How it works
Share the link with your team. Everyone picks a side on each dilemma — results update live so you can see where the group stands. No sign-up needed to play.
This template includes 10 work-appropriate Would You Rather questions designed to spark conversation without crossing any lines. Each question uses Questiory’s This or That interaction, and results are displayed as a Split visualization so you can compare both sides at a glance.
The 10 questions in this template
- Work from anywhere in the world or have a 4-day work week forever
- Always know the right answer or always ask the right question
- Have unlimited creativity or have unlimited focus
- Lead a small team you love or be part of a huge project that changes everything
- Never have another meeting or never write another email
- Master every tool instantly or master one skill deeply over 10 years
- Always be early or always be perfectly on time
- Work with your best friend or work with someone who challenges you constantly
- Have a mentor who’s a CEO or have a mentor who’s a world traveler
- Know what your career looks like in 10 years or be surprised by every opportunity
50+ Would You Rather questions for every team situation
Use these to swap into the template or build your own rounds. Pick 5–10 per session — that’s the sweet spot.
For teams that are just meeting. Low-stakes, fun questions to get people comfortable.
- Have the best office view in the building or the most comfortable chair ever made
- Only communicate through memes for a day or only speak in questions for a day
- Have a personal theme song that plays when you enter a room or have a personal narrator for your workday
- Be famous inside your company or be anonymous but incredibly influential
- Have free lunch at work every day or leave one hour early every day
- Share an office with your favorite celebrity or work from your dream vacation spot
What do you actually value? These spark real conversations about priorities.
- Have a high-paying job you tolerate or a lower-paying job you absolutely love
- Work 4 long days or 5 shorter days
- Have unlimited PTO that you feel guilty using or 20 fixed days you take without question
- Start work at 6am and finish at 2pm or start at 11am and finish at 7pm
- Never work weekends again or never work past 5pm on weekdays
- Have a 5-minute commute to a boring office or a 1-hour commute to an amazing one
Where are you headed? Good for teams reflecting on growth and goals.
- Be the best at one thing or be pretty good at everything
- Get promoted to management or become the top individual contributor
- Work on something brand new with high risk or improve something proven with steady results
- Have a job title that sounds impressive or a job role that's actually meaningful
- Learn a new skill every month or go deep on one skill for a year
- Work at a tiny startup with huge equity or a big company with big stability
How do you work with others? Reveals collaboration styles and preferences.
- Always work in a team or always work solo
- Have a manager who gives too much feedback or one who gives almost none
- Be the one presenting the idea or the one building it behind the scenes
- Work with a genius who's hard to get along with or a great teammate who's average at the job
- Have meetings where everyone talks or meetings where everything is a shared doc
- Always be the newest person on the team or always be the most experienced
The eternal debate. Perfect for hybrid and distributed teams.
- Only work from home forever or only work from the office forever
- Have a fancy home office setup or a budget to work from coffee shops and coworking spaces
- Never turn on your camera again or never use Slack again
- Have your team in the same timezone or have your team spread across the world
- Attend all meetings from a beach or skip all meetings entirely
- Have the best internet in the world at home or live next door to the office
What kind of leader are you? Great for offsites and management workshops.
- Make a fast decision that might be wrong or take a long time to make the right one
- Lead a team through a crisis or lead a team through rapid growth
- Be the leader everyone likes or the leader everyone respects
- Give hard feedback in person or give it in writing
- Have a team that always agrees with you or a team that constantly challenges you
- Be in charge of strategy or be in charge of execution
How does your brain work? Fun for workshops and brainstorming sessions.
- Solve one impossible problem or improve 100 small things
- Have the idea or have the plan to execute it
- Work with no constraints and no budget or tight constraints and unlimited budget
- Brainstorm alone first, then share or brainstorm live with the whole team
- Design the perfect product nobody uses or build an ugly product millions love
- Automate your entire job or make your job twice as creative
Just for laughs. End-of-week energy or when the team needs a break.
- Have a rewind button for your last email or a pause button for any meeting
- Accidentally reply-all something embarrassing or accidentally unmute yourself in a meeting
- Have your Slack status always show what you're actually doing or have your browser history shared with your team
- Only eat lunch at exactly noon forever or never know when your lunch break is
- Have a robot assistant that's very literal or a human assistant that's very dramatic
- Give a presentation in pajamas or attend every meeting standing up
When to use it
- Start of a meeting — pick 5 questions, takes 3 minutes, warms everyone up
- Team building sessions — use a full round of 10 to reveal personalities and spark conversation
- Onboarding — new hires get to know coworkers without the awkward small talk
- Remote teams — works perfectly async or live on a call
- Workshops & offsites — use topic-specific questions to set the tone for the session
- End of week — close with the fun round to send everyone off laughing
Customize it
Search for “Would You Rather” in the template library and click Use template. A copy is added to your account — swap in any of the questions above, add more rounds, or mix in other interactions like word clouds or voting.
Want more icebreaker ideas? Try our 5-minute team games or online icebreaker activities.