60 questions to help you unleash your team’s best thinking


“The best leaders tell less and ask more.” — Liz Wiseman, author of Multipliers


Sure, great leaders are curious and ask a lot of questions. But which ones? And when?

Deployed wisely, thoughtful questions can clarify and advance thinking — both yours and your direct reports’ — and can open the door to innovation and better performance. Use this list to spark ideas.

To seek your direct reports’ perspective on ideas, situations, or decisions:
  1. What does this situation look like from your perspective? What makes you say that?
  2. Could you say more about what do you mean by X?
  3. How are you feeling about this?
  4. What do you think is the crux of this issue? Why?
  5. What’s the most important thing that we need to consider? Why?
  6. What’s the most exciting or interesting part of this?
  7. What’s the most difficult part of this issue? Why?
  8. What impact is this having/could this have?
  9. What do you think I should I know about this that I might not know?
  10. What would be the most helpful thing to take away from this conversation in order to make progress?
  11. What have you tried so far? And why hasn’t it worked?
  12. What is the number one hurdle getting in the way of our progress and what would change if we could remove that hurdle?
  13. What is it that we’re trying to achieve here?
  14. What would a successful outcome look like? Let’s describe it in detail.
To push your team to challenge assumptions, see potential pitfalls, and consider additional options:
  1. What’s the biggest opportunity you think we’re missing out on?
  2. How is this situation different from what we’ve faced before?
  3. How is this situation similar to situations we’ve faced before? How might that experience be affecting our perspective now?
  4. How have things changed since last time we did this that might lead us to change our approach?
  5. What important information could we be missing?
  6. What do people who disagree with this say and what are the merits of those perspectives?
  7. What’s another way to interpret the data or information?
  8. If we had twice as long to do this work, what might we have time to explore or develop that we’re not looking at now?
  9. If we had half the budget to pursue this idea, what key elements would we still want to keep?
  10. If we knew that a competitor was pursuing a similar idea, what would our version have that would set it apart?
To expand your direct reports’ view of possible ideas or solutions:
  1. I’m curious what ideas you have for how to address this?
  2. What are some possible solutions you see?
  3. If we couldn’t do it the way you’re suggesting, what are some other ways we could get the outcome we want?
  4. What have we learned here that we can apply for next time?
  5. What are some ways we can prevent this from happening again?
  6. If we forget about finding a perfect solution, what are the options we can think of now?
  7. If we forget about feasibility concerns for now, what is the ideal outcome we want?
  8. Who has a different perspective and could give us additional ideas for how to handle this?
  9. What other sources could we consult?
  10. What do we not yet know or understand about this situation that we’d like to know? How might we go about finding that out?
  11. What are some possible paths we could take to reach our goal?
  12. What people or resources could we tap to help us reach our goal?
To help your direct reports evaluate ideas and solutions to determine whether they’re worth pursuing:
  1. Of the solutions/ideas we’ve listed, what are the top one or two you think are worth considering further? Why?
  2. We’ve said that we want to achieve X — how could we define that as a goal using the phrase “We want to get from X to Y by when”?
  3. What do you see as the pros and cons of this idea?
  4. What do we stand to learn by trying this idea?
  5. How would this idea contribute to our business goals or solve the problem of X?
  6. How would this fit in with everything else we’re doing?
  7. Let’s say this idea ends up failing. What are some reasons why?
  8. Let’s say this idea succeeds beyond our expectations. What are some reasons why?
  9. If this approach doesn’t work, what’s the worst-case scenario of what would happen? The best-case scenario?
  10. What haven’t we discussed yet that could be important to the success of this idea?
  11. What factors that are out of our control might affect the implementation or outcome of this idea?
  12. What else could we do to increase the likelihood of success of this idea?
  13. Who else might have a valuable perspective on this? What do you think their input might be? Should we seek their input?
  14. Whose work would be impacted by this decision? What do you think their input might be? Should we seek their input?
  15. What other information do we need and from whom before deciding whether to move forward with this?
To shift any discussion from ideas toward action:
  1. What are some good next steps?
  2. To implement that idea, what would the specifics look like?
  3. Based on this discussion, what’s one thing we should commit to doing to make progress and when?
  4. What people and resources do you need to make this solution happen?
  5. What’s a reasonable time frame for this?
  6. How should we measure progress?
  7. As you pursue this, at what point would my input or feedback be helpful?
  8. What are milestones along the way that would alert us to whether we’re headed in the right direction?
  9. What obstacles do we anticipate getting in our way and how might we get around those obstacles?