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Would you rather questions for work.

Would you rather questions for work give your team two choices about the workday, meetings or office life, and everyone picks one. All 60 here are safe for any workplace and run as a quick 2-option poll.

Sample

Run as a live poll

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.?

Ask it live as a 2-option poll – everyone votes from their phone, free for 100 people.

All 60 questions

Every question works as a 2-option live poll: the two choices are the answers.

Workday

  1. 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.?
  2. Would you rather have no emails for a week or have no meetings for a week?
  3. Would you rather clear your inbox to zero every day or never open your inbox before lunch?
  4. Would you rather have a perfectly organized desk or have a perfectly organized computer desktop?
  5. Would you rather do your hardest task first thing or save it for the afternoon?
  6. Would you rather have an assistant who handles your email or have an assistant who handles your calendar?
  7. Would you rather take a long lunch break or finish an hour early?
  8. Would you rather learn a new tool every month or master the tools you already have?
  9. Would you rather write every report as a one-page summary or share every report as a three-minute video?
  10. Would you rather always know the answer to “quick question?” or never be asked a quick question again?
  11. Would you rather let a robot do your to-do list in the order it picks or do it yourself in your own order?
  12. Would you rather have a week with no deadlines or have a week with no interruptions?
  13. Would you rather have a fully booked calendar with no surprises or have an empty calendar and constant interruptions?
  14. Would you rather have Mondays off or have Fridays off?
  15. Would you rather finish one big project a year or finish a small project every week?

Remote and office

  1. Would you rather work from a mountain cabin with slow Wi-Fi or work from a busy café with great Wi-Fi?
  2. Would you rather work from home every day or work in the office every day?
  3. Would you rather have a standing desk or have a desk by the window?
  4. Would you rather have the best office chair you’ve ever sat in or have a huge second screen?
  5. Would you rather share an office with a coworker who chats all day or share one with a coworker who never speaks but hums?
  6. Would you rather work in an office with free snacks or work in an office with a rooftop garden?
  7. Would you rather have a two-hour train commute where you can read or have a 40-minute drive?
  8. Would you rather work in an open-plan office or work in a small private office?
  9. Would you rather have three office days and two home days or work fully remote with a team trip every month?
  10. Would you rather work from a different city every month or work from the same desk forever?
  11. Would you rather have a team playlist that plays all day or have a strict quiet zone?
  12. Would you rather use a beach as your video call background or use a library as your video call background?
  13. Would you rather sit next to the coffee machine or sit next to the quietest corner?
  14. Would you rather have an office dog or have an office cat?
  15. Would you rather have a home office with a door or have a home office with a view?

Meetings

  1. Would you rather cap every meeting at 15 minutes or have half as many meetings of any length?
  2. Would you rather present at every meeting or take the notes at every meeting?
  3. Would you rather join a meeting with no agenda or join a meeting with a 20-item agenda?
  4. Would you rather hold every meeting standing up or hold every meeting on a walk?
  5. Would you rather have one long meeting on Monday or have a short meeting every day?
  6. Would you rather run a meeting with no slides or run a meeting where the slides do all the talking?
  7. Would you rather always speak first or always speak last?
  8. Would you rather have all your meetings at 8 a.m. or have all your meetings at 5 p.m.?
  9. Would you rather have someone write your meeting notes or have someone do your action items?
  10. Would you rather ban laptops in meetings or ban phones in meetings?
  11. Would you rather lead a workshop for 50 people or have a one-to-one with the CEO?
  12. Would you rather answer questions live in a big meeting or answer them in writing afterward?
  13. Would you rather pass a talking stick round the room or give each speaker a two-minute timer?
  14. Would you rather start every meeting with an icebreaker or never have an icebreaker again?
  15. Would you rather pitch an idea to the whole company or pitch it to one tough critic?

Team

  1. Would you rather work on a team of 3 or work on a team of 30?
  2. Would you rather plan the team social or be surprised by it?
  3. Would you rather do a team escape room or take a team cooking class?
  4. Would you rather have a team trophy that moves to the star of the week or have no awards at all?
  5. Would you rather celebrate wins with a team lunch or celebrate with a shout-out in front of the whole company?
  6. Would you rather be the team’s go-to person for tech problems or be the go-to person for spreadsheets?
  7. Would you rather share one big goal with the whole team or each have your own goal?
  8. Would you rather let your team choose your next project or choose it yourself?
  9. Would you rather swap jobs with a teammate for a day or shadow the CEO for a day?
  10. Would you rather be on a team that argues a lot and ships fast or be on one that agrees a lot and moves slowly?
  11. Would you rather write the team’s welcome guide or give every new starter the welcome tour?
  12. Would you rather keep the office plants alive forever or book every meeting room forever?
  13. Would you rather have a team volunteering day or have a team learning day?
  14. Would you rather work for a week with a famous inventor or work for a week with a famous explorer?
  15. Would you rather have a team that sends memes all day or have a team that only sends calendar invites?

How to play would you rather at work

Read one question out, give everyone five seconds to choose, then ask one person from each side why. One question takes about two minutes and works at the start of a stand-up, a weekly meeting or a new joiner’s first team call.

  • In the office. Ask people to raise a hand for the first option, then the second. Ask the smaller group to make their case before you move on to the agenda.
  • On a video call. Run it as a live poll so everyone votes at once without unmuting. The split shows on screen, and you call on one person from each side.
  • At a team day. Play three rounds, then pair up people who voted differently most often. It is a light way to learn how teammates like to work.

Why these questions are work-safe

None of them touch health, money, religion, politics, appearance or family status, so nobody has to choose between sharing and sitting out. They stick to things everyone at work has an opinion on: meetings, mornings, desks, tools and teams.

FAQ

Questions about this list

What are good would you rather questions for work?
Questions about how people like to work: meetings, mornings, desks and tools. They are easy to answer, they split the room, and the answers tell you something useful about your team. “Would you rather have no emails for a week or no meetings for a week?” is a good first one.
Are these questions safe for any workplace?
Yes. They leave out health, money, religion, politics, appearance and family status, so nobody has to share anything private to answer.
How do I use would you rather in a virtual meeting?
Ask the question in the chat for an A or B answer, or run it as a live poll so everyone votes at once without unmuting. Then ask one person from each side to explain their pick.
How long should a would you rather icebreaker take?
About two minutes for one question. At a workshop or team day, play three or four rounds and let people argue a little.
Can my team vote live?
Yes. Make a RiLiFi poll with the question and the two choices as answers, then share the PIN or QR code. People vote from their phones and the bar chart fills as votes come in. The free plan covers 100 people per session.