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60+ Would You Rather Questions for Work and Team Icebreakers

Safe-for-work icebreakers for meetings, onboarding and team building.

Would You Rather questions for work are light, inclusive icebreakers for meetings, onboarding, team building and virtual calls. Nothing personal, nothing awkward, just quick questions that get coworkers talking.

How to play

Open a meeting with one question and give everyone 30 seconds to answer. In video calls, use the chat or a quick poll to vote first, then ask a few people to explain. Want to play online instead? Press the Play button above to vote on each question and see what percentage of players agreed with you.

60 Work Would You Rather Questions

1. Would you rather have a four-day workweek or have a two-hour lunch break every day?

Longer weekends or a relaxed midday.

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2. Would you rather work from home forever or work from a beautiful office forever?

Pajamas or a great view.

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3. Would you rather have a boss who gives you lots of praise or have a boss who gives you lots of freedom?

Recognition or independence.

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4. Would you rather never have another meeting or never have to answer another email?

Calendar freedom or inbox freedom.

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5. Would you rather have free lunch at work every day or have free coffee and snacks all day?

One big perk or all-day fuel.

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6. Would you rather have a desk by the window or have a desk next to the coffee machine?

Sunlight or first sip.

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

Early birds or night owls at work.

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8. Would you rather be able to read your coworkers' minds in meetings or be able to mute anyone in a meeting?

Insight or silence.

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9. Would you rather have a nap pod at the office or have a game room at the office?

Rest or play on breaks.

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10. Would you rather get a raise or get an extra week of vacation?

More money or more time.

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11. Would you rather bring your pet to work every day or bring your favorite snack chef to work every day?

Office dog or office snacks.

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12. Would you rather work on a small, close team or work at a huge company with many teams?

Family vibe or big opportunities.

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13. Would you rather present in front of 500 people or write a 50-page report?

Stage fright or writer's block.

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14. Would you rather have the fastest computer in the office or have the most comfortable chair in the office?

Speed or comfort.

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15. Would you rather never have to commute again or have a commute in a self-driving limo?

Zero travel or luxury travel.

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16. Would you rather have a mentor who is a famous CEO or have a mentor who is a famous inventor?

Leadership or innovation.

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17. Would you rather have every meeting be 15 minutes or have every meeting have snacks?

Short or sweet.

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18. Would you rather work in a quiet library-like office or work in a buzzing open-plan office?

Calm or energy.

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19. Would you rather have unlimited sick days or have unlimited training budget?

Rest or growth.

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20. Would you rather have a standing desk or have a treadmill desk?

Stand up or walk it out.

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21. Would you rather be the person who always has a pen or be the person who always has a charger?

Two office heroes.

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22. Would you rather lead the team or be the team's go-to expert?

Boss or specialist.

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23. Would you rather celebrate wins with a team lunch or celebrate wins with an early finish?

Food or freedom.

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24. Would you rather have a coworker who tells great jokes or have a coworker who always helps you meet deadlines?

Laughs or lifelines.

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25. Would you rather work on one big project all year or work on lots of small projects?

Deep focus or variety.

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26. Would you rather get a company trip to the beach or get a company trip to the mountains?

Sand or snow team building.

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27. Would you rather have music playing in the office all day or have total silence all day?

Soundtrack or quiet focus.

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28. Would you rather learn a new skill at work every month or get a new gadget at work every month?

Brain upgrade or desk upgrade.

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29. Would you rather work for a company that changes the world or work for a company with amazing perks?

Purpose or perks.

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30. Would you rather answer phones for an hour or answer emails for three hours?

Fast talk or long typing.

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31. Would you rather have a coffee chat with a different coworker each week or have a team game every Friday?

One-on-one bonding or group fun.

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32. Would you rather work in a treehouse office or work in an office on a boat?

Leafy or wavy.

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33. Would you rather have your own office with a door or have a desk next to your work best friend?

Privacy or friendship.

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34. Would you rather be famous in your industry or be loved by your team?

Reputation or relationships.

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35. Would you rather have the perfect to-do list app or have a personal assistant for one hour a day?

Organized or supported.

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36. Would you rather get every Friday afternoon off or get your birthday week off?

Weekly treat or yearly treat.

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37. Would you rather wear a uniform every day or have to dress up formally every day?

Easy mornings or sharp looks.

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38. Would you rather have a hilarious team chat or have a super productive team chat?

Fun or efficient.

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39. Would you rather work in a different country for a year or work from a different city each month?

Deep roots abroad or digital nomad.

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

Fun exit or peaceful breaks.

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41. Would you rather brainstorm with sticky notes or brainstorm on a whiteboard?

Colorful squares or big marker ideas.

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42. Would you rather get feedback every day or get feedback once a year?

Constant tweaks or one big talk.

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

Talk the talk or write it right.

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44. Would you rather have a company that closes for the whole holiday season or have a company that gives you any two weeks you want off?

Shared break or flexible break.

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45. Would you rather have lunch at your desk with a show or have lunch outside in a park?

Screen break or fresh air.

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46. Would you rather always know the Wi-Fi password or always find a free meeting room?

Everyday office superpowers.

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47. Would you rather have a job with a great title or have a job with a great team?

Status or people.

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48. Would you rather have casual Fridays every day or have pizza Fridays every week?

Comfort or cheese.

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49. Would you rather have a coworker who brings homemade cookies every Monday or have one who makes amazing coffee every morning?

Sweet starts or strong starts.

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50. Would you rather retire at 50 with a modest income or work until 70 doing something you love?

Early freedom or lasting passion.

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51. Would you rather work with robots that do all the boring tasks or work with a team that makes everything fun?

Efficiency or enjoyment.

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52. Would you rather have every Monday be a half day or have every Friday be a half day?

Easy start or early finish.

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53. Would you rather be the first one in the office or be the last one to leave?

Quiet morning or quiet evening.

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54. Would you rather have your desk be super tidy or have your desk be cozy and decorated?

Minimal or personal.

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55. Would you rather have your job be fully remote or have your job include travel every month?

Home base or on the go.

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56. Would you rather get a team trophy or get an individual award?

We or me.

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57. Would you rather never have to use a printer again or never have to join a video call again?

Two daily frustrations. Pick one to delete.

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58. Would you rather write the company newsletter or plan the company party?

Words or celebrations.

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59. Would you rather have a quiet room for focus or have a fun room for breaks?

Concentrate or recharge.

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60. Would you rather have the best boss with an average salary or have an average boss with the best salary?

People or pay.

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Frequently asked questions

How do you play work Would You Rather?

Read a question out loud, everyone picks one of the two options, and each person explains why. No answering "both" or "neither". You can also tap a question here to vote online and see how other players chose.

Are these work questions family friendly?

Yes. Every question on WouldYouRather.info is clean and safe for kids, classrooms, families and work events.

How many work questions are there?

This page has 60 work Would You Rather questions, and we add new ones regularly.

More Would You Rather questions