53 great questions to help you navigate difficult conversations

I recently asked a Zoom room full of 20 senior leaders and executives what questions they ask when navigating difficult conversations. In less than 2min this group generated 53 great questions that I’ve included below (unedited, so as to preserve the magic) for you legends to use.

Maybe, just maybe, this list will make your next difficult conversation just a little less ‘difficult’ and a little more generous, empathetic and curious:

  1. How can I support?
  2. What are your thoughts on this?
  3. How does that make you feel?
  4. What’s the biggest challenge here for you?
  5. Firstly ask about how they are…
  6. What are some options you can think of here?
  7. I’d love to hear your perspective and what I might be missing…
  8. What is your greatest struggle at the moment?
  9. What are your blockers and how can I help?
  10. What is keeping you up at night?
  11. How do you think I can best support you ?
  12. If you could change one thing what would it be?
  13. What else might we do…?
  14. What’s your POV on…..?
  15. Can we walk though your position?
  16. What can we do to clear the way for you on this?
  17. What is your biggest challenge?
  18. How do you see this being resolved?
  19. What are 3 other ways forward?
  20. How can I help to navigate through this?
  21. How could the team support you through this?
  22. What’s your idea of success?
  23. Have you resolved situations like this before?
  24. How can we help make this better?
  25. How can I help?
  26. Is there anything we/I could do to help
  27. Interesting you said x, what is it that you mean by x?
  28. What’s your definition of success in this situation?
  29. Can you explain the problem to me?
  30. Do you mind running me through…
  31. What’s the one thing you need right now to help you?
  32. What do you think about that? How can I help?
  33. Let’s focus on what you want to achieve next
  34. How do you feel about this?
  35. What would be your ideal outcome?
  36. Follow up question to what’s keeping you up at night….what else is there?
  37. What is your number one goal/objective
  38. I would what makes it difficult for you to complete this task so that i am able to support you in a way that adds value for you
  39. What is the outcome you are seeking to achieve?
  40. And what else?
  41. How can I help you achieve your goals?
  42. I need your help with something..
  43. What are the things we can control in this situation?
  44. What does success look like for you?
  45. Why do you think that matters?
  46. If I were to help, what would that look like for you?
  47. What is stopping you from being the best version of yourself?
  48. What does success look like to you?
  49. How can I help you achieve your goals? What goals are you hoping I can assist you with?
  50. Can you please help me understand why this is a priority?
  51. Is there anything we have not discussed which you feel we need to?
  52. Is there anything that is going on outside of work/this project which is causing you stress? How can we help you?
  53. What do you think we need to improve?