120 what if questions: funny, deep and safe for work
Twenty what if questions in each of six groups: funny, work, superpowers, what if I, world and deep. Plus four ways to use them in a meeting.
A what if question hands people a scenario and lets them run with it. There’s no wrong answer and nothing personal to share, so even the quietest person on the call has something to say. Start a meeting with one, or give a whole round to the funny list at your next team social.
Funny what if questions
Silly enough to get a laugh, specific enough that everyone has an answer.
1. What if animals could talk? Which one would be the rudest?
2. What if you had a theme song that played every time you walked into a room?
3. What if your refrigerator could talk? What would it complain about?
4. What if your houseplants could rate how well you look after them?
5. What if you were a kitchen appliance? Which one would you be?
6. What if you could only speak in questions for a whole day?
7. What if you could only communicate with emojis for a week?
8. What if a narrator described everything you did out loud? Whose voice would it be?
9. What if you had to enter a talent show tomorrow? What's your act?
10. What if gravity switched off for one hour every Friday?
11. What if you could only eat food of one color for a month? Which color?
12. What if your pet had a job? What would it be?
13. What if you were the main character in a cartoon? Which cartoon?
14. What if you could make one silly rule that everyone had to follow?
15. What if your car could talk? What would it say about your driving?
16. What if you had a robot sidekick? What would you name it?
17. What if you could hire a stunt double for one boring task? Which task?
18. What if a coin toss decided all your weekend plans?
19. What if you got paid in snacks? Which snack?
20. What if you swapped voices with a cartoon character for a day?
What if questions for work
Hypotheticals about the job that make people laugh and, now and then, surface a real idea.
21. What if meetings could last no longer than 15 minutes?
22. What if you could delete one work task forever? Which one?
23. What if email disappeared tomorrow? How would we work?
24. What if every Friday afternoon were for learning something new?
25. What if you swapped jobs with a teammate for a week?
26. What if our team had a mascot? What would it be?
27. What if you could add one perk to the office?
28. What if you had to explain your job to a five-year-old?
29. What if every meeting started with a two-minute game?
30. What if you could work from anywhere for a month? Where would you go?
31. What if our team ran a food truck? What would we sell?
32. What if you had a whole day with no meetings? What would you finish?
33. What if you could learn any work skill in a day? Which one?
34. What if our team had a motto? What would it be?
35. What if you could fix one annoying tool we use?
36. What if a customer shadowed us for a day? What should they see?
37. What if you were CEO for a day? What would you change first?
38. What if you had to teach a workshop tomorrow? What's the topic?
39. What if our team were a band? What would you play?
40. What if you could go back to your first day here? What would you tell yourself?
Superpower what if questions
The classic hypothetical, with a catch on most of them so the answers get creative.
41. What if you could fly, but only three feet off the ground?
42. What if you could pause time for 10 minutes a day?
43. What if you understood every language on Earth?
44. What if you could teleport, but only to places you've already been?
45. What if you could talk to animals?
46. What if you could turn invisible, but only when nobody was looking?
47. What if you could read minds, but couldn't switch it off?
48. What if you had a perfect memory?
49. What if you could breathe underwater?
50. What if you never needed to sleep?
51. What if you could master any instrument instantly?
52. What if you could rewind the last 30 seconds once a day?
53. What if you could see 10 minutes into the future?
54. What if you could shrink to the size of an ant?
55. What if you could copy any skill by watching someone do it once?
56. What if you could control the weather in your town?
57. What if you had super speed, but only for chores?
58. What if you could make any meal appear, once a day?
59. What if your superpower were totally useless? What would it be?
60. What if you could give your whole team one superpower?
What if I questions to ask yourself
Small experiments to try on your own life. Swap I for you and they work in a team meeting too.
61. What if I said yes to every invitation for a month?
62. What if I learned one new word every day for a year?
63. What if I took a different route home every day this week?
64. What if I tried a hobby I've always assumed I'd be bad at?
65. What if I spent one hour a week with no screens?
66. What if I asked for feedback on one thing every Friday?
67. What if I wrote down one win every day?
68. What if I cooked a recipe from a different country every week?
69. What if I read 20 pages a day? How many books would that be in a year?
70. What if I finally signed up for that class?
71. What if I swapped one meeting a week for a walk-and-talk?
72. What if I taught someone the thing I'm best at?
73. What if I started every day with my hardest task?
74. What if I spent a weekend somewhere new, an hour from home?
75. What if I turned off notifications for one afternoon?
76. What if I kept a list of things I'm curious about?
77. What if I gave one genuine compliment every day?
78. What if I said no to one thing a week?
79. What if I volunteered one Saturday a month?
80. What if I wrote a letter to myself to open in a year?
What if the world worked differently?
Big hypotheticals about how life would change. Good for a long lunch or a team that likes to debate.
81. What if everyone had to switch careers every 10 years?
82. What if there were no clocks?
83. What if every city had free public transit?
84. What if cars had never been invented?
85. What if dinosaurs still roamed the Earth?
86. What if the internet went down worldwide for a week?
87. What if people could hibernate through winter?
88. What if everyone spoke the same language?
89. What if every weekend were three days long?
90. What if money didn't exist?
91. What if we lived on the Moon? What would you miss most?
92. What if a day had 30 hours?
93. What if books were the only entertainment?
94. What if every home came with a robot chef?
95. What if schools added one brand-new subject? What should it be?
96. What if the oceans were fresh water?
97. What if everyone spent one year living in another country?
98. What if each season lasted a whole year?
99. What if you could visit any time in history for one day?
100. What if every workplace had a nap room?
Deep what if questions
Questions that take a minute to answer. Best in small groups, and always with the option to pass.
101. What if you knew you couldn't fail? What would you try?
102. What if you could ask your future self one question?
103. What if you could relive one day of your life?
104. What if you could master one thing completely, but nothing else?
105. What if you had to live by one rule? What would it be?
106. What if you could give your younger self one piece of advice?
107. What if you got a do-over on one decision?
108. What if you picked one word to guide your year?
109. What if you had to teach one life lesson to a room of strangers?
110. What if money weren't a factor in choosing your work?
111. What if you could have dinner with anyone from history?
112. What if you could keep only five things you own?
113. What if you could change one thing about how people treat each other?
114. What if you wrote your own job description from scratch?
115. What if you could solve one problem in your town?
116. What if you knew exactly how others saw you? Would you want to?
117. What if you had a paid year to learn anything you wanted?
118. What if you were remembered for one thing? What should it be?
119. What if you could trade places with anyone for a day?
120. What if your 80-year-old self wrote you a note? What would it say?
How to use what if questions in meetings
Four formats, from a five-minute opener to a full breakout round.
1. Round the room
Open a meeting with one what if question and give everyone 20 seconds to answer. Five minutes, every voice heard before the agenda starts.
Try: What if you could delete one work task forever?
2. The what if chain
One person answers, then turns their answer into the next what if for the person after them. The chain gets stranger with every turn, which is the fun.
“I'd fly to Lisbon.” Next: What if you had to live in Lisbon for a year?
3. Pitch it
Give each breakout room one world-changing what if and three minutes. Each team pitches how life would change; everyone votes for the best pitch.
Try: What if every weekend were three days long?
4. Question of the week
Post one what if in Slack or Teams on Monday and pin the best reply on Friday. It keeps a remote team talking without another meeting.
Try: What if our team ran a food truck? What would we sell?
- Pick from the funny or superpower lists for new groups; save deep questions for teams that know each other.
- Ask one follow-up: “Why that one?” gets a better story than a second question.
- Answer first yourself. It shows the level of detail you want and makes passing feel normal.
- Keep it hypothetical. A what if is a safe way in, so don't turn it into a real-life interrogation.
- Write down the good work ideas. Now and then a joke answer is worth trying.
Want a fresh question every day instead? Our question of the day picks one for you, and these team meeting games fill a longer slot.
Need a different kind of question? Try our would you rather questions, get to know you questions, yes or no questions and hot seat questions.
Want someone to run this for your team?
Teams that love a good what if usually love improv. A live host can run an improv class, a game show or trivia for about an hour on Zoom, with nothing for you to prepare. Book about 2 weeks ahead, or get a free quote.
