Work-Safe Would You Rather Questions
Work-safe Would You Rather questions for meetings, team socials and icebreakers without intrusive or inappropriate topics.
Best for
team meetings, workshops, onboarding and office socials.
How to play this set
Use one or two questions at the start of a session. Keep explanations optional and avoid choices about protected characteristics, health, pay or personal relationships.
- Would you rather open every document on its oldest version with everyone noticing immediately, whenever a colleague shares their screen or unmute during the quietest moment of every call and be unable to blame the software, whenever a colleague shares their screen?
- Would you rather have every emoji you use name the person you hoped would reply, every weekend for five years or have every reaction you remove announce the exact second you noticed it, every weekend for five years?
- Would you rather never lose your luggage but receive no refund when plans change, for your next twenty trips or pay full price for every train but remain comfortable for the entire journey, for your next twenty trips?
- Would you rather make every snack completely healthy but you eat beside the kitchen door, for your next hundred meals or queue twenty minutes for any restaurant but the meal is always exactly as expected, for your next hundred meals?
- Would you rather complete your morning routine in five minutes but accidentally describe one at breakfast, whenever you have an early start or forget every dream immediately but begin each day very slowly, whenever you have an early start?
- Would you rather begin every meeting with your camera already on but notice the problem before anyone else, twice a week without warning or begin every lunch break when someone needs a favour and be unable to blame the software, twice a week without warning?
- Would you rather have every voice note you send reveal how many times you reopened it, twice a week without warning or have every message request announce the exact second you noticed it, twice a week without warning?
- Would you rather arrive everywhere thirty minutes early but cannot change the journey afterwards, on the outward journey or take the first available parking space but remain comfortable for the entire journey, on the outward journey?
- Would you rather get every food delivery free but everyone at the table notices, whenever you are paying or follow every recipe without shortcuts but the meal is always exactly as expected, whenever you are paying?
- Would you rather wake fully rested after four hours but yawn through every social event, with no way to catch up later or nap only when genuinely exhausted but begin each day very slowly, with no way to catch up later?
- Would you rather receive every calendar invitation at the least convenient time with your real name highlighted, whenever your manager is nearby or let every meeting overrun by exactly seventeen minutes with your real name highlighted, whenever your manager is nearby?
- Would you rather have every typing indicator you trigger include the first version you nearly sent, every weekday for one year or have every incoming voice note show your live facial reaction, every weekday for one year?
- Would you rather teleport to any familiar place but let everyone see that you received the advantage, whenever the weather is terrible or keep the cheapest travel seat but nobody comments on your choice, whenever the weather is terrible?
- Would you rather receive unlimited portions of your favourite food but the order or recipe is read aloud, every Friday night or wait exactly forty minutes for every meal but nobody judges your choice, every Friday night?
- Would you rather have unlimited energy every morning but snore like a printer, every weekend or take thirty minutes to fall asleep but give up one evening hour, every weekend?
- Would you rather see every deadline reminder while someone watches after only a ten-second warning, once a day without warning or rename every shared document after your worst nickname with your real name highlighted, once a day without warning?
- Would you rather have every work or school message display your honest mood at the time, once a day without warning or have every missed call show your live facial reaction, once a day without warning?
- Would you rather always find the perfect parking space but lose control of one small travel detail, on the journey home or travel normally to every new place but nobody comments on your choice, on the journey home?
- Would you rather cook every recipe perfectly but you must share with anyone who asks, whenever someone else is paying or order your favourite food only once a month but nobody judges your choice, whenever someone else is paying?
- Would you rather take the perfect nap on command but crash completely at 8pm, during every holiday or gain energy slowly throughout the morning but give up one evening hour, during every holiday?
- Would you rather end every presentation with your worst typo highlighted while everyone stays completely silent, for your next working week or stop every printer only when your turn arrives with your real name highlighted, for your next working week?
- Would you rather have every serious text you send include your weekly screen-time total, for seven days or have every forwarded message show your live facial reaction, for seven days?
- Would you rather receive every flight upgrade free but arrive wearing yesterday's clothes, on every commute or risk one delayed bag each year but nobody comments on your choice, on every commute?
- Would you rather have every meal arrive instantly but the smoke alarm celebrates loudly, at every takeaway or keep every snack exactly as unhealthy but nobody judges your choice, at every takeaway?
- Would you rather fall asleep within thirty seconds but wake with one song stuck in your head, for the next seven nights or spend one peaceful hour getting ready but give up one evening hour, for the next seven nights?
- Would you rather freeze on your worst expression in every video call and be unable to explain why, whenever a deadline is close or play every work voice note through the office speakers while your closest colleague watches, whenever a deadline is close?
- Would you rather have every message you leave on read include how long you spent on it, whenever you are in public or have every group chat mention reveal how long you waited to respond, whenever you are in public?
- Would you rather get every train ticket half price but accept one uncomfortable part of the journey, whenever you have heavy luggage or arrive everywhere two minutes late but carry only your own belongings, whenever you have heavy luggage?
- Would you rather never wait for a restaurant table but someone watches your first bite, during every holiday or pay double for every delivery but every item is correct, during every holiday?
- Would you rather remember every dream clearly but wake at exactly 5am, whenever you sleep away from home or sleep eight uninterrupted hours but follow a strict routine, whenever you sleep away from home?
- Would you rather hear every message from your boss through the loudest notification while your closest colleague watches, with no way to blame the software or personally end every reply-all thread while your closest colleague watches, with no way to blame the software?
- Would you rather have every late-night reply show your current battery percentage, until your next birthday or have every read receipt reveal how long you waited to respond, until your next birthday?
- Would you rather know every delay before leaving home but carry one extra bag, until your next birthday or join every travel queue normally but carry only your own belongings, until your next birthday?
- Would you rather always receive the largest portion but one favourite extra is unavailable, and everyone at the table notices or eat every takeaway slightly cold but every item is correct, and everyone at the table notices?
- Would you rather never feel tired at work or school but announce the time aloud when waking, starting tonight or use five different alarms but follow a strict routine, starting tonight?
- Would you rather send every email with your first draft attached with no undo button, whenever a colleague shares their screen or unmute during the quietest moment of every call while your closest colleague watches, whenever a colleague shares their screen?
- Would you rather have every message you delete show how quickly you expected an answer, every weekend for five years or have every reaction you remove reveal how long you waited to respond, every weekend for five years?
- Would you rather skip every travel queue but sit beside the busiest part of the vehicle, for your next twenty trips or pay full price for every train but carry only your own belongings, for your next twenty trips?
- Would you rather make every takeaway perfectly hot but it leaves a slight toothpaste aftertaste, for your next hundred meals or queue twenty minutes for any restaurant but every item is correct, for your next hundred meals?
- Would you rather never need an alarm again but wear one item backwards, whenever you have an early start or forget every dream immediately but follow a strict routine, whenever you have an early start?
- Would you rather open every document on its oldest version but notice the problem before anyone else, twice a week without warning or begin every lunch break when someone needs a favour while your closest colleague watches, twice a week without warning?
- Would you rather have every emoji you use reveal how many times you reopened it, twice a week without warning or have every message request reveal how long you waited to respond, twice a week without warning?
- Would you rather never lose your luggage but cannot change the journey afterwards, on the outward journey or take the first available parking space but carry only your own belongings, on the outward journey?
- Would you rather make every snack completely healthy but everyone at the table notices, whenever you are paying or follow every recipe without shortcuts but every item is correct, whenever you are paying?
- Would you rather complete your morning routine in five minutes but yawn through every social event, with no way to catch up later or nap only when genuinely exhausted but follow a strict routine, with no way to catch up later?
- Would you rather begin every meeting with your camera already on while your closest colleague watches, whenever your manager is nearby or let every meeting overrun by exactly seventeen minutes after only a ten-second warning, whenever your manager is nearby?
- Would you rather have every voice note you send show your current battery percentage, every weekday for one year or have every incoming voice note display your honest first thought, every weekday for one year?
- Would you rather arrive everywhere thirty minutes early but carry one extra bag, whenever the weather is terrible or keep the cheapest travel seat but control every small travel detail, whenever the weather is terrible?
Common questions
What makes an icebreaker work-safe?
It should be easy to answer without revealing health, religion, politics, family status, finances or other sensitive personal information.
How long should a work icebreaker take?
One question can take two minutes: ten seconds to choose and roughly a minute for a few voluntary explanations.