Simple Questions as Conversation Catalysts




Questions make great meeting icebreaker/conversation catalysts. Having a supply of good questions on hand makes it easier to introduce one when doing so is the right call in a meeting or conversation.

Too often, we make breaking the ice too complicated. While longer community-building activities or icebreakers are valuable, they are not the only option available to us.  Leaders and facilitators always need to be thinking about how to strengthen connections among participants in ways that honor their needs and the time available. We are trying to help reveal the positions and perspectives people bring to a conversation. 

While I continue to work on a short book/manifesto on this topic, I have shared below 70+ simple questions you can immediately use as conversation catalysts in your own efforts.  Some are relatively all-purpose, low-risk, and can be used simply to get people sharing. Others are more specific and can be drawn on more purposefully to help achieve a meetings objectives. 

This list is by no means exhaustive, so consider crafting your own conversation catalysts. In doing so, this summary of Warren Berger’s A More Beautiful Question (PDF) may be helpful.

  1. With what people or in what situations do you most feel the need to censor yourself? Why?
  2. If you were going to write a book, what would it be about?
  3. What is a work of art (movie, performance, book, et al) that you return to regularly? Why?
  4. Tell me about an experience that significantly shaped your beliefs about giving & receiving feedback.
  5.  Fill in the blank. I wish more people supported _________.
  6.  What new law would you like to see passed (or existing law removed) and why?
  7. For what opinion, perspective, or type of person are you most challenged to display empathy? Why might that be?
  8. Tell me about something difficult you figured out on your own how to handle/do.
  9. Tell me about a time when you were surprised to change your mind about something.
  10. How can we create an environment that allows people to BE more of who they are, not just DO more of what we want?
  11. If you could make all your colleagues follow one piece of advice, what would it be and why?
  12. How might we make more progress in the areas that matter most for those who most need it?
  13. When an idea you want to advance meets resistance, how do you typically respond?
  14. What's one thing you really wish our ___ (company, org, neighborhood) would try to make happen?
  15. Tell me about the last time you felt really inspired.
  16. Finish this sentence. I don't think it is fair that ... Follow with everyone discussing fairness and deciding what is just.
  17. What would enable you to exercise more initiative?
  18. How do you decide where to spend the capital of your convictions and commitment?
  19. How do you currently define success? How, if at all, has that changed for you over time and why?
  20. Tell me about the last time you felt "stuck" and what you did to break free.
  21. To whom and what do you hold yourself accountable and why?
  22. When (and/or with whom) are you most generous? Why? When (and/or with whom) are you most selfish? Why?
  23. Tell me about a choice you made whose risk only became apparent in hindsight.
  24. What is the most rewarding recent conversation you had?
  25. What is a normal item/detail that matters a great deal to you and why?
  26. What would you need to be more brave where (with whom) you most want to do so?
  27. Tell me about a time that fully engaged your heart, head, and hands, your passion and your talents.
  28. What is an unpopular opinion you hold and how does your perspective differ from others?
  29. If someone asks you to pay/do your fair share, how do you decide what that would include?
  30. What is unnecessarily difficult or complex to do in our organization and how would you simplify it?
  31. What is something you wish you had been told/discovered sooner?
  32. What do we need to learn in our ___ (org or profession)? What do we need to forget?
  33. What's a misperception people might have of you?           
  34. When you discover you need to learn something, how do you most often go about doing so?
  35. Share a ritual you have that helps account for your success.
  36. Confess an unpopular opinion that you hold.
  37. Create a business card with your title for an imaginary business you think should exist.
  38. What advice have you received that you chose to ignore ... and why?
  39. "What sci-fi gadget do you most wish existed in real life?" Courtesy of The Atlantic, 11/15 issue
  40. Who should play you in the movie about your life and why?
  41. When did you last feel like the "other," someone outside the group? What was that like? How did you act?
  42. What do you think you'll need to get better at or learn more about in the coming months?
  43. Talk about a time when you were very certain about something, but eventually learned it was not true.
  44. What is something you learned (or relearned) about yourself in the past 3 months?
  45. What do we already know that we could apply better here?
  46. What do you do to help others succeed?
  47. If you could make everyone in your organization read three books, what would they be and why?
  48. How might you (we) be participating in systems or power structures that marginalize others or perpetuate injustice?
  49. To whom are you most accountable and how? 
  50. If you had $10,000 and wanted to do the most good possible with it, how would you spend it?
  51. What does it mean to be a critical thinker and how would you become one on a topic new to you?
  52. What book did you learn the most from this year and what is one takeaway that has had staying power?
  53. Tell me about how you arrived at where you are today.
  54. In what situations do you most feel privileged and how?
  55. What is something that others find risky, but you do not? 
  56. What is a choice you have made that others failed to understand? 
  57. What is something you once could never imagine doing, but yet you subsequently did? What changed?
  58. What makes you cry or get emotional?  What makes you cry or get emotional?
  59. What do you most value in a collaborator or colleague and why?
  60. In what ways have you felt silenced? 
  61. If you could know with certainty all that would happen to you in the future, would you want that information?  Why or why not? 
  62. What makes you different?
  63. What do you require to be at your best?
  64. What is something you wish we were better at as an organization? How might we move in that direction? 
  65. What is one thing you think we could (should) stop doing? Why? 
  66. What is something you wish we were better at as an organization? How might we move in that direction?
  67. What do you most hope others respect you for?
  68. If you were to run for public office, what would be one of your primary campaign issues? 
  69. What message would you like to find in a fortune cookie? 
  70. What 2-3 experiences most influenced who you currently are? 
  71. Tell me about a time when you took action because you thought something was unfair or unjust. 
  72. What made your week? (source: Robert Glazer, Acceleration Partners)
  73. Talk about a time when you felt most fulfilled professionally.
  74. How do you (could you) use your social capital to benefit others? 
  75. For which public figure (politician, celebrity, et al) do you have a very strong bias (positive or negative)? What has led to this perception/belief?
  76. What is a leadership belief or practice that you wish more people would embrace?
  77. With which people or in what situations do you feel a greater obligation to say yes? Why?
  78. What does is usually required for you to change your mind about something? 

1 comment:

Joan Eisenstodt said...

LOVE these! They are so fun and perfect! When I use the '3 things in common/1 uniqueness' exercise in sessions, I suggest too that people use those outcomes as conversation starters. You know.. all those in their group loved Brussels sprouts and one can then say to someone else, "I learned how many people like Brussels sprouts. What's your take on them?"

Fun! Thanks for helping many.