Would You Rather Questions for Work

Meetings run smoother when people feel at ease. Use these would you rather questions for work to open a stand up, welcome a new hire or warm up a remote call in two minutes, with topics that stay neutral, friendly and inclusive.

For speedy picks, see this or that for teams.

1. 1.

   Would you rather spill coffee on your own keyboard or spill water on a coworkers notebook?
2. 2.

   Would you rather accidentally leave yourself unmuted during a yawn or have your video freeze on an awkward face?
3. 3.

   Would you rather commute behind a slow tractor every single day or wait for a train that is always ten minutes late?
4. 4.

   Would you rather type loud enough for the whole floor to hear or use a mouse that constantly disconnects?
5. 5.

   Would you rather sit directly under the freezing air conditioning or have your desk next to the noisy kitchen microwave?
6. 6.

   Would you rather run out of ink halfway through printing a report or realize the printer is entirely out of paper?
7. 7.

   Would you rather forget your security badge at home on a Monday or lock your keys inside your car in the parking lot?
8. 8.

   Would you rather drink lukewarm decaf for the rest of your career or eat stale breakroom donuts every morning?
9. 9.

   Would you rather present a slide deck with a glaring typo or call a client by the completely wrong name?
10. 10.

    Would you rather work with someone who hums constantly or sit beside a colleague who loudly crunches ice?
11. 11.

    Would you rather share your screen while a silly text pops up or have a cat walk across your keyboard on a call?
12. 12.

    Would you rather try to fix a jammed paper shredder or untangle a massive pile of computer cords?
13. 13.

    Would you rather endure an hour long meeting that could be an email or read a ten page email that could be a short chat?
14. 14.

    Would you rather show up an hour early to an empty building or arrive exactly on time but sweat from running?
15. 15.

    Would you rather bring tuna fish for lunch in a tiny breakroom or microwave leftover broccoli in the shared kitchen?
16. 16.

    Would you rather only communicate using spreadsheet cells or draft all your memos in comic sans font?
17. 17.

    Would you rather wear a heavy winter coat inside all day or walk around the office in bright fuzzy slippers?
18. 18.

    Would you rather discover you wore mismatched shoes to the office or realize your shirt is completely inside out?
19. 19.

    Would you rather have a chair that slowly sinks to the floor or use a monitor that randomly flickers to black?
20. 20.

    Would you rather listen to elevator music at your desk all day or hear the fax machine dialing sound on loop?
22. 21.

    Would you rather accidentally wave at someone waving to the person behind you or hold the elevator door for someone walking incredibly slow?
23. 22.

    Would you rather give a presentation where the projector dies or host a video call where your internet drops out?
24. 23.

    Would you rather find out someone took your labeled yogurt or watch a coworker take the last cup of fresh coffee?
25. 24.

    Would you rather stand during every single team meeting or sit on an exercise ball instead of a regular chair?
26. 25.

    Would you rather drop your lunch directly onto the carpet or spill your water bottle all over your own lap?
27. 26.

    Would you rather navigate a confusing maze of office cubicles or work in a completely silent open plan space?
28. 27.

    Would you rather use sticky notes for every piece of documentation or write all your notes on the back of receipts?
29. 28.

    Would you rather forget the passcode to the main entrance or cannot remember the shortcut to lock your screen?
30. 29.

    Would you rather always get stuck at the red light near the office or walk three blocks in the pouring rain?
31. 30.

    Would you rather pack a delicious lunch but leave it on the counter or buy an expensive sandwich that tastes terrible?
32. 31.

    Would you rather have a virtual background you cannot turn off or use a webcam that makes everything look green?
33. 32.

    Would you rather type out a long message only to accidentally delete it or send a message before you finished typing it?
34. 33.

    Would you rather deal with a headset that pinches your ears or wear an earpiece that constantly falls out?
35. 34.

    Would you rather try to explain a joke that nobody understood or laugh out loud at something during a quiet moment?
36. 35.

    Would you rather find a huge ink stain on your favorite sweater or notice a coffee drip on your crisp white shirt?
37. 36.

    Would you rather rely on a stapler that always jams on the first try or use scissors that are impossibly dull?
38. 37.

    Would you rather have to restart your computer during a deadline or wait for a mandatory software update to finish?
39. 38.

    Would you rather walk into a glass door while people are watching or trip over a rug in the middle of the lobby?
40. 39.

    Would you rather carry a massive box of supplies up three flights of stairs or assemble a complicated new desk by yourself?
41. 40.

    Would you rather get stuck in a conversation by the water cooler or hide in the restroom to avoid small talk?
42. 41.

    Would you rather notice your webcam was on after you sneezed heavily or realize your microphone caught you talking to your dog?
43. 42.

    Would you rather keep a messy desk with piles of random papers or maintain a spotless desk but never find a pen?
44. 43.

    Would you rather attempt to read handwriting that looks like scribbles or transcribe an audio file with terrible background noise?
45. 44.

    Would you rather bring a cake for a coworker who hates sweets or organize a card for someone who already left?
46. 45.

    Would you rather commute in a car with no working radio or ride a bus where the heating is stuck on high?
47. 46.

    Would you rather click a link that plays loud music in a silent room or drop a heavy binder on a hard floor?
48. 47.

    Would you rather need to borrow a charger from a stranger or beg the IT department to unlock your account again?
49. 48.

    Would you rather always volunteer to take the meeting minutes or be forced to schedule everyone else on the calendar?
50. 49.

    Would you rather leave your umbrella at home on a stormy day or bring a huge golf umbrella on a perfectly sunny day?
51. 50.

    Would you rather sit next to the constantly ringing mainline phone or have your desk right by the busy entrance doors?

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