120 Fun Questions of the Day for Work

Teams collaborate more effectively when every member is engaged. And people are more engaged when their brains are actively focused on the problem, issue, or task at hand. How can you get your colleagues mentally engaged? Ask questions.

When starting team or workplace conversations, talking “at” people – especially using “should” statements – can be met with passive resistance, leading to zoning out or disengaging.

Questions, on the other hand, stimulate the mind to explore ideas, actively process information, engage in critical thinking, and formulate responses. Incorporating fun and interesting daily questions into the workplace routine can help enhance communication, foster team collaboration, and create a positive work environment.

Using fun or insightful questions of the day for work, whether directly related to a task at hand or completely separate from work topics, gets people mentally stimulated. This practice can energize team interactions while reducing stress and boosting morale.

Wondering where to begin – and how to keep this going? Bookmark this blog post as a resource you can use, featuring an extensive collection of work-related or at least safe-for-work questions you can incorporate in your workplace. This post will cover 11 types of questions:

Icebreaker Questions of the Day for Work
Questions of the Day to Get to Know Your Team
Fun Questions of the Day for Work
Work-Appropriate Would-You-Rather Questions
Questions about Likes and Dislikes
“Either/Or” Questions of the Day for Work
Trivia Questions of the Day for Work
Deep Questions of the Day for Work
Team Building Questions of the Day for Work
Team Improvement Questions of the Day for Work
Fun Team-Related Questions of the Day for Work

Why Use Questions of the Day at Work?

Getting into the routine of asking fun, thought-provoking daily questions at work provides a number of benefits, including:

Improving team bonding – Answering lighthearted questions creates shared experiences that foster a sense of camaraderie among coworkers.

Encouraging personal connections – Team members get to know each other beyond work roles, building trust and rapport.

Promoting creativity – Imaginative or quirky questions activate creative thinking in a low-pressure, stress-free way.

Breaking up monotony – A daily dose of fun adds variety and energy to the workday, especially during routine tasks.

Boosting morale – Starting the day with a smile or laugh can improve mood and workplace satisfaction.

Enhancing communication – Opens up casual conversation across departments and roles, promoting a more open work culture and improving communication skills in the workplace.

Supporting inclusion – Encourages participation from everyone, regardless of position or background, leveling the playing field.

Creating positive rituals – Builds a consistent, uplifting rhythm into the day that teams can look forward to.

Revealing shared interests – Helps uncover common hobbies, values, or experiences that can deepen team relationships.

Work questions of the day can help lighten the mood during meetings, add life to stand-ups, help employees develop stronger workplace relationships, and spark interesting conversations.

These questions are tools for HR professionals and managers can use to cultivate a strong team culture while maintaining a work-appropriate balance. While work friends are different from “real life” friends, developing solid workplace bonds enhances collaboration and increases employee engagement.

141 Ideas for Questions of the Day for Work

The next 11 sections of this post will provide ideas for questions to ask at work to match different goals and occasions – from questions that help employees get to know each other better to questions that require deep reflection to inquiries about team development and improvement.

Icebreaker Questions of the Day for Work

Icebreaker questions are a great way to kick off a meeting or learn more about new employees during their orientation and onboarding process. They help set the mood and get people thinking and talking.

Icebreakers can deal with a wide range of topics. They generally aren’t work-related, though they can be. Here are 10 questions to break the ice and get conversations flowing.

1. What’s your favorite season and why?
2. If you could only eat one meal for the rest of your life, what would it be?
3. What’s the most interesting place you’ve traveled to?
4. If you could time travel, which period would you choose to visit first?¹
5. What’s your favorite way to unwind after a long workday?²
6. What’s your favorite way to spend time when on vacation?⁴
7. Where in the world do you most want to visit?⁶
8. If you could host a talk show or game show, which one would you want to be on?
9. If you were stranded on a deserted island, what book or object would you bring?²
10. What superpower do you most envy, and how do you wish you could use it?³

Questions of the Day to Get to Know Your Team

Thoughtful and meaningful questions are a fantastic way to learn about coworkers and individual team members, their preferences, and their unique perspectives. The best questions help you get to know the person better while also being fun to think about and answer.

Here are 20 questions to help you discover more about the people you work with.

11. What book has had the biggest impact on your life and why?³
12. Who has been a vital mentor or inspirational figure in your life?
13. What’s one skill you’ve always wanted to learn?
14. What’s your best or favorite childhood memory?
15. What does success mean to you?
16. What’s one thing you’re passionate about outside of work?
17. What’s something you’ve always wanted to do but haven’t done yet? Why not?²
18. What’s been the best day of your life so far?²
19. What would you say is your best attribute or your “superpower”?
20. What’s been your biggest life lesson?³
21. If you could switch jobs with anyone for a week, what role would you choose?²
22. What’s the best piece of career advice you’ve ever received?
23. What’s the worst piece of advice you’ve ever been given?²
24. What advice would you give yourself if you were starting your career again?³
25. If you could choose any person on earth to mentor you for a week, who would you select and why?
26. What’s something you’ve accomplished that you’re super proud of?³
27. What inspired you to pursue your current career path?³
28. What’s the most exciting project you’ve worked on in your career?³
29. What is one thing you’ve done that was outside of your comfort zone?⁵
30. What’s one thing you could teach us about, and why are you passionate about it?⁵

Keeping it Lighthearted: Fun Questions of the Day for Work

In stressful and disconnected work environments, finding ways to maintain team cohesion and workplace culture has become more challenging – and more important – than ever. One simple yet remarkably effective approach is implementing light, fun questions of the day that combine humor, thoughtfulness, and a touch of the unexpected.

These questions are designed to keep the workplace fun and lively, striking a balance between lighthearted engagement and genuine connection. Here are 10 fun, quirky questions of the day to get you started.

31. If your life had a theme song, what would it be?
32. What’s the weirdest thing you’ve ever eaten?
33. What’s one job you would never want to do?
34. What’s your go-to dance move?
35. What’s your favorite TV show or movie of all time?
36. What’s your favorite movie soundtrack?³
37. What was your first concert? What was the best concert you’ve ever been to?²
38. If aliens landed on Earth, who would you recommend they talk to?²
39. What’s one team-building activity you think every company should try?²
40. Which historical figure would you most like to have a Zoom meeting with?³

Work Appropriate Would-You-Rather Questions

“Would you rather” scenarios are effective icebreakers that foster imaginative thinking while remaining professional. Topics can range from amusing to practical to thought-provoking.

These types of questions offer several benefits for teams. They can be a fun way to spark conversation, get to know colleagues better, and even identify potential areas for team improvement.

Here are 10 helpful examples of work-appropriate “would you rather” type questions.

41. Would you rather have free coffee every day or free lunch every Friday?
42. Would you rather organize team-building events or lead strategy meetings?
43. Would you rather work at the beach or in a log cabin?
44. Would you rather be exceptionally good at one professional skill or moderately good at five different skills?
45. Would you rather have the ability to solve any technical problem or the ability to mediate any interpersonal conflict?
46. Would you rather have an office with an amazing view but uncomfortable furniture or no windows but the most ergonomic setup possible?
47. Would you rather tackle one large project at a time or juggle multiple smaller projects?
48. Would you rather have flexible working hours but strict deadlines or fixed hours with more flexible timelines?
49. Would you rather be the funniest or most intelligent person in the room?³
50. Would you rather have the ability to perfectly prioritize tasks or the ability to work twice as fast?

Questions about Likes and Dislikes

Simple questions about likes and dislikes help coworkers get to know each other’s favorite and least favorite foods, activities, colors, songs, or pretty much anything else. Following up on any of these with a “why?” question can often spark interesting conversations.

Here are 15 examples of questions about likes and dislikes. The only limit is your imagination!

51. What is your favorite food?
52. What is a food you hated as a child but like now?
53. What’s your least favorite chore?
54. What’s your favorite color and something it reminds you of?
55. What’s your favorite type of work project to tackle and why?
56. What’s one office supply or tool you couldn’t work without?
57. What’s your least favorite business buzzword or phrase?
58. What background noise helps you focus best: music, silence, or ambient sounds?
59. What’s your favorite way to learn something new: reading, watching videos, or interactive workshops?
60. What’s a work-related book or resource you’ve found particularly valuable?
61. What’s your favorite season and how does it affect your work habits?
62. What’s something you collect or would collect if you started a collection?
63. What’s your stance on the Oxford comma?
64. What’s your opinion on pineapple as a pizza topping?
65. What’s your preference: digital or physical calendars and to-do lists?

“Either/Or” Questions of the Day for Work

Simple either/or questions are ideal for occasions when there isn’t much time to spend on an icebreaker. These questions work great in groups, where participants can instantly see where other team members agree with them, on which topics they differ – and if there are any responses that surprise the team.

Again, imagination is your only limit on these. Here are 15 examples to get your creative juices flowing.

66. Cats or dogs?
67. Sunrise or sunset?
68. Sweet or savory?
69. Breakfast or dinner?
70. Email or phone call?
71. Early meetings or late meetings?
72. Multitasking or deep focus?
73. Planning ahead or adapting on the fly?
74. Windows open or air conditioning?
75. Digital notes or handwritten notes?
76. City or small town?
77. Laptop stickers or pristine laptop?
78. Desk plants or desk photos?
79. Emojis or no emojis?
80. Scheduled meetings or spontaneous discussions?

Trivia Questions of the Day for Work

Trivia questions are a great test of general knowledge and long-term memory. They get everyone engaged without sharing personal information.

You can pull hundreds of trivia questions and answers from sources like Today, Parade, TriviaMaker, and Laurel Gaming. Or you can deliver an authentic game show experience at your next corporate event with our Trivia Blast Live! program or any of our virtual trivia games. For trivia questions of the day at work, here are a few sets of questions and answers as a starting point.

81. Approximately how far away is the moon from Earth? (Answer: Any answer from 225,000 miles to 253,000 miles is close enough)
82. What is the smallest country in the world? (Answer: Vatican City; Monaco is #2)
83. Who painted the Mona Lisa? (Answer: Leonardo da Vinci)
84. How many police cars were destroyed during the filming of The Blues Brothers in 1980? (Answer: 60)
85. What is the largest mammal on earth? (Answer: The Blue Whale)

Deep Questions of the Day for Work

Deep questions go beneath the surface and encourage people to really consider their responses – without being uncomfortable or intrusively personal. Here are 10 deep questions for team members to ponder and respond to.

86. What would you most like to be remembered for?
87. What does success mean to you – personally or professionally?
88. What motivates you to do your best work?
89. How do you handle failure or setbacks?
90. What value or principle do you try to live by every day?
91. How do you approach conflict or disagreement at work?
92. What is one change that would make you happier at work?
93. What’s the most valuable lesson you’ve learned from a mistake you made?⁵
94. How do you define leadership?⁵
95. What’s one dream you’ve yet to achieve, and what’s holding you back?⁵

Team Building Questions of the Day for Work

These questions are designed to elicit feedback about how team members feel about the team generally and their experience with the team to date. Here are 10 example “current state of the team” questions.

96. Are you able to easily approach anyone on the team?¹
97. What is a discussion topic you would like to address with the rest of the team?¹
98. What is the most important factor for effective team collaboration?
99. What do you think makes our team unique?³
100. What is one thing we do well as a team?
101. What aspect of your personality adds most to the team?
102. Using only one word for each person, and without using any word twice, what unique quality or skill does each person bring to our team?
103. What’s been the most fun moment our team has shared?⁵
104. What’s a challenge our team overcame that you’re proud of?⁵
105. What do you think is the first thing you need to do when starting a new project?

Team Improvement Questions of the Day for Work

These questions help “take the temperature” of team member feelings about collaboration and effectiveness, and generate ideas for improving team dynamics. Here are 5 key questions to help teams reach a higher level of performance.

106. What’s the best team experience you’ve ever had, and why?
107. What’s the most significant issue affecting the team right now?⁴
108. How can we ensure that everyone on the team is heard, and that their ideas are valued?
109. What would you like to learn from another team member?⁴
110. How would you describe our team’s approach to resolving conflicts? How could we improve here?

Fun Team-Related Questions of the Day for Work

To wrap up this collection of workplace questions, and expand on the “Fun Questions of the Day for Work” section above, here are 10 fun, lighthearted, and imaginative team-related queries.

111. If our team had a theme song, what would it be?²
112. If our team were a band, what would our debut album cover look like?⁵
113. If our team was stranded on a deserted island, who would you want to take charge?²
114. Which fictional family do you think our work team is most like and why?³
115. Which fictional character would you like to invite to our next team meeting?³
116. Which team member would you nominate to join Mount Rushmore?³
117. You’ve been designated team chef for the day. What’s on the menu?⁴
118. If our team were to write a book, what should its title be and why?⁵
119. If our team were a sports team, what would our mascot be and why?⁵
120. Which team achievement do you think should go into our team’s “Hall of Fame”?⁵

Tips for Using Good Questions of the Day for Work

Implementing questions of the day effectively requires a thoughtful approach that balances consistency with spontaneity. The goal isn’t simply to ask random questions, but to create moments of connection that energize your team and strengthen workplace relationships. To make this practice both sustainable and impactful:

• Integrate questions into existing routines like daily stand-ups, team Slack channels, or the first few minutes of regular meetings.
• Match questions to your meeting purpose; for example, use lighthearted either/or questions to break the ice in Monday morning meetings, but save more reflective questions for retrospectives or planning sessions.
• Tailor questions to your team’s personality. The most engaging questions reflect the unique culture and interests of your specific team. Technical teams might enjoy hypothetical “Would you rather” scenarios with a technology twist, while creative teams might prefer questions that spark innovative thinking.
• Involve the team in question selection. Sustain long-term enthusiasm by inviting team members to submit questions or take turns choosing the question of the day. This shared ownership not only provides fresh material but also gives insight into what colleagues find interesting or important.

Creating Long-term Engagement Through Questions

Consistent, thoughtful, context-appropriate use of questions for the day can enhance teamwork, inspire innovation, and boost workplace morale. As noted above, using these questions can provide a wide range of benefits, from building stronger personal connections and fostering creativity to supporting inclusion and uncovering shared interests.

Using questions of the day is a simple yet effective way to enhance engagement and camaraderie within professional teams. They can help get endorphins flowing through shared laughter and challenge team members to think beyond the surface.

Find ways to incorporate these simple ideas into your daily and weekly routines, and you’ll see the benefits of deeper connection and improved communications. When you’re ready to explore team building strategies that take collaboration and communication to a higher level, contact Best Corporate Events and let’s get a conversation started.

Sources:

1. 1. 103 Check-in Questions for Meetings, Workhuman Blog, https://www.workhuman.com/blog/check-in-questions/
   2. 130 Icebreaker Questions for Work That Actually Work, Asana, https://asana.com/resources/icebreaker-questions-team-building
   3. 101 Icebreaker Questions for Work: The Perfect Tool for Breaking Down Barriers, Necatar HR Blog, https://nectarhr.com/blog/icebreaker-questions-for-work
   4. 71 Great Check-In Questions for Engaging Meetings, Deel, https://www.deel.com/blog/check-in-questions-for-meetings/
   5. Ice Breaker Questions: The Ultimate Guide for Team Building, Evivve, https://evivve.com/icebreaker-questions-the-ultimate-guide-for-team-building/
   6. 70 Icebreaker Questions for Any Meeting or Presentation, Mentimeter, https://www.mentimeter.com/blog/meetings/icebreakers-for-meetings-and-presentations