Starting a new job is exciting, but it can also feel a little intimidating. You’re learning new responsibilities, adapting to a different workplace culture, and meeting people you’ve never worked with before. For many people, introducing themselves and making conversation with unfamiliar colleagues can be just as challenging as learning the job itself.
Building positive relationships at work doesn’t happen overnight. It usually begins with small conversations that help people discover shared interests and become more comfortable with one another. Whether you’re attending a team meeting, onboarding with new hires, or participating in a company social event, having a simple way to break the ice can make interactions feel much more natural.
One of the easiest ways to encourage conversation is by using “This or That” questions. These quick, lighthearted prompts invite people to choose between two options, making them fun, low-pressure, and easy for everyone to answer. They can spark laughter, reveal surprising preferences, and create opportunities for follow-up conversations that strengthen workplace relationships.
Icebreaker activities like these don’t just make meetings more enjoyable—they also help build trust, improve communication, and foster a more connected team. When colleagues feel comfortable talking with one another, collaboration becomes easier and the workplace often becomes more welcoming and inclusive.
In this article, you’ll discover a collection of fun “This or That” questions designed specifically for work environments. Whether you’re meeting new coworkers, leading a team-building activity, or looking for an easy conversation starter, these questions can help everyone get to know each other in an engaging and memorable way.
And if you’re looking for even more conversation starters to energize your next team meeting or workplace event, there is a free download waiting for you at the end.
What Are This or That Questions?
Using questions about a range of topics, you ask whether someone prefers X or Y. There is no wrong or right, no scores being kept, and it’s all about fun. In a game of this or that, you learn a great deal about the players, whether they are family, friends, colleagues, or even strangers.
By offering a choice between items, the player has to choose something, and they usually share a little something about why they prefer one choice over the other. The questions are what make it so much fun to play.
In a “this or that game,” it’s not about whether you like apples or bananas (but you can, of course, ask these too as a warm-up). Instead, you ask really challenging questions that reveal beliefs, moral values, principles, and sneaky streaks.
A question like “would you rather go to prison for a crime or frame someone else for it?” can really open a wide discussion, which is guaranteed to be heaps of fun.
When deciding on this or that questions, it’s important to choose open-ended questions that will invite further explanation and conversations. The right this or that questions can form excellent conversation starters to further encourage team spirit.
Why Play the This or That Questions Game at Work?
Employees hate boring team-building activities, which are usually not relevant to them. But using this or that questions, you can really get to know something unique about your colleagues, laugh together, and surprise everyone (including yourself) – all the elements of great teamwork, right?
A game of this or that is a wonderful icebreaker, and it gets the ball rolling without putting anyone on the spot (everyone is on the spot with clever questions), but since it’s a game, nobody takes offense.
While you can enjoy a game of this or that with friends with some pizza and beer, you can also use the game to welcome new employees to the company during a staff lunch, weekend team-build, or at company retreats.
A great way to get creative juices flowing is to use a short session of “this or that” when you gather for a brainstorming session.
To make it fair, you can toss the questions in a hat, passing it down the boardroom table for everyone to have a chance to choose and answer. It’s a surefire way to ensure nobody keeps mum during the meeting that follows.
141 Fun This or That Questions for Work
Decide on the this or that questions that will work best for your workplace, keeping in mind that while you may know much about your colleagues yet, the questions should be somewhat relatable.
Here is a broad selection of this or thats to encourage a great adventure of answers and surprises as you and your colleagues (and your boss too!) share and laugh together.
Funny This or That Work Questions
1. Lose your cell phone or car keys?
2. Get fired or arrested?
3. Wrap up in an itchy jacket or develop a blister?
4. Have someone pop your pimple or get a wedgie?
5. Get locked out of your apartment or slip in the shower?
6. Crash your car or get run over by your ex?
7. Bring a pet snake or pet spider to work?
8. Get caught taking dodgy selfies in the company bathroom or while plucking a nose hair in the kitchen?
9. Forget to wear underwear or wear the wrong shoes together?
10. Grow a unibrow or lose your hair?
Thought-Provoking This or That Questions for Work
11. Work for one company until retirement or get promoted through six companies?
12. Walk on water or dive to the bottom of the ocean?
13. Friends for life or family forever?
14. A blue pill or take the red one?
15. Shack up in the city or buy a haunted mansion in the countryside?
Using this or that questions, you can really get to know something unique about your colleagues, laugh together, and surprise everyone.
16. Death by execution or by life sentence?
17. Amnesia, forgetting who you are, or forgetting your soulmate?
18. Live like a saint or party to hell?
19. Grow by six inches (#winkwink) or win the lottery?
20. Be catfished or cheat on your partner?
Common Fears This or That Work Questions
21. Cut off your hand to escape or burn while running from a building?
22. Onion breath or something in your teeth?
23. Tempt fate under a ladder or smash a mirror?
24. Face ghosts or run from zombies?
25. Listen to someone chewing loudly or nails scraping on a chalkboard?
26. Stuck in a crowd or locked in isolation?
27. Buried alive or sinking to the bottom of the sea?
28. Run down by a bull or run over by a garbage truck?
29. Dive into a tub of maggots or a bag of rats?
30. Die of hunger or thirst?
Pop Culture and Entertainment This or That Work Questions
31. Queen or Beach Boys?
32. Bourne or Bond?
33. Madonna or Taylor Swift?
34. Justin: Bieber or Timberlake?
35. The British royals or the Kardashians?
36. The Witcher or Game of Thrones?
37. Tattoos or piercings?
38. Football or wrestling?
39. Mac or Windows?
40. Squid Games or Alice in Borderland?
Travel This or That Questions for Your Team
41. Romantic trip to Paris or Rio?
42. Miss the connecting flight or lose your luggage?
43. Have action-packed holiday excursions or spend time on the sofa for the week?
44. Holiday in ice or on the beach?
45. New Years in Times Square or on the Eiffel Tower?
46. Hot air balloon ride or a sunset cruise?
47. Get abducted by sea pirates or bitten by a blood-sucking malaria-infested mosquito?
48. Fall in love in a foreign country or meet your beau on a road trip at home?
49. Backpack through Asia or jet to Russia?
50. Northern Lights or Niagara Falls?
Physical This or That Work Questions
51. Small hands or large feet?
52. Dumbbells or resistance bands?
53. Gym or road runner?
54. Extra fingers or a missing thumb?
55. Makeup perfection or a pleasing, authentic face?
56. No hair or beer gut?
This or that questions are fun and take all the pressure off, and you quickly get to know something about people in a short timespan.
57. Smooth skin with tattoos or wrinkled with liver spots?
58. Glasses or braces?
59. Bad breath or terrible sinus drip?
60. Wear a toupee or be bald?
Food and Drink This or That Questions for Work
61. Pizza or hotdogs?
62. Beer or wine?
63. Same meal every day or spicy chili every day?
64. Coke or Pepsi?
65. Enjoy only Bloody Maries or only water for the next year?
66. Cheese sandwich or mac ‘n cheese every evening?
67. Vegetarian or vegan?
68. Broccoli or Brussel sprouts?
69. Give up nachos or tacos?
70. Reese’s or M&Ms?
Work-Related This or That Questions
71. Watercooler chat time or smoke breaks?
72. Work like a slave or drag your feet?
73. Chatty colleagues or quiet workspace?
74. Answer emails or call customers?
75. Dream job with a small 401(k) or a terror job with shares and a huge 401(k)?
76. Brainstorm with your colleagues or work on a solo project?
77. Bigger pay and longer hours or less pay and more time off?
78. Most productive in the morning or afternoon?
79. Love pressure or hate it?
80. Open office space or remote work space?
Controversial This or That Questions for Your Coworkers
81. Undergo gender-affirming surgery or have a permanent hangover?
82. Kill a priest or go to prison?
83. Pineapple or watermelon on pizza?
84. McDonald’s vs Burger King?
85. Round pizza or square pizza?
86. Worst to have: circumcision or vasectomy?
87. Huge tongue or broken nose?
88. Chipotle or Taco Bell?
89. Extra toes or extra fingers?
90. Xbox or PlayStation?
Hobbies and Interests This or That Questions for Your Work Mates
91. Extreme ironing or bubble football?
92. Throat singing or competitive frog jumping?
93. Collect trivia or photos?
94. Comedy Central or Disney Channel?
95. Hobby horse racing or Nascar tickets?
96. Host colleagues with potluck or barbeque?
97. Enjoy street food in Deli or sample sushi at a Japanese market?
98. Visit a museum or attend a show?
99. Indoor rock climbing or naked ziplining?
100. Club hopping or bar cruising?
101. Herb gardening or vegetable patch?
Bosses and Careers This or That Questions
102. Dictator director or incompetent CEO?
103. Forgetful team leader or freeloading colleague?
104. Mid-level management with great colleagues or upper management with the devil as CEO?
105. Pay raises or company shares?
You ask really challenging questions that reveal beliefs, moral values, principles, and sneaky streaks.
106. Work uniform or work from home?
107. Free donuts in the office kitchen or free coffee?
108. Do what you studied or learn on the job?
109. Long commute to work or walk to work?
110. Company gym or grocery card?
Lifestyle This or Thats
111. Zen garden or high-rise apartment?
112. Slacks or tights?
113. Sneakers or boots?
114. Fuel economy car or V8 ride?
115. Weekends with family or clubbing?
116. Sit-down dinner or TV-dinners?
117. Eat while working or take a break?
118. Exercise or meditate?
119. Backpack or suitcase?
120. Shop in person or order online?
121. Pay by credit card or pay in cash?
Fantasy This or That Questions for Your Teammates
122. Spiderman or Captain America?
123. Wonder Woman or Supergirl?
124. The Joker or Harley Quinn?
125. Gandalf or Mr Spock?
126. Aang or Korra?
127. Ariel, the Little Mermaid, or Cinderella?
128. Han Solo or Darth Vader?
129. The Rocky Horror Picture Show: Frank-N-Further or Riff Raff?
130. Never Ending Story or Peter Pan?
131. Books or movies?
Animal This or That Work Questions
132. Crocodile or shark?
133. Dogs or cats?
134. Dogs: face lick or sniff crotch?
135. Cows for pets or food?
136. Stung by a bee or bitten by a spider?
A great way to get creative juices flowing is to use a short session of “this or that” when you gather for a brainstorming session.
137. Which came first: Chickens or eggs?
138. Pet whale or pet dinosaur?
139. Train a kangaroo or tiger?
140. Pets indoors or outside only?
141. Indoor skunk or porcupine?
Free Download: Icebreaker Questions
The Icebreaker Questions printable includes a variety of fun, engaging conversation starters designed to help coworkers, teams, students, and groups connect more easily. Use them during meetings, training sessions, workshops, onboarding events, or team-building activities to encourage participation, spark conversations, and create a more comfortable atmosphere.
Download your copy and make every introduction a little easier—one question at a time.
(The link opens up a Google Drive folder where you can get the PDF download for the Cards in a variety of sizes)
Final Thoughts about This or That Questions for Work
You can have loads of fun when you, your boss, and colleagues indulge in this or that questions for the work environment. It’s all about getting to know your team, sharing, laughs, and giggles, and if there’s time, elaborate on why you chose this over this.
Work through a category at a time or choose random this or thats to engage in. If you enjoyed these this or that questions for work, check out these good ice breaker questions for virtual meetings or these 180+ fun this or that questions for adults.
And if you want more interesting questions to ask, be sure to check out these blog posts:
