Looking for new ways to stoke the flames of conversation at work? Trying to nurture those fledgling relationships between colleagues to bring the team closer together? And have you already been through our lists of ice-breaker questions, get-to-know-you-questions, and this-that questions?!
Well, would you rather questions for the workplace are a natural next step. These fun inquiries present 2 competing options for teammates to choose from – providing easy laughs, conversation starters, and opportunities to learn about one another in the process. To help you get the ball rolling, we’ve put together an entire article full of them! Read on for 300 would you rather questions to use in the office.
Our go-to Would you rather questions for work
Lack the time to go through this list in its entirety? Don’t worry. Containing 20 of the best would you rather questions for work teams, this first section should have everything you need.
1. Would you rather work on a remote team or in a traditional office?
2. Would you rather work in a client-facing role or behind the scenes?
3. Would you rather work on a team that prioritizes efficiency or creativity?
4. Would you rather have complete freedom or strict instructions?
5. Would you rather have tight or relaxed work deadlines?
6. Would you rather work on projects that are highly profitable or socially impactful?
7. Would you rather be a big fish in a small pond or the other way around?
8. Would you rather have lots of responsibility at work or none at all?
9. Would you rather work at home in your pajamas or in the office in a suit?
10. Would you rather eat lunch at your desk and go home early or eat lunch outside with colleagues and leave work at the regular time?
11. Would you rather have a team lunch every day or a happy hour once a week?
12. Would you rather play music in the office or work in silence?
13. Would you rather work long hours for more money or a 4-day week for less?
14. Would you rather work in a team of super ambitious or super laidback people?
15. Would you rather start work early and go home early or start late and go home late?
16. Would you rather work on innovative projects or those that are tried and tested?
17. Would you rather be rich and famous or poor and happy? Why?
18. Would you rather have a full-time job and financial stability or be able to work from anywhere and have a less predictable income?
19. Would you rather have more paid vacation time or more paid training?
20. Would you rather have a highly specialized role or one with a broad range of responsibilities?
Funny Would you rather questions
The best would you rather questions put a smile on people’s faces! In this section, we’ll run through 20 queries that should prompt some laughs.
21. Would you rather wear a clown nose or clown makeup to work every day?
22. Would you rather work at a desk made of Jello or marshmallows?
23. Would you rather give your next big presentation in a tutu or your pajamas?
24. Would you rather say everything in your best British accent or sing everything you say?
25. Would you rather have to do the Gangnam Style dance whenever the phone rings or play the kazoo whenever your boss talks to you?
26. Would you rather work in an office that’s freezing cold or scorching hot?
27. Would you rather work in an office that plays Mongolian throat singing or death metal all day long?
28. Would you rather do your job blindfolded or standing on tiptoes?
29. Would you rather work in an office with no air-conditioning or no coffee machine?
30. Would you rather work in an office where everyone has to dress like cavemen or superheroes?
31. Would you rather have to speak in rhyme all day or in a different accent every hour?
32. Would you rather give presentations upside down or while spinning in circles?
33. Would you rather use an abacus instead of a calculator or a quill instead of a pen?
34. Would you rather wear a Hawaiian shirt or a tuxedo to work each day? Why?
35. Would you rather your boss was a ghost or a vampire? Why?
36. Would you rather do a cartwheel whenever you enter the office or a roly-poly on your way out of it?
37. Would you rather work in an office where no one was allowed to talk or where everyone had to shout as loud as possible to communicate?
38. Would you rather eat lunch with your hands or drink coffee through a straw?
39. Would you rather wear a cowboy hat or a top hat to work each day? Why?
40. Would you rather work in an office that’s always decorated for Christmas or that’s always decorated for Halloween?
Thoughtful Would you rather questions for work
Just because these types of team-building questions usually have humor at their core doesn’t mean you can’t get deep and meaningful with them too! Here are 20 thoughtful would you rather questions to spark conversations with more substance.
41. Would you rather work somewhere with high potential for career growth or somewhere with a great work-life balance?
42. Would you rather have a clear line of progression through a company or the chance to explore many different roles within it?
43. Would you rather work in a small, agile startup or a large, slow-moving corporation?
44. Would you rather prioritize results or company culture? Why?
45. Would you rather place the emphasis on innovation or tradition?
46. Would you rather work on projects with a long or short time horizon? Why?
47. Would you rather receive lots of support or autonomy from your manager?
48. Would you rather focus on eco-friendly initiatives or profits above all else?
49. Would you rather work somewhere that celebrates individual or team achievements? Why?
50. Would you rather work somewhere with a flat organizational structure or a hierarchical one?
51. Would you rather work for a company where everyone earns the same high salary or where you can earn more as you take on additional responsibility?
52. Would you rather prioritize short or long-term goals? Why?
53. Would you rather plan or execute a project?
54. Would you rather work in the same place your whole career or change roles/organizations every 6-12 months?
55. Would you rather work in an office culture that prioritizes competition or collaboration?
56. Would you rather take risks or pursue easy wins?
57. Would you rather prioritize workplace productivity or employee well-being?
58. Would you rather spend more time working or playing?
59. Would you rather be able to talk to foreign clients in their native language or work overseas in an English-speaking country?
60. Would you rather travel for work or work in the local community?
Silly Would you rather questions
Tired of the meaningful questions? Want to lift the mood in the office by getting back to the silliness instead? This section should do the trick.
61. Would you rather have hands for feet or feet for hands?
62. Would you rather have a pet unicorn or a pet dragon?
63. Would you rather have a monkey’s tail or an elephant’s trunk?
64. Would you rather be unable to stop sneezing or yawning?
65. Would you rather have a case of hiccups or giggles on a permanent basis?
66. Would you rather have a third eye or a third hand?
67. Would you rather have an oversized head or one oversized foot?
68. Would you rather have a personal butler or a personal chef?
69. Would you rather be able to speak every language fluently or be able to talk to animals?
70. Would you rather have a super sense of smell or have incredible sight?
71. Would you rather be superman or batman?
72. Would you rather have a mono-brow or no eyebrows at all?
73. Would you rather see 200 years in the past or 200 years into the future?
74. Would you rather be best friends with Wonder Woman or Captain America?
75. Would you rather fall in love with your dream partner or win $1 million?
76. Would you rather go to jail for a decade or be in a coma for a year?
77. Would you rather be permanently overdressed or under-dressed?
78. Would you rather be omnipotent or omniscient?
79. Would you rather go without a smartphone or give up drinking for a year?
80. Would you rather stop talking or stop using the internet for a month?
81. Would you rather eat your weight in chocolate or ice cream?
82. Would you rather be respected by everyone or be able to control them?
83. Would you rather know what people are thinking or be able to shoot laser beams from your eyes?
84. Would you rather be really tall or really small?
85. Would you rather spend or save your money?
86. Would you rather wear the same underwear for a week or the same socks for a month?
87. Would you rather dance like Shakira or sing like Ariana Grande?
88. Would you rather have a pause button or a rewind button for life?
89. Would you rather die young with no regrets or live for ages and have lots?
90. Would you rather have a third nipple or an extra finger?
Random Would you rather questions
Fact: not all would you rather questions fit into neat little boxes. Here are 30 totally random ones on a wide range of topics that prove it:
91. Would you rather be able to control the time or the temperature?
92. Would you rather lose your hearing or your sense of taste?
93. Would you rather go on a company retreat to Santa Cruz or Las Vegas?
94. Would you rather do an escape room or murder mystery game on a team-building retreat?
95. Would you rather watch Netflix all day or see a live theatre production?
96. Would you rather do improv or live comedy in front of a crowd?
97. Would you rather do a bungee jump or a skydive? Why?
98. Would you rather spend the night in the world’s most haunted house or live outside for a week?
99. Would you rather get a papercut whenever you turn a page or bite your tongue whenever you eat a meal?
100. Would you rather have a food fight or a water fight? Why?
101. Would you rather be the best at something nobody else really cares about or average at something everyone loves?
102. Would you rather win the lottery or get an extra 10 years of life added on?
103. Would you rather go back in time or into the future for 24 hours?
104. Would you rather be stuck on a broken ski lift or a broken rollercoaster?
105. Would you rather read a good book or watch an awesome movie?
106. Would you rather go to space or go deep sea diving in a submarine?
107. Would you rather know what happens in your future or revisit a special moment in your past?
108. Would you rather have so much to do that you’re stressed or so little to do that you’re bored?
109. Would you rather have too much stuff or too little stuff?
110. Would you rather be 5 minutes late or 50 minutes early?
111. Would you rather have lots of good friends or one best friend?
112. Would you rather be indoors or outdoors?
113. Would you rather be the best player on a losing sports team or sit on the bench of a winning one?
114. Would you rather live in the nicest house in a bad neighborhood or the worst house in a great neighborhood?
115. Would you rather be good-looking or super smart?
116. Would you rather be visited by a ghost or an alien?
117. Would you rather never stand in line or never hit a red light while driving ever again?
118. Would you rather be Homer Simpson or Peter Griffin?
119. Would you rather fly first-class for free on every flight or never have to pay for food again?
120. Would you rather be the richest person in the world or the happiest person in the world?
Would you rather questions about travel
Let’s move on to some subject-specific would you rather questions for work. To start, here are 30 that relate to globe-trotting and gallivanting.
121. Would you rather travel the world on a tight budget for a year or do it in luxury for a month?
122. Would you rather go on a cruise and get seasick or a backpacking trip and get lost in the wilderness?
123. Would you rather stay in a luxury hotel and be pampered or stay in a rustic cabin and unplug from technology?
124. Would you rather travel to the Sahara Desert or Antarctica?
125. Would you rather take a guided tour or explore somewhere on your own? Why?
126. Would you rather go on a road trip or a cruise? Why?
127. Would you rather go to a theme park and throw up or a national park and get lost?
128. Would you rather go on a scenic drive or a scenic flight? Why?
129. Would you rather explore a big city or remote countryside?
130. Would you rather have an adventurous experience or a cultural one?
131. Would you rather go on a food tour or a shopping trip?
132. Would you rather laze on a beach or ski down a mountain?
133. Would you rather explore a historic site or a theme park?
134. Would you rather spend lots of money to fly business class or save some money and fly economy?
135. Would you rather explore a far-flung destination or your own backyard?
136. Would you rather stay at a boutique hotel or a bed and breakfast? Why?
137. Would you rather spend a week in London or Paris? Why?
138. Would you rather travel solo or in a group? Why?
139. Would you rather eat from street food stalls or fancy restaurants?
140. Would you rather pack/travel light or take lots of luggage?
141. Would you rather see the Northern Lights or the Great Barrier Reef?
142. Would you rather see the Colosseum in Rome or the Great Wall of China?
143. Would you rather spend time in a modern metropolis or a historical town?
144. Would you rather go wine or beer tasting?
145. Would you rather go on safari or go scuba-diving?
146. Would you rather sail around the world on a yacht or cycle around it on a bike?
147. Would you rather go on vacation with friends or family?
148. Would you rather hang out with ex-pats and speak your own language or mingle with the locals and not understand everything they say?
149. Would you rather be by yourself on a tropical island or surrounded by countless people in a city?
150. Would you rather be able to speak every language in the world or teleport anywhere at any time?
Would you rather questions about animals/wildlife
Would your team rather be at the zoo than be talking on zoom? Time to find out with these 30 would you rather questions related to animals, pets, and wildlife.
151. Would you rather see lions on safari or swim with dolphins?
152. Would you rather ride an elephant or an ostrich?
153. Would you rather be as fast as a cheetah or strong as an ox?
154. Would you rather hug a koala bear or see baby turtles?
155. Would you rather stroke a tarantula or hold a snake?
156. Would you rather swim with great white sharks or see a grizzly bear in the wild?
157. Would you rather be able to climb like a monkey or swim like a fish? Why?
158. Would you rather be woken up by a dog barking or a cockerel crowing?
159. Would you rather have a pet dog or a pet cat? Why?
160. Would you rather have too many pets or none at all?
161. Would you rather fight a tiger or a bear?
162. Would you rather be as slow as a sloth or as smelly as a skunk?
163. Would you rather be a squid or a seahorse?
164. Would you rather have a pet otter or a pet beaver?
165. Would you rather be able to talk to spiders or snakes?
166. Would you rather live on dry land or in the ocean?
167. Would you rather be best friends with a gorilla or a panda?
168. Would you rather go on a whale-watching tour or on a jungle trek?
169. Would you rather ride a camel or a horse? Why?
170. Would you rather be surrounded by a pack of wolves or hyenas?
171. Would you rather be a dark horse or an underdog?
172. Would you rather be sly as a fox or as proud as a peacock? Why?
173. Would you rather be as quiet as a mouse or as hungry as a horse? Why?
174. Would you rather be as wise as an owl or happy as a clam? Why?
175. Would you rather be as innocent as a lamb or as slippery as an eel? Why?
176. Would you rather be as tall as a giraffe or as tiny as an ant?
177. Would you rather have a pet monkey or a pet parrot?
178. Would you rather own a farm or a zoo?
179. Would you rather swim with sharks or dolphins?
180. Would you rather have a pet lion or a pet elephant?
Would you rather questions about socializing
Do you have a team full of introverts or extroverts? What sort of things do they like doing with friends and family outside of the office? Time to find out with the following 20 would you rather questions for the workplace.
181. Would you rather go to a huge party or a small gathering of close friends?
182. Would you rather have a night on the town or stay in to watch a movie?
183. Would you rather be the life and soul of the party or a quiet observer on the sidelines?
184. Would you rather chat with a stranger or catch up with an old friend? Why?
185. Would you rather go to a concert or comedy show? Why?
186. Would you rather go to a networking event for work or a high school reunion?
187. Would you rather go to a folk festival or a dance festival?
188. Would you rather go to a food festival or a music festival?
189. Would you rather have dinner or drinks for a first date?
190. Would you rather give an impromptu speech or stay completely silent?
191. Would you rather chat with friends online or meet up in person?
192. Would you rather go to a fancy restaurant or a casual eatery in town?
193. Would you rather have a picnic or a BBQ? Why?
194. Would you rather talk one-on-one or in a group setting?
195. Would you rather walk around a museum or spend the day at a theme park?
196. Would you rather go to a nightclub or a bar?
197. Would you rather have post-work drinks or have dinner with the team?
198. Would you rather go to church or attend a political rally?
199. Would you rather go a week without talking or a week without socializing?
200. Would you rather eat out or eat in?
Would you rather questions about hobbies
Learning about people’s hobbies is a great way to find things to talk about and to select future team-building activities you know your employees will engage with. Here are 20 would you rather questions on the topic!
201. Would you rather go hiking or biking?
202. Would you rather collect stamps or coins?
203. Would you rather paint like Picasso or play piano like Paul Procopolis?
204. Would you rather cook dinner or do the dishes?
205. Would you rather do a Sudoku or a crossword?
206. Would you rather be a photographer or videographer?
207. Would you rather read a fiction or non-fiction book?
208. Would you rather write poetry or read poetry?
209. Would you rather go rock climbing or bungee jumping?
210. Would you rather go scuba diving or fishing?
211. Would you rather watch the baseball or NFL?
212. Would you rather play sports or watch sports?
213. Would you rather play computer games or board games?
214. Would you rather play the guitar or the accordion? Why?
215. Would you rather speak a second language fluently or play an instrument like a professional?
216. Would you rather be a carpenter or a blacksmith? Why?
217. Would you rather go hunting or visit the local zoo?
218. Would you rather be good at knitting or gardening?
219. Would you rather be a professional artist or musician?
220. Would you rather be the lead singer or the lead guitarist in a band?
Would you rather questions about daily routines
Would the team rather wake up early or go to bed late? Spend their day at the gym or watching Netflix on the couch? Here are 20 would you rather questions about their daily routine that’ll reveal all!
221. Would you rather have a set routine or be more spontaneous?
222. Would you rather wake up early or stay in bed all morning?
223. Would you rather have a cup of coffee or tea in the morning?
224. Would you rather take a nap in the afternoon if you’re tired or power through?
225. Would you rather cook dinner or pay for takeout?
226. Would you rather clean the house every week or do it only when necessary?
227. Would you rather plan ahead or live in the moment?
228. Would you rather have a glass of water or a glass of wine with dinner?
229. Would you rather work less and earn less or work more and earn more?
230. Would you rather make your bed or leave it messy?
231. Would you rather grab breakfast on the go or wake up early to have it at home?
232. Would you rather spend the evening watching Netflix or listening to music?
233. Would you rather go for a run or go to the gym?
234. Would you rather go to bed late and wake up late or go to bed early and wake up early?
235. Would you rather eat breakfast in bed or at a local café?
236. Would you rather listen to music or a podcast while commuting to work?
237. Would you rather go do yoga or squeeze in a workout during your lunch break?
238. Would you rather eat less or exercise more to lose weight?
239. Would you rather have a big breakfast and no coffee or a cup of coffee and no breakfast each morning?
240. Would you rather be responsible for the housework or the cooking?
Would you rather questions about food/drinks
Next up, we’re going through 20 would you rather questions about food and drinks to ask the group. From disputes about the best snacks to foods you could or could never give up, this section’s sure to spark some fun team discussions.
241. Would you rather eat steak or lobster for dinner?
242. Would you rather eat an entire chocolate cake or cheesecake?
243. Would you rather give up chocolate or potato chips forever?
244. Would you rather drink beer or wine to unwind after work?
245. Would you rather eat cake or cookies for a snack at work?
246. Would you rather have a grape stuck up your nose or some spinach stuck in your teeth?
247. Would you rather eat something overcooked or undercooked?
248. Would you rather try the vegan diet or the carnivore diet for a whole month?
249. Would you rather fast for a day or eat so much that you threw up?
250. Would you rather have ketchup or mayonnaise on every meal?
251. Would you rather eat KFC or Chick Fil A?
252. Would you rather have pasta for breakfast every morning or pancakes for dinner every night?
253. Would you rather eat every meal with chopsticks or your fingers?
254. Would you rather eat an entire raw onion or an entire bulb of raw garlic?
255. Would you rather give up sugar or salt for the next 10 years?
256. Would you rather eat meals you have to microwave or meals you can eat raw?
257. Would you rather live in a world without pizza or a world without pasta?
258. Would you rather eat Chinese takeout or McDonald’s fries for the rest of your life?
259. Would you rather never eat grilled cheese again or never eat mac n cheese again?
260. Would you rather eat waffles or pancakes for dessert every day?
Difficult Would you rather questions to answer
Last but not least, here are 40 questions you and the team should struggle to answer! With pros and cons on either side, they’re sure to elicit opposing viewpoints and trigger more light-hearted debates between co-workers.
261. Would you rather be able to control the weather or control the time?
262. Would you rather solve world hunger or end wars at will?
263. Would you rather be able to teleport or read minds?
264. Would you rather take the red pill or the blue pill in the Matrix?
265. Would you rather live in a world where cars didn’t exist or planes didn’t exist?
266. Would you rather be able to breathe underwater or fly?
267. Would you rather be able to run at the speed of light or travel to other planets?
268. Would you rather have chronic insomnia or chronic pain?
269. Would you rather be able to turn into any animal or any person at will? Why?
270. Would you rather live in a world without weapons or psychopaths?
271. Would you rather get rid of crime in the US or famine around the globe?
272. Would you rather be as rich as Elon Musk or smart as Albert Einstein?
273. Would you rather never spend time in nature again or never use technology again?
274. Would you rather have complete control of the elements (fire, wind, earth, and water) or complete control of other people?
275. Would you rather be able to eat whatever you want, whenever you want, or be the fittest person on the planet?
276. Would you rather have a personal chef or a personal trainer?
277. Would you rather be able to control light or control sound?
278. Would you rather be friends with Ironman or Thor?
279. Would you rather have the perfect family or the perfect friends?
280. Would you rather have 1 wish that’s guaranteed to come true or 3 wishes with a 50/50 chance of coming true?
281. Would you rather be the tallest person on the planet or the smallest person on the planet?
282. Would you rather be a lone wolf or a sheep in a herd?
283. Would you rather listen to one song for the rest of your life or never be able to listen to the same song more than once?
284. Would you rather know when you’re going to die or what you’re going to die of?
285. Would you rather go on a silent retreat for a week or on vacation with someone who never stops talking?
286. Would you rather have to crawl everywhere or sprint everywhere you go?
287. Would you rather be famous for something embarrassing or totally unknown?
288. Would you rather have a fantastic imagination or a photographic memory?
289. Would you rather earn more working from the office or earn less working from home?
290. Would you rather have your life turned into a movie or a book? Why?
291. Would you rather have someone ignore you at all times or be mean to you whenever you talk? Why?
292. Would you rather never be rejected ever again or never fail at anything ever again?
293. Would you rather be better at managing your time or managing your money?
294. Would you rather have an exciting life that’s dangerous or a dull life that’s safe?
295. Would you rather be liked by everyone you meet or possess everything you want?
296. Would you rather buy your dream house or take your dream trip?
297. Would you rather never use shampoo again or never use toothpaste again?
298. Would you rather work standing up at all times or work kneeling down at all times?
299. Would you rather have to make everyone at work a hot drink every time you make yourself one, or never have anyone else at work make you a hot drink?
300. Would you rather have no control over what you say at work or no control over what you do at work?
Try these Would you rather questions at work
Would you rather questions for work are an effective way to stimulate conversation in the office, lighten the mood, boost camaraderie, and help co-workers get to know each other. Whether you use them as a group warm-up before meetings or to learn more about candidates in job interviews, we hope the 300 options above will prove useful in the coming weeks and months!
Looking for more opportunities to put them into action? Why not go on a team-building retreat together? Specifically designed to unite teams in a fun, unique, and relaxed environment, it’d be a perfect place to try these questions out for size. Furthermore, if you want all the benefits with none of the hassle, Surf Office can organize the whole thing for you! Contact us today to learn more.
