Get to Know Your Coworkers: The 30 Best What If Questions to Ask

Want to really get to know your remote team? Ask them some of these unique and fun 'what if' questions.

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By the Offsyte Team, February 7, 2023

Sometimes the best way to get to know your coworkers is just rapid-fire questions. The more you send their way, the more you get a sense of what they're like. One way to do this is with 'what if' questions. You can pose these as what-if scenarios, funny what-if questions, and more.

The most important thing is to make the exercise a good mix of light-hearted and serious. Funny what-if questions and serious what-if questions can both provide a window into someone's personality, just in different ways. Here are 30 of the best what-if questions to ask your remote team during your next meeting.

  1. What if you hit the lottery today — would you keep working?
  2. What if you could time travel — where would you go and when?
  3. What if you were our CEO? What changes would you make?
  4. What if you could change one thing about yourself? What would you change?
  5. What if you could live forever, would you want to?
  6. What if you could understand animals?
  7. What if you had superpowers? What would they be?
  8. What if you could give yourself a raise? Would you and why?
  9. What if you had to pick one thing to bring to a deserted island? What would you bring?
  10. What if you had to switch roles with one of your team? Who would you pick?
  11. What if you could only eat one thing for the rest of your life?
  12. What if you woke up and found you were one of the last 50 people on Earth?
  13. What if a movie was made about your life? Who would play you?
  14. What if you had to work in an office full-time?
  15. What if you could live one day over again? What day would it be?
  16. What if you had to give $5 billion away in order to keep $1 billion? What would you do with it?
  17. What if you could make one of your dreams a reality?
  18. What if you could change one thing about remote working?
  19. What if you had the power to cure one disease? What would you cure and why?
  20. What if you could work only three days a week? Would that be a good thing or a bad thing?
  21. What if a previous boss had to describe you in five words? What would they choose?
  22. What if you could tell when people were lying? What would you do?
  23. What if you were an Olympic athlete? What sport would you choose and why?
  24. What if you could retire tomorrow? Would you?
  25. What if you found a bag containing $4 million in cash? What would you do with it?
  26. What if you could make time stand still?
  27. What if you never had to attend a meeting ever again?
  28. What if you could talk to your 15-year-old self?
  29. What if you had to choose between hearing or seeing?
  30. What if you could change places with anyone famous? Who would it be and why?

More to Know About the Best What If Questions to Ask

Some common questions people have about what-if questions for work.

What are some good what-if questions to ask your team?

The best what-if questions for work are those that are unique and fun. You don't want to be too serious when trying to learn more about your team.

What are some funny what-if questions to ask coworkers?

If you're trying to find fun questions to ask coworkers, think silly first. You almost want to channel your inner child, as the most basic questions can also be the most fun.

What are some examples of what-if questions?

A what-if question is just what it sounds like — a question posed with "what if" at the beginning. It can be about anything, from work to the latest movie you've seen.

Get Started!

Looking for more 'what if' questions to ask your remote team? Check out Offsyte's icebreaker events. There are plenty of options that are sure to make your next meeting much more interesting.

Get more team-nurturing insights

We're always looking for new ways to help you deepen relationships with your team. We'll email you the newest findings as we discover them. No spam. We promise.

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