Icebreaker questions for work and team meetings

Safe for a room with your manager in it. Good for standups, onboarding and offsites.

1. Describe a typo you sent at work that you still cringe about.
2. A manager ten years younger than you, or one thirty years older?
3. Never have I ever let an AI write something and sent it under my own name.
4. Leave a voicemail for the head of a company you admire, out loud, right now.
5. What's the best or strangest perk any job has ever given you?
6. A manager who inspects every single thing you do, or one you can never get hold of?
7. Never have I ever spent my own birthday working a full day.
8. Invent an anthem for your workplace on the spot and sing the chorus.
9. What job did you want at age ten, and how far are you from it today?
10. Camera on for every online meeting forever, or never allowed to switch it on again?
11. Never have I ever blamed my connection to escape a meeting early.
12. Give the player beside you the most over-the-top confident handshake you can manage.
13. What's the one thing you always do on the way to work, no matter what?
14. A one-minute commute with regular late nights, or a long journey and never any overtime?
15. Never have I ever checked work email while on paid leave.
16. Celebrate an imaginary signed contract with a high five for everyone within reach.
17. Which work thought sneaks into your head on a day off and refuses to leave?
18. Two hours each way to a job you love, or five minutes to one you feel nothing about?
19. Never have I ever drifted off to sleep in the middle of a meeting.
20. Talk for sixty seconds using only corporate buzzwords. No actual information allowed.
21. How do you actually end your emails, and what do you secretly wish you could write instead?
22. A full suit every day of your life, or the exact same casual outfit every day of your life?
23. Never have I ever woken up tired because I spent the night dreaming about my job.
24. Act out a normal day at your job without a single word. Everyone guesses your role.
25. Explain your job the way you'd explain it to a six-year-old.
26. A four-day week that pays less, or five days at exactly what you earn today?
27. Never have I ever lost a colleague's name halfway through introducing them.
28. Give a thirty-second motivational speech to kick off everyone's workday.
29. What was the very first job you got paid for, and how long did you last?
30. Move to a new company every two years, or stay at one place for forty?