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The Ultimate List Of "Would You Rather" Questions For Work

5 min read   |  
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If you think employee engagement is hard, try engaging your employees during a morning meeting or a mid-week brainstorming session. We wouldn't want to be a part of it unless we had something exciting to break the ice with like some funny "Would you rather" questions for work.

"Would you rather" questions are a fun and unique approach to garner a lot of interaction among the team members.

When combined with a funny premise, the "why" part of the question will almost certainly yield some hilarious answers. It's a fantastic team-building activity to get to know your coworkers and employees by sharing all of the ridiculous decisions you end up making.

So, without further ado, let's look at some amazing "Would you rather" questions for work that our team happens to love:

48 Best "Would You Rather" Questions For Work That Make For Perfect Icebreakers

In this list of 48 short "Would you rather" questions, you'll find that some are funny, some are unique, and some are quite deep. Whatever question you choose, it will certainly make your team sit up and take notice.

1. Would you rather live in a tiny apartment in the city or a house in the middle of nowhere?

2. Would You Rather be always slightly hot or slightly cold?

3. What would you choose if you had the option of chewing cold, hard ice cream or eating hot, steaming food without blowing it?

4. Would you rather become a chess grandmaster or an elite kickboxer?

5. Which useless superpower would you choose out of the following?

  • No wet socks ever
  • Never have to wash hair
  • Cry on command
  • Get 10 dollars cash every year

6. Which would you rather do?

  • In the sport of your choice, set a world record at the Olympics.
  • Become the leader of your nation.
  • Record a super hit song that will be remembered for ages to come.
  • Invent something that people use daily.
  • Become an astronaut and walk on a new planet.

7. Would you rather live a regular boring life or that something unexplainable happens to you every day?

8. Which would you choose: being the best at a terrible job or being the worst at your dream job?

9. What would you choose if you had to pick between wearing clown shoes every day or wearing a clown hat for the rest of your life?

10. If given the choice of not showering for a week or not brushing your teeth for a week, what would you choose?

11. Would you rather get a paper cut every time you read a book or never be allowed to pick up a book ever again?

12. Which one would you choose: the superhuman ability to read minds or having all of your lies believed?

13. Would you rather eat only fried food or eat only boiled food for the rest of your life?

14. Which would you rather be— a great boss but a terrible human being or a bad boss but a great human being?

15. Would you rather lose the ability to cry or cry at least once a day for the rest of your life?

16. Here is a difficult "would you rather eat only…" question. If given the choice of eating mayonnaise with every dish or eating sriracha with every dish for the rest of your life, which one would you pick?

17. Would you rather have a magic van that can transport you anywhere and time-travel you back in time or a magic ring that absorbs all of the knowledge inside a book?

18. Would you rather be able to turn sand into water or air into sand?

19. Would you rather be able to eat whatever you want and be perfectly healthy, or have to sleep only one hour every day and be completely rested?

20. Would you rather own an elephant the size of a hamster or a hamster the size of an elephant?

21. What would you pick if you could either spend the rest of your life in space or live during prehistoric times?

22. Would you rather battle King Kong or Gorilla?

23. Out of these two weird food combinations, what would you pick— peanut butter with your burger or Flaming Hot Cheetos with cream cheese?

24. Would you rather accomplish something amazing for humanity but be regarded as one of the worst individuals ever, or do nothing and be remembered as a hero to everyone?

25. Which one is the right choice: cereal first or milk first?

26. Would you rather have the power of stopping time whenever you wanted or the ability to turn invisible?

27. Would you rather have hiccups for the rest of your life or feel the need to sneeze but be unable to do so for the rest of your life?

28. You can either have a great job or a great boss. Which would you choose?

29. Do you prefer to get the good news first or the bad news first?

30. Would you rather travel 100 years in the future or 100 years in the past?

31. You can only eat sweet or spicy foods for the rest of your life. Which would you pick?

32. Would you rather work a short shift of intense work or a long shift of relatively relaxed work for the same pay?

33. Would you rather tell your past self something or ask your future self a question?

34. You can either see how the universe came to be or how it will end. What would you choose?

35. Would you rather settle all of your disagreements with a game of "paper, rock, scissors" or "hide-and-seek"?

36. Which would you choose if you had to pick between not being able to eat sugar or salt for the rest of your life?

37. Would you rather have the ability to forget anything you want or remember everything you've ever done?

38. Would you rather spend your Friday evening at home or spend time at your favorite restaurant?

39. Cooking or takeout. What would you pick?

40. You can choose between two minor but magical abilities. You can either be instantly ready in the morning or instantly ready for bed at night. What would you choose?

41. Are you Team DC or Team Marvel?

42. Which one is superior— pie or cake?

43. Would you rather land your dream job with bad pay or get a bad job with a dream pay?

44. Christmas or Halloween. What's your pick out of these two holidays?

45. Would you rather play the main character in a bad movie or a supporting role in a good movie?

46. Pineapple over pizzas. Is that a "yes" or "no" from your side?

47. Would you rather never listen to old music again or never listen to new music again?

48. You can strike off either Monday or Friday from your workweek. What would you choose?


Do you have any other "Would you rather" questions for work that you use frequently? We'd love to hear them!

This article is written by Barasha Medhi who is a part of the marketing team at Vantage Circle. Barasha can be found either searching for interesting HR buzzwords to write about or looking at pictures of cozy Bel Air mansions. For any related queries, contact editor@vantagecircle.com.

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