200 Would You Rather Questions for Work (2026)

How to run it

Two minutes, not twenty

Pick three questions, not thirty. An opener that runs long stops being an opener and becomes the meeting.
Everyone answers, including you, and you go first. Whoever runs the meeting sets the ceiling for how honest anyone else will be.
One sentence of reasoning each, no more. The reason is the interesting part, but a round table of monologues kills it.
Nobody may pass, but anybody may pick a different question. Refusing to choose defeats the format; refusing a particular topic is fair.

On a video call, put the two options in the chat and ask for a reaction emoji before anyone speaks. It takes twenty seconds, it stops the room anchoring on whoever unmutes first, and it gives quiet people a way in that does not require them to interrupt.

Which block to use. A first meeting with strangers: openers, then absurd. A team that works together daily: office, meetings, tech — the shared grievances. An offsite or a retro with a group that trusts each other: team, then real. Do not start with the last block, ever.

Safe openers for the first two minutes

Nothing personal, nothing anyone has to think about. These exist to get voices into the room before the real meeting starts.

start work at seven and finish at three or start at ten and finish at six
have a window seat with a terrible view or have no window and an excellent chair
take a proper lunch break alone or take a short one with the team
work in complete silence or work with background music somebody else chose
have unlimited coffee or have unlimited snacks
have a standing desk or have a genuinely good chair
get every Friday afternoon off or arrive an hour late every single day
sit near a colleague who talks constantly or sit near one who never speaks at all
take your birthday off or take an extra day at Christmas
always be first into the office or always be last out
have a twenty-minute commute you hate or have an hour-long one you enjoy
have a laptop that is always fast or have internet that is always fast
know the name of everyone in the building or have everyone in the building know yours
have four short meetings or have one long one
get feedback the moment something happens or get it once a quarter and in detail
share an office with one other person or sit in an open plan with forty
have the best desk in the worst room or the worst desk in the best room
have a printer that always works or have a coffee machine that always works
have a manager who is always available or have one who never interrupts you
be given very clear instructions or be given complete freedom

Remote, hybrid and the commute

The block that reliably splits a team down the middle. Expect the answers to say more about people's living situations than their opinions about work.

work from home permanently or be in the office every day
have a perfect home setup and no colleagues nearby or have a mediocre desk and a team you like
never commute again or never take a video call again
work from anywhere but always at fixed hours or work fixed hours nowhere but your desk, but choose the hours
do a two-hour commute twice a week or do a thirty-minute one five times
have your camera on for everything or have a camera that never works
work from a coffee shop or work from a library
live near the office in a small flat or live far away in a large house
have a colleague permanently in another time zone or have one permanently in another room
take every meeting walking or take every meeting sitting in one place
do four calm days at home and one chaotic office day or do five steady days in the office
have a home office with a door that closes or have a desk in the living room with much better light
never see your team in person or see them every single day
have flexible hours and no clear boundaries or have fixed hours and a hard stop
commute by train with a guaranteed seat or commute by bike in any weather
work from a beach with unreliable wifi or work from a basement with perfect wifi
have work know your home address or have work know your personal phone number
take calls in your car or take calls in a corridor
relocate for a job you would love or stay put for a job you like
work somewhere that trusts you completely or work somewhere that checks in constantly

Office life

Small grievances, strongly held. Good for a Friday, and good for finding out what is quietly annoying everybody.

sit next to the kitchen or sit next to the printer
work somewhere always slightly too cold or work somewhere always slightly too warm
have a desk by the door or have one by a window with a draught
share a fridge with people who label everything or share one with people who label nothing
have an extremely loud keyboard or have an extremely loud chair
be invited to every office social or be invited to none
have a strict dress code or have no guidance at all and get it wrong occasionally
have your screen visible to the whole room or sit facing a blank wall
sit near someone who microwaves fish or sit near someone who takes every call on speaker
have an excellent canteen ten minutes away or have a bad one downstairs
be responsible for a plant on your desk or be responsible for a fish
work in a beautiful building with bad equipment or work in an ugly one with excellent equipment
have a lift that is always slow or have no lift and be on the fifth floor
have hot-desking or have a fixed desk you are not allowed to personalise
have a superb coffee machine five minutes away or have a mediocre one at arm's reach
have your team spread across three floors or have all of them in one small room
have soundproof booths and no meeting rooms or have meeting rooms and no booths
have someone else decorate your space or have a completely bare one
have a fire drill every month or never have one at all
have a bad chair and a large monitor or have a good chair and a laptop screen

Meetings

Everyone has strong feelings and nobody usually says them out loud. Use two or three, not the whole block, or the meeting becomes about meetings.

have every meeting start on time and overrun or have them start late and end on time
have no agenda at all or have an agenda nobody follows
sit through a meeting you did not need or miss one you did
present to fifty strangers or present to five people who know your work
have every meeting standing or have every meeting seated for an hour
put all meetings on Monday or spread them through the week
be the person taking notes or be the person running it
have a meeting that could have been an email or have an email that should have been a meeting
be interrupted constantly or never be asked a single question
have every meeting recorded or have no record of any of them
run one two-hour workshop or run four thirty-minute calls
have every meeting back to back in the morning or have them scattered across the day
be told your idea is bad immediately or have it politely ignored
run a retrospective nobody prepared for or run a planning session that overruns badly
have a chair who cuts people off or have one who lets everybody talk
always be the first to speak or always be the last
have one meeting-free day a week or leave an hour early every day
have your camera freeze mid-sentence or have your microphone cut out
sit through sixty slides or sit through ten minutes with no visuals at all
have every decision made in the room or have every decision made afterwards

Career and ambition

These change the temperature. Better one-to-one or with a small group than as a warm-up for twenty people.

be promoted early and struggle or be promoted late and be ready
be genuinely excellent at one thing or be good at five
have a title above your actual work or have work well above your title
change career entirely at thirty-five or stay and go very deep
become a manager or stay senior and hands-on
work for someone brilliant and difficult or someone kind and mediocre
take a pay cut for a better team or take a raise for a worse one
be indispensable or be easily replaceable and completely free to leave
get honest feedback that stings or get encouragement that is vague
work on something important that fails or something small that actually ships
have your work credited to the team or be singled out personally
be known outside the company or be quietly valued inside it
join a company of twenty people or join one of two thousand
have one long stint on your CV or have many short ones
learn everything from your own mistakes or learn it from someone else's
always be the least experienced person in the room or always be the most
have a career you planned or have one that happened to you and worked out
be the person who fixes things or be the person who prevents them
take a sabbatical and fall behind or keep going and burn slightly out
have a mentor or have a rival

Money, hours and everything around them

The most honest block. People answer these quickly and the answers are worth paying attention to.

get a twenty per cent raise or get a four-day week
have unlimited holiday you feel guilty taking or have twenty-five fixed days you take fully
get one extra week off a year or finish an hour earlier every day
get an unpredictable large bonus or get a smaller guaranteed one
have an excellent pension or have more money now
have private healthcare or have a much better office
get lunch free or get a shorter day
have a company car or have a travel budget
get training paid for or get conference travel paid for
have a bigger salary and a long commute or have less money and a five-minute walk
hold equity that might be worth a great deal or hold cash that definitely is
get a gym membership or get a therapy budget
get a remote work allowance or get a laptop you keep
get a raise nobody knows about or get public recognition and no raise
take six months of paid leave once or take two extra weeks every year
get a sabbatical after five years or get a bonus after five years
have a personal assistant for a year or have a personal trainer for a year
work somewhere with full salary transparency or work somewhere with complete privacy
have a share of the profits or have a fixed salary above the market
have a job that pays enough and asks little or one that pays a lot and asks a lot

Working with other people

The block that earns its place. Everything here is a real trade-off somebody in the room has actually made.

work with people you like on a boring project or work with people you tolerate on a brilliant one
be on a team that argues openly or be on one that agrees quietly
be the newest person on the team or be the longest-serving
have to give hard feedback or have to receive it
work with someone who over-promises or work with someone who under-communicates
inherit a mess with a good team or get a clean slate alone
be trusted and left completely alone or be supported and checked on often
work with someone much faster than you or work with someone much slower
share credit for a success or carry the blame for a failure alone
be on a team that socialises or be on one that goes straight home
be the person who says the awkward thing or be the person who smooths it over
have clear roles and rigid boundaries or have blurred roles and real flexibility
onboard someone badly or be onboarded badly
work closely with a friend or keep work and friendship completely separate
work with someone brilliant and unreliable or someone reliable and average
say something to a colleague who might be struggling or say nothing and risk being wrong
be on a team where everyone thinks like you or be on one where nobody does
be liked and not respected or be respected and not liked
lose your best colleague to a promotion or lose them to another company
be on a team of five or be on a team of fifteen

Tools, systems and everything that breaks

Light, specific, and it surfaces genuine complaints about your stack without anyone having to file a ticket.

have one tool that does everything badly or have ten that each do one thing well
get every notification or get none
lose your entire inbox or lose your entire calendar
have search that actually works or have folders that actually make sense
type twice as fast or read twice as fast
have a second monitor or have a much better laptop
never update anything again or update every week
have every file in one place or have an excellent memory for where things are
have automated reports nobody reads or have manual ones everybody reads
use a password manager and remember nothing or memorise every password
have an assistant that drafts everything roughly or one that does a single thing perfectly
lose an hour a week to a bad tool or lose a day a month to migrating tools
have all your work visible inside the company or have it private by default
have version history or have unlimited undo
use whatever tools you like or have everything standardised
have IT that is slow but always right or have IT that is fast but often wrong
have a heavy laptop that lasts all day or a light one with three hours of battery
stay in a system you know is bad or learn a new one that might be worse
have perfect documentation and no colleagues to ask or have great colleagues and no documentation
have every meeting transcribed or never write anything down at all

The ridiculous ones

For four in the afternoon, the last day before a holiday, or a call where nobody has any energy left.

attend every meeting as a puppet or write every email in rhyme
have your job title be an animal or have your email signature be a haiku
present with slides that advance on their own or present with no slides and no notes
have a compulsory office song each morning or have a compulsory office stretch
have your desk inside a lift or have it in a stairwell
do stand-up actually standing on the desk or do it lying down
have every email copied to the whole company or have every email deleted after a day
have a horn sound whenever you finish a task or have a sad trombone whenever you miss one
high-five everyone on arrival or bow to everyone on leaving
have your work calendar visible to your family or have your family calendar visible to work
wear a costume you choose or wear one chosen for you
have a colleague who is a highly competent dog or one who is a deeply incompetent human
have your performance review staged as a musical or staged as a silent film
have a swear jar or have a jargon jar
communicate only in emoji or communicate only in formal letters
have your annual goals written by a stranger or written by yourself five years ago
have to arrive by scooter or have to leave by fire pole
be followed everywhere by a company mascot or have a theme tune play whenever you speak
hold every meeting in the dark or hold every meeting outdoors in any weather
name every project after a cheese or name every project after a former colleague

The ones that start a real conversation

Save these for a team that already trusts each other. In the wrong room they land as an interrogation; in the right one they are the reason people remember the session.

know exactly what your manager thinks of you or never know
be told early that the company is struggling or be protected from it until it is decided
do work that matters and work long hours or do work that does not and keep reasonable ones
be very good at your job and slightly bored or be stretched and slightly out of your depth
stay in a role you have outgrown with people you love or move on alone
be paid fairly and never told you are doing well or be praised constantly and underpaid
know a decision is wrong and say so or stay quiet and be proven right later
have a career that impresses people or have one you would choose again
believe in the mission and endure bad management or have good management and no mission
be the reason someone stayed or be the reason someone left for something better
have your best years at work already behind you or have them ahead but a long way off
take the safe option and always wonder or take the risk and possibly regret it
know your job will be automated within five years or not know
be completely honest in an exit interview or be diplomatic
work for someone you would never work for again and learn enormously or work for someone pleasant and learn little
be respected by people you do not respect or be dismissed by people you do
turn down a promotion for your health or take it and manage somehow
find out you were the second choice or never find out
have a job that fits your life or have a life that fits your job
retire knowing you built something or retire knowing you were kind to everyone you worked with

Why this works at all

People badly misjudge how much colleagues want to be asked

The standard objection to an icebreaker is that it is forced, awkward, and that nobody wants to do it. Half of that is right. The awkwardness is real — and it turns out to be systematically overestimated by the people feeling it.

Michael Kardas, Amit Kumar and Nicholas Epley tested exactly this across a series of experiments published in the Journal of Personality and Social Psychology in 2022. They paired people up and assigned them either shallow small talk or deliberately deeper questions, and — the important part — asked both groups to predict beforehand how awkward it would feel and how much the other person would care about the answer.

The predictions were wrong in a consistent direction. Deeper conversations turned out less awkward, more enjoyable and more connecting than the participants had expected. Their hypothesis, in their own framing, was that people systematically underestimate how caring and interested other people are in their more personal revelations — and that this miscalibration is itself the barrier to having those conversations at all.¹

Which is a fairly precise description of what happens in a team meeting. Everyone privately assumes their colleagues would rather not be asked anything, so nobody asks, so nobody finds out they were wrong.

The practical read: the block of questions at the bottom of this page is likely to work better than you expect, and the openers at the top are likely to feel more pointless than they are. Which is not an argument for opening a Monday stand-up with someone’s biggest regret — it is an argument for not stopping at coffee preferences forever.

The thing an icebreaker is actually for

Cheap disagreement now, expensive disagreement avoided later

A would-you-rather round makes people disagree out loud about something that costs nothing. That is not a side effect — on a team it is close to the whole point.

The concept that names this is psychological safety, and the foundational study is Amy Edmondson’s, published in Administrative Science Quarterly in 1999. She defined team psychological safety as a shared belief that the team is safe for interpersonal risk-taking, and measured it across 51 work teams at an office-furniture manufacturer of roughly 5,000 employees.

Two findings are worth carrying into a meeting. Psychological safety was associated with learning behaviour — asking questions, admitting errors, seeking feedback — while team efficacy, the belief that the team is capable, was not, once psychological safety was controlled for. And learning behaviour mediated the relationship between psychological safety and actual team performance.²

In plain terms: a team that believes it is competent is not the same as a team where it is safe to say something wrong, and it is the second one that learns and performs. Confidence is not the ingredient. Permission is.

A silly forced choice is a very low-stakes rehearsal of that permission. Someone says the unpopular thing about pineapple, the room disagrees, nothing bad happens. It is a small rehearsal, and no round of questions substitutes for a manager who responds well when the stakes are real. But it is a rehearsal, and it costs two minutes.

What goes wrong

Five ways to make everyone hate this

Making it compulsory and public with no way out. The fastest route to resentment. “Anyone may swap a question” costs you nothing and removes almost all of the objection.

Asking questions you would not answer yourself. If you would not tell the team your own answer to the last block, do not ask it. Seniority makes this worse, not better — a question from a manager is never quite optional.

Using the personal blocks with people who have just met. The research above says depth works better than expected; it does not say depth works on day one with strangers who report to you. Start at the top of the page.

Running it every single week. Novelty is doing a lot of the work. Fortnightly stays fun; weekly becomes a ritual people schedule around.

Turning it into a performance review. Nothing anyone says in a round of these should ever come back later. If it might, you are not running an icebreaker.

Free printable

Ten more rounds, printable

The Bonus Round Pack is a printable PDF with ten rounds that aren’t in Party Battle Book and aren’t on this page — useful for an offsite where you want something on the table instead of on a screen. Prints fine in black and white.

Questions about the questions

Common ones

How long should an icebreaker actually take?

Two to five minutes for a regular meeting, and it should be over before anybody wonders when it will be. Three questions with a one-sentence answer each is about right for a team of six. Anything longer needs to be the point of the session rather than the opening of it.

What works on a video call specifically?

Put both options in the chat and ask for a reaction emoji before anyone speaks. It removes the anchoring problem — on a call the first person to unmute shapes every answer after them — and it lets quiet people participate without interrupting. Then ask two people to explain, not everybody.

Are these safe to use with a team I manage?

The first eight blocks, yes. The last two are a different matter: a question from a manager is never fully optional, however casually it is asked. The rule that makes it safe is that you answer first and anyone may swap a question for another without explaining why.

Does an icebreaker actually improve anything, or is it theatre?

Honestly, on its own it is close to theatre. What it does is rehearse low-stakes disagreement, which is the observable behaviour underneath psychological safety — and psychological safety is what Edmondson’s work links to learning behaviour and then to performance. A round of questions does not create that. A manager who responds well when someone is wrong creates it. The questions just give people something harmless to be wrong about first.

What about a fully remote team across time zones?

Run it asynchronously. Post one question in the team channel, everyone answers when they are online, and it accumulates over a day instead of a minute. It loses the energy of a live room and gains the participation of the half of the team who were asleep.

Can we use these in interviews or onboarding?

Onboarding, yes — the openers block is close to ideal for a first-week introduction. Interviews, no. The power imbalance is at its most extreme there, nothing anybody says is voluntary, and answers to hypotheticals tell you very little about how someone works.

Sources

Where the research on this page comes from

Kardas, M., Kumar, A., & Epley, N. (2022). Overly shallow?: Miscalibrated expectations create a barrier to deeper conversation. Journal of Personality and Social Psychology, 122(3), 367–398. doi:10.1037/pspa0000281.
Edmondson, A. (1999). Psychological safety and learning behavior in work teams. Administrative Science Quarterly, 44(2), 350–383. Field study of 51 work teams at a manufacturer of office furniture with roughly 5,000 employees. doi:10.2307/2666999.

Both are peer-reviewed and widely replicated in citation, not in every particular. Where this page draws a practical conclusion the studies do not themselves make — for instance that a two-minute round of questions rehearses psychological safety — it is flagged as an inference rather than a finding.

Keep going

More from this side of the house

The same game cut for a different room: 200 questions for teens, or the whole would-you-rather collection with the full rules.

If you are putting together an offsite rather than an opener, Party Battle Book has 117 rounds across seven kinds — charades, bluffs, debates, letter storms — one page per round, no phones and no setup. It travels better than a slide deck.

For the other thing the office does together: twenty Christmas party games with the rules in full, seventeen of which are safe in a room that includes your manager.

Everything on the party and games shelf