Would You Rather Questions for Work: Team Icebreakers

Work-appropriate would you rather questions

A good meeting icebreaker takes two minutes, gets everyone talking and never puts anyone on the spot. These would you rather questions are made for exactly that. They are about workspaces, meetings, coffee, team outings and dream perks, like choosing between a nap pod and a game room, or between a company band and a company sports team. Nothing touches on salaries, health, politics or anyone's private life.

How to use them with a team

Start the meeting with one question. Share your screen, read it out, and let everyone answer in one sentence. Tap the most popular option to close the round.
Hands up or chat. In the room, people raise a hand; on a call, they type 1 or 2 in the chat. Quick and painless.
Follow-up question. The facilitator picks one person from each side and asks a short "why?" That is usually where the team learns something new.

42 would you rather questions

Would you rather have a four-day workweek or be able to work from anywhere in the world?
Would you rather have a standing desk or have a treadmill desk?
Would you rather have unlimited free coffee at work or have unlimited free snacks at work?
Would you rather only have meetings on Mondays or never have meetings before 10 a.m.?
Would you rather give a presentation to 500 people or write a 50-page report?
Would you rather have an office with a window or have a desk next to the best coffee machine?
Would you rather work with an office dog or be in charge of keeping the office plant alive?
Would you rather communicate only by email or communicate only by video call?
Would you rather have a team lunch every Friday or finish an hour early every Friday?
Would you rather work on a project you love with a tight deadline or work on a dull project with a relaxed deadline?
Would you rather have a mentor from another industry or have a mentor from your own team?
Would you rather learn new software every month or use the same old software forever?
Would you rather take a team trip to the mountains or take a team trip to the beach?
Would you rather run every meeting or take notes in every meeting?
Would you rather work in a quiet office or work in a lively open space?
Would you rather get praised in front of the whole company or get a private handwritten thank-you note?
Would you rather work early mornings or work late afternoons?
Would you rather have a company band or have a company sports team?
Would you rather always have the right cable or always have a printer that works?
Would you rather have a team karaoke night or have a team trivia night?
Would you rather bring your pet to work or bring your favorite armchair to work?
Would you rather have a strict dress code with a free wardrobe or wear whatever you want but buy it yourself?
Would you rather eat lunch alone with a great view or eat lunch in the cafeteria with your team?
Would you rather have a nap pod at the office or have a game room at the office?
Would you rather work on a team of three or work on a team of thirty?
Would you rather get your birthday off or get a long weekend every quarter?
Would you rather present your work with slides or present your work without any slides?
Would you rather have a robot assistant or have a human assistant?
Would you rather work in a treehouse office or work in a houseboat office?
Would you rather have the fastest computer in the building or have the comfiest chair in the building?
Would you rather organize the holiday party or be in charge of the holiday party playlist?
Would you rather switch desks every week or keep the same desk for ten years?
Would you rather start every meeting with a joke or end every meeting with a compliment?
Would you rather learn sign language with your team or learn to cook a new cuisine with your team?
Would you rather have a job with an impressive title or have a job with a great team?
Would you rather answer every email within five minutes or answer all your emails once at the end of the day?
Would you rather have a company retreat in a castle or have a company retreat on a ranch?
Would you rather never fill out an expense report again or never fill out a timesheet again?
Would you rather be famous at work for your cookies or be famous at work for your spreadsheets?
Would you rather get a free lunch every day or get a free book every month?
Would you rather work alongside your best friend or work alongside your favorite celebrity?
Would you rather have a meeting room with a ball pit or have a meeting room with hammocks?

How it works

Read the question
Two options appear in two big boxes. Read them out loud: every question comes from this page’s list.
Pick your side
Everyone chooses. Tap the winning option and it is highlighted for the whole group to see.
Get the next one
Tap again or press Next question. The counter shows how far you are, with no repeats until the end of the list.

Any suggestions for improvement?

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Ready-made versions

Would you rather Funny would you rather Kids would you rather Hard would you rather Teen would you rather Couples would you rather Food would you rather Christmas would you rather Animal would you rather Travel would you rather

Tips for team leads and facilitators

Weekly stand-ups: one question per week builds a small ritual that new hires pick up quickly.
Remote and hybrid teams: answers in the chat let quieter people join in without unmuting.
Workshops and offsites: use answers to form groups, for example everyone who chose the treehouse office against everyone who chose the houseboat. For bigger groups, the team generator splits people at random.
Holiday parties: mix in a few questions while people arrive, so nobody stands around waiting.

Keep it optional: anyone can say "pass" and nobody keeps score.

Questions

Are these questions appropriate for work?

Yes. They stay on safe topics like workspaces, meetings, coffee and team activities, with nothing personal or divisive.

How long does an icebreaker take?

One question takes one or two minutes with a small team. For a longer warm-up, run five questions back to back.

Do they work for remote teams?

Yes. Share your screen on the call, read the question and ask people to answer 1 or 2 in the chat.

Can we use these questions when onboarding new hires?

Yes. They give new team members an easy way to share a little about themselves without anything personal. Ask one question in their first team meeting and let a couple of veterans answer first.

Are these would you rather questions free?

Yes. The page is free, funded by ads, and needs no account or app. It works in your browser.

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