The 50 Most Powerful Questions Leaders Can Ask

Guest Post by Mike Myatt

Originally posted @

The best leaders don’t engage in monologues; they stimulate conversations.

They understand conversations are not competitions to be won, but opportunities to enrich, inspire, challenge, illuminate and learn. So, what makes for great dialogue? Great questions.

I’ve always said, a leader’s job is not to leverage their people, but to create leverage for their people. Put another way, smart leaders find out what their people need to be successful and then provide those things to them – a difficult task for the disengaged leader…

Whether you like it or not, your success as a leader will be largely tied to your team building ability. Not only do great leaders understand how to recruit a top executive team, but they also understand how to build cohesion among team members through collaboration while addressing specific situational and contextual needs. They understand how to use intelligent questions to advance the betterment of those they lead.

The best leaders always have a great feel for the pulse of their organization. They realize the importance of being consistently, purposefully and intensely engaged with their team. They understand how to unlock hidden value and unleash creativity and passion with the use of well-timed questions.

I was recently asked the following question by one of our readers: “What’s the most powerful question of all?” My belief is that there is no perfect question, just the right question for the moment. My specific response was as follows:

“My belief is that the most powerful question of all is the one that works within the context of the situation at hand. The question must be appropriate to the person(s) being addressed, the timing must be spot-on, but most importantly it must unlock the door to reveal the needed input/feedback/information.

Relying on any single question to serve as the omnibus catch-all question is dangerous. I’m not sure what the most powerful question in the world is, but I know that the most powerful question of the moment changes frequently …”

Therefore, in the text that follows I’ll provide you with a resource that is immediately actionable, and highly productive – a list of questions (in no particular order) that can be used across situations, constituencies and reporting lines. I have found that one of the most effective ways for leaders to lead their team is by helping them refine and justify their reasoning through the use of intelligent questions. This serves to not only align interests and areas of focus, but also to facilitate the exchange of insights, and to acquire useful knowledge and information – it also builds stronger relationships. Contrary to the beliefs of some, dialogue is a healthy thing. I strongly recommend to all leaders that they routinely ask team members the following questions:

1. Why? (my personal favorite and the most powerful one-word question on the planet)

2. Other than your title, why should anyone be led by you?

3. How can I help you with that? What do you need from me in order to make that happen?

4. That’s an interesting thought, what process did you go through to reach that conclusion?

5. What’s our biggest risk in this, and what’s your fallback position?

6. What rules should we be breaking?

7. What do we need to do today to pull the future toward us and beat our competition to the future?

8. What if we did nothing at all, what would happen?

9. Are you passionate about this? If not, how do we make that happen?

10. Are we missing anything here?

11. What makes our culture unique and how do we protect that?

12. Are your efforts at work making your family stronger or putting them at risk? How can I help you here?

13. Where do our best ideas come from and how can we spawn more creativity?

14. Aside from profit motive, how does this change lives – how does this make the world a better place?

15. Why is this important to you?

16. How do we know what our [team, organization, culture, business] need to look like three years out?

17. What does this accomplish for us?

18. What are you doing on a daily basis to build into other leaders?

19. What can we do to drive decisions down closest to the point of impact?

20. What are people thinking, but afraid to express?

21. What can we do to operationalize our vision, values and strategy?

22. Which members of our team are underperforming, and how can we help them do better?

23. If we fail in this can we live with that?

24. How does this add value to our [fill in the blank]?

25. Can you give me a bit more detail on the logic used to arrive at your [costs, timing, return estimates, etc.]?

26. How will this impact [individual, team, business unit, competitive advantage, brand perception, customer satisfaction, etc.]?

27. What are the greatest challenges you face in pulling this off, and how do you plan to deal with them?

28. What can I do to lead better?

29. Where do you see “X” account in [insert time period] and what can we do to (improve customer satisfaction, increase influence with key stakeholders, increase the life-cycle value, etc.)?

30. Which markets, partners, clients, or other opportunities can add significant value to our business?

31. What’s your greatest current frustration and how can I help you with that?

32. What specific steps can you take to increase your area’s contribution margin?

33. Does this add value to our core business? How? Why?

34. Does this effectively and efficiently support our values, vision, and strategy? How? Why?

35. What can you offer as validation of proof of concept?

36. What’s our biggest miss, and how do we resolve it?

37. Who or what are we missing and how do we solve that?

38. What motivates [insert person’s name]? What’s really important to them?

39. What will be the key performance indicators for this? How will we measure them, and what hurdles do we need to hit to be successful?

40. Do you have the necessary resources (financial, technology, talent, infrastructure, etc.) to hit your objectives?

41. How can we improve the risk management, governance, control, and reporting functions for this?

42. What’s are biggest risk and how do we mitigate it?

43. Why do people come to work here, and why do they leave?

44. Why should we make this investment? How does it drive revenue, profit, brand equity, competitive advantage, etc. What are the potential risks vs. possible rewards and what is the downside of not making the investment?

45. What are your biggest obstacles and barriers to success? What are your plans to deal with them and what do you need from me?

46. How do you know if all your resources are properly aligned and connected?

47. What are the weakest points in your area and how do you plan to deal with them?

48. Who are your strongest leaders and how are you developing them to handle more responsibility?

49. What are you doing to attract new talent?

50. How would you feel if this discussion was public knowledge – would you be comfortable with that? If not, why not?

Great leaders not only view their interactions with team members as coaching and mentoring opportunities, but also as learning opportunities for themselves. When leaders don’t take the time to get to know their team members on a very personal basis, they simply won’t build the trust necessary to successfully weather the many different and often difficult seasons of leadership. Because all leaders face good times and bad, it is essential that strong, caring, and loyal relationships are established so that candor and collaboration can occur irrespective of the situation at hand.

While the aforementioned list of questions is clearly not exhaustive, it offers some insight into where a CEO should focus their efforts and attention…Perhaps best of all it places you in a constant position of being an active listener, learner, and mentor. If you have a favorite question(s) you use to focus and/or refine your team’s thinking that you’d like to share, please leave a comment below…


Mike Myatt


Mike Myatt, is a leadership advisor to Fortune 500 CEOs and Boards, Author of Hacking Leadership (Wiley), and Chairman at N2Growth. Follow him on Twitter @MikeMyatt



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