60 Would You Rather Questions for Work & Team Building

Team building doesn't have to be awkward trust falls and forced fun. Would You Rather questions are a simple, effective way to help colleagues connect without crossing professional boundaries.

Why Would You Rather Works at Work

The best team activities are low-stakes and inclusive. Would You Rather questions let people share personality without oversharing personal details. Everyone can participate regardless of role or tenure.

Safe for Any Workplace

1. Would you rather have unlimited vacation but no pay raise, or double salary but only 2 weeks off?
2. Would you rather always be 10 minutes late, or always be 20 minutes early?
3. Would you rather have a 4-day work week with 10-hour days, or 5-day week with 8-hour days?
4. Would you rather work from home forever, or have the corner office?
5. Would you rather have a great boss at an okay company, or an okay boss at a great company?
6. Would you rather give up email, or give up meetings?
7. Would you rather have free lunch every day, or leave an hour early?
8. Would you rather sit in an open office with great colleagues, or have a private office alone?
9. Would you rather work on one big project, or many small projects?
10. Would you rather have a standing desk, or the comfiest chair ever made?

Team Meeting Starters

1. Would you rather present to 1000 strangers, or have a difficult conversation with 1 colleague?
2. Would you rather lead every meeting, or never speak in meetings?
3. Would you rather have your Slack messages read aloud, or your calendar made public?
4. Would you rather only communicate via email, or only via video call?
5. Would you rather work with your best friend, or keep work and personal life separate?

Fun Office Scenarios

1. Would you rather have free WiFi everywhere, or free coffee everywhere?
2. Would you rather have a nap room at work, or a game room?
3. Would you rather wear a suit every day, or pajamas every day?
4. Would you rather have a funny email signature you can't change, or a professional photo that's slightly blurry?
5. Would you rather have your browser history visible to IT, or your lunch always stolen from the fridge?

When to Use These

Monday meetings: Energize the week with a quick round.

New team members: Great icebreaker for onboarding.

Virtual calls: Break the awkward silence before meetings start.

Team offsites: Mix with other activities.

End of week: Fun way to wind down on Friday.

Tips for Facilitators

1. Go first - Model vulnerability by answering first.
2. Keep it moving - 30 seconds per person max.
3. No pressure - Let people pass if they want.
4. Mix it up - Don't always use the same questions.
5. Read the room - Skip questions that might be sensitive.

Play Icebreaker Questions →