The Top 25 Questions Great Leaders Ask

Guest Post by Don Metznik

“Judge a man by his questions rather than his answers.”


Do great leaders ask great questions? Or do leaders become great because they ask great questions?  Either way, what are those great questions?

Join me on my quest to find them.

They are not to be found on some mountaintop, nor are they found in sacred books. I took a simpler route and went to the fountain of all knowledge; I Googled “Questions great leaders ask.”

Here is the outcome from 10 pages worth of search results.


I wasn’t looking for the obvious questions, like “what are my strengths,” because, well, they are obvious. Interestingly, what appeared to be brilliant and unique questions weren’t immediately identifiable. And no great leaders surfaced! Of course, the best questions may be squirreled away like some secret Coke formula, available only to large clients paying huge sums and requiring blood oaths not to reveal them.

However, some questions rose to the top. These tended to be inner focused, that is, questions that one asks oneself in brutal honestly. Others tended to be those directed to team members. In other words, the best questions were not focused on demonstrating one’s brilliance but on teamwork and service to others. These are the gutsy questions that I believe reflect great leadership.

You decide.


Here are what I believe are the top 25 great questions that anyone who is or wishes to be a great leader will ask.

From Forbes via James Slavet of Greylock Partners
Questions great leaders ask themselves every day

1. What can I do to make sure my employees are consistently acknowledged and appreciated for what they do?
2. What can I do to to support my employees to stay open to learning and to keep getting better all the time?

From Forbes via Josh Linkner
What leaders ask their teams

3. What is everyone thinking, but nobody has the courage to say?
4. If someone was going to come along and put us out of business, what would he or she do?
5. Are we focusing on preserving the problem to which we are a solution, or are we innovating our way to success?

From Forbes via Brett Nelson
Questions you ask yourself under the hood

7. How committed am I?
8. Is my product/service a real business?
9. How much power do my customers have?
10. How much power do my suppliers have?
11. Does my business have a moat around it?

From Leadership Thoughts via Martin Webster
Questions you ask your teams

12. Is there anything I can do for you?
13. What can we do better?
14. What is holding us back?

From Talent Quest

15. Am I being honest?
16. Am I inspiring others?
17. Am I being courageous?

From Inc.
Influential Leaders

18. I would like you to discuss my idea with your teammates. Will you see what they think, then give me completely unfiltered feedback?

From Center Source via Evan Owens

19. Where are we manufacturing energy?

From The Mojo Company
Just between you and the mirror

20. Do you rely completely on facts, logic, and proof? Or do you use intuition and foresight–gut and instinct–to balance those things?
21. Do you place an over-emphasis on speed and fast action? Or do you focus on gaining understanding; adapting to organizational environments; and balancing the need for progress with the need for appropriate buy-in, input, and decentralized decision-making?
22. Do you equate patience with indecision? Or do you value listening and observation in order to make good decisions?
23. Do you get annoyed when others won’t think or act the way you want them to? Or are you thankful for the variety and use it as an opportunity?
24. Do you believe leadership is about control? Or do you believe leadership is about finding ways not to have so much of it?


25. Why? (Could it be anything else? Several sources suggest that asking “why” five times will get at the root of any problem.)


In Great Leaders Don’t Have All the Answers, Robert S. Kaplan takes us into the mental inner sanctum of some leaders and this is where self-doubt and confusion reside. Kaplan says,

“As a leader, you don’t need to have all the answers or have  superhuman traits. Instead you need to focus on asking the right questions, engaging your team and focusing on what you’re actually doing.   All great leaders  have moments of doubt and go through periods of struggle.  Focus on having the wisdom to  ask the right questions of yourself  and others, and have the courage to act on what you  learn.”

Question: How’s your customer acquisition doing? Download this easy 20-Point Customer Acquisition Checklist and find out.

Note from Bob:  Let’s make it 29 Great Questions!  Here are my favorite four questions:

26.  What do you think about ____________?

27.  Wow – What else?

28.  Wow – Please tell me more?

29.  Wow – What else?  

(Many times you will get the best insights the 3rd time you ask “What else/Please tell me more?”)



Don Metznik is a marketing therapist at, helping the anxious and fearful overcome the stress of marketing, and Chief Volunteer at Starve Hunger Now (, dedicated to helping communities feed more hungry people through better strategy, communication, and technology.


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