Would You Rather Questions for Work

Would you rather questions for remote teams

For teams that know each other mostly as squares on a screen.

1. 1.Would you rather work from a beach with bad Wi-Fi or work from a basement with perfect Wi-Fi?
2. 2.Would you rather have your cat walk across your keyboard on every call or have your dog bark at every delivery on every call?
3. 3.Would you rather work with a team twelve time zones away or work with a team that sits right behind you?
4. 4.Would you rather stay on mute through your whole update or unmute by accident while singing along to music?
5. 5.Would you rather work from a hammock all day or work from a treadmill desk all day?
6. 6.Would you rather only use a cartoon avatar on video calls or keep a funny hat filter you can't turn off?
7. 7.Would you rather have every video call be audio-only or have every video call require a fun hat?
8. 8.Would you rather have your internet cut out at the start of every big call or have your laptop start a big update right before every presentation?
9. 9.Would you rather be known on every call for your amazing bookshelf or be known on every call for your amazing houseplants?
10. 10.Would you rather share your screen with 47 tabs open or share your screen with 300 files on your desktop?
11. 11.Would you rather join every call with a leaf blower running outside or join every call from a chair that squeaks?
12. 12.Would you rather have a virtual coffee chat every day or play a team game every Friday?
13. 13.Would you rather work from a new city every month or work from a perfect home office forever?
14. 14.Would you rather use one giant monitor or use three small monitors?
15. 15.Would you rather work from a cabin in the woods or work from a high-rise with a city view?
16. 16.Would you rather have your video freeze on a goofy face or have your audio make you sound like a robot?
17. 17.Would you rather start every call with a five-minute icebreaker or end every call with a terrible pun?
18. 18.Would you rather take a real one-hour lunch away from screens every day or finish thirty minutes early every day?
19. 19.Would you rather never have a video call again or never have a phone call again?
20. 20.Would you rather have a team chat full of memes or have a team chat so quiet you can hear crickets?

Would you rather questions about office life

Desks, kitchens, elevators and the eternal fight over the thermostat.

1. 21.Would you rather have the office's best view and its worst chair or have the office's best chair and its worst view?
2. 22.Would you rather pick a new desk every morning or keep the same desk with a wobbly chair forever?
3. 23.Would you rather share a kitchen with someone who microwaves fish or share a kitchen with someone who never washes their mug?
4. 24.Would you rather take the stairs to the 12th floor or ride the slowest elevator in the city?
5. 25.Would you rather be in charge of the office playlist or be in charge of the office thermostat?
6. 26.Would you rather have an office dog or have an office cat?
7. 27.Would you rather have a slide between floors or have a nap pod on every floor?
8. 28.Would you rather sign every birthday card in the office or plan every office party?
9. 29.Would you rather reply-all with a thumbs-up to 500 people or share your grocery list in the team channel by accident?
10. 30.Would you rather have the coffee machine break every Monday or have the Wi-Fi go down every Friday?
11. 31.Would you rather have a standing desk stuck at the highest setting or have a desk chair that slowly sinks all day?
12. 32.Would you rather sit near a coworker who narrates everything they do or sit near a coworker who sighs every ten minutes?
13. 33.Would you rather get stuck in an elevator with your manager for an hour or sit next to your manager on a five-hour flight?
14. 34.Would you rather have a costume day every month or have a pajama day every month?
15. 35.Would you rather be in charge of cleaning out the office fridge or be in charge of fixing the printer?
16. 36.Would you rather work in a glass office everyone can see into or work in a cozy room with no windows?
17. 37.Would you rather have your desk right next to the boss or have your desk next to the noisiest team?
18. 38.Would you rather use a keyboard with a sticky space bar or use a mouse that double-clicks on its own?
19. 39.Would you rather get a lot of emails that start with “per my last email” or get a lot of messages that start with “quick question”?
20. 40.Would you rather have someone always use your favorite mug or have someone always take your favorite seat in the break room?

Would you rather questions for team meetings

Quick picks about meetings themselves, short enough to open a stand-up.

1. 41.Would you rather have every meeting last 15 minutes or have one meeting a week that lasts three hours?
2. 42.Would you rather present to 500 people or present to five very serious people?
3. 43.Would you rather have every meeting be a walking meeting or have every meeting be a standing meeting?
4. 44.Would you rather always go first in the round of updates or always go last in the round of updates?
5. 45.Would you rather take notes in every meeting or run the slides in every meeting?
6. 46.Would you rather sit through a meeting that could have been an email or read an email that should have been a meeting?
7. 47.Would you rather present with your slides in the wrong order or present with no slides at all?
8. 48.Would you rather start every meeting with a one-minute dance break or end every meeting with a team cheer?
9. 49.Would you rather have meetings only on Mondays or have meetings only on Fridays?
10. 50.Would you rather answer a question you didn't quite hear or ask the question everyone has been thinking?
11. 51.Would you rather pass a talking stick in every meeting or have a buzzer that goes off after 60 seconds?
12. 52.Would you rather hold every meeting at a picnic table outside or hold every meeting in a room full of beanbags?
13. 53.Would you rather lead the icebreaker every week or pick the team lunch every week?
14. 54.Would you rather sit in a meeting with 30 people and say nothing or sit in a meeting with three people and talk the whole time?
15. 55.Would you rather get a meeting invite called “quick chat” with no details or get a meeting invite for 7 a.m. on a Monday?
16. 56.Would you rather say “you're on mute” fifty times a week or be told “you're on mute” fifty times a week?
17. 57.Would you rather work on a team that agrees on everything or work on a team that debates everything?
18. 58.Would you rather have every meeting start five minutes late or have every meeting run five minutes over?
19. 59.Would you rather ask “any questions?” and get total silence or get twenty questions at 4:59 on a Friday?
20. 60.Would you rather give your next update as a short poem or give your next update as a sports play-by-play?

Would you rather questions about dream jobs and careers

Career daydreams for the five minutes before the meeting starts.

1. 61.Would you rather taste new ice cream flavors for a living or name new paint colors for a living?
2. 62.Would you rather be a lighthouse keeper or be a park ranger?
3. 63.Would you rather run a cozy bakery or run a cozy bookstore?
4. 64.Would you rather be the voice of a cartoon character or write the jokes for a comedy show?
5. 65.Would you rather work on a cruise ship or work at a ski resort?
6. 66.Would you rather be a museum curator or be a movie set designer?
7. 67.Would you rather be the weather reporter on the morning news or be the voice of the announcements at the airport?
8. 68.Would you rather design toys for a living or design board games for a living?
9. 69.Would you rather spend a season at a research station in Antarctica or spend a season on a research ship at sea?
10. 70.Would you rather be a professional organizer or be a professional party planner?
11. 71.Would you rather be a puppeteer or be a magician?
12. 72.Would you rather make puzzles for a living or design escape rooms for a living?
13. 73.Would you rather work in the world's biggest library or work in the world's biggest aquarium?
14. 74.Would you rather run your own food truck or run your own bed-and-breakfast?
15. 75.Would you rather draw cartoons for a living or write children's books for a living?
16. 76.Would you rather be a train conductor or be a ship captain?
17. 77.Would you rather switch careers every five years or stay in one career your whole life?
18. 78.Would you rather host a game show or be a contestant on a game show every week?
19. 79.Would you rather solve mysteries for a living or crack secret codes for a living?
20. 80.Would you rather pilot a hot air balloon or pilot a submarine?

Would you rather questions about team perks and snacks

Snacks, outings and team traditions, the easy way into any icebreaker.

1. 81.Would you rather have free snacks but no coffee or have free coffee but no snacks?
2. 82.Would you rather get a free team lunch every Friday or leave at 3 p.m. every Friday?
3. 83.Would you rather take a team cooking class or go to a team bowling night?
4. 84.Would you rather win employee of the month or have the team name a snack after you?
5. 85.Would you rather have a team mascot or have a team theme song?
6. 86.Would you rather have a team potluck every month or have a catered lunch every month?
7. 87.Would you rather have a team that celebrates every win with cake or have a team that celebrates every win with a silly trophy that gets passed around?
8. 88.Would you rather spend a team volunteer day at a food bank or spend a team sports day at the park?
9. 89.Would you rather have an office karaoke night or have an office trivia night?
10. 90.Would you rather win the office chili cook-off or win the office costume contest?
11. 91.Would you rather get a surprise day off or know every day off a year ahead?
12. 92.Would you rather do a team scavenger hunt or do a team talent show?
13. 93.Would you rather play a board game at lunch or go for a team walk at lunch?
14. 94.Would you rather take a team photo in matching shirts or take a team photo in silly hats?
15. 95.Would you rather learn a coworker's hidden talent or teach the team your hidden talent?
16. 96.Would you rather share a fun fact about yourself every Monday or share your weekend highlight every Monday?
17. 97.Would you rather work on a team of five or work on a team of fifty?
18. 98.Would you rather have a coworker who bakes cookies every week or have a coworker who fixes every tech problem?
19. 99.Would you rather have a no-meeting Wednesday or have a no-email Friday?
20. 100.Would you rather have a ping-pong table at work or have a rooftop garden at work?

How to use would you rather in a 10-minute team meeting

Would you rather is one of the easiest icebreakers for work because nobody has to share anything personal. Everyone picks one of two options and says why in a sentence. The full deck and house rules are on the full Would You Rather game.

1. 1Pick a group before the meeting. Meetings and Office life are safe openers. Dream jobs works when people are new to each other.
2. 2Share your screen or put the page on the room display, and read the first question out loud.
3. 3Ask everyone to vote at once: hands up, thumbs in the chat, or a quick poll.
4. 4Call on two people, one from each side, for a one-sentence reason. Keep it moving.
5. 5Stop after three to five questions. Ten minutes is plenty, and people will ask for it again next week.

Tips for remote and hybrid teams

On a video call, voting in the chat works better than talking over each other. Ask everyone to type A or B, wait until the answers land, then reveal the count. The person in the smallest group gets to explain first.

For hybrid meetings, read the question in the room and on the call at the same time, and call on someone remote first. It's a small habit that keeps the people on the screen from becoming an audience. More ideas for virtual teams are in our video call games.

Keeping it comfortable for everyone

Every question here stays away from pay, health, age, family plans, relationships, religion and politics. Nobody is asked to confess a mistake or rate a coworker. The worst thing anyone admits is liking a no-email Friday.

Let people pass on any question, and never make anyone explain an answer they would rather keep short. If you want a longer warm-up with games beyond this one, browse our icebreaker games.

Questions