72 Would You Rather Questions for an Office Icebreaker

These would you rather questions for work are designed for one thing: getting a room of colleagues talking without anyone feeling put on the spot. No personal finances, no politics, no awkward Monday-morning regrets. Every pair is balanced, every answer is defensible, and the whole game runs in under thirty minutes.

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How to Play

Read each prompt aloud, or pass the printed card to whoever is facilitating. Everyone votes simultaneously, either by raising a hand, holding up a finger for Option A or two fingers for Option B, or simply calling out their choice. After the vote, give the room sixty seconds to argue their corner, then move on. No wrong answers, no score to keep, no pressure to explain. Six rounds of twelve pairs means you have more than enough material to fill a lunch session or a team warm-up, and the rounds escalate gently from low-stakes office trivia to bigger career hypotheticals, so you can stop after any round and the energy will still feel complete.

Round One: Harmless Office Choices

Start here: these are the lowest-stakes pairs in the deck, light enough to break the ice before anyone has touched their coffee.

1. Would you rather have a standing desk or a classic sit-down desk with a cushioned chair?
2. Would you rather work in an open-plan office or in a private office with a glass wall?
3. Would you rather have a second monitor or a much faster laptop?
4. Would you rather sit next to the window with afternoon glare or in the middle of the room with perfect lighting?
5. Would you rather have unlimited stationery supplies or unlimited snacks in the kitchen?
6. Would you rather start every day with a ten-minute team standup or end every day with a five-minute wrap-up call?
7. Would you rather have your desk face a wall or face the rest of the room?
8. Would you rather share a printer that never jams or have your own printer that occasionally does?
9. Would you rather have a perfectly tidy desk with nothing on it or a personalised desk covered in plants and photos?
10. Would you rather use a physical notebook for all your notes or go fully digital with no paper at all?
11. Would you rather have a dedicated quiet room available all day or a well-stocked lounge where colleagues can drop in?
12. Would you rather keep the office temperature slightly too warm or slightly too cold?

Round Two: Meetings and Emails

Nearly everyone in the room has a strong opinion about meetings and inboxes, which makes this round the one that tends to get loudest.

1. Would you rather attend one two-hour meeting or four thirty-minute meetings that cover the same ground?
2. Would you rather receive fifty short emails a day or ten long emails that each require a careful reply?
3. Would you rather present to your own team or present to a group of senior stakeholders you have never met?
4. Would you rather be the person who runs every meeting or the person who never has to run one?
5. Would you rather have all your meetings before noon or all of them after two in the afternoon?
6. Would you rather have your camera on for every video call or be voice-only for every call?
7. Would you rather reply to every message within five minutes or batch all replies once a day?
8. Would you rather sit through a meeting that could have been an email or read a twenty-paragraph email that could have been a two-minute chat?
9. Would you rather be the person who always takes the meeting notes or the person who never does?
10. Would you rather have a recurring weekly meeting that never gets cancelled or no recurring meetings at all?
11. Would you rather give feedback to a colleague face-to-face or in a written message they can read in their own time?
12. Would you rather miss one important meeting because of a calendar clash or attend a meeting you were not supposed to be in?

Round Three: Working From Home

This round splits rooms reliably because everyone has a different relationship with remote work, and no position sounds unreasonable.

1. Would you rather work from home every day with a fixed schedule or come into the office three days a week on your own terms?
2. Would you rather have a dedicated home office with a door or work from a comfortable corner of your living room?
3. Would you rather join every video call in smart-casual dress or always wear exactly what you would wear in the office?
4. Would you rather cook lunch at home every day or have lunch provided when you are in the office?
5. Would you rather have your internet cut out during a presentation or your microphone stop working right before you are introduced?
6. Would you rather work from home with a pet in the room or work from a co-working space with strangers?
7. Would you rather receive a home-office allowance to spend on furniture or a monthly stipend for a co-working membership?
8. Would you rather have every team social event online or have every team social event require travel?
9. Would you rather be the first person on a remote team to go back to the office full-time or the last one?
10. Would you rather work from home in a city with no outdoor space or commute forty minutes to an office with a rooftop terrace?
11. Would you rather have the company track your working hours remotely or be trusted completely with no check-ins at all?
12. Would you rather have a slow but stable home broadband connection or fast broadband that drops out once a week?

Round Four: Commuting

Commute stories bond a room fast. Use this round to remind everyone they are not suffering alone.

1. Would you rather commute forty-five minutes by train with a guaranteed seat or twenty minutes standing in a packed carriage?
2. Would you rather cycle to work in all weather or drive in daily rush-hour traffic?
3. Would you rather arrive at the office fifteen minutes early every day or cut it so close that you are never quite late?
4. Would you rather listen to a work-relevant podcast on your commute or use the time to read fiction and completely switch off?
5. Would you rather have your commute fully paid by the company or receive a cash allowance and sort it yourself?
6. Would you rather commute ninety minutes each way to a job you love or ten minutes to a job that is just fine?
7. Would you rather sit next to a loud phone caller every morning or stand next to someone eating a strong-smelling breakfast?
8. Would you rather have a company parking spot that is a ten-minute walk from the entrance or no spot but drop-off at the door?
9. Would you rather have your commute cut in half but lose your flexible hours or keep flexible hours and keep the long commute?
10. Would you rather arrive at work already buzzing from an active commute or arrive calm after a quiet ride?
11. Would you rather your commute involve a short ferry crossing or a short cable-car ride?
12. Would you rather commute to a different city two days a week with all costs covered or stay local every day with no travel budget?

Round Five: Career Trade-Offs

This is where the room gets genuinely thoughtful. Keep the tone curious, not interrogative, and remind everyone there is no performance review attached.

1. Would you rather be the most skilled person on your team with no path to promotion or be promoted quickly into a role that stretches you past your comfort zone?
2. Would you rather earn twenty percent more in a role with high pressure or earn your current salary in a role with half the stress?
3. Would you rather work for a company whose mission you believe in with average pay or work for a company whose mission means nothing to you with excellent pay?
4. Would you rather have a manager who gives constant detailed feedback or a manager who gives you complete autonomy and checks in monthly?
5. Would you rather be known as the most creative person in your field or the most reliable?
6. Would you rather change careers completely at the peak of your current one or stay in your field and become one of its best-known voices?
7. Would you rather lead a team of two very talented people or manage a team of ten who are still developing?
8. Would you rather work a four-day week with a proportional pay cut or a five-day week with four weeks extra annual leave?
9. Would you rather take a sideways move that opens a completely new area or wait two years for the promotion you already know is coming?
10. Would you rather have your name on a project that fails publicly or be uncredited on a project that succeeds spectacularly?
11. Would you rather give a keynote at a major industry conference or publish a widely-read piece of work under your own name?
12. Would you rather spend the first half of your career building deep expertise in one area or spend it gaining broad experience across five?

Round Six: The Last Round Before Coffee

End on something lighter: these are the slightly absurd, entirely harmless hypotheticals that close a session on a good note rather than a philosophical one.

1. Would you rather have a robot that writes all your emails or a robot that attends all your meetings and gives you a summary?
2. Would you rather work in an office where the background music is always jazz or always lo-fi beats?
3. Would you rather have a nap pod available at the office or a fully equipped gym?
4. Would you rather have a professional chef cook lunch in the office every day or have a generous monthly meal-delivery credit for home?
5. Would you rather your job title be wildly impressive but mean nothing to outsiders or be completely plain but immediately understood by everyone?
6. Would you rather have the power to pause any meeting the moment it goes off-topic or the power to send any email directly to the right person without searching for their address?
7. Would you rather work a regular schedule in a treehouse office with no phone signal or in a sleek city skyscraper with floor-to-ceiling windows?
8. Would you rather every work trip include one extra day for sightseeing or always fly home the same evening to sleep in your own bed?
9. Would you rather have a company mascot that attends every all-hands meeting or a company anthem that plays at the start of every Friday?
10. Would you rather be given a surprise afternoon off with no notice or know three weeks in advance that you have a surprise free day coming?
11. Would you rather have a colleague who remembers every birthday and organises every team event or a colleague who always covers your shift when you need it?
12. Would you rather have the last word in every meeting or always be the person who asks the question that saves everyone an hour of confusion?

How to Keep It Moving and When to Stop

The only thing that kills a good round of would you rather questions for work is letting the debate run until everyone goes quiet from exhaustion. Set a visible timer for sixty to ninety seconds per pair and stick to it, even when the room is animated. Momentum is the point.

If a pair lands flat, because the split is nine to one and no one wants to defend the minority view, skip it without apology and go straight to the next card. You printed twelve for a reason: you will never need all twelve in one sitting.

Stop after any complete round if the energy is still good. Ending while people still want more is better than grinding through every prompt to reach the full seventy-two. Save the remaining cards for the next session, a work Christmas party, or any moment the team needs a quick reset. For more team-friendly games in the same spirit, the office Halloween party games list and the Thanksgiving games for work collection both follow the same principle: low stakes, high participation, no one singled out. Print the cards on cardstock, run them through a laminator if the deck will be reused, and clip each round together with a binder ring so you can grab exactly the set you need.

Frequently Asked Questions

How many players do you need to play Would You Rather at work?

The game works with as few as four people and as many as thirty. Larger groups benefit from a quick show of hands rather than going around the room individually, which keeps the energy up and the session on schedule.

How long does a full game of 72 questions take?

With sixty to ninety seconds of discussion per pair, one round of twelve questions takes roughly fifteen to twenty minutes. Six full rounds would run to about ninety minutes, so most teams pick two or three rounds that fit their session slot.

Are these questions suitable for a professional setting?

Yes. Every pair here avoids salary specifics, personal relationships, politics and anything that could feel intrusive in a workplace. The prompts are designed to be answerable in a meeting room without anyone feeling uncomfortable.

How do I print and use the card sheets?

Download the sheet, print on heavy cardstock, and cut along the marked lines. A standard home office laminator adds durability if the deck will be reused across multiple sessions. Clip each round together with a binder ring so they stay organised.

Can I use these questions for a virtual team session?

Absolutely. Read each prompt aloud on the call and ask participants to type A or B in the chat simultaneously so no one is influenced by seeing others vote first. The chat log also doubles as a light record of team preferences.

What is the best round to start with for a group that does not know each other well?

Start with Round One: Harmless Office Choices. The stakes are low enough that even quiet participants tend to vote and occasionally defend their answer, which builds confidence before the later rounds ask bigger questions.