Nothing kills Monday morning dread quite like a good “Would You Rather” question. Whether your team is remote, hybrid, or crammed into the same conference room, these questions turn awkward silences into actual conversations. They work for icebreakers, team lunches, Slack channels, or those five minutes before a meeting when everyone is just staring at their screens.
We put together 100 work-friendly questions that are fun without crossing any HR lines. Pick a few for your next standup or dump the whole list into your team chat and watch people debate for hours.
How to play “Would You Rather”
The rules are dead simple. Someone reads a question with two options, and everyone picks one. No “both” answers, no “neither” – you have to commit. The real fun starts when people explain their choice. You’ll learn things about your coworkers you never expected.
Go around the table (or the Zoom call), give everyone a turn to answer, and let the conversation flow. One question can easily fill five minutes if the group gets into it. For larger teams, try polling tools or just a show of hands.
Play “Would You Rather” online
Want an endless supply of questions without scrolling through a list? Our app serves up fresh questions on the spot, so you can keep the game going as long as you want.
Would You Rather questions for team meetings
Kick off your next meeting with one of these. They’re quick, light, and get people talking before you dive into the agenda.
1. Would you rather have unlimited PTO but never get a raise, or get a massive raise but only two weeks of vacation?
Time is money, but money is also money.
2. Would you rather present to the entire company with no preparation or write a 50-page report by tomorrow?
Stage fright or carpal tunnel – pick your poison.
3. Would you rather have your boss read all your texts or your coworkers read all your emails?
Suddenly everyone is very careful about what they type.
4. Would you rather always be five minutes late to every meeting or always be 30 minutes early?
One makes you look unreliable. The other means a lot of sitting alone in conference rooms.
5. Would you rather never have another meeting again or never have to answer another email?
The dream question. Watch how fast people answer this one.
6. Would you rather give every presentation in a karaoke style or have to start every meeting with a joke?
Either way, your reputation is about to change.
7. Would you rather have back-to-back meetings every day or answer 200 emails every day?
The classic office dilemma that nobody actually wants to face.
8. Would you rather have your webcam always on during remote meetings or always have your microphone unmuted?
Dogs barking, kids screaming, or just your face on display all day. Tough call.
9. Would you rather lead a team of 50 people or work completely alone on every project?
Some people thrive on collaboration. Others thrive on silence.
10. Would you rather have to stand during every meeting or have every meeting last twice as long?
Your legs versus your sanity.
11. Would you rather only be able to communicate through memos or only through voice notes?
Old school paperwork or a modern podcast-style workplace.
12. Would you rather have your Monday meetings moved to Friday afternoon or your Friday afternoons filled with new project kickoffs?
Both options hurt in different ways.
13. Would you rather always have to share your screen during calls or never be able to share your screen?
Hope your desktop is clean. Or hope you’re really good at describing things verbally.
14. Would you rather sit next to someone who talks on the phone all day or someone who eats loudly at their desk?
The open office soundtrack nobody asked for.
15. Would you rather have a meeting that could have been an email or an email thread that should have been a meeting?
The eternal workplace paradox.
16. Would you rather always be the one taking notes in meetings or always be the one presenting?
Scribe or spotlight – where do you fall?
17. Would you rather have a meeting with no agenda or a meeting that runs 45 minutes over?
Chaos now or chaos later.
18. Would you rather your boss always cancels meetings last minute or always adds meetings last minute?
The relief of a cancellation versus the dread of a surprise invite.
19. Would you rather have to use only your phone for work or only your laptop with no mouse?
Thumb typing everything or trackpad frustration for life.
20. Would you rather give a TED Talk to your whole industry or write a best-selling book about your job?
Public speaking glory or literary fame – both sound terrifying.
21. Would you rather always have to work with your least favorite software or always have a slow internet connection?
Buffering circles or a terrible UI. The ultimate tech torture.
22. Would you rather have every meeting recorded and posted publicly or have no meetings but triple the emails?
Accountability or inbox overload.
23. Would you rather be in charge of the office playlist or the office thermostat?
Two things that cause more workplace conflict than anything else.
24. Would you rather have a two-hour commute to your dream job or a five-minute walk to a boring job?
This one reveals what people truly value.
25. Would you rather always have to dress business formal or always wear a company-branded polo shirt?
Suit and tie every day, or become a walking billboard.
Would You Rather questions for coworkers
These are perfect for lunch breaks, coffee chats, or team Slack channels. Get to know the people you spend 40 hours a week with.
26. Would you rather have free lunch at work every day or be able to leave two hours early on Fridays?
The foodie versus the freedom lover.
27. Would you rather sit in an open office or a tiny private cubicle?
Social butterfly or hermit crab – no judgment either way.
28. Would you rather have a coworker who never stops talking or one who never responds to messages?
The over-communicator or the ghost.
29. Would you rather accidentally reply-all with something embarrassing or accidentally send a personal text to your boss?
Both make you want to disappear.
30. Would you rather have a work best friend who’s terrible at their job or a work rival who’s incredible at theirs?
Loyalty versus competition.
31. Would you rather share an office with someone who microwaves fish every day or someone who clips their nails at their desk?
The two most controversial office behaviors, head to head.
32. Would you rather always have to eat lunch alone or always have to eat lunch with your boss?
Solo recharge time or mandatory small talk.
33. Would you rather work with someone who takes credit for your ideas or someone who blames you for their mistakes?
Neither is great, but one stings a little more.
34. Would you rather have a coworker who always borrows your stuff or one who always comments on what you’re eating?
“Can I borrow your charger?” versus “Is that healthy?”
35. Would you rather be the youngest person on your team or the oldest?
Fresh perspective or seasoned experience.
36. Would you rather work with your best friend or your sibling?
Mixing personal and professional – what could go wrong?
37. Would you rather have a desk next to the bathroom or next to the break room?
Constant foot traffic either way, but with very different sound effects.
38. Would you rather have a coworker who’s always positive or one who’s brutally honest?
Sunshine and rainbows versus cold hard truth.
39. Would you rather always be the one to organize team events or never be invited to them?
Party planner or the one left out.
40. Would you rather have a coworker who always one-ups your stories or one who never remembers your name?
“Oh, that happened to me but worse” versus “Hey… you.”
41. Would you rather work on a team where everyone agrees on everything or a team that debates every decision?
Harmony or healthy conflict.
42. Would you rather have a coworker who hums all day or one who constantly taps their pen?
The office background music nobody requested.
43. Would you rather carpool with your boss every day or share a hotel room with a coworker on every work trip?
Forced proximity, two different flavors.
44. Would you rather be known as the office prankster or the office snack supplier?
Fun or food – both earn you popularity.
45. Would you rather have your coworker’s phone alarm go off during every meeting or have yours go off once during a presentation to the CEO?
Chronic annoyance or one moment of pure horror.
46. Would you rather train a new hire every month or never get any help on your projects?
Teaching endlessly or doing it all yourself.
47. Would you rather work with someone who’s always late but brilliant, or always on time but mediocre?
Talent versus reliability.
48. Would you rather have an office dog or an office nap room?
Two perks that would solve most workplace problems.
49. Would you rather have a coworker who spoils every show you’re watching or one who sends you 50 memes a day?
Entertainment ruined or entertainment overload.
50. Would you rather always know when a coworker is talking about you or never find out?
Blissful ignorance or full awareness.
Funny Would You Rather questions for work
Time to loosen things up. These questions are still work-appropriate but designed to get people laughing.
51. Would you rather accidentally call your boss “mom” in a meeting or trip and fall during a presentation?
Both will haunt you for years.
52. Would you rather have to wear a suit to work from home or pajamas to the office?
Blazer on the couch or fuzzy pants in the boardroom.
53. Would you rather your work computer only play circus music or have your chair replaced with an exercise ball?
A bouncy commute or a very entertaining office soundtrack.
54. Would you rather have your browser history projected in the break room or your search history read aloud at the company meeting?
“Why is there a spider in my house” hits different when 200 people hear it.
55. Would you rather have an email signature that’s a random inspirational quote every time or one that always includes a cat GIF?
Motivational or adorable – your clients won’t know what hit them.
56. Would you rather accidentally leave yourself unmuted while singing or while complaining about the meeting?
Both are career-defining moments.
57. Would you rather be able to teleport to work or be able to read your boss’s mind?
Skip the commute or know exactly what they really think of your ideas.
58. Would you rather have your keyboard randomly type in ALL CAPS or have autocorrect change every third word?
STOP YELLING or stop making nonsense – pick one.
59. Would you rather have to do 10 pushups before every meeting or tell a dad joke to start every call?
Physical fitness or comedic torture.
60. Would you rather have a desk that’s always slightly sticky or a chair that squeaks every time you move?
The mysterious stickiness or the world’s loudest seat.
61. Would you rather have to narrate everything you do at work out loud or have theme music play every time you enter a room?
“And now I’m opening my email” or dramatic orchestral swell.
62. Would you rather only be able to type with one finger or only be able to talk in a whisper at work?
Hunt-and-peck for life or permanent library voice.
63. Would you rather have your lunch stolen from the fridge every day or have to eat the same lunch every day for a year?
The fridge thief strikes again, or hello turkey sandwich #365.
64. Would you rather have your out-of-office reply always be a haiku or always include a fun fact about you?
“I am not here now / emails will go unanswered / back on the third, bye.”
65. Would you rather have a parrot that repeats everything said in meetings or a goat that lives under your desk?
Office wildlife, your choice.
66. Would you rather have your face as the company screensaver or your voice as the hold music?
Digital immortality at its finest.
67. Would you rather get caught sleeping at your desk by the CEO or get caught dancing alone in the elevator?
One shows exhaustion, the other shows moves.
68. Would you rather have to type every email in rhyme or start every conversation with a compliment?
Roses are red, the deadline is near… versus being suspiciously nice to everyone.
69. Would you rather have your desk permanently covered in glitter or have a fog machine that goes off every time you sit down?
Sparkle or drama – make your entrance.
70. Would you rather accidentally send a love letter to the company-wide mailing list or pocket-dial your boss during a rant about work?
Cringe in writing or cringe in real time.
71. Would you rather have to speak in corporate buzzwords for an entire day or only communicate through emojis?
“Let’s circle back and synergize” or a series of carefully chosen thumbs up and fire emojis.
72. Would you rather have an office chair that randomly reclines all the way back or a desk that slowly gets lower throughout the day?
Surprise nap position or gradual floor desk.
73. Would you rather have hiccups during every important call or sneeze every time you try to make a point?
“So what I’m trying to say is– achoo”
74. Would you rather have your Slack status always show what you’re actually doing or have your webcam turn on at random times?
“Currently: watching YouTube” or surprise face reveal.
75. Would you rather have to end every email with “sent from my toaster” or “this message will self-destruct”?
Questionable tech or spy thriller vibes.
Would You Rather questions for work events
Heading to a team outing, offsite, or holiday party? Pull these out when the conversation needs a boost.
76. Would you rather have a team retreat at the beach or in the mountains?
Sand between your toes or fresh mountain air – the classic offsite debate.
77. Would you rather do karaoke at the company party or compete in an office talent show?
Sing your heart out or show off a hidden skill.
78. Would you rather have unlimited budget for office snacks or unlimited budget for office decorations?
A well-fed team or an Instagram-worthy workspace.
79. Would you rather win “Employee of the Year” or get a surprise extra week of vacation?
A plaque on the wall or sand between your toes.
80. Would you rather have the company holiday party at a fancy restaurant or at a bowling alley?
Black tie or bowling shoes.
81. Would you rather do an escape room with your team or a cooking class?
Problem-solving under pressure or food fights – both build character.
82. Would you rather have your team building activity be a scavenger hunt or a trivia night?
Running around town or flexing your random knowledge.
83. Would you rather have an office with a slide instead of stairs or a rooftop garden?
Fun commute between floors or peaceful lunch spot.
84. Would you rather have your company sponsor your gym membership or your Netflix subscription?
Gains or entertainment – the modern benefits question.
85. Would you rather attend a work conference in Tokyo or in New York?
Sushi or pizza, bullet trains or yellow cabs.
86. Would you rather have a team cooking competition or a team sports day?
Iron Chef: Office Edition or the company Olympics.
87. Would you rather have your team offsite at a theme park or a vineyard?
Roller coasters or wine tasting.
88. Would you rather have a professional DJ at every team lunch or a company movie theater?
Beats while you eat or films on the clock.
89. Would you rather plan the perfect team event with no budget or have unlimited budget but only 30 minutes to plan?
Creativity versus chaos.
90. Would you rather have the office throw you a huge birthday party or get your birthday off as a paid holiday?
Cake with coworkers or cake in bed.
91. Would you rather compete against your boss in a video game tournament or a bake-off?
Button mashing or butter creaming.
92. Would you rather have a team-building activity where you build something together or one where you compete against each other?
Cooperation or rivalry – both reveal true colors.
93. Would you rather have your work event at a comedy club or an arcade?
Laughing together or trash-talking over air hockey.
94. Would you rather have a “work from anywhere” month or a permanent four-day work week?
Bali with a laptop or every weekend is a long weekend.
95. Would you rather have an office pool table or an office coffee bar with a barista?
Trick shots between tasks or a perfect latte on demand.
96. Would you rather have a company field day with three-legged races or a company game night with board games?
Outdoor chaos or indoor strategy.
97. Would you rather have your team go go-karting or rock climbing?
Speed demons or summit seekers.
98. Would you rather have an annual company talent show or an annual company roast?
Show off your skills or hear what your coworkers really think.
99. Would you rather win the office fantasy football league or win the office chili cook-off?
Sports bragging rights or culinary glory.
100. Would you rather have your last day at a job be a giant party or a quiet, personal goodbye with each coworker?
Go out with a bang or go out with meaning.
Need more icebreakers? Our Would You Rather for friends works great for casual team bonding, and our funny Would You Rather questions are always a hit. New to the game? Check out how to play Would You Rather.
These 100 questions should keep your team entertained for plenty of meetings, lunches, and offsites to come. If you want even more options across different categories, check out our full collection of “Would You Rather” questions and keep the fun going.
