Would you Rather Questions for Work

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Would You Rather questions are one of the best things you can drop into a work setting because they require absolutely nothing. No supplies, no preparation, no budget. Just one question and suddenly the room is alive with opinions, arguments, and laughter over things that have nothing to do with the agenda.

We have used these at the start of team meetings, during lunch breaks, at end of year parties, and on those video calls where the energy is flat before anyone has even said good morning. Every single time they work. Someone gives an unexpected answer, someone else cannot believe it, and the conversation takes off from there.

Here are over 100 Would You Rather questions for work covering every type of work setting, coworkers, team meetings, remote workers, office parties, and everything in between. Scroll to the category that fits your situation and start there.

Funny Would You Rather Questions for Work

These are the ones that get people laughing before they even finish answering. Perfect for the start of a meeting or as a warmup before a team activity.

1. Would you rather have no lunch break but finish an hour early or have a two hour lunch break but stay two hours late?
2. Would you rather have to do the chicken dance every time you answer the phone or wear a clown wig to every meeting?
3. Would you rather fight one hundred duck-sized horses or one horse-sized duck in the break room?
4. Would you rather have your boss read every email you send before it goes out or have your coworkers hear every thought you have during meetings?
5. Would you rather have a printer that works perfectly but makes a sound like a foghorn every time or a silent printer that jams every third page?
6. Would you rather be copied on every email in the company for a week or have no email access at all for a month?
7. Would you rather give a presentation in your pajamas to the whole company or show up to a formal event in full business attire when everyone else is in casual clothes?
8. Would you rather have unlimited snacks in the office but only one flavor forever or a rotating snack selection but only one item per day?
9. Would you rather work with someone who talks constantly or someone who never speaks at all?
10. Would you rather your computer made dial-up sounds every time you opened a new tab or your keyboard autocorrected every third word to something random?
11. Would you rather have to use a typewriter for all your emails or send messages only through carrier pigeons for a month?

Would You Rather Questions for Remote Workers

These are for the work from home crew. The ones who have accidentally unmuted themselves, appeared on camera in something questionable, and know exactly how many steps it takes to get from their desk to the fridge.

1. Would you rather work from home forever with no office perks or go back to the office full time with free food every day?
2. Would you rather have your video always on during calls or never be allowed to use video at all?
3. Would you rather work in total silence at home or have background noise you cannot control?
4. Would you rather have perfect WiFi but no natural light or a beautiful sunny workspace with unreliable internet?
5. Would you rather commute an hour each way for a great office environment or work from a mediocre home setup with no commute?
6. Would you rather your pet appear on every video call or have a family member walk in the background of every meeting?
7. Would you rather have scheduled check-in calls every hour or have complete independence with no check-ins at all?
8. Would you rather work from a coffee shop every day with no guaranteed seating or from home with no dedicated desk?
9. Would you rather have a virtual background that glitches constantly or no virtual background and whatever is behind you is always visible?
10. Would you rather work across three different time zones every week or always work the same hours but they are overnight?

Would You Rather Questions for Team Meetings

Drop one of these at the start of a meeting before you get into the agenda. It takes sixty seconds, gets everyone talking, and resets the energy in the room better than any formal icebreaker activity ever does.

1. Would you rather have every meeting be a standing meeting or every meeting be at least ninety minutes long?
2. Would you rather present to a room of strangers or a room of people you know well?
3. Would you rather be the person who runs every meeting or never have to run one again?
4. Would you rather have all your meetings on Mondays to get them out of the way or spread them evenly across the whole week?
5. Would you rather have no agenda for every meeting or a detailed agenda that nobody follows?
6. Would you rather have one three hour meeting per week or six thirty minute meetings scattered throughout?
7. Would you rather always go first when sharing updates or always go last?
8. Would you rather have a meeting that could have been an email or an email chain that should have been a meeting?
9. Would you rather present your idea to a small skeptical group or a large enthusiastic one?
10. Would you rather work in a team where everyone agrees all the time or a team where everyone debates everything?

Want more Would You Rather Questions? Here is a full list of Would You Rather Questions for all occasions.

Would You Rather Questions for Work Parties and Events

Perfect for an end of year party, a team celebration, or any work event where you want to get people mixing and talking outside of the usual work context.

1. Would you rather attend a work party where you know everyone or one where you know nobody but the food is incredible?
2. Would you rather do karaoke in front of your whole company or give a five minute speech about yourself to the whole room?
3. Would you rather be in charge of organizing the work party or just show up and enjoy whatever someone else planned?
4. Would you rather have a formal sit-down work dinner or a casual backyard BBQ with the team?
5. Would you rather win a work award in front of everyone or receive a private bonus with no public recognition?
6. Would you rather have a team building activity outdoors in perfect weather or a cozy indoor escape room?
7. Would you rather do a Secret Santa with a generous budget or a bring-a-plate potluck with no assigned dish?
8. Would you rather sit next to your best work friend at the party or be strategically placed next to someone new?
9. Would you rather work at a company with legendary Christmas parties or one with generous bonuses and no party at all?
10. Would you rather give a toast at the work party or be the person someone else toasts?

Deep Would You Rather Questions for Work

These slow things down in a good way. Perfect for a team retreat, a mentoring conversation, or any work setting where people are ready to talk about something more meaningful than snacks and meeting schedules.

1. Would you rather have a job you love that pays just enough or a job you tolerate that makes you financially comfortable?
2. Would you rather be the most skilled person on your team or the most liked?
3. Would you rather have a brilliant boss who is difficult to work with or a mediocre boss who is easy to get along with?
4. Would you rather be recognized publicly for your work or know privately that your contribution made the biggest difference?
5. Would you rather work for a company whose values you believe in completely at lower pay or a company whose values you are indifferent to at significantly higher pay?
6. Would you rather have complete job security in a role you have outgrown or an exciting new role with no guarantees?
7. Would you rather know exactly where your career will be in ten years or have complete uncertainty and complete possibility?
8. Would you rather work hard for thirty years and retire early or work moderately your whole life and never fully retire?
9. Would you rather be the person who has all the ideas or the person who executes them better than anyone else?
10. Would you rather leave a job that is comfortable but going nowhere or stay and try to change it from the inside?

Need more ideas? Check out these fun Ice Breaker Questions for work.

Office and Work Would You Rather Questions

These questions are perfect for your work mates.

1. Would you rather have unlimited snacks in the office but only one type, or a variety of snacks but limited to one per day?
2. Would you rather have a desk only in black and white, or a colorful desk?
3. Would you rather start your workday with a funny joke over the intercom or a surprise dance party in the breakroom?
4. Would you rather have a super comfy chair but a tiny desk or a spacious desk with an uncomfortable chair?
5. Would you rather have a talking pet parrot as your office companion or a robot assistant that tells cheesy jokes?
6. Would you rather have a work uniform that’s incredibly stylish but a little impractical or a super comfy uniform that’s not so fashionable?
7. Would you rather have a never-ending supply of coffee but it’s always decaf or only get one cup of super strong coffee per day?
8. Would you rather attend a team-building event where everyone wears silly hats or one where everyone participates in a karaoke competition?
9. Would you rather have a job where you get to wear pajamas but have no meetings, or a job with a strict dress code but frequent pizza parties?
10. Would you rather have a private office with no windows or a window seat in an open plan office?
11. Would you rather work four ten hour days or five eight hour days?
12. Would you rather have a job with lots of travel or one where you never have to leave your city?
13. Would you rather earn more money at a stressful job or earn less at a relaxed one?
14. Would you rather be promoted above your comfort zone or stay in a role you are great at?
15. Would you rather work for a tiny startup with big potential or a large established company with stability?
16. Would you rather take a pay cut to work with people you love or take a pay rise to work with people you find difficult?
17. Would you rather have a one hour lunch break every day or finish an hour earlier? Would you rather have a mentor who pushes you hard or one who supports you gently?
18. Would you rather know what your coworkers earn or have your own salary kept completely private?

Work This or That Questions

• Email or phone call for quick communication at work?
• Open office layout or private cubicles for your workspace?
• Candy or donuts?
• Casual Fridays or a consistent dress code throughout the week?
• Windows or Mac for your work computer?
• Have Tuesday off work or have Thursday off work?
• Decorate the office for Halloween or for Christmas?
• Have an office dog or an office cat?
• Noise-canceling headphones or airpods?
• Lose your phone or lose your keys?
• Drive to work or walk to work?
• Work from home or work from office?
• Coffee or tea?
• In person meetings or zoom call?
• Eat a salad or tacos for lunch?
• Get to work early or leave work late?
• More annual leave or higher salary?
• Work Christmas Eve or New Year’s Eve?
• Have more family time or more money?
• Monday meeting or Friday meeting?

Using “Would You Rather” questions at your workplace is an excellent way to create a positive atmosphere. These simple yet entertaining queries can serve as icebreakers, team-building activities, and a much-needed break from the daily grind.

So, the next time you’re looking to add some fun to your work day, don’t hesitate to pose some “Would You Rather” questions and watch as your coworkers laugh and chat.

Still looking for more fun Questions? try these 500+ Fun Questions for Any Group

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