Would You Rather Questions for Work

A good work icebreaker takes thirty seconds, includes everyone, and doesn't make anyone uncomfortable. These 77 would you rather questions for work are written for exactly that. Would you rather have a meeting that could have been an email, or an email that should have been a meeting? Work from a beach or from a treehouse? They touch on office life, habits, and hypotheticals, never on anything personal or divisive.

Managers and team leads use them to open a weekly meeting, warm up a remote call, or add some fun to onboarding. Share your screen with party mode on, read one question, and let people answer in chat or unmute. It takes a minute and gets quieter teammates talking. They also work well for trainings, workshops, and all-hands meetings where you need a light start.

How to play

1. Pick one question to open your meeting or standup.
2. Share your screen with party mode on, or read it aloud.
3. Have everyone answer in chat or with a quick show of hands.
4. Reveal the vote split and move on to the agenda.

All 77 Would You Rather Questions for Work

1. Would you rather share a desk with a coworker or share a computer with a coworker?
2. Would you rather work a 10-hour day four days a week or work a 6-hour day six days a week?
3. Would you rather write the office newsletter or organize the office softball team?
4. Would you rather have your boss follow you on social media or have your coworkers see your old yearbook?
5. Would you rather work for a startup with big risk or work for a big company with steady pay?
6. Would you rather teach a new hire everything or learn a brand-new role from scratch?
7. Would you rather work from home forever or work from a beach office forever?
8. Would you rather sit next to a loud chewer or sit next to a loud phone talker?
9. Would you rather have a job you love that pays okay or have a job you tolerate that pays great?
10. Would you rather win Employee of the Month or win the office chili cook-off?
11. Would you rather get a raise or get a better job title?
12. Would you rather be an expert on everything but never promoted or be promoted fast but always learning on the fly?
13. Would you rather have your Zoom background be stuck on a tropical beach or have it stuck on outer space?
14. Would you rather have your side hustle become your full-time job or have your full-time job pay like a side hustle and a half?
15. Would you rather have a boss who micromanages or have a boss who never answers questions?
16. Would you rather give a presentation with no slides or give a presentation with slides but no notes?
17. Would you rather have your team always agree or have your team always challenge each other?
18. Would you rather get your name on the building or get your name on the patent?
19. Would you rather work with your best friend or work with a stranger who's brilliant?
20. Would you rather have your typing sounds broadcast to the whole office or have your stomach growls broadcast to the whole office?
21. Would you rather never have another performance review or never have another team-building exercise?
22. Would you rather have a coworker who loves reply-all or have a coworker who never replies at all?
23. Would you rather spend a week job-swapping with your boss or spend a week job-swapping with the intern?
24. Would you rather have a two-hour lunch break or leave work two hours early every day?
25. Would you rather work in a quiet cubicle or work in a lively open office?
26. Would you rather have a remote job with no coworkers to chat with or have an office job with the best coworkers?
27. Would you rather be the office's go-to tech helper or be the office's go-to party planner?
28. Would you rather have a four-day workweek or have six weeks of paid vacation?
29. Would you rather be known as the office jokester or be known as the office genius?
30. Would you rather have a job with a fancy title or have a job with a flexible schedule?
31. Would you rather have a 30-minute commute by train or have a 15-minute commute by car?
32. Would you rather have your office holiday party be karaoke or have it be an ugly sweater contest?
33. Would you rather work the night shift or work the weekend shift?
34. Would you rather wear a suit every day or wear a uniform every day?
35. Would you rather have a workspace with a dog allowed or have a workspace with a free barista?
36. Would you rather work at a zoo or work at a museum?
37. Would you rather present to the CEO unprepared or present to the whole company fully prepared?
38. Would you rather have your camera stuck on during every call or have your mic stuck unmuted during every call?
39. Would you rather get feedback every day or get feedback once a year?
40. Would you rather have your email inbox always at zero or have your calendar always empty?
41. Would you rather always know what your boss thinks of you or never worry about what your boss thinks of you?
42. Would you rather have every coworker call you by the wrong name or have every coworker mispronounce your name?
43. Would you rather be the first one in the office or be the last one to leave?
44. Would you rather have a boss who's your age or have a boss who's 20 years younger?
45. Would you rather answer every call with a jingle or sign every email with a haiku?
46. Would you rather have a nap pod at work or have a massage chair at work?
47. Would you rather lead a team of 20 or be the top expert with no reports?
48. Would you rather be amazing at public speaking or be amazing at negotiating?
49. Would you rather lose all your work files or lose all your work emails?
50. Would you rather have Fridays off or have Monday mornings off?
51. Would you rather be in charge of the office fridge cleanup or be in charge of the office plant care?
52. Would you rather have unlimited PTO but a busy team or have three weeks off with coverage guaranteed?
53. Would you rather have a coworker who eats fish in the microwave or have a coworker who hums all day?
54. Would you rather be the office birthday card organizer forever or be the office coffee maker forever?
55. Would you rather get to pick your coworkers or get to pick your boss?
56. Would you rather have a desk by the window or have a desk by the snack drawer?
57. Would you rather be the boss of a job you hate or be the intern at a job you love?
58. Would you rather have a free cafeteria at work or have a free gym at work?
59. Would you rather have a coworker who takes credit for your ideas or have a coworker who never helps with group work?
60. Would you rather get promoted every year or get to choose your own projects?
61. Would you rather have a video call with your cat filter stuck on or have a call where your screen share shows your shopping cart?
62. Would you rather have a job with a great team and okay pay or have a job with great pay and an okay team?
63. Would you rather have a job that's always busy or have a job that's always slow?
64. Would you rather have a standing desk that won't go down or have a chair that won't stop spinning?
65. Would you rather have your job be 100 percent meetings or have your job be 100 percent spreadsheets?
66. Would you rather get free lunch every Friday or get free coffee every day?
67. Would you rather have a job that changes the world with no credit or have a job that gets you credit but changes little?
68. Would you rather go to a conference in Las Vegas or go to a conference in Orlando?
69. Would you rather say "let's circle back" every sentence or say "per my last email" every sentence?
70. Would you rather get a corner office or get to work from anywhere?
71. Would you rather have a 7 a.m. meeting every day or have a 6 p.m. meeting every day?
72. Would you rather have the office thermostat stuck at 60 or have it stuck at 80?
73. Would you rather have your kid crash every video call or have your pet crash every video call?
74. Would you rather have every meeting be an email or have every email be a meeting?
75. Would you rather take a sabbatical for six months or get a 20 percent raise?
76. Would you rather switch jobs every two years or stay at one company for 30 years?
77. Would you rather be stuck in an all-day meeting or be stuck answering 200 emails?

Questions people ask

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