Most Powerful Questions Leaders Can Ask

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’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– 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.

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