100 Would You Rather Questions for Coworkers
 Whether you’re starting a new job or there’s a new face in the office, you can improve team dynamics by simply asking a good question or two. To help get to know your coworkers, try a few of these would you rather questions. Whether you choose a goofy or serious question is up to you!
About Work
- Would you rather work 80 hours one week and have the next week off or work 40 hours for the week (spread across seven days including weekends) for two weeks?
- Would you rather be the CEO of a company or another executive?
- Would you rather do something you love and make just enough money to get by or do something you hate but make billions of dollars?
- Would you rather work in a big city or a small town (if you could have the same job both places)?
- Would you rather bike or drive to work?
- Would you rather have a constant supply of the best coffee in the world at your office or a constant supply of the best snacks in the world at your office?
- Would you rather get paid your entire salary plus benefits all at once for the year or get paid little by little throughout the year?
- Would you rather have way more work than you could ever accomplish in a day and be stressed or have hardly any work at all and be bored?
- Would you rather have an office where you could wear pajamas to work or work in a really fancy office?
- Would you rather work for a very small company or a very large company?
- Would you rather work in Los Angeles or in New York City?
- Would you rather have a terrible boss but a great job or a great boss but a terrible job?
- Would you rather receive catered lunch every day at work but never get to choose what you order or pack your own lunch every day?
- Would you rather work an extra hour but get an hour of break time or work with no breaks but leave an hour earlier?
- Would you rather commute two hours to your dream job or live two minutes from a mediocre job?
- Would you rather have a job where you talk to people all day or a job where you stay at your desk by yourself all day?
- Would you rather have a job where you don’t write at all or a job where you write all the time?
- Would you rather have plenty of time to work on an eventually unused project or frantically rush to finish a surprisingly important project?
- Would you rather be good at any new skill you tried but always work on new things or work with the same skills and specialize your work?
- Would you rather work longer but fewer days a week or shorter but more days of the week?
- Would you rather work on a big team or just with one other person?
- Would you rather come in late to work and leave late or come in early and leave early?
- Would you rather have a very stressful job but have a lot of responsibility or have a minimally stressful job but with little responsibility?
- Would you rather run a country or a business?
- Would you rather be the manager whose job is to delegate or the worker who gets to do the actual work?
- Would you rather have your dream job but you can’t retire for 50 years or a terrible job, but you get to retire in 10 years?
- Would you rather eat the oldest thing in the office fridge or clean the office bathroom?
- Would you rather never have a meeting again or be in meetings all day every day for a year straight?
- Would you rather sit in a loud part of the office or a quiet part?
- Would you rather wear headphones at work or have music playing over a speaker?
- Would you rather speak at an important conference or host an important meeting face-to-face at the office?
- Would you rather be the oldest person in the office or the youngest?
- Would you rather be famous in your career field or celebrity famous?
Coordinate an office potluck with a sign up. SAMPLE
Silly Questions
- Would you rather be a famous celebrity or live like a hermit?
- Would you rather be the best in the world at a super obscure sport or just pretty good at a very popular sport?
- Would you rather have to listen to one song (chosen by you) play over and over for a week or have multiple songs (chosen by someone else) play over and over for a week?
- Would you rather always be slightly too warm or slightly too cold (no matter what temperature the world around you is)?
- Would you rather be able to read minds or be able to see the future?
- Would you rather lose all your technology devices or lose every picture that’s ever been taken of you?
- Would you rather have to wear clown shoes every day or have to wear bunny ears every day?
- Would you rather not have heating or not have air conditioning?
- Would you rather be an amazing chef or be an amazing driver?
- Would you rather pick up painting or sewing?
- Would you rather hear every word spoken to you as if it’s to the tune of your least favorite song or have to sing everything you speak but to any tune you want?
- Would you rather live in a tiny house or in a house that’s too big for the number of people living in it?
- Would you rather be a public speaker or be a shark diver?
- Would you rather be able to fly or be able to teleport?
- Would you rather live for 1,000 years or live for only 30 years?
- Would you rather have no elbows or have no knees?
- Would you rather eat only sour foods or only salty foods?
- Would you rather have one dog that lived for your whole life or multiple dogs, but all dogs that you really loved?
- Would you rather have feet that never stopped growing or hands that never stop growing?
- Would you rather eat spicy dessert food or spicy breakfast food every day?
- Would you rather have to eat all your meals holding silverware with your feet or drink all your drinks holding the cup with your feet?
- Would you rather be able to turn invisible but have no control over when it happens or be able to fly but have no control over when it happens?
- Would you rather have all the money you could ever need or have every meal you eat to be the best meal of your life?
- Would you rather swim the Atlantic Ocean or bike across the United States?
- Would you rather have a super fancy car or a super fancy house?
- Would you rather have an unlimited supply of cell phone data or an unlimited supply of gas in your car?
- Would you rather have 10 dogs or no dogs at all?
- Would you rather never have to eat again or never have to go to the bathroom again?
- Would you rather visit the seven wonders of the world or get to plan your own trip to seven interesting places?
- Would you rather be a singer who makes one amazing album or three pretty good albums?
- Would you rather always be itchy or always be cold?
- Would you rather have hair down to your ankles or be bald?
- Would you rather only drink soy milk or only eat gluten-free?
Organize a company community service day with a sign up. SAMPLE
About Your Coworkers
- Would you rather have a big family or a small family?
- Would you rather live somewhere tropical or somewhere cold?
- Would you rather spend the majority of your time by yourself or a majority of your time with other people?
- Would you rather always be running late or always be running early?
- Would you rather be able to read faster than anyone on the planet or be able to run faster than anyone on the planet?
- Would you rather write a New York Times bestseller or win an Olympic gold medal?
- Would you rather have a name everyone misspells or a name everyone forgets?
- Would you rather live in the mountains or at the beach?
- Would you rather have 20 kids or have no kids?
- Would you rather always be traveling or never be able to travel again?
- Would you rather live in France or Italy?
- Would you rather be a famous singer and have the voice you have now or a famous dancer and have the dance skills you have now?
- Would you rather work at Disney World (the park) or at Apple (the corporate headquarters)?
- Would you rather live in the same state until you die or have to live in a different state every year for the next 50 years?
- Would you rather travel exclusively by plane or exclusively by submarine (if there was no time difference)?
- Would you rather eat the same food every day or, once you eat a certain food, you’re never able to eat it again?
- Would you rather have to eat super healthy every day or have to work out every day?
- Would you rather always hit every red light at a stoplight or get a flat tire once a month?
- Would you rather only have room temperature water for the rest of your life or only have ice cold water?
- Would you rather never be able to remember anyone’s name or never be able to remember directions?
- Would you rather be the president but you’re bad at it or have a job nobody knows about, but you’re really good at it?
- Would you rather be able to play any instrument or speak any language?
- Would you rather go camping or go on a cruise?
- Would you rather eat a bug or get stung by a bee?
- Would you rather give up deodorant or give up toothpaste?
- Would you rather be great at ping pong or great at croquet?
- Would you rather eat pizza every single day or never eat pizza again?
- Would you rather sit down all day or stand all day?
- Would you rather be a great swimmer or a great runner?
- Would you rather be friends with Oprah or Simon Cowell?
- Would you rather have a vegetable garden or a flower garden?
- Would you rather act in a movie or sing on an album?
- Would you rather have a lion as a pet or have a hawk as a pet?
- Would you rather give up your GPS or Netflix?
Your coworkers will be giggling with you in no time.
Kayla Rutledge is a college student who spends most of her time writing, singing for her church and eating quesadillas.
Additional Resources
100 Would You Rather Questions
25 Office Party Games to Kick Off Meetings
20 Quick Icebreakers for Meetings
40 Get to Know You Questions for Meetings
100 Icebreaker Questions for Work
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