Would You Rather Questions for Work

All 50 Would You Rather questions

A question shows how players split once it has 10 answers, marked “early” until it has 30.

1. 1

   Would you rather have a 4-day work week or work from anywhere you want?

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2. 2

   Would you rather never have another meeting or never answer another email?

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3. 3

   Would you rather have a desk with an amazing view or have a desk right next to the snacks?

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4. 4

   Would you rather work from a beach or work from a cabin in the woods?

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5. 5

   Would you rather present to 500 people or write a 20-page report?

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6. 6

   Would you rather have a golden retriever as a coworker or have a robot as a coworker?

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7. 7

   Would you rather be stuck on mute forever or have your camera stuck on forever?

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8. 8

   Would you rather only communicate in GIFs or only communicate in voice memos?

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9. 9

   Would you rather cap every meeting at 15 minutes or get one meeting-free week every month?

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10. 10

    Would you rather be the office DJ or be in charge of team snacks?

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11. 11

    Would you rather swap jobs with your manager for a day or swap jobs with someone on another team for a day?

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12. 12

    Would you rather have a nap pod at work or have a game room at work?

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13. 13

    Would you rather start at 6 a.m. and finish at 2 p.m. or start at 11 a.m. and finish at 7 p.m.?

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14. 14

    Would you rather work in total silence or work with music always playing?

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15. 15

    Would you rather bring a pet to work every day or get a free catered lunch every day?

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16. 16

    Would you rather be great at public speaking or be great at writing?

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17. 17

    Would you rather work on one big project all year or work on ten small projects?

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18. 18

    Would you rather be known as the team's problem solver or be known as the team's morale booster?

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19. 19

    Would you rather have your dream job in a boring city or have an okay job in your dream city?

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20. 20

    Would you rather keep every browser tab open forever or close every tab right now?

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21. 21

    Would you rather have Fridays off or have Mondays off?

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22. 22

    Would you rather get career advice from your 10-year-old self or get career advice from your 80-year-old self?

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23. 23

    Would you rather have the office always a bit too cold or have the office always a bit too warm?

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24. 24

    Would you rather sit in a meeting that could have been an email or write an email that should have been a meeting?

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25. 25

    Would you rather have plants everywhere in the office or have art everywhere in the office?

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26. 26

    Would you rather instantly understand any spreadsheet or write any email in one second?

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27. 27

    Would you rather accidentally reply-all to the whole company or share your screen with 40 tabs open?

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28. 28

    Would you rather do the same tasks every day or do totally different tasks every day?

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29. 29

    Would you rather have a team retreat at a theme park or have a team retreat at a cozy cabin?

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30. 30

    Would you rather plan the office party or host the team trivia night?

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31. 31

    Would you rather have a private office with no window or have an open desk by a big window?

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32. 32

    Would you rather get an extra week of vacation or get a brand-new laptop every year?

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33. 33

    Would you rather never forget a name or never forget a deadline?

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34. 34

    Would you rather be a world-class chess player or be a world-class karaoke singer?

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35. 35

    Would you rather go on a work trip to Tokyo or go on a work trip to Paris?

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36. 36

    Would you rather commute by boat or commute by cable car?

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37. 37

    Would you rather have your job featured in a documentary or have your job turned into a sitcom?

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38. 38

    Would you rather start every meeting with a joke or start every meeting with a fun fact?

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39. 39

    Would you rather have your office on a cruise ship or have your office in a treehouse?

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40. 40

    Would you rather win the team award for best snacks or win the team award for best playlist?

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41. 41

    Would you rather take a 1-hour lunch break or leave an hour early every day?

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42. 42

    Would you rather know every keyboard shortcut or type twice as fast?

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43. 43

    Would you rather read every unread email right now or delete every unread email right now?

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44. 44

    Would you rather learn a new skill from a coworker or teach your favorite skill to the team?

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45. 45

    Would you rather have a robot that takes your meeting notes or have a robot that answers your emails?

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46. 46

    Would you rather have an office with a slide or have an office with a rooftop garden?

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47. 47

    Would you rather have a team mascot or have a team theme song?

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48. 48

    Would you rather have a pirate captain as your manager or have a wizard as your manager?

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49. 49

    Would you rather pick every project you work on or pick everyone you work with?

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50. 50

    Would you rather answer every message right away or check messages only twice a day?

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