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100 engaging prompts for community conversation

Updated: Nov 29, 2022

Everyone has something interesting to say, and people want to hear our thoughts!

Engaging with people in public spaces through conversation and connection benefits our own professional development, and builds the community we all so desperately crave. It benefits everyone. Sharing is caring!

That said, thinking out loud on social media, at an event, in a Medium article, or even in a meeting, can be challenging. First you need the confidence to take a chance and share your ideas. Still, it can be difficult to even come up with something to talk about.

If you're in need of some inspiration, give this list of 100 conversation prompts a gander. See what strikes you and start putting pen to paper (or fingers to keys, voice to text, etc.)

Experiment, iterate, and have fun!

You can also download a PDF here.

🎙 ✍️ 👩🏾‍💻 📠

The 100 Prompts

1. Your manifesto

2. Your mission

3. People, places, or things that inspire you

4. An accomplishment

5. A time when you found your voice

6. A cause you are passionate about

7. Something that frustrates you, with solutions

8. Your values and beliefs, and how you adhere to them in your work

9. A favorite quote, and why it’s meaningful

10. A challenge you overcame and what you learned

11. A progress update

12. What you learned in your first job

13. The expectations you had for your career when you were younger and how it’s

played out

14. Celebrate a colleague

15. Something you learned today

16. A favorite resource (book, podcast, etc.)

17. Advice based on an experience

18. Something you learned at a recent event

19. What motivates you

20. The story of how you got to where you are

21. Advice you would give your younger self

22. A time you proved something to yourself

23. A lesson you learned at work

24. The best advice you ever got from a manager

25. Something radically honest

26. Ask for feedback

27. Ask for help

28. Industry trends

29. A solution to a common problem or challenge (e.g., time management, prioritizing,


30. A prompt or question

31. Something you’re proud of

32. What’s going on in your life, at work, with your business

33. What you’ve been thinking about

34. What you’ve been talking about with others

35. The skills you use the most or the least

36. Something you’re grateful for

37. Something you would do if you knew you couldn’t fail

38. A time you took a leap or went outside your comfort zone

39. An opportunity for self-improvement and how you’re addressing it

40. A deep question you want to answer by the time you’re 85 years old

41. An educated prediction for the future

42. Something you can’t stop thinking about

43. A problem you would like to solve, and a request for ideas

44. An overview of your career path and insights you’ve gained

45. How you got your last job or client

46. Describe the qualities of your ideal coworker

47. How you use your education/training in your job

48. A giveaway - favorite book, conference ticket, mentoring

49. What you enjoy about working in your industry

50. Your ideal job - the what, the where, the why

51. Experiences with burnout

52. Reflections on workplace culture

53. Your take on current events

54. Working with challenging stakeholders

55. A goal and how you plan to achieve it

56. Introduce or reintroduce yourself

57. Something you’re looking for

58. Advice for getting a job in your field

59. Productivity tips

60. Advice for newbies

61. The most challenging aspect of your job

62. The steps you took to achieve a goal

63. Something you would do differently if you could go back in time

64. Your origin story; the origin story of your business

65. Roundup of links on a favorite topic

66. Conduct a poll

67. Where you see yourself in 6 or 12 months

68. The best part of your workday/workweek

69. An interview with someone in your field

70. A key takeaway from an article you read

71. A how-to guide

72. A major realization and what you did next

73. A message to your teenage self

74. The best/worst boss you ever had

75. Thank someone

76. How you take care of yourself

77. How you got into your field

78. A time someone changed your perspective

79. Your top career tips

80. A guest post from someone in your field

81. Your favorite tools/apps

82. Something you’d like to change about your field

83. An unpopular opinion

84. Lists! My top 5…. 10 methods for…

85. Who you are outside of work

86. Your top favorite social media accounts

87. The state of diversity, equity, and inclusion in your field and how it can improve

88. A day in the life

89. A new idea

90. Extend an invite to the community

91. How you maintain your work/life balance

92. What fascinates you

93. Make an argument against something that others believe to be correct

94. An announcement

95. Something you wish people knew about you; assumptions they make

96. Insider tips and tricks

97. Your take on something controversial

98. A review of a product or service that others are interested in

99. A template

100. A reality check


1. Be authentic--be yourself! Showcase your personality

2. Remember your audience and what they’re interested in - relevance!

3. Encourage engagement

4. Make it visual with an image, gif, meme or video

5. Put captions on videos

6. Touch on the why -- why is this thing you’re talking about important?

7. Turn your social media posts into blog posts or Medium articles

8. Draft on paper or in a doc before publishing it in public so you focus on the content

rather than worrying about the platform interface

9. Emojis! 👽 💓 👀

10. Promptly respond to comments to continue the conversation

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