Would You Rather Questions for Work

How to play

1. Read the question out and give everyone a few seconds to pick a side. No fence-sitting: you have to choose.
2. Go around and have each person say why. The reasons are the game.
3. Tap the side the room (or you) picked to see how everyone else on Online List Maker answered.
4. On a TV or shared screen, open Play with a group: the room votes out loud, then press Show how everyone voted.

All 67 questions

1. Would you rather always be 10 minutes late or always be 20 minutes early?
2. Would you rather be the funniest person in the room or be the smartest person in the room?
3. Would you rather work at a movie theater or work at an ice cream shop?
4. Would you rather have a summer job at a camp or have a summer job at a beach snack shack?
5. Would you rather have your first job at a fancy restaurant or have your first job at a theme park?
6. Would you rather have autocorrect change every word to banana or have your keyboard add three exclamation points to everything?
7. Would you rather have a 5-minute commute to a cramped office or have a 45-minute commute to a beautiful office?
8. Would you rather work from home forever or work in an office with your favorite people?
9. Would you rather have every meeting last 15 minutes or have half as many meetings?
10. Would you rather accidentally reply-all to the whole company or forget your camera is on during a video call?
11. Would you rather have a coworker who talks nonstop or have a coworker who never says a word?
12. Would you rather work four 10-hour days or work five 8-hour days?
13. Would you rather never send another email or never sit in another meeting?
14. Would you rather present to the CEO with no prep or present to the whole company after a week of prep?
15. Would you rather be stuck in an elevator with your boss for an hour or sit through a three-hour meeting with no agenda?
16. Would you rather get free lunch every day or get free fancy coffee every day?
17. Would you rather be the best presenter in the company or be the best problem-solver in the company?
18. Would you rather learn a brand-new skill every year or become the top expert in one skill?
19. Would you rather have a boss who checks in every hour or have a boss you hear from once a month?
20. Would you rather use a standing desk forever or use a treadmill desk forever?
21. Would you rather write every email in rhyme or write every email in all caps?
22. Would you rather dress formally every day in the office or work from home but keep your camera on all day?
23. Would you rather work a steady 9-to-5 or set your own hours but always be reachable?
24. Would you rather have a coworker who microwaves fish or have a coworker who sings at their desk?
25. Would you rather have your dream job in a tiny town or have a pretty good job in your favorite city?
26. Would you rather commute by boat or commute by cable car?
27. Would you rather have an office dog or have an office cat?
28. Would you rather have your computer restart every day at noon or have the Wi-Fi drop every day at 3pm?
29. Would you rather present your work to a room of experts or present your work to a room of five-year-olds?
30. Would you rather start every meeting with a dance break or end every meeting with a group high-five?
31. Would you rather pick any job title you want or pick any place in the world to work from?
32. Would you rather take one long vacation a year or take a long weekend every month?
33. Would you rather have a mentor who is brutally honest or have a mentor who is endlessly encouraging?
34. Would you rather never write another report or never make another slide deck?
35. Would you rather have a job that's fun but chaotic or have a job that's calm but a little boring?
36. Would you rather take a 2-hour lunch break or leave 2 hours early every Friday?
37. Would you rather work at a scrappy startup or work at a big established company?
38. Would you rather answer every work question with a song lyric or answer every work question with a movie quote?
39. Would you rather give a presentation while wearing a costume or give a presentation in a language you're still learning?
40. Would you rather work on a team where everyone agrees or work on a team that argues but gets better results?
41. Would you rather have your job change completely every year or do the exact same job for twenty years?
42. Would you rather have a button that fixes any printer jam or have a button that ends any meeting five minutes early?
43. Would you rather have a corner office with no window or have an open desk with an amazing view?
44. Would you rather start work at 6am and finish at 2pm or start work at noon and finish at 8pm?
45. Would you rather have a team lunch every Friday or have a team trip once a year?
46. Would you rather try being a zookeeper for a day or try being a chef for a day?
47. Would you rather have a job where you travel every week or have a job where you never travel?
48. Would you rather spend a workday without a keyboard or spend a workday without a mouse?
49. Would you rather have your desk move to a random spot every Monday or sit in the same spot for the next ten years?
50. Would you rather get a handwritten thank-you note from your boss or get a shout-out in front of the whole company?
51. Would you rather have the office thermostat stuck at freezing or have it stuck at sweltering?
52. Would you rather be in charge of the office playlist or be in charge of the office snack order?
53. Would you rather give an all-hands presentation with your mic stuck on mute or give one with your dog barking the whole time?
54. Would you rather have a job you love that pays just enough or have a job you don't mind that pays a lot?
55. Would you rather move far away for your dream job or stay near family in an okay job?
56. Would you rather do world-changing work no one knows is yours or do ordinary work everyone admires you for?
57. Would you rather be great at saying no or be great at asking for help?
58. Would you rather be brilliant but bad at explaining or be average but a wonderful teacher?
59. Would you rather have the courage to say what you think or have the wisdom to know when to stay quiet?
60. Would you rather be the smartest person in a room of strangers or be the least smart person in a room of geniuses?
61. Would you rather win an award for a project you barely worked on or get no credit for a project you poured yourself into?
62. Would you rather fall asleep for five random minutes every day or yawn loudly whenever someone talks to you?
63. Would you rather be a professional pillow tester or be a professional water slide tester?
64. Would you rather be a famous chef or be a famous food critic?
65. Would you rather give up coffee or give up dessert?
66. Would you rather be a travel writer or be a tour guide?
67. Would you rather do a Secret Santa at work or do a white elephant gift swap at work?

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