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Team Building & Retreats tips
Published on
August 23, 2025
70 Best Get To Know You Questions: The #1 List for Fun
Building stronger relationships in the workplace starts with one simple but essential action: asking the right questions to get to know someone. It doesn't matter whether your team is in-person, remote, or hybrid: investing effort to get to know your colleagues, managers, and leaders, inside and outside the office, is an excellent way to open the door to collaboration, initiate meaningful conversations, and promote a healthy, productive company culture.
If it's not yet clear to you how important it is to get to know your team, these stats can help you with the big picture:
Gallup has found that employees with “a best friend at work” are more than twice as likely to be engaged. Teams with strong social bonds experience higher morale, increased collaboration, less burnout, and improved job performance.
According to Forbes, people who feel connected to their colleagues report 91% greater personal growth and 101% greater professional growth. These connections reduce loneliness, anxiety, and stress at work.
Harvard Business Review reports that when people feel a genuine sense of belonging at work, they are more motivated and nearly 3.5 times more likely to contribute at their fullest potential.
Asking thoughtful, get-to-know-you questions helps teams break the ice, build rapport, and set the stage for more meaningful conversations. At TeamOut, with our track record of organizing over 1,000 corporate events and retreats, we know that asking fun, deep, or icebreaker questions contributes to a space where everyone can share stories, reveal preferences, and show vulnerability. This helps people feel seen and included and contributes to a workplace culture that values openness, diversity, and trust.
In this article, you’ll discover the #1 list of over 70 questions to get to know someone at work. These questions to ask can be implemented during meetings, corporate retreats, virtual hangouts, or any team-building event. These questions are also meant to ease social anxiety and help everyone feel included. Discover TeamOut's compilation, which builds stronger teams, improves communication skills, and fosterslasting bonds crucial for every high-performing team.
Want to generate your own questions ? Try our free Get to know you questions generator 👇
Icebreaker questions are great to get to know someone better in a group or at the start of a meeting. They’re fun, low-pressure, and set the stage for engaging small talk.
How to Ask: Try as a quick opener before meetings or during virtual calls.
When to Use: Use at the start of a gathering, orientation, or team-building session.
Why These Questions Work: Icebreakers lead to positive first impressions and support professional networking by encouraging initial connections in virtual and in-person environments.
Cultural Considerations: Make sure questions are universally relatable and non-intrusive. Avoid family-related inqueries, for example.
Common Challenges and Solutions: Some people may feel shy or reluctant to participate; offering easy options encourages participants to answer and helps everyone feel included.
Icebreaker Get-to-Know Questions:
What’s your favorite way to start the workday?
Do you have a go-to snack or drink during work hours?
What’s the most interesting place you’ve ever worked from?
Would you rather work from the beach or a cozy cabin?
If you could swap jobs with anyone here for a day, who would it be and why?
What’s the most fun part of your current role?
Would you say you’re a morning person or a night owl?
What’s one office supply you can’t live without?
What song gets you in the right mood for work?
Do you prefer meetings in-person or virtual?
2. Quick and Random Questions to ask to Get to Know Your Team
These are the best questions to ask to get people talking, laughing, or just sharing fun facts. They can be introduced in game sessions, or when you want a combination of interesting questions to get to know someone better.
How to Ask: Throw out these simple questions to keep the conversation light and fun.
When to Use: Use to quickly energize the group or fill time gaps in meetings.
Why These Questions Work: Quick, random questions help break monotony, inject fun and interesting moments into meetings, and support spontaneous interactions for new friends and established teams alike.
Cultural Considerations: Keep questions universally fun and appropriate to ask in a corporate setting.
Common Challenges and Solutions: Random questions sometimes feel silly; reassure the team that sharing fun facts is a great way to get to know each other and encourage playful participation.
11. What’s your favorite ice cream flavor? 12. What’s one thing you absolutely dislike as a food? 13. What’s a talent or skill (big or small) that’s totally useless but fun? 14. What’s your “guilty pleasure” song or movie? 15. What’s a fun fact most people don’t know about you? 16. If you could instantly master any skill, what would it be? 17. What’s the last show you binge-watched?
3. Personal Interests & Hobbies to Get to Know Someone
These are the best questions to get to know someone outside of their job title. They are a way to get people share their perspective on various subjects, give insights on personal interests, reveal hobbies, and find common ground.
How to Ask: Ask during a team lunch, corporate retreat, or casual chat.
When to Use: Use when conversation needs a personal touch or when you aim to build trust between team members.
Why These Questions Work: There are great questions because exploring hobbies and interests builds bridges across teams, sparking informal conversations and revealing shared backgrounds for ongoing rapport.
Cultural Considerations: Encourage sharing, but respect those who prefer not to discuss private life. Moreover, even though these are interesting questions, remember some participants are introverts and struggle being on the spotlight.
Common Challenges and Solutions: Not everyone feels comfortable divulging personal details; providing a variety of questions (serious, light, recent, childhood) helps team members find topics they can answer confidently.
Great Questions to Get to Know Your Colleagues Interests:
18. What’s a hobby you wish you had more time for? 19. What’s your favorite way to unwind after a busy week? 20. What’s one fun or interesting hobby you’ve picked up recently? 21. Do you have a personal passion project outside of work? 22. What book, movie, or TV series would you recommend to everyone here? 23. Are you currently learning any new skills for fun? 24. What’s your favorite outdoor activity? 25. What’s your favorite way to get moving or stay active? 26. What type of art, music, or performance do you love most? 27. What’s the most interesting travel destination on your bucket list?
4. Interesting Questions about Work History & Career Insights for Deeper Conversations
These work-centric questions are a great way to get to know an employee by exploring their career journey, perspective, and professional aspirations. Asking questions to understand their experiences helps build empathy and trust while supporting meaningful professional conversations.
How to Ask: Use these questions during 1:1 meetings, onboarding, or “get to know your coworker” features where open-ended questions encourage storytelling.
When to Use: Best suited for mentorship meetups, onboarding sessions, or career development conversations to start deeper career-related discussions.
Why These Questions Work: Questions for getting to know career histories provide insight into professional growth and aspirations, promoting empathy and respectful understanding within teams, which builds stronger workplace relationships.
Cultural Considerations: In some cultures, discussing past job changes or salary can be taboo or sensitive. Adapt questions to focus on skills learned or future aspirations rather than specifics that might intimidate or embarrass.
Common Challenges and Solutions: Some employees may feel intimidated by sharing sensitive job transitions or hierarchy-related topics. Gently remind team members that they can share only what they’re comfortable with. You can start conversations by sharing your career path to set a welcoming tone.
Work History and Career Insight Questions:
28. What inspired you to choose your current career? 29. What was your very first job, and what did you learn from it? 30. What’s the greatest lesson you’ve learned during your career so far? 31. If you could give one career tip to your younger self, what would it be? 32. What’s one project you’re especially proud of? 33. What’s the best advice a coworker ever gave you? 34. What’s your favorite part about our company culture? 35. What’s one skill you’d like to develop in the next year? 36. Would you rather work on many small tasks or one big project? 37. What motivates you to do your best work?
5. Fun and Light-Hearted Questions
Fun and light-hearted questions are a great way to bring positive energy into team meetings or social settings. These questions can help ease social anxiety and create bonds by promoting friendship through humor and relaxed conversation starters.
How to Ask: Use these as simple conversation starters or in a question game to get everyone involved and smiling.
When to Use: Ideal whenever you want to keep the conversation going, lift the mood, or warm up a new or nervous group.
Why These Questions Work: These questions foster social bonding by encouraging laughter and informal interactions, which improve group dynamics and help team members feel more comfortable around each other.
Cultural Considerations: Avoid jokes or references that might be misunderstood or offensive; keep topics universally fun and appropriate to the workplace to maintain inclusiveness.
Common Challenges and Solutions: Humor and what’s considered “funny” can vary widely across cultures and individuals. Our TeamOut advice is to provide a combination of silly and straightforward questions and allow people to opt into answering those they enjoy.
List of Fun Questions to Get to Know Someone:
38. If you could have any superpower at work, what would it be? 39. If you were a character from a movie or show, who would you be? 40. Would you rather always have to sing instead of speak or dance everywhere you go? 41. What’s the funniest thing that’s happened to you on a workday? 42. What’s your go-to comfort food? 43. What's an unusual fact about you that people may not expect? 44. What’s the weirdest job you’ve ever had? 45. If you were an animal, which one best matches your working style? 46. What emoji do you use the most at work? 47. If you had to eat the same lunch every day for a month, what would it be?
6. "Would You Rather" Questions
“Would you rather” questions are an engaging way to share preferences and ignite lively discussions. These questions are an excellent approach to get started and keep conversations moving smoothly in any group setting.
How to Ask: Present these "would you rather" questions during group meetings or breakout sessions to encourage everyone’s participation quickly and easily.
When to Use: Perfect for kickoff activities in team-building sessions or icebreaker games that get people talking without intimidation.
Why These Questions Work: "Would you rather" questions reveal personality traits in a fun and non-threatening way, boosting engagement and making social interactions more dynamic.
Cultural Considerations: Customize the scenarios to avoid inappropriate options. Certain humor or choices may be unfamiliar or uncomfortable in different regions, so tailor accordingly.
Common Challenges and Solutions: Some people may overthink answers or feel pressured to choose “right” responses. Don't forget to emphasize that there are no wrong answers and keep the pace with rapid-fire questioning to maintain energy.
"Woud You Rather" Questions:
48. Would you rather work four 10-hour days or five 8-hour days? 49. Would you rather have a coffee break with your CEO or your favorite celebrity? 50. Would you rather never check your email again or never attend meetings again? 51. Would you rather always take notes by hand or always type on your phone? 52. Would you rather brainstorm in silence or with background music? 53. Would you rather always be a team lead or always be a team member? 54. Would you rather work in an office with a view of the city or the mountains? 55. Would you rather dress up for work every day or wear pajamas? 56. Would you rather commute 15 minutes or have free lunch every day? 57. Would you rather present to a big audience or write a long report?
7. Deep Questions & Meaningful Conversation Starters
These deep questions allow you to get to know personal values, aspirations, and promote vulnerability between team members. These questions help build deeper conversations and lie a foundation for emotional intelligence and empathy at work.
How to Ask: Introduce deeper questions gradually, perhaps starting by sharing your own insights to encourage others to open up without feeling intimidated.
When to Use: Appropriate for team retreats, trust-building workshops, or after rapport has been established to encourage meaningful and intimate conversations.
Why These Questions Work: Asking deep questions helps colleagues reveal personal stories at a deeper level, which builds trust, empathy, and stronger workplace friendships.
Cultural Considerations: Be mindful that in some cultures, vulnerability and intimate sharing may not be common or welcome in workplace settings. Tailor your approach to fit the group’s cultural comfort zones and norms around openness.
Common Challenges and Solutions: These questions can intimidate some team members who aren’t used to sharing personal details. Provide a respectful “pass” and remind the team that sharing is voluntary to maintain comfort and openness.
Deep Questions that are Appropriate to Ask:
58. What’s a value you try to live by at work and in life? 59. What accomplishment are you most proud of (at work or outside)? 60. What’s something you’ve changed your mind about recently? 61. Who in your life inspires you to be your best self? 62. What’s one thing you’d like to be remembered for? 63. What’s a risk you’re glad you took? 64. How do you handle setbacks or failure? 65. What do you want to pursue in the next five years? 66. What does “success” mean to you? 67. How do you stay motivated through challenges?
8. Reflective and Perspective Questions
Reflective questions are a thoughtful way to draw out perspectives and personal experiences, which promotes critical thinking and self-awareness. These questions serve as conversation starters that deepen team insight and encourage mutual understanding.
How to Ask: Use these questions during team reflections, annual reviews, or project wrap-ups as a way to start an important conversation and explore diverse viewpoints.
When to Use: Best used in settings oriented towards growth, learning, and feedback, where team members feel safe to share their insights.
Why These Questions Work: Reflective questions support self-awareness and empathy by discovering lessons learned and common aspirations that benefit the whole group’s collaboration and dynamics.
Cultural Considerations: Not all workplace cultures encourage public introspection; keep participation optional and respect different communication styles, especially in environments where direct sharing might feel too personal.
Common Challenges and Solutions: Reflection may be uncomfortable or unfamiliar for some people; balance these deeper questions with simple ones, allow silence for thought, and never force anyone to answer more deeply than they want.
68. What’s the best piece of advice you’ve ever received? 69. How do you define a “good day” at work? 70. What’s a mistake you learned from (and how did it help you grow)? 71. What’s one thing you wish more people understood about you? 72. What’s a skill you admire in others but don’t have yourself? 73. When do you feel most productive or “in the zone”? 74. What’s one thing about our workplace culture you’d keep forever? 75. What kind of legacy do you want to leave in your professional life? 76. What does teamwork mean to you? 77. How do you approach balancing work and life?
Why Certain Questions Build Connections?
Certain questions build connection more effectively because they invite openness, vulnerability, and shared experience at a deeper level. Asking the right questions goes beyond small talk and encourages exchanges that reveal personal values, preferences, and stories.
These connections deepen your relationships by fostering empathy, trust, and rapport, especially when they are used to understand intimate insights. Questions that invite storytelling or reflection serve as great conversation starters because they create space for people to reveal personal perspectives in a way that feels safe and engaging. Whether you ask simple questions or more profound ones, the key is to choose questions on this list that suit your group’s comfort and purpose, helping you keep the conversation flowing naturally.
Questions for Introverts vs. Extroverts
Getting to know someone well often means recognizing different comfort zones in social interaction.
Introverts generally prefer personal questions that allow time for thought and answers without pressure, making deep questions or open-ended questions to ask easier for them to engage with at their own pace. For introverts, questions that allow reflection or sharing a hobby can invite deeper conversation without immediate spotlight,
Extroverts may thrive on fun and funny questions or questions game settings where they can share in energetic ways. They often enjoy questions that spark group dynamics or humorous debate, like "would you rather" questions.
Either way, start by asking questions that match your team members' style. You'll avoid intimidating or overwhelming participants. Tailoring your approach helps make everyone feel included and creates new friends through meaningful interaction.
Inclusive Question Options
To ensure conversations include different personalities and backgrounds, here are three inclusive questions that work well in corporate or mixed settings:
“What’s a hobby or pastime that helps you recharge outside of work?”. This question is personal but neutral, allowing people to share at their comfort level.
“If you could travel anywhere to experience a new culture, where would you go and why?” This is an interesting question that invites sharing of personal perspective without pressure.
“What’s one thing you appreciate about the team or workplace culture here?” This question encourages positive conversation that focuses on a common experience and inclusion rather than personal disclosure.
These inclusive questions help you get to know employees with sensitivity, inviting participation from both introverts and extroverts, and contribute to building friendship and trust while keeping conversation light, fun, and interesting.
Wrapping Up
TeamOut's comprehensive collection of 70+ get-to-know-you questions provides a variety of options tailored to different team dynamics and situations. Whether you’re looking for icebreakers or delve into deep questions to get meaningful insights, knowing how and when to ask someone will help foster connection, improve communication, and build stronger relationships.
At TeamOut, we leverage our proven expertise from organizing over 1,000 corporate retreats and events, maintaining a 95% satisfaction rate to ensure exceptional experiences. Through partnerships with more than 4,000 venues worldwide, we save you up to 30 hours of research, streamlining the planning of your next team-building event or retreat.
Schedule a free call today to explore how TeamOut can support you in creating a seamless, impactful retreat or event that your team will remember. This is your chance to deepen relationships and spark conversations that drive collaboration and boost morale!
Frequently Asked Questions
1. How do I select questions that respect different backgrounds?
Choose questions that are inclusive and neutral, avoiding topics related to politics, religion, or personal finances, and focus on hobbies, interests, and professional objectives to ensure everyone feels comfortable and included.
2. How can I encourage shy or reluctant team members to join in?
Use simple, light-hearted questions to start, allow optional participation, and create a safe environment where team members feel no pressure to answer if uncomfortable, gradually easing into deeper questions as trust builds.
3. How do I handle nervous questioners?
Encourage preparing simple, light-hearted questions ahead of time and practicing active listening. Remind nervous participants that it’s normal to feel anxious and that questions are meant to foster positive connection, not judgment.
4. How do I respond to questions effectively?
Show genuine interest by maintaining eye contact, giving verbal affirmations, and asking follow-up questions that invite deeper conversation to keep the dialogue natural and engaging.
5. How can I make sure I respect everyone's boundaries?
Avoid personal or intimate questions that might intimidate, especially early on. Always observe body language and verbal cues, and respect if someone prefers not to answer or wants to skip a question.
Thomas Mazimann, a French entrepreneur and former international kayaking athlete, transitioned from sports to tech after moving to the U.S. He co-founded TeamOut, revolutionizing team gatherings.
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