The 15 Best Would You Rather Questions for Work

Ask your coworkers some of these would you rather questions and get to know them much better.

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By the Offsyte Team, February 15, 2023

The best teams are teams that feel connected to each other. When you care about who you work with, their success — and your team's success — becomes as important as your own.

One of the easiest ways to get to know someone better is to simply ask them questions. To keep things interesting, we highly recommend asking "would you rather" questions. They can be fun or serious, but the goal for every would you rather question is to increase your team's bond. Here are some of the best "would you rather" questions for work — some are silly and some are serious. They're all sure to get some good conversations going.

  1. Would you rather work remotely, at an office, or hybrid?
  2. Would you rather be famous or extremely wealthy?
  3. Would you rather work at a job that you don't like but pays well, or work at a job you like but doesn't pay well?
  4. Would you rather get rid of Zoom forever or email forever?
  5. Would you rather be a manager or a CEO?
  6. Would you rather have super strength or x-ray vision?
  7. Would you rather work long hours for four days per week and get a three-day weekend, or work short hours for five days per week and get to leave early every day?
  8. Would you rather travel back in time or into the future?
  9. Would you rather start work earlier and leave earlier, or start work later and leave later?
  10. Would you rather give up pizza or french fries forever?
  11. Would you rather get paid more or have more vacation days?
  12. Would you rather have one million Instagram followers or one million dollars?
  13. Would you rather work in silence or with music playing?
  14. Would you rather be an astronaut or a deep-sea diver?
  15. Would you rather switch roles with your boss or another member of your team?

More to Know About Would You Rather Questions for Work

Some common questions people have about would you rather questions.

What are good questions for "would you rather?"

The best "would you rather" questions evoke an interesting answer. Think of something silly, serious, or in-between, just try to make your question unique no matter what direction you go.

Is "would you rather" a good icebreaker?

Yes, would you rather questions are good icebreakers with your colleagues. They're low-stakes, fun questions that get everyone talking.

What are some fun questions to ask coworkers?

Fun questions to ask coworkers can be about anything. What you want to focus on is coming up with something that is likely to spark a conversation. The more talking, the more you get to know your team.

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