders of small and medium-sized businesses, I have found that the greatest leaders ask themselves the toughest, most provocative questions. I collect great questions, and will add those above to my list. In my new book I share 500+ questions that probe 18 compelling topics the successful people I have worked with examine regularly. Most of my clients have enjoyed answering (and debating!) these questions with their senior leadership teams. I hope you do as well.

  • Diana

    How does work and family life relate to eachother? Do you feel a connection in any way with one to the other?  Can you separate realistically your values to family and friends as compared to partners and employees (co-workers)?

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  • Diana

    I read this post a few weeks ago and followed the link in it to “Lose it!”  Since then, I have exercised regularly and have kept my calorie intake below my goal mark for all but the first couple of days. Shedding a few ounces a day, I have already lost eight pounds. Thanks for this inspiring post! Reading it was the boost I needed to make positive changes in my life. 

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  • http://www.frymonkeys.com Alan Kay

    A great list, as always. I like to start interviews with leaders by asking,
    ‘What pleases you most in the work you have been doing?’ I keep asking, ‘What else”, and ‘How do you manage to do that?”. That allows me to then ask, ‘What’s the one thing that’s troubling you that are working on?’ You get refreshingly open answers to both sets of questions. 

  • http://www.facebook.com/people/Luz-Gonzales/791804125 Luz Gonzales

    Michael: Norman Vincent Peale was my inspiration when I started in college, in 1959 . He used to send every student a small booklet per month and I was always anxious to read every one. Later I came across the book Think and Grow, Rich by Napoleon Hill, which he  autographed for me and I still keep to this day. All these years God has  been my inspiration and  as young man I learned to memorized the Scriptures. Now that my son has introduced me to you, I enjoy every thing you have to say. I am an evangelist and have travel all over Latin America and thank God for guys like you, I stay upbeat and motivated. God eternally bless you.

    • http://michaelhyatt.com Michael Hyatt

      Thanks, Luz. I appreciate your kind words!

  • http://pulse.yahoo.com/_EWBNZ6YNARCYIV25PXS7HQZAEY Justin

    Great set of questions.  I will be asking everyone I know these questions. 
    The grammer in the following is wrong.  You have “ensure the your organization”.  It should be “the” or “your”.”How do you ensure the your organization and its activities are aligned with your “core values”?” 

    • http://michaelhyatt.com Michael Hyatt

      Thanks for catching that. It is fixed.

  • Frank

    Question for a leader: Articulate for me a time-line of your typical work day.

  • http://www.facebook.com/mato.attila Attila Mátó


  • Craig Mckown

    I typically ask other leaders if they are someone else!  Example…ask Andy Stanley if he is Rob Bell :)

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  • http://twitter.com/rajkhera rajkhera

    Michael, I really enjoyed your list of questions for leaders, especially the one about aligning core values with subordinates – absolutely key to making everyone in an organization row in the same direction.

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  • Nicolek Umutoni

     I would be interested in reading your answers to these questions too :).

  • http://runningwithhorses.wordpress.com/ Steve Hawkins

    Great questions Mike. Thanks for sharing.

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  • CindyD

    I absolutely love these questions and wish they had been asked of me when I was applying for a leadership promotion.  

  • CindyD

    I would like to know your answers as well.  

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  • Irena-rox

    Awesome questions! Definatley helping me with my assignment! Thanks!

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  • http://twitter.com/circle86 Circle86.com

    Excellent set of questions :) 

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  • Susiezimm

    I am a Graduate Nursing student getting ready to interview a nursing leader.  Thank you for posting these great questions.  I used most of them for my project.

  • Gordon Tredgold
  • Sam Adeyinka

    I really love this cus i’m about to interview one of my mentors and i was trying to know what to ask him. this helped. Thanks…….x

  • Sam Adeyinka

    Hello Mr. Dan, how is everything sir? I trust God you and your family are doing well…..x

  • Swati

    Can you please provide with the questionnaire for managers classified in three divisions of leadership 1) leading self, 2) leading others 3) leading organization ????