As a Taproot employee and pro bono junkie, I watch a lot of new groups come together: teams on pro bono projects, pro bono consultants at orientations, nonprofits at training sessions learning how to manage pro bono on their own.
The icebreaker question–that time-honored way of breaking down barriers and helping groups get comfortable–can really make it work. Or not. Inspired by some really awkward team moments, I created this list of inappropriate icebreakers and broke it out at our last staff retreat. Try one at your next board meeting or workshop!
1. Please tell us your name, your title, and how much you make.
2. What’s the worst budget mistake you’ve made, and how did you cover it up?
3. What is your favorite way to waste time at work without getting caught?
4. If this retreat were an island, who would you kick off?
5. What is the worst thing you’ve done to someone in this room?
6. What was your longest relationship and why did it end?
7. Tell us your work alias: the name of the one person you’d take with you to your next job plus the name of the company you wish you actually worked for.
8. When was the last time you thought, I really need a drink?
9. What’s the most outrageous thing you’ve ever done for God?
10. If you could be any microorganism for 24 hours, what would you be?
11. What breakfast cereal best represents your personal philosophy?
12. Assume there is a whole different concept of reality (like the Matrix). Describe it to us in three sentences or less.
13. When in your childhood did you feel most deprived?
14. What part of your body would you most like to get pierced? You can choose anything from the neck down.
15. Describe the person sitting next to you in terms of 3-5 pizza toppings.
16. When you are using the bathroom at someone else’s house, do you leave anything behind different than it was when you got there?
17. Tell us about the last time you vandalized something.
18. If you were to put a razor in some kind of Halloween candy, what candy would it be?
19. You’ve just shoved someone in the trunk of your car. Who is it?
20. If you could be invisible in this room for 30 minutes, what would you do?
21. Turn to the person next to you and tell them what you like least about them.
22. If you had some funky cold medina and you had to give it to someone in this room, who would you give it to?
23. Say I tell you I’m going to break your arms or your legs. Which do you choose?
24. Tell us something that you’ve never wanted to share with anyone in your family.
25. Hand your wallet or your purse to the person next to you. Let them find something interesting in it and share it with the group.
26. Have you ever had a recurring dream about someone in this room? If so, tell us about it. If not, make one up.
27. What is one thing you have with you on this retreat that you’d be totally devastated about if someone stole it from you? Where is that item right now?
28. How often do you clean between your toes?
29. What’s the nastiest habit you have?
30. If you could eliminate one thing you do in the bathroom every day so that you never had to do it again, what would you eliminate?
31. When was the last time you vomited, and what did it taste like?
