40 Stupid Questions to Reframe Your Next Meeting

One well-timed and innocently-asked stupid question can be a powerful tool for reframing problems, redirecting conversation, and encouraging a decision-oriented mindset.

On a particularly busy and brain-busting day a few weeks back, I noticed that I was asking the same type of questions over and over. I started tracking these “stupid” questions in a text document. It’s been useful to review this list periodically, and have pulled it up during meetings when I was feeling stuck.

You’re invited to steal your favorite questions and build your own stupid questions list.

Scott’s Stupid Questions

  1. Why?
  2. So what?
  3. And?
  4. Why not?
  5. How?
  6. What do we need to do next?
  7. What if we didn’t do this?
  8. What’s the absolute worst thing that can happen?
  9. What are we trying to decide right now?
  10. What decision do we need to make today?
  11. What if we flipped a coin?
  12. What’s the absolute bare minimum it has to do?
  13. Is there a service that will do this for us?
  14. Can we just pay someone to do this?
  15. Are we sure no one has done this work already?
  16. Does (so and so) still care about this project?
  17. If I’m not at the meeting can you get by?
  18. Will it go away if we ignore it?
  19. Why now?
  20. Is this worth fixing?
  21. Can we scrap it and start over?
  22. Where did this idea come from?
  23. Why there?
  24. Can it be shorter?
  25. Can it be faster?
  26. Can we give them more?
  27. What does (doing x) actually cost?
  28. Is anyone taking notes?
  29. Is 30 minutes enough?
  30. Will this get edited by anyone?
  31. Do we have all of the information?
  32. How do we know that that’s true?
  33. Do we believe this is possible?
  34. Why did it happen that way the first time?
  35. Will anyone care?
  36. What are we concerned about?
  37. Are we actually worried about this?
  38. Is a meeting necessary?
  39. Can’t we just ask them?
  40. Has anyone asked?
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