Adding Fun to the Workplace with Would You Rather

Would you rather always be 2 hours early, or 2 hours late? Or, would you rather be a perfect artist or a perfect mathematician?

A game with two choices, Would You Rather games have been a staple for group gatherings around the world. Once players get over their initial reactions to the absurdity of picking between two good or bad options, their answers often reveal some nugget of truth about themselves.

Beyond that, Would You Rather is also a versatile tool to break the ice, start a conversation, or strengthen existing bonds. Because the games can be played with anywhere from 2 to 20 players, it works well in both smaller, more intimate settings as well as larger groups.

More importantly, an under looked application of the game is playing in the workplace.

At first glance, Would You Rather doesn't seem like a great fit for a work environment. It's typically played among friends and family, where the participants are more relaxed in answering and already have a baseline understanding of each other.

But these traits make the game perfect for the workplace. By having coworkers answer personal questions, the game opens a new window for teams to understand and bond with each other. Rather than having each person's boundaries and beliefs bubble up during a work meeting, Would You Rather allows for healthy discussion and disagreement in a casual environment.

Below, we'll talk about how, why, and when to play Would You Rather and provide a list of tailored questions for your first game.

How to play Would You Rather

The rules behind Would You Rather are pretty simple. For each question, players are given two choices and have to select one of the choices while explaining their reasoning behind the pick. For example, for a question like, “would you rather be a perfect artist or a perfect mathematician,” I would pick being an artist. As an artist, I could capture the world in all of its beauty and that's important to me.

That's the core to the game. Rather than trying to win or select the right answer, the purpose of Would You Rather is to allow players to express themselves and detail their thought process. So players aren't allowed to choose both options or skip the question. Instead, they have to select a single one before the next question is revealed.

Beyond the basic rules, finding the right questions for Would You Rather is important. Some questions, like “would you rather fight 100 ducks-sized horses or 1 horse-sized duck”, are great for their comedic value but provide little in terms of team bonding. On the other hand, questions like “would you rather have a four-day workweek or a six-day workweek” can evoke unpleasant memories (such as working on a Saturday).

There's no single “perfect” question. Instead, a great round should have a healthy blend of general questions as well as personal ones. A good rule of thumb would be 80% general questions and 20% personal questions.

A general question could be, “would you rather have great penmanship or type 180 words per minute?” On the other hand, a personal question could be, “would you rather have all meetings start exactly on time, or have all meetings end on time?” or “would you rather start work an hour later or leave work an hour earlier?”

Before the game starts, the organizer should write down all of the questions on sheets of paper. Participants should only be able to see one question at a time and the time to discuss each question should be around 1 to 3 minutes depending on the energy.

One other thing that an organizer can do is also ask the players for new questions before the game starts. This allows players to feel empowered in building the game together.

Finally, it's also important to take into account the context around the game. Playing in the middle of the workday might mean more general questions, while an end of day game has room for more personal ones.

All in all, the experience around Would You Rather is crucial to engaging the players. At Fun Country, we've spent a lot of time thinking about how to bring the magic of Would You Rather to an online environment. We've built the game such that anyone can submit questions and players answer by moving their faces to the response.

In doing so, the gaming experience becomes much smoother than when the game's played on tools like Zoom or Google Meets. Instead of everyone shouting out their answers, players can think about their reasoning, hear other responses, and learn about their coworkers. There's also a built-in timer to keep the game from becoming stale, and any player can also elect to move on to the next question.

Why play Would You Rather

Team bonding is often a squishy phrase that's not very actionable. Would You Rather is a great practicable tool for companies to start or improve their team's cohesion.

As we've written in the past, remote companies often struggle with creating a culture of connection. Coworkers don't have the chance to talk over a water cooler, go to lunch together, or simply be in each other's presence.

Would You Rather is a good starting point to recreating that culture. It gives different coworkers the platform to speak and express their personality in a safe and casual environment. Their answers draw upon their personal life experiences or passions, something that's not easily shown in the day to day working environment.

For example, a question as simple as, “would you rather live in a loud city or live on a secluded farm,” can signal what type of working style someone has. Choosing a loud city might mean an emphasis on teamwork and collaboration, whereas choosing a secluded farm may mean that the person is better suited for deep work.

Another question, “would you rather travel to your favorite place every year or go to a new destination each year,” can imply if a person is more process oriented or focused on new challenges. Or maybe that person is more risk-adverse.

One thing to note is that these answers shouldn't be taken as the unchangeable truth. Someone could simply prefer the farm life over the city life but still be an extroverted person. The answers only give a view into someone's preferences. When extrapolating answers, players should be aware that these are data points rather than personality traits.

Further, a single round in Would Your Rather will cycle through dozens of questions. While they're not played with the express intention of figuring each coworker's working style, the details in answering so many questions naturally shine a light on their preferences. Plus, what's better than smiling and laughing together while learning more about each other?

When to play Would You Rather

The big barrier to Would You Rather is getting started. It's easy to get a group of coworkers together, it's very difficult to get them to open up and start sharing.

That's why the first game of Would You Rather for the company should be played in a more relaxed environment. Instead of introducing the game during a morning standup, organizers can instead strategically start the game during company happy hours or after work has finished for the game.

During this first game, success hinges on the energy of the participants. It's important that the game keeps a brisk pace and everyone is engaged. In a larger group, organizers should keep individual answers to less than one minute and intentionally create opportunities for players to explain their choices. This can be as simple as asking why someone chose an option, or something more complex like asking the group to see if anyone agrees with the explanation.

The final note to the first game is limiting the questions to more general ones that aren't intensely personal. A bad question is, “would you rather lose your spouse or lose your parents?” This might be a good question in a smaller setting but would kill the mood when posed during the first game.

Once the first game is complete, continue the momentum by adding the game to a weekly opt-in gaming session. Teams can choose to participate and learn more about their coworkers. The key in these games is to make sure that the questions are prepared ahead of time. Low quality Would You Rather games are often caused because the players aren't interested in the questions.

Beyond that, success in implementing Would You Rather within a company is dependent on the recognition that the game gets. While it's hard to argue with the smiles and laughter that comes with Would You Rather, it's important for the organizer to consistently organize new sessions and invite new parts of the company to join.

When the same coworkers participate in every session, they can dive into more personal parts of themselves. However, over time, this group starts to solidify and makes it hard for newcomers to join in. A healthy game should be accommodating to both new players as well as veterans.

180 Would You Rather Questions to Use With Coworkers

Here are plenty of Would You Rather questions to get your group started. We've broken them into categories: General, Funny, and Personal.

General:

1. Would you rather have the ability to read minds or have the ability to fly?
2. Would you rather have an extra hour every day or have the power to stop time for an hour every day?
3. Would you rather have a lifetime supply of books or a lifetime supply of movies?
4. Would you rather spend a year living at the top of a mountain or a year living on a beach?
5. Would you rather be a famous author or a famous musician?
6. Would you rather live without music or live without television?
7. Would you rather never be able to use social media sites/apps again or never watch another movie or TV show?
8. Would you rather be the best player on a losing team or the worst player on a winning team?
9. Would you rather always be 10 minutes late or always be 20 minutes early?
10. Would you rather never be able to use a touchscreen or never be able to use a keyboard and mouse?
11. Would you rather be able to speak all languages or be able to communicate with animals?
12. Would you rather explore space or the deepest part of the ocean?
13. Would you rather have free Wi-Fi wherever you go or have free coffee whenever you want?
14. Would you rather be completely invisible for a day or be able to fly for a day?
15. Would you rather be stranded on a deserted island with all the supplies you need or be in a bustling city but have no money?
16. Would you rather have the ability to teleport anywhere or be able to create legal money at will?
17. Would you rather have an unending summer or an unending winter?
18. Would you rather spend a day without your phone or a day without your friends?
19. Would you rather visit 100 years in the past or 100 years in the future?
20. Would you rather have the best house in a bad neighborhood or the worst house in a good neighborhood?
21. Would you rather be a famous director or a famous actor?
22. Would you rather be able to breathe underwater or fly through the air?
23. Would you rather be a world-class athlete or a renowned scientist?
24. Would you rather live in a place where it's always day or always night?
25. Would you rather have a golden voice or a silver tongue (persuasive)?
26. Would you rather live in a world of magic or a world of advanced technology?
27. Would you rather be a superhero or a super villain?
28. Would you rather never have to sleep again or never have to eat again (and have no negative health effects)?
29. Would you rather be able to control fire or water?
30. Would you rather go to a music concert or a comedy show?
31. Would you rather have the ability to never get stuck in traffic or never get a cold?
32. Would you rather always have to wear shoes one size too big or one size too small?
33. Would you rather live without heat and AC or live without social media?
34. Would you rather never be able to travel more than 50 miles from home or live in hotels never staying in one place for more than 3 days?
35. Would you rather have all your clothes fit perfectly or have the most comfortable pillow, blankets, and sheets in existence?
36. Would you rather always know the truth or always live in blissful ignorance?
37. Would you rather always be able to find a parking spot or never have to wait in line?
38. Would you rather never lose your phone again or never lose your keys again?
39. Would you rather have the ability to stop time or the ability to travel in time?
40. Would you rather live in a treehouse or a castle?
41. Would you rather live in a virtual reality where you are all powerful or in the real world?
42. Would you rather have free international first-class tickets or never have to pay for food at restaurants?
43. Would you rather be able to control machines with your mind or animals with your mind?
44. Would you rather have a photographic memory or be able to forget anything you want?
45. Would you rather go deep-sea diving or bungee jumping?
46. Would you rather have a constantly changing face or a constantly changing voice?
47. Would you rather be able to teleport but get extremely tired after each use or be able to fly but only as fast as you can run?
48. Would you rather always speak your mind or never speak again?
49. Would you rather be forced to dance every time you heard music or be forced to sing along to any song you heard?
50. Would you rather live without music or live without television?
51. Would you rather be too hot or too cold?
52. Would you rather have telekinesis (the ability to move things with your mind) or telepathy (the ability to read minds)?
53. Would you rather be able to run incredibly fast or be incredibly strong?
54. Would you rather be locked in an amusement park or a library overnight?
55. Would you rather be an unknown major league baseball player or a famous badminton star?
56. Would you rather be unable to use search engines or unable to use social media?
57. Would you rather only be able to use a fork (no spoon) or only be able to use a spoon (no fork)?
58. Would you rather have a noisy neighbor or a nosy neighbor?
59. Would you rather live in a cave or live in a treehouse?
60. Would you rather always know where you left things or always know what people are thinking about you?
61. Would you rather never be able to read again or never be able to speak again?
62. Would you rather spend the rest of your life with a sailboat as your home or an RV as your home?
63. Would you rather be a character in an action-packed thriller or a romantic comedy?
64. Would you rather spend a year at sea or a year in the mountains?
65. Would you rather always feel an itch that you can't reach or always have a tiny rock in your shoe?
66. Would you rather never lose your phone again or never lose your keys again?
67. Would you rather live at the top of a tall New York City apartment building or at the top of a mountain?
68. Would you rather be able to control animals (but not humans) with your mind or control electronics with your mind?
69. Would you rather have unlimited international first-class tickets or never have to pay for food at restaurants?
70. Would you rather see what was behind every closed door or be able to guess the combination of every safe on the first try?
71. Would you rather have all traffic lights you approach be green or never have to stand in line again?
72. Would you rather be the first person to explore a planet or be the inventor of a drug that cures a deadly disease?
73. Would you rather have a horrible short-term memory or a horrible long-term memory?
74. Would you rather be completely invisible for one day or be able to fly for one day?
75. Would you rather be locked in a room that is constantly dark for a week or a room that is constantly bright for a week?
76. Would you rather live without the internet or live without AC and heating?
77. Would you rather be able to teleport anywhere or be able to read minds?
78. Would you rather your shirts always be two sizes too big or one size too small?
79. Would you rather live without music or without television?
80. Would you rather be fluent in all languages or be a master of every musical instrument?

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Funny:

1. Would you rather have unlimited sushi for life or unlimited tacos for life?
2. Would you rather have a pet dinosaur or a pet dragon?
3. Would you rather always have to sing rather than speak or dance everywhere you go?
4. Would you rather have unlimited pizza or unlimited burgers?
5. Would you rather have a pet unicorn or a pet phoenix?
6. Would you rather have to write everything you say out by hand or only be able to speak in rhymes?
7. Would you rather always have to sing rather than speak or dance all your movements?
8. Would you rather fight 100 duck-sized horses or one horse-sized duck?
9. Would you rather have a tail or have wings (but you can't fly)?
10. Would you rather be able to only whisper or only shout?
11. Would you rather always get first dibs or the last laugh?
12. Would you rather always talk in rhymes or sing instead of speak?
13. Would you rather have to announce to everyone around you whenever you have to fart or pee your pants daily?
14. Would you rather have a permanent clown face or permanent clown clothes?
15. Would you rather always have to enter rooms by announcing your name or always have to do cartwheels out?
16. Would you rather be forced to high-five everyone you make eye contact with or be required to yell "I don't know you!" to every person you see in a grocery store?
17. Would you rather have to start every sentence with “According to my calculations,” or end every sentence with “and that’s how I saved the world”?
18. Would you rather your only mode of transportation be a donkey or a giraffe?
19. Would you rather only be able to communicate with whispers or only be able to communicate with shouts?
20. Would you rather always smell like a pungent garlic or always smell like a fish?
21. Would you rather wear a tuxedo/dress every single day or wear a bathing suit every single day?
22. Would you rather sneeze cheese or have your tears be chocolate flavored?
23. Would you rather have to use a public toilet that is terribly dirty and dark or one that has a snake in it?
24. Would you rather your only mode of transportation be a small rowboat or ride on the back of an ostrich?
25. Would you rather sweat maple syrup or sneeze confetti?
26. Would you rather have your mouth always taste like onions or have silent but uncontrollably deadly farts?
27. Would you rather burp the sound of a gong or sneeze with the force of a hurricane?
28. Would you rather only be able to wear one color each day or have to wear seven colors each day?
29. Would you rather have a 10-inch long belly button that sways to music or accordions for legs?
30. Would you rather have a singing voice like an opera star's or a whistle with a range of six octaves?
31. Would you rather always wear clown makeup or always wear a clown wig?
32. Would you rather be forced to dance every time you heard music or be forced to sing along to any song you heard?
33. Would you rather have a hand twice as big as it should be or one half as big?
34. Would you rather smell like eggs when you burp or have a green cloud appear when you fart?
35. Would you rather give up bathing for a month or give up the internet for a month?
36. Would you rather be a chicken-sized elephant or an elephant-sized chicken?
37. Would you rather always have a booger in your nose that moves when you breathe in and out or a piece of food stuck between your two front teeth?
38. Would you rather have to fart loudly every time you have a serious conversation or have to burp after every kiss?
39. Would you rather eat a whole jar of mayonnaise or drink a bottle of hot sauce?
40. Would you rather have to eat a whole onion or a whole lemon?
41. Would you rather always have to skip everywhere or run everywhere?
42. Would you rather have a head the size of a tennis ball or the size of a watermelon?
43. Would you rather live in a world where huge, friendly gummy bears walk around or live in a world where hoverboards exist?
44. Would you rather fight one horse-sized duck or 100 duck-sized horses?
45. Would you rather fart loudly every time you are in a serious meeting or have to burp after every time you kiss?
46. Would you rather never be able to eat warm food or never be able to eat cold food?
47. Would you rather always wear earmuffs or a nose plug?
48. Would you rather have to read aloud every word you read or sing everything you say out loud?
49. Would you rather have the neck of a giraffe or the nose of an elephant?
50. Would you rather have a foot-long nose or a foot-long tongue?

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Personal:

1. Would you rather travel back in time to meet your ancestors or travel to the future to meet your descendants?
2. Would you rather live in a world where there are no problems, or live in a world where you rule?
3. Would you rather go back to the past and fix all your mistakes or go to the future to see what it's like?
4. Would you rather have a rewind button or a pause button for your life?
5. Would you rather have the ability to see one year into your own future or one year into the future of anyone but yourself?
6. Would you rather have unlimited money, power, and respect or unlimited love, trust, and loyalty?
7. Would you rather lose all of your memories or never be able to create new ones?
8. Would you rather donate your body to science or donate your organs to people who need them?
9. Would you rather go back to age 5 with everything you know now or know now everything your future self will learn?
10. Would you rather have the chance to rewrite your past or have the certainty to foresee your future?
11. Would you rather experience a constant feeling of being underrated or being overrated?
12. Would you rather be known for your kindness or your intelligence?
13. Would you rather be able to change one event from your past or have the guarantee of changing one event in your future?
14. Would you rather be unable to express your emotions or have them be exaggeratedly expressed all the time?
15. Would you rather lose all of your old memories or never be able to create new ones?
16. Would you rather live with constant regret or constant fear?
17. Would you rather live a short, impactful life or a long, mundane one?
18. Would you rather be born with wisdom or gain it through experience?
19. Would you rather be forced to hide your true beliefs every day or shout them out once every hour?
20. Would you rather live in peace but in ignorance or in turmoil but with knowledge?
21. Would you rather have your dreams come true but have a short life or live a long and healthy life with no dreams coming true?
22. Would you rather be universally loved but personally lonely or be universally hated but loved by the one who matters most to you?
23. Would you rather always be slightly lying or always be brutally honest?
24. Would you rather live one 1000-year life or ten 100-year lives?
25. Would you rather be able to stop time or able to manipulate time but you age accordingly?
26. Would you rather know the date of your death or the cause of your death?
27. Would you rather be happy but alone forever or unhappy but with the love of your life?
28. Would you rather have deep conversations every day or have small talk every day?
29. Would you rather betray your closest friend for your greatest personal gain or sacrifice your greatest personal gain for your closest friend?
30. Would you rather be seen as someone who always over-delivers or as someone who under-promises?
31. Would you rather be successful professionally with a poor private life or have a prosperous private life but a frustrating professional one?
32. Would you rather let go of your pride or your fear?
33. Would you rather be extremely lucky but have a short life or have an extremely long life with no luck?
34. Would you rather love with a broken heart or live without any feelings at all?
35. Would you rather spend your life chasing your dreams, even if you might never reach them, or be content with what you have?
36. Would you rather achieve great things but be alone or lead an average life surrounded by loved ones?
37. Would you rather make a difference in the world but be forgotten after you die or do nothing but be remembered forever?
38. Would you rather have to painfully relive all your past mistakes once a year or be unable to learn from your mistakes?
39. Would you rather live in your dreams but never achieve them or achieve your dreams but never live them?
40. Would you rather have a painful truth or a comforting lie?
41. Would you rather always know what people think of you or never know?
42. Would you rather have a lifetime of regret or a moment of shame?
43. Would you rather be unable to forgive or unable to apologize?
44. Would you rather age mentally but not physically or age physically but not mentally?
45. Would you rather have an infinite amount of time or an infinite amount of money?
46. Would you rather always feel like you’re not enough or feel like you’re too much?
47. Would you rather live without love or live without hope?
48. Would you rather be able to erase your fears or your failures?
49. Would you rather lose all of your money and valuables or all of the pictures you have ever taken?
50. Would you rather be an average person in the present or a king of a large country 2500 years ago?