12 Great Questions Leaders Ask Other Leaders

Excerpted from Chapter 26 of “Now That’s a Great Question.”


Click HERE to listen to Chapter 26 “12 Great Questions Leaders Ask Other Leaders”

When you connect with other leaders, what do you ask them?

Have you ever had the opportunity to spend time with another leader that you would love to learn from, and felt tongue-tied? These opportunities can happen spontaneously, like during a refreshment break at a conference, or finding yourself seated next to a leader on an airplane.

Or maybe you are scheduled for a one-on-one breakfast/lunch/coffee time. Or maybe you have had the opportunity to hear a great leader speak who then opened it up to Q & A and you didn’t know what to ask. (Did you know that every speaker I know is always very grateful for the person who instantly raises their hand to ask the first question?)

Here are my “Baker’s Dozen”:

You might want to start by asking, “May I ask you a question?” (I have never had anyone say, “No.”) You might also preface your question with, “I’m curious”, then ask one of the questions below:

  1. What are your favorite questions to ask those you lead?
  2. How did you get your start?
  3. What is your “Secret Sauce”? i.e. what are the 3–5 leadership principles that you have discovered and executed that have contributed to your success?
  4. What would you say has been your greatest accomplishment?
  5. Who opened doors for you?
  6. What role does God play in your life & leadership?
  7. What has been your greatest failure? And what did you learn from it?
  8. Can you please talk to me about execution? What do you do to ensure that your strategic plans actually become reality?
  9. What do you do to keep your family Priority #1?
  10. What do you do to take care of your staff?
  11. What are the keys to developing the next generation of leaders in your world?
  12. How do you continually deepen your personal relationships with your clients/customers/staff/peers/ leaders?
  13. What questions are you asking yourself lately?

If their answer to any question leaves you wanting to know more, go ahead and ask,:

“Can you please tell me more about that?”

And, of course, you will want to thank them for their answers and time.

Head’s Up! Don’t be surprised if, after they answer your question, they return the favor by asking you the very same question(s).

If you are asking your questions in a meeting or over a meal, be mindful of the clock. But also be aware that many times they will enjoy the interaction so much, they will extend the time.


  • You will gain valuable insights.
  • The leader you are interacting with will appreciate how your thoughtful questions actually provided an opportunity for them to explore more deeply their own thoughts.
  • You will almost always come away with a new friend, or will have deepened your relationship with an old friend.
  • You will no longer feel tongue-tied!

You have just listened and/or read “Chapter 26” from “Now That’s a Great Question.”  You can request your free download of the entire Audiobook and/or eBook by clicking HERE 

Bob Tiede


Bob has been on the staff of Cru for 52 years. He currently serves on the U.S. Leadership Development Team and is passionate about seeing leaders grow and multiply their effectiveness. Bob and his wife, Sherry, live in Plano, TX and are blessed with 4 incredible children and 8 remarkable grandchildren.


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