100 Would You Rather Questions for Work

Prompts (100)

• 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.?

  Workday
  start work at 6 a.m. and finish at 2 p.m.start at 11 a.m. and finish at 7 p.m.

• 2. Would you rather have a perfectly empty inbox or have a perfectly empty to-do list?

  Workday
  have a perfectly empty inboxhave a perfectly empty to-do list

• 3. Would you rather have a laptop battery that never runs out or have passwords that never expire?

  Workday
  have a laptop battery that never runs outhave passwords that never expire

• 4. Would you rather never wait for a slow computer again or never hunt for a lost file again?

  Workday
  never wait for a slow computer againnever hunt for a lost file again

• 5. Would you rather get every Friday afternoon free or get every Monday morning free?

  Workday
  get every Friday afternoon freeget every Monday morning free

• 6. Would you rather get one uninterrupted hour every day or get one fully uninterrupted day every week?

  Workday
  get one uninterrupted hour every dayget one fully uninterrupted day every week

• 7. Would you rather know exactly how long every task will take or know exactly which tasks you can safely skip?

  Workday
  know exactly how long every task will takeknow exactly which tasks you can safely skip

• 8. Would you rather have a desk that tidies itself or have a calendar that books itself?

  Workday
  have a desk that tidies itselfhave a calendar that books itself

• 9. Would you rather type twice as fast or read twice as fast?

  Workday
  type twice as fastread twice as fast

• 10. Would you rather learn a new skill from an online course or learn it by shadowing a teammate for a day?

  Workday
  learn a new skill from an online courselearn it by shadowing a teammate for a day

• 11. Would you rather bike to work in perfect weather or ride a train where you always get a seat?

  Workday
  bike to work in perfect weatherride a train where you always get a seat

• 12. Would you rather have every deadline pushed back a week or have every project cut to half its size?

  Workday
  have every deadline pushed back a weekhave every project cut to half its size

• 13. Would you rather get a mentor for your current role or get a mentor for a skill you have always wanted?

  Workday
  get a mentor for your current roleget a mentor for a skill you have always wanted

• 14. Would you rather never see a pop-up notification again or never sit through a surprise software update again?

  Workday
  never see a pop-up notification againnever sit through a surprise software update again

• 15. Would you rather work four long days with the fifth day for learning or work five normal days with no extra learning time?

  Workday
  work four long days with the fifth day for learningwork five normal days with no extra learning time

• 16. Would you rather finish a task perfectly but late or finish it on time but just good enough?

  Workday
  finish a task perfectly but latefinish it on time but just good enough

• 17. Would you rather be the person everyone asks for help or be the person who always knows where to find the answer?

  Workday
  be the person everyone asks for helpbe the person who always knows where to find the answer

• 18. Would you rather cap every meeting at 15 minutes or have one two-hour meeting a week and no others?

  Meetings
  cap every meeting at 15 minuteshave one two-hour meeting a week and no others

• 19. Would you rather be in charge of sharing the screen or be in charge of keeping time?

  Meetings
  be in charge of sharing the screenbe in charge of keeping time

• 20. Would you rather start every meeting with a two-minute icebreaker or end every meeting with a two-minute stretch?

  Meetings
  start every meeting with a two-minute icebreakerend every meeting with a two-minute stretch

• 21. Would you rather run a meeting with zero slides or sit through one with 60 slides?

  Meetings
  run a meeting with zero slidessit through one with 60 slides

• 22. Would you rather have a meeting-free day every week or have a meeting-free first week of every month?

  Meetings
  have a meeting-free day every weekhave a meeting-free first week of every month

• 23. Would you rather get an automatic summary of every meeting or never have a meeting recorded at all?

  Meetings
  get an automatic summary of every meetingnever have a meeting recorded at all

• 24. Would you rather join a brilliant brainstorm that runs long or join a dull meeting that ends early?

  Meetings
  join a brilliant brainstorm that runs longjoin a dull meeting that ends early

• 25. Would you rather give a five-minute update live or record a video update people watch later?

  Meetings
  give a five-minute update liverecord a video update people watch later

• 26. Would you rather get every agenda a day in advance or get every decision written up within an hour?

  Meetings
  get every agenda a day in advanceget every decision written up within an hour

• 27. Would you rather collect ideas on sticky notes on a wall or collect them in an anonymous online poll?

  Meetings
  collect ideas on sticky notes on a wallcollect them in an anonymous online poll

• 28. Would you rather book the meeting room with the best snacks or book the one with the best chairs?

  Meetings
  book the meeting room with the best snacksbook the one with the best chairs

• 29. Would you rather have a countdown timer on screen in every meeting or have a friendly referee who keeps everyone on topic?

  Meetings
  have a countdown timer on screen in every meetinghave a friendly referee who keeps everyone on topic

• 30. Would you rather work with a team that over-communicates or work with a team that under-communicates?

  Meetings
  work with a team that over-communicateswork with a team that under-communicates

• 31. Would you rather have one long all-hands meeting a quarter or have a ten-minute team huddle every morning?

  Meetings
  have one long all-hands meeting a quarterhave a ten-minute team huddle every morning

• 32. Would you rather hold meetings in a room with a stunning view or hold them in a room with flawless video and sound?

  Meetings
  hold meetings in a room with a stunning viewhold them in a room with flawless video and sound

• 33. Would you rather ask the first question in a Q&A or wait for the very last question slot?

  Meetings
  ask the first question in a Q&Await for the very last question slot

• 34. Would you rather have meetings that always start on time or have meetings that always end on time?

  Meetings
  have meetings that always start on timehave meetings that always end on time

• 35. Would you rather get a monthly book allowance or get a monthly lunch allowance?

  Office perks
  get a monthly book allowanceget a monthly lunch allowance

• 36. Would you rather have a bookable quiet room for deep focus or have a lounge with comfy sofas for breaks?

  Office perks
  have a bookable quiet room for deep focushave a lounge with comfy sofas for breaks

• 37. Would you rather get free parking forever or get a free public transit pass forever?

  Office perks
  get free parking foreverget a free public transit pass forever

• 38. Would you rather get a brand-new laptop every year or get a brand-new desk chair every year?

  Office perks
  get a brand-new laptop every yearget a brand-new desk chair every year

• 39. Would you rather pick your own start time every day or get every other Friday off?

  Office perks
  pick your own start time every dayget every other Friday off

• 40. Would you rather get free noise-canceling headphones or get a private phone booth you can book anytime?

  Office perks
  get free noise-canceling headphonesget a private phone booth you can book anytime

• 41. Would you rather have a table tennis table in the office or have a giant puzzle table everyone adds to?

  Office perks
  have a table tennis table in the officehave a giant puzzle table everyone adds to

• 42. Would you rather get a surprise day off once a quarter or get one planned extra week off once a year?

  Office perks
  get a surprise day off once a quarterget one planned extra week off once a year

• 43. Would you rather get a home-office equipment budget or get a commuting budget?

  Office perks
  get a home-office equipment budgetget a commuting budget

• 44. Would you rather have a free yoga class at lunch or have a free cooking class after work?

  Office perks
  have a free yoga class at lunchhave a free cooking class after work

• 45. Would you rather have a desk that raises and lowers at the touch of a button or have a chair that reclines all the way back?

  Office perks
  have a desk that raises and lowers at the touch of a buttonhave a chair that reclines all the way back

• 46. Would you rather get a team award with a silly trophy every month or get a big team celebration once a year?

  Office perks
  get a team award with a silly trophy every monthget a big team celebration once a year

• 47. Would you rather have an on-site bike repair stand or have an on-site shoe-shine and tailor service?

  Office perks
  have an on-site bike repair standhave an on-site shoe-shine and tailor service

• 48. Would you rather have a craft corner for breaks or have a mini putting green for breaks?

  Office perks
  have a craft corner for breakshave a mini putting green for breaks

• 49. Would you rather get a free language-learning subscription or get free music lessons?

  Office perks
  get a free language-learning subscriptionget free music lessons

• 50. Would you rather work in a building with a gym or work in a building with a park right outside?

  Office perks
  work in a building with a gymwork in a building with a park right outside

• 51. Would you rather be known for the best desk snacks or be known for the best potluck dish?

  Food
  be known for the best desk snacksbe known for the best potluck dish

• 52. Would you rather have perfect coffee that takes ten minutes to brew or have average coffee ready in ten seconds?

  Food
  have perfect coffee that takes ten minutes to brewhave average coffee ready in ten seconds

• 53. Would you rather never wait in line for the microwave again or never find a full office fridge again?

  Food
  never wait in line for the microwave againnever find a full office fridge again

• 54. Would you rather have a weekly team breakfast or have a weekly afternoon tea break?

  Food
  have a weekly team breakfasthave a weekly afternoon tea break

• 55. Would you rather get a soup bar every winter or get an ice cream cart every summer?

  Food
  get a soup bar every winterget an ice cream cart every summer

• 56. Would you rather have a chef cook a team lunch once a week or have fresh fruit delivered every day?

  Food
  have a chef cook a team lunch once a weekhave fresh fruit delivered every day

• 57. Would you rather give up coffee at work for a month or give up snacks at work for a month?

  Food
  give up coffee at work for a monthgive up snacks at work for a month

• 58. Would you rather have a breakfast-food potluck or have a dishes-from-around-the-world potluck?

  Food
  have a breakfast-food potluckhave a dishes-from-around-the-world potluck

• 59. Would you rather be in charge of ordering lunch for 30 people or be in charge of cleaning up after it?

  Food
  be in charge of ordering lunch for 30 peoplebe in charge of cleaning up after it

• 60. Would you rather have a waffle maker in the office kitchen or have a toaster oven in the office kitchen?

  Food
  have a waffle maker in the office kitchenhave a toaster oven in the office kitchen

• 61. Would you rather get a smoothie blender for the kitchen or get a popcorn machine for the kitchen?

  Food
  get a smoothie blender for the kitchenget a popcorn machine for the kitchen

• 62. Would you rather eat lunch at a picnic table outside every day or eat lunch at a cozy cafe table every day?

  Food
  eat lunch at a picnic table outside every dayeat lunch at a cozy cafe table every day

• 63. Would you rather have office snacks that are always healthy or have office snacks that are always a surprise?

  Food
  have office snacks that are always healthyhave office snacks that are always a surprise

• 64. Would you rather find a hot breakfast waiting every Monday or find a dessert cart rolling by every Friday?

  Food
  find a hot breakfast waiting every Mondayfind a dessert cart rolling by every Friday

• 65. Would you rather have the team lunch always be pizza or have the team lunch always be a build-your-own taco bar?

  Food
  have the team lunch always be pizzahave the team lunch always be a build-your-own taco bar

• 66. Would you rather bake for the team once a month or wash the shared mugs once a month?

  Food
  bake for the team once a monthwash the shared mugs once a month

• 67. Would you rather work from home in your comfiest sweater or work from the office with the best coffee in town?

  Remote vs in-office
  work from home in your comfiest sweaterwork from the office with the best coffee in town

• 68. Would you rather work remotely from a different city every month or work every day in a stunning office you love?

  Remote vs in-office
  work remotely from a different city every monthwork every day in a stunning office you love

• 69. Would you rather have a long commute with a podcast you love or have no commute and no lunch buddies?

  Remote vs in-office
  have a long commute with a podcast you lovehave no commute and no lunch buddies

• 70. Would you rather have flawless home internet forever or have a perfectly quiet home forever?

  Remote vs in-office
  have flawless home internet foreverhave a perfectly quiet home forever

• 71. Would you rather have your whole team in one office or have teammates around the world so someone is always awake?

  Remote vs in-office
  have your whole team in one officehave teammates around the world so someone is always awake

• 72. Would you rather make every video call audio-only or make every phone call a video call?

  Remote vs in-office
  make every video call audio-onlymake every phone call a video call

• 73. Would you rather join a call where your screen keeps freezing or join a call with an echo nobody can fix?

  Remote vs in-office
  join a call where your screen keeps freezingjoin a call with an echo nobody can fix

• 74. Would you rather have your home desk face a window or have it face a blank wall with zero distractions?

  Remote vs in-office
  have your home desk face a windowhave it face a blank wall with zero distractions

• 75. Would you rather go to the office on two fixed days a week or go in on any two days you choose each week?

  Remote vs in-office
  go to the office on two fixed days a weekgo in on any two days you choose each week

• 76. Would you rather set up your home office in a converted closet or set up a desk in the corner of the living room?

  Remote vs in-office
  set up your home office in a converted closetset up a desk in the corner of the living room

• 77. Would you rather have a team chat that is quiet and useful or have a team chat that is busy and fun?

  Remote vs in-office
  have a team chat that is quiet and usefulhave a team chat that is busy and fun

• 78. Would you rather have a virtual coffee chat with a random coworker every week or have a team game session online every month?

  Remote vs in-office
  have a virtual coffee chat with a random coworker every weekhave a team game session online every month

• 79. Would you rather work at a coworking space full of strangers or work alone at home with total control?

  Remote vs in-office
  work at a coworking space full of strangerswork alone at home with total control

• 80. Would you rather have a webcam that always makes you look well-rested or have a microphone that removes every background noise?

  Remote vs in-office
  have a webcam that always makes you look well-restedhave a microphone that removes every background noise

• 81. Would you rather commute to work by ferry or commute on foot through a park?

  Remote vs in-office
  commute to work by ferrycommute on foot through a park

• 82. Would you rather have the office open only on rainy days or have it open only on sunny days?

  Remote vs in-office
  have the office open only on rainy dayshave it open only on sunny days

• 83. Would you rather have every remote meeting start exactly on time or have every remote meeting end with ten free minutes?

  Remote vs in-office
  have every remote meeting start exactly on timehave every remote meeting end with ten free minutes

• 84. Would you rather have a desk inside a greenhouse or have a desk beside a tiny indoor fountain?

  Silly hypotheticals
  have a desk inside a greenhousehave a desk beside a tiny indoor fountain

• 85. Would you rather have a printer that never jams but sings while it prints or have a silent printer that jams once a day?

  Silly hypotheticals
  have a printer that never jams but sings while it printshave a silent printer that jams once a day

• 86. Would you rather have an elevator that plays your favorite tune or have an escalator that moves twice as fast?

  Silly hypotheticals
  have an elevator that plays your favorite tunehave an escalator that moves twice as fast

• 87. Would you rather change desks every day by random draw or keep the exact same desk for ten years?

  Silly hypotheticals
  change desks every day by random drawkeep the exact same desk for ten years

• 88. Would you rather have every email you send read aloud in a movie-trailer voice or have it narrated like a nature documentary?

  Silly hypotheticals
  have every email you send read aloud in a movie-trailer voicehave it narrated like a nature documentary

• 89. Would you rather have a teleporter to work or have a pause button for your inbox?

  Silly hypotheticals
  have a teleporter to workhave a pause button for your inbox

• 90. Would you rather redo one past presentation with a time machine or preview one future meeting with a crystal ball?

  Silly hypotheticals
  redo one past presentation with a time machinepreview one future meeting with a crystal ball

• 91. Would you rather work in an office inside a castle or work in an office on a space station?

  Silly hypotheticals
  work in an office inside a castlework in an office on a space station

• 92. Would you rather have your laptop read every notification aloud or have it buzz like a phone for every notification?

  Silly hypotheticals
  have your laptop read every notification aloudhave it buzz like a phone for every notification

• 93. Would you rather have a clone who handles all your Mondays or have a clone who handles all your Fridays?

  Silly hypotheticals
  have a clone who handles all your Mondayshave a clone who handles all your Fridays

• 94. Would you rather get the superpower of instant focus or get the superpower of never forgetting a name?

  Silly hypotheticals
  get the superpower of instant focusget the superpower of never forgetting a name

• 95. Would you rather commute by zipline or commute by hot-air balloon?

  Silly hypotheticals
  commute by ziplinecommute by hot-air balloon

• 96. Would you rather have your job title chosen by a five-year-old or have your job title chosen by a fortune cookie?

  Silly hypotheticals
  have your job title chosen by a five-year-oldhave your job title chosen by a fortune cookie

• 97. Would you rather have the office guarded by a friendly dinosaur or have the front desk run by a polite robot?

  Silly hypotheticals
  have the office guarded by a friendly dinosaurhave the front desk run by a polite robot

• 98. Would you rather swap jobs for a day with a lighthouse keeper or swap jobs for a day with a museum night guard?

  Silly hypotheticals
  swap jobs for a day with a lighthouse keeperswap jobs for a day with a museum night guard

• 99. Would you rather know the answer to every work question but explain it badly or explain anything brilliantly but need to look it up first?

  Silly hypotheticals
  know the answer to every work question but explain it badlyexplain anything brilliantly but need to look it up first

• 100. Would you rather have every room in the office be a different season or have every floor be a different decade?

  Silly hypotheticals
  have every room in the office be a different seasonhave every floor be a different decade

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