Would you rather questions for work

40 questions. Work-friendly choices about offices, meetings and careers, safe for any team.

1. Would you rather have a four-day workweek with longer days or a five-day week with shorter days?
2. Would you rather have a desk that looks out over the ocean or one that looks out over a city skyline?
3. Would you rather have every meeting be a walking meeting or every meeting be held standing up?
4. Would you rather have an office with a cozy fireplace or one with a mini putting green?
5. Would you rather give a ten-minute presentation with no slides or a one-minute presentation with fifty slides?
6. Would you rather communicate only by email for a month or only by video call for a month?
7. Would you rather start work at 6 a.m. and finish at 2 p.m. or start at noon and finish at 8 p.m.?
8. Would you rather have your desk right next to the coffee machine or in the quietest corner of the office?
9. Would you rather master a new software tool overnight or become an instant expert at public speaking?
10. Would you rather have unlimited office snacks or a nap pod you can use anytime?
11. Would you rather work in a silent library-style office or a buzzing open space with music playing?
12. Would you rather have your dream job title or your dream team of coworkers?
13. Would you rather keep a perfectly clean inbox or a perfectly tidy desk?
14. Would you rather lead a project you know little about or support a project you know inside out?
15. Would you rather have every meeting start with a joke or end with a two-minute dance break?
16. Would you rather type twice as fast or read twice as fast?
17. Would you rather spend one month a year working from anywhere in the world or work from home every Friday all year?
18. Would you rather have a team chat full of GIFs or a team chat where only words are allowed?
19. Would you rather switch careers every five years or stay in one field your whole working life?
20. Would you rather present to a room of 500 people or to three top experts in your field?
21. Would you rather write the company newsletter every week or plan the team party every month?
22. Would you rather have a laptop that never needs charging or a printer that never jams?
23. Would you rather solve one huge problem a year or a hundred small problems a week?
24. Would you rather have a meeting-free Monday or a meeting-free Friday?
25. Would you rather be known as the team's best listener or its best problem solver?
26. Would you rather learn a new skill from a mentor or teach your favorite skill to a new hire?
27. Would you rather keep your camera on for every video call or have audio-only calls forever?
28. Would you rather work in an office on a houseboat or an office inside a greenhouse full of plants?
29. Would you rather map out a project step by step or dive in and adjust as you go?
30. Would you rather get quick feedback after every task or one big review at the end of each quarter?
31. Would you rather try the job you dreamed of as a child for one week or design a brand-new role for yourself?
32. Would you rather have a five-minute walk to work or a one-hour train ride where you can read?
33. Would you rather brainstorm alone first or brainstorm out loud with the whole team?
34. Would you rather tackle your hardest task first thing in the morning or save it for after lunch?
35. Would you rather work on a team of two or a team of twenty?
36. Would you rather have a robot that takes perfect meeting notes or a robot that keeps every meeting on time?
37. Would you rather receive a handwritten thank-you note or a shout-out in front of the whole team?
38. Would you rather spend a day shadowing a chef or a day shadowing an air traffic controller?
39. Would you rather name the company's next product or design its new logo?
40. Would you rather have an office dog or an office cat?