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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  • okjedi

    A great set of questions. Thank you!

  • http://www.linkedin.com/in/willarmstrong will armstrong

    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!

  • Monika Miko

    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:)

  • JimMartin

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

  • Monika Miko

    Yes. Yes. Would love that!

  • Bre

    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.

  • http://www.higherlevelgroup.com/danieldecker.html Daniel Decker

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

  • http://www.rose-publishing.com Gretchen Goldsmith

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

  • http://joannebrunette.blogspot.com/ JoBrunette

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

  • Cal

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

    • Michael Hyatt

      That's a very interesting idea. Hmmm.

      • Joel Ceballos

        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.

  • Phil Bandy

    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."

  • http://www.godsabsolutelove.com patriciazell

    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.

  • http://catalystconference.com CatalsytLeader

    yes, what are your answers!

  • Allen Resha

    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!

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  • Forrest Long

    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.

  • Michael Hyatt

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

  • http://MyGemofWisdom.com Angie Breidenbach

    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.

  • http://www.stephenblandino.com Stephen Blandino

    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!

  • http://www.jrbriggs.com J.R. Briggs

    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?

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  • http://blog.threestarleadership.com Wally Bock

    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.

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  • http://www.yourfbs.co.uk Ed Hart

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

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  • PaulWallis

    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.

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  • http://jodyfransch.wordpress.com Jody T Fransch

    What a fantastic post! I really appreciated it…

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  • http://charlesstone.net charles stone

    superb questions to ask ourselves. I will retweet.

  • http://thoughtsaboutnothing.com Kyle Reed

    I would like to ask you Mr Hyatt, can you do a blog post with answers to these questions like I was asking you them.

  • http://www.lauraclick.com Laura

    These are fantastic! I would especially love to know how you answered #3. Did you ever do the video follow up to these as mentioned in the comments? If so, where can I find it? I'd love to see what you said.

    • Michael Hyatt

      I have not, but reading these comments, I am motivated to do so. Thanks.

  • http://www.colinfaulknerblog.com Colin_Faulkner

    So do we get to see your answers?

    • Michael Hyatt

      I probably should take these one at a time and create a series of blog posts. Thanks for the reminder.

  • Michael Hyatt

    No, I have never done it—but I need to. Thanks for the “vote.”

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  • culturesmithconsulting

    One of my favorite questions to ask leaders is, "What have you learned the hard way?"

    Would love to hear your reply on that one, as you have a chance.

    • http://martialpreneur.com Kevin

      Ooo…I like that one!

  • http://www.kaylomarketing.com Nigel

    Great Set of Questions. I will definitely use them with the VP of Google, Shona Brown today at an Alumni Dinner!

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  • http://www.gendads.com Gary Taylor

    These is almost as provoking as the one question my soninlaw posed to our 12 year old's rite of passage kid AND me on our manhood backpack. ( described in my blog http://www.gendads.com) "OK, guys, Jesus is right up the trail. You can ask him two questions. You have ten minutes to get it together." Now I ask Hyatteers: What two questions would YOU ask Jesus? Then with your knowledge of Scripture, what do you believe will be His answer?

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  • Sandra

    Have just discovered this blog and want to thank you for sharing. I am about to embark on some interviews of CEOs and these will be excellent questions to ask. Thank you.

  • Ezekiel Clarke

    Michael, I´m an Assistant Pastor in Panama City, Panama and am passionate about Leadership Development (my own and helping others to grow). I´m about to start interviewing some leaders I know and admire (as a result of reading your post). My question for you would be: Should I send them the questions in advance or ask them right at the moment of the interview? What do you suggest?

    Ezequiel Clarke

    • http://michaelhyatt.com Michael Hyatt

      Ask them what they prefer. Some may prefer them in advance.

  • 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.

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  • 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.

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  • 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 ????