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Would You Rather Questions for Work

Looking for would you rather questions to ask at work? Sometimes these icebreaker games can help you to get to know your coworkers better. And help to establish a positive and healthy relationship so that work becomes slightly easier. When you’re at work, you’re going to need appropriate questions to ask. Give these a try!

Fun questions

  • Would you rather attend a team-building activity that’s an escape room or go on an off-site retreat?
  • Would you rather have a group lunch with colleagues every day or once a month?
  • Would you rather work in the office or work remotely?
  • Would you rather have a standing desk or sit in a comfortable chair?
  • Would you rather have an open office space or individual cubicles?
  • Would you rather wear casual clothes to work or dress professionally?
  • Would you rather take a break every hour for five minutes or take one long break during the day?
  • Would you rather collaborate with teammates on projects or work independently? Would you rather have a quiet workspace or listen to music while working?
  • Would you rather be able to take vacation days whenever you want or receive a bonus at the end of the year?
  • Would you rather have team-building activities that involve physical activity or problem-solving exercises?
  • Would you rather have one long meeting in the morning or smaller meetings throughout the day?
  • Would you rather participate in group brainstorming sessions or tackle projects on your own?
  • Would you rather have flexible hours or strict working hours?
  • Would you rather work from home or at a shared coworking space?
  • Would you rather be able to work with flexible deadlines or have tight deadlines?
  • Would you rather be rewarded for individual performance or team performance?
  • Would you rather receive feedback in public or private?
  • Would you rather start your day earlier and finish earlier, or stay later and take a lunch break?
  • Would you rather complete projects individually or as a group?
Would you rather questions for work
Would you rather questions for work

Silly questions

  • Would you rather do a presentation in front of the team or take the blame for a mistake you didn’t make?
  • Would you rather have a superpower to fly or read minds? 
  • Would you rather have unlimited money or unlimited time?
  • Would you rather have a pet elephant or a pet monkey?
  • Would you rather live without the internet or without AC and heating?
  • Would you rather have a never-ending summer vacation or a never-ending supply of your favorite food?
  • Would you rather be able to speak every language or have the ability to talk to animals?
  • Would you rather be the world’s greatest dancer or the world’s greatest singer?
  • Would you rather have x-ray vision or super strength?
  • Would you rather be famous or have the power of invisibility?
  • Would you rather be a superhero or a villain?
  • Would you rather have the ability to fly or to be able to stop time?
  • Would you rather have one wish granted or ten wishes granted?
  • Would you rather never experience heartbreak or never feel physical pain? 
  • Would you rather have a perfect memory or be able to run faster than the speed of light?
  • Would you rather never have to sleep again or never have to eat again?
  • Would you rather have an extra hour of work each day or take a pay cut?
  • Would you rather spend an hour filling out paperwork or listen to your boss drone on in a meeting?
  • Would you rather work late nights or get up early in the morning?
  • Would you rather take on a new project or do extra hours of busy work?
  • Would you rather have a new job with more responsibility or stay in your comfort zone?
  • Would you rather work with a difficult coworker or work alone?
  • Would you rather work on a project that you’re passionate about or something mundane?
  • Would you rather have your own office or work from home?
  • Would you rather attend networking events or stay in the office all day?
  • Would you rather take an extra long lunch to relax or spend it working through a problem?
Would you rather questions for work
Would you rather questions for work

Career questions

  • Would you rather work in a corporate environment or start your own business?
  • Would you rather work as an attorney or a doctor?
  • Would you rather have job security or a higher salary?
  • Would you rather work with people who challenge and inspire you or those who support and encourage you?
  • Would you rather have a job that gives you lots of free time or one that pays very well?
  • Would you rather take a job in another city or stay close to home?
  • Would you rather be an entrepreneur or work for someone else?
  • Would you rather be constantly learning and adapting your skills or have the security of knowing what to expect?
  • Would you rather climb the corporate ladder or take a risk and start your own company?
  • Would you rather specialize in one field or learn multiple skills to broaden your horizons?
  • Would you rather work alone or with a team of like-minded professionals?
  • Would you rather have a job that is physically demanding but well paid or one that is mentally stimulating but not as well paid?
  • Would you rather take a job with flexible hours and little structure or one with a consistent schedule and clear expectations?
  • Would you rather work in an industry where you can make a big impact on the world, or in one that offers more stability and security?
  • Would you rather have a job that allows you to travel or one with consistent hours?
  • Would you rather work for a prestigious company or a startup?

Workplace questions

  • Would you rather have a job that involves lots of travel or one with a regular 9-5 office schedule?
  • Would you rather work in an open office layout or have a private cubicle?
  • Would you rather attend meetings all day or stay in your office and complete projects?
  • Would you rather work in a team environment or on individual projects?
  • Would you rather work for a large corporation or a small business?
  • Would you rather wear formal clothing to work or dress casually every day?
  • Would you rather have a job with flexible hours or one with set hours?
  • Would you rather take on extra responsibilities at your current job or look for something completely new and different?

More fun games to play

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Fact checked:
Board reviewed by Marianne Tomlinson, LCSW (Couples and Family Therapy). Content is rigorously reviewed by a team of qualified and experienced fact checkers. Learn more.

About the author

Ryan Sanderson (LCSW) Ryan is a game and relationship enthusiast who enjoys all things quizzes, games, fun, love, relationships, and family. He's a licensed social worker and helps families, couples, and children in need. He's spoken about love and relationships on Salon.com, Forbes, and Mirror, to name a few.

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