All 67 Would You Rather Questions for Work
- Would you rather be a morning person or a night owl?
- Would you rather never have to sleep again or sleep 12 hours every night?
- Would you rather give up cheese or give up chocolate forever?
- Would you rather eat your favorite meal every day or never eat it again?
- Would you rather give up all desserts or give up all fried foods?
- Would you rather only eat ice-cold food or only eat piping-hot food forever?
- Would you rather listen to the same 10 songs forever or watch the same 5 movies forever?
- Would you rather binge-watch an entire series in one sitting or savor one episode per week?
- Would you rather live in your favorite video game world or your favorite movie universe?
- Would you rather meet your favorite musician or your favorite actor?
- Would you rather attend a Broadway show or a blockbuster movie premiere?
- Would you rather travel solo and be completely independent or travel with friends and share the experience?
- Would you rather explore ancient ruins or futuristic cities?
- Would you rather have every trip planned to the minute or figure it out as you go?
- Would you rather meet a celebrity who's incredibly boring or a stranger who's absolutely hilarious?
- Would you rather always be the host or always be the guest?
- Would you rather win $10,000 guaranteed or take a 50/50 chance at $1 million?
- Would you rather live in a fully automated smart home or a home with no tech at all?
- Would you rather give up social media forever or eat the same dinner for the rest of your life?
- Would you rather speak every language fluently or play every musical instrument perfectly?
- Would you rather have a photographic memory or genius-level creativity?
- Would you rather read fiction that transports you or non-fiction that teaches you?
- Would you rather live in a bustling city or the peaceful countryside?
- Would you rather have infinite time but limited money or infinite money but limited time?
- Would you rather be able to pause time whenever you want or rewind time once per day?
- Would you rather never wear shoes again or never wear sleeves again?
- Would you rather work out intensely three times a week or moderately every day?
- Would you rather be able to breathe underwater or run at superhuman speed?
- Would you rather be able to fly or turn invisible?
- Would you rather read anyone's thoughts or predict anyone's future?
- Would you rather talk to animals or instantly understand any human language?
- Would you rather perform live on stage in front of hundreds or star in a major film?
- Would you rather spend a year in the Harry Potter universe or the Star Wars universe?
- Would you rather have dramatic seasons or the same perfect weather year-round?
- Would you rather have long summer days or long winter nights?
- Would you rather finish an amazing project or start an exciting new adventure?
- Would you rather be the funniest person alive or the most intelligent person alive?
- Would you rather work four 10-hour days or five 8-hour days?
- Would you rather have a two-hour lunch break every day or finish work an hour early?
- Would you rather never attend another meeting or never write another email?
- Would you rather have a personal assistant or a personal chef?
- Would you rather work from a beach hut or a mountain cabin for a month?
- Would you rather present to the CEO or to a room of 500 strangers?
- Would you rather have unlimited vacation days or a 20% raise?
- Would you rather work with a perfectly organized but slow teammate or a brilliant but chaotic one?
- Would you rather always have a tidy inbox or always have a tidy desk?
- Would you rather have your dream job in a city you dislike or an okay job in your favorite city?
- Would you rather have cameras always on in meetings or never be able to use video?
- Would you rather have a standing desk or a treadmill desk?
- Would you rather receive public praise or a private thank-you note?
- Would you rather lead a team or be the top expert on one?
- Would you rather have a long train commute with a great book or a five-minute walk to work?
- Would you rather only communicate by chat or only by phone for a month?
- Would you rather work in a library-quiet office or a buzzing open space?
- Would you rather get a new laptop every year or a new office chair every year?
- Would you rather go back to school for a year or take a year-long sabbatical?
- Would you rather have a perfect memory for names or for faces?
- Would you rather give a TED talk or write a bestselling book?
- Would you rather fix bugs all day or write documentation all day?
- Would you rather have a team offsite at a ski lodge or a beach resort?
- Would you rather start work at 6 a.m. or finish work at 8 p.m.?
- Would you rather sit next to a coworker who hums all day or one who reads their emails out loud?
- Would you rather know everyone's honest opinion of you or never hear any feedback at all?
- Would you rather have free coffee for life or free lunch every Friday?
- Would you rather learn to code in a day or learn to draw in a day?
- Would you rather be stuck in an elevator with your CEO or with your favorite celebrity?
- Would you rather have a robot that does your chores or one that answers your emails?
Tips for Using Would You Rather Questions for Work
- Poll first, discuss second: A quick vote gets everyone involved in seconds, even on a large call.
- Ask for the why: The choice is the hook. The reasoning behind it is what helps people get to know each other.
- Make your own: Swap in options from your product or industry for an inside-joke version your team will remember.
More Icebreaker Questions
Want a mix? The random icebreaker generator draws from every category at once. For recurring meetings, try the check-in question generator.
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