300 would you rather questions for work

Two choices. A surprisingly good conversation.

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Rated general. Everyone can skip.

Showing 1-100 of 100 questions

Easy openers

  1. Would you rather explore a promising idea nobody has tested or build a template for repeated work?

  2. Would you rather solve a small recurring annoyance or work alongside someone with a different specialty?

  3. Would you rather work alongside someone with a different specialty or present an idea with a clear story?

  4. Would you rather improve the way a team starts projects or get feedback after polishing one example?

  5. Would you rather write a concise project guide or get feedback early while an idea is rough?

  6. Would you rather improve the way a team hands projects over or plan a team walk with an optional conversation?

  7. Would you rather plan a team lunch with an optional game or plan a team walk with an optional conversation?

  8. Would you rather have a team library of useful resources or be known for making difficult things clear?

  9. Would you rather learn a tool through a guided lesson or celebrate learning from an unsuccessful experiment?

  10. Would you rather present an idea with a clear story or write a concise project guide?

  11. Would you rather work from a quiet individual room or swap roles in a practice exercise?

  12. Would you rather improve the way a team hands projects over or improve the way a team starts projects?

  13. Would you rather build a template for repeated work or protect an hour for focused work?

  14. Would you rather record decisions in a shared notebook or protect an hour for focused work?

  15. Would you rather get feedback after polishing one example or be known for asking useful questions?

  16. Would you rather have a team hour for sharing useful skills or be known for asking useful questions?

  17. Would you rather have a meeting-free morning each week or record decisions in a shared notebook?

  18. Would you rather work from a bright shared studio or protect an hour for focused work?

  19. Would you rather present an idea with a clear story or explore a promising idea nobody has tested?

  20. Would you rather have a team library of useful resources or plan a team lunch with an optional game?

  21. Would you rather protect an hour for useful collaboration or explore a promising idea nobody has tested?

  22. Would you rather plan a team walk with an optional conversation or write a concise project guide?

  23. Would you rather explore a promising idea nobody has tested or present an idea with a simple prototype?

  24. Would you rather plan a team lunch with an optional game or record decisions in a shared notebook?

  25. Would you rather celebrate learning from an unsuccessful experiment or create a short project walkthrough?

  26. Would you rather solve a small recurring annoyance or create a short project walkthrough?

  27. Would you rather get feedback after polishing one example or swap roles in a practice exercise?

  28. Would you rather plan a team lunch with an optional game or improve the way a team starts projects?

  29. Would you rather build a template for repeated work or create a short project walkthrough?

  30. Would you rather have a short discussion with one precise goal or map decisions on a shared diagram?

  31. Would you rather work alongside someone with a different specialty or swap roles in a practice exercise?

  32. Would you rather be known for making difficult things clear or explore a promising idea nobody has tested?

  33. Would you rather protect an hour for useful collaboration or learn a tool through a guided lesson?

  34. Would you rather have a meeting-free afternoon each week or present an idea with a simple prototype?

  35. Would you rather celebrate finishing a difficult task or have a meeting-free afternoon each week?

  36. Would you rather map decisions on a shared diagram or improve the way a team starts projects?

  37. Would you rather be known for making difficult things clear or have a meeting-free afternoon each week?

  38. Would you rather get feedback early while an idea is rough or learn a shortcut that saves ten minutes?

  39. Would you rather start a project with a quiet sketching session or work alongside someone with a different specialty?

  40. Would you rather build a checklist for repeated work or work alongside someone with a different specialty?

  41. Would you rather have a meeting-free afternoon each week or get feedback early while an idea is rough?

  42. Would you rather protect an hour for useful collaboration or work from a quiet individual room?

  43. Would you rather pair up to solve an unfamiliar problem or work from a bright shared studio?

  44. Would you rather write a concise project guide or have a meeting-free morning each week?

  45. Would you rather build a template for repeated work or get feedback early while an idea is rough?

Everyday surprises

  1. Would you rather have a clear agenda with room for questions or solve a small recurring annoyance?

  2. Would you rather pair up to solve an unfamiliar problem or protect an hour for focused work?

  3. Would you rather work alongside someone with a different specialty or protect an hour for focused work?

  4. Would you rather be known for making difficult things clear or have a team hour for sharing useful skills?

  5. Would you rather solve a small recurring annoyance or present an idea with a simple prototype?

  6. Would you rather start a project with a quiet sketching session or be known for asking useful questions?

  7. Would you rather have a clear agenda with room for questions or celebrate finishing a difficult task?

  8. Would you rather learn a tool through a guided lesson or pair up to solve an unfamiliar problem?

  9. Would you rather get feedback early while an idea is rough or record decisions in a shared notebook?

  10. Would you rather write a concise project guide or solve a small recurring annoyance?

  11. Would you rather work from a quiet individual room or celebrate learning from an unsuccessful experiment?

  12. Would you rather be known for making difficult things clear or improve the way a team starts projects?

  13. Would you rather start a project with a quiet sketching session or have a short discussion with one precise goal?

  14. Would you rather start a project with a quiet sketching session or explore a promising idea nobody has tested?

  15. Would you rather get feedback early while an idea is rough or learn a tool through a small real task?

  16. Would you rather build a template for repeated work or work alongside someone with a similar approach?

  17. Would you rather map decisions on a shared diagram or protect an hour for useful collaboration?

  18. Would you rather learn a shortcut that saves ten minutes or present an idea with a clear story?

  19. Would you rather map decisions on a shared diagram or protect an hour for focused work?

  20. Would you rather record decisions in a shared notebook or solve a small recurring annoyance?

  21. Would you rather improve the way a team starts projects or have a team hour for sharing useful skills?

  22. Would you rather start a project with a quiet sketching session or have a meeting-free afternoon each week?

  23. Would you rather have a team hour for sharing useful skills or have a team library of useful resources?

  24. Would you rather get feedback after polishing one example or present an idea with a clear story?

  25. Would you rather map decisions on a shared diagram or build a template for repeated work?

  26. Would you rather improve the way a team starts projects or plan a team walk with an optional conversation?

  27. Would you rather improve the way a team starts projects or start a project with a quiet sketching session?

  28. Would you rather learn a shortcut that saves ten minutes or learn a tool through a small real task?

  29. Would you rather work from a quiet individual room or get feedback early while an idea is rough?

  30. Would you rather get feedback early while an idea is rough or be known for asking useful questions?

  31. Would you rather work from a bright shared studio or be known for making difficult things clear?

  32. Would you rather present an idea with a simple prototype or work alongside someone with a similar approach?

  33. Would you rather get feedback early while an idea is rough or teach a shortcut that saves everyone five minutes?

  34. Would you rather celebrate finishing a difficult task or protect an hour for focused work?

  35. Would you rather protect an hour for focused work or explore a promising idea nobody has tested?

  36. Would you rather create a short project walkthrough or be known for asking useful questions?

  37. Would you rather be known for asking useful questions or swap roles in a practice exercise?

  38. Would you rather present an idea with a clear story or solve a small recurring annoyance?

  39. Would you rather solve a small recurring annoyance or get feedback after polishing one example?

  40. Would you rather have a team hour for sharing useful skills or map decisions on a shared diagram?

  41. Would you rather solve a small recurring annoyance or have a meeting-free afternoon each week?

  42. Would you rather learn a shortcut that saves ten minutes or celebrate finishing a difficult task?

  43. Would you rather have a meeting-free morning each week or learn a tool through a small real task?

  44. Would you rather pair up to solve an unfamiliar problem or build a template for repeated work?

  45. Would you rather protect an hour for focused work or learn a shortcut that saves ten minutes?

How to play with work

Read both choices aloud. Everyone chooses one, then shares why. There are no correct answers. For work groups, make participation optional, avoid judging answers, and allow about 30 seconds per person. Keep personal follow-ups optional.

Let's play

A quick round

Pick ten prompts and keep each answer to one sentence. Stop when the group wants to talk more.

A story round

Use fewer prompts and invite an optional follow-up. Let the person answering decide how much to share.

A paper round

Print a small set, cut out the cards, and let willing players draw a prompt. Keep a skip pile on the table.

Make it your game.

Simple rules, plenty of room for your group.

How do you play would you rather with work?

Read both choices aloud. Everyone chooses one, then shares why. There are no correct answers. For work groups, make participation optional, avoid judging answers, and allow about 30 seconds per person. Keep personal follow-ups optional.

Can we play without an account or an app?

Yes. Open play mode in your browser, read a prompt aloud, and move to the next one. Every control also works without JavaScript.

Can I print these questions as cards?

Yes. Choose Print cards, select how many you want, and download a PDF with cut lines and an optional rules card. Printing is free.

Can someone skip an uncomfortable question?

Always. Skip without explaining, choose another prompt, or stop the round. Nobody owes the group a personal answer or a performance.

Are these questions appropriate for this group?

This bank is rated general. Kids and school banks are separate from adult banks. All our content is non-explicit, and even flirty prompts stay light.

Try a different kind of question.