Looking for a fun way to get the conversation started and break the ice with your team? Check out our list of the best 200+ “This or That” questions, a simple and easy tool that helps your employees get to know each other better. They're an excellent choice if you’re meeting new colleagues or want long-time team members to learn something new while keeping your group engaged.
The game is self-explanatory: each “This or That” question gives a binary choice, two options to choose from, like “Would you rather live by the sea or in the mountains?”, prompting a super fun and low-pressure way to know someone’s preferences and sense of self. These thought-provoking and sometimes silly questions help corporate teams relax and can be used as a fun party game, icebreaker, or even for one-on-one chats.
These questions help your team open up and connect, so you better make a game out of it and get everyone talking. At TeamOut, with a track record of organizing over 1,000 corporate events and retreats, we know first-hand how to implement fun team-building experiences that your crew will cherish over time.
Discover 200 questions that will keep you away from clichés like "coffee or tea?" and let the stories emerge naturally from your employees' preferences.
Want to generate your own questions ? Try our free generator 👇
The Problem with Complex Team-Building Activities
Most retreat planners default to elaborate activities:
- Trust exercises that make introverts uncomfortable
- Physical challenges that exclude team members with different abilities
- Competitive games that create winners and losers
- Sharing circles that demand vulnerability from strangers
These activities often backfire because they require comfort levels that don't exist yet. People participate politely but don't genuinely connect.
The Power of Simple Choice Questions
This or that questions work because they're low-stakes. There's no wrong answer to "reading minds or predicting the future?", but the follow-up conversation reveals personality, habits, and stories.
Simple binary choices accomplish three things:
- Remove pressure, as no one can fail at stating a preference
- Spark natural follow-ups. For example, "Why reading minds?" leads to fun stories
- Level the playing field, creating a place where introverts and extroverts participate equally
The magic happens in the "why" behind each choice, not the choice itself.
200+ Best This or That Questions
Icebreaker Questions for New Teams
These questions are supreme choices for first-day introductions when people are still learning names:
Basic Preferences
- Morning person or night owl?
- Beach vacation or mountain retreat?
- Text message or phone call?
- Spotify or Apple Music?
- Summer or winter?
- Summer company retreat or winter company offsite?
- Dogs or cats?
- Books or movies?
- City or countryside?
- Pizza or burgers?
Work Style Basics
- Email or Slack?
- Open office or private workspace?
- Meetings or deep work time?
- Collaboration or independent work?
- Deadline pressure or steady pace?
- Morning meetings or afternoon meetings?
- Video calls or audio only?
- Taking notes by hand or typing?
- Standing desk or sitting?
- Background music or silence while working?
Would You Rather Questions to Ask for Deeper Connections
Use these after initial introductions, typically on day two:
Career and Growth
- Would you rather be the smartest person in the room or the most creative?
- Lead a small team or be part of a large one?
- Work four 10-hour days or five 8-hour days?
- Have unlimited vacation or unlimited professional development budget?
- Be known for innovation or reliability?
- Work from anywhere or have the perfect office setup?
- Master one skill completely or be good at many skills?
- Start your own company or be employee #1 at a startup?
- Give presentations or write detailed reports?
- Solve technical problems or solve people problems?
Life Philosophy
- Would you rather read minds or predict the future?
- Have the ability to fly or be invisible?
- Live in the past or live in the future?
- Be famous or wealthy?
- Have more time or more money?
- Know how you'll die or know when you'll die?
- Be able to speak every language or play every instrument?
- Never age or never get sick?
- Control fire or control water?
- Time travel or teleportation?
- Live forever or have the ability to resurrect one person?
- Always tell the truth or always lie?
- Always know when someone is lying or always get away with lying?
- Cure all diseases or solve world hunger?
- Be famous for something embarrassing or remain anonymous?
- Give up social media or TV for a year?
- Only be able to whisper or only be able to shout?
- Be able to talk to animals or understand all plants?
- Experience one amazing year or ten average years?
- Face a fear head-on or avoid it forever?
- Live in a world without music or without books?
- Control your dreams or watch them like movies?
- Have the power to heal others or to teleport?
- Have super strength or super speed?
- Lose all your memories or never be able to make new ones?
Professional Get-to-Know Questions
These questions are ideal for working lunches or coffee breaks:
Career Journey
- First job or current job?
- Startup environment or established company?
- Remote work or office environment?
- Meetings or email communication?
- Team leader or team player?
- Early deadlines or last-minute hustle?
- Focus on details or big picture?
- Solo work or collaboration?
- Goal-oriented or process-oriented?
- Frequent breaks or power through?
- Set schedule or flexible hours?
- Morning person at work or night owl at work?
- Data-driven decisions or intuition?
- Structured tasks or creative freedom?
- Work from home or coworking space?
- Networking events or small group meetings?
- Formal dress code or casual dress?
- Public speaking or written reports?
- Fast-paced work or steady pace?
- Prefer mentorship or self-learning?
- Innovation or tradition?
- Long-term planning or short-term goals?
- Individual contributor or management track?
- Technical skills or soft skills focus?
- Fast-paced projects or long-term planning?
- Client-facing work or internal projects?
- Creative work or analytical work?
- Teaching others or learning from others?
- Building new things or improving existing things?
Problem-Solving Style
- Research thoroughly or trust your gut?
- Ask for help immediately or try to figure it out first?
- Perfectionist approach or "good enough" and iterate?
- Big picture thinking or attention to detail?
- Innovation or optimization?
- Work alone first or brainstorm with others?
- Written communication or verbal discussion?
- Structured approach or flexible method?
- Data-driven decisions or intuition-based choices?
- Risk-taking or playing it safe?
Creative Board Game Alternative Questions
When you need structured fun without actual games:
Rapid-Fire Preferences
- Marvel or DC?
- Star Wars or Star Trek?
- Harry Potter or Lord of the Rings?
- Netflix or YouTube?
- Podcasts or audiobooks?
- Comedy or drama?
- Action movies or romantic comedies?
- Live music or recorded music?
- Concerts or theater?
- Museums or amusement parks?
Fun Hypotheticals
- Would you rather fight one horse-sized duck or 100 duck-sized horses?
- Always be 10 minutes late or 20 minutes early?
- Speak every language fluently or play every instrument perfectly?
- Never use social media again or never watch TV again?
- Have dinner with any historical figure or any living celebrity?
- Win the lottery or live twice as long?
- Be able to fly or be invisible?
- Know the answer to every question or be able to speak every language?
- Control the weather or never have to sleep?
- Be the funniest person alive or the smartest person alive?
- Build a castle or a spaceship?
- Explore a dungeon or conquer a kingdom?
- Trade with other players or battle opponents?
- Gather resources or complete quests?
- Play as a hero or a villain?
- Use magic or technology?
- Move stealthily or charge boldly?
- Craft weapons or build defenses?
- Role-play or solve puzzles?
- Collect cards or roll dice?
- Play cooperatively or competitively?
- Choose power or strategy?
- Upgrade skills or gain new abilities?
- Play for points or for survival?
- Control the board or control the cards?
- Take risks or play it safe?
- Focus on offense or defense?
- Trade secrets or share alliances?
- Recruit allies or sabotage opponents?
- Win by luck or by skill?
Video Game Style Quick-Fire Questions
These "this or that" questions are especially effective for energizing afternoon sessions:
Gaming Preferences
- Mario or Sonic?
- PC gaming or console gaming?
- Single-player or multiplayer?
- Strategy games or action games?
- Retro graphics or modern graphics?
- Competitive play or cooperative play?
- Fantasy settings or sci-fi settings?
- Puzzle games or racing games?
- Mobile gaming or a dedicated console?
- Voice chat or text chat?
- FPS or RPG?
- Open world or linear story?
- Single-player or co-op?
- Stealth or action?
- Role-playing or strategy?
- Fantasy or sci-fi?
- Indie or AAA?
- First-person or third-person?
- Casual or hardcore?
- PvP or PvE?
- Mobile or desktop?
- Graphic-heavy or minimalist?
- Achievements or story?
- Loot or crafting?
- Fast-paced or tactical?
- Character customization or fixed characters?
- Save often or save manually?
- Leaderboard or personal best?
- Mute or voice chat?
Quick Choices
- Cake or pie?
- Chocolate or vanilla?
- Sweet or salty snacks?
- Hot weather or cold weather?
- Ocean or mountains?
- Sunrise or sunset?
- Rain or snow?
- Camping or hotels?
- Road trip or flying?
- Cooking or ordering takeout?
Miscellaneous Questions Game
- Attend a poetry slam or a stand-up comedy night?
- Take a spontaneous road trip or plan every detail?
- Wear mismatched socks for a week or eat the same lunch every day for a week?
- Solve a crossword puzzle or complete a jigsaw puzzle?
- Grow your own vegetables or shop at a farmers’ market?
- Watch a sunrise from the mountains or a sunset over the ocean?
- Host a dinner party at home or book a table at a trendy new restaurant?
- Trade places with a character from a classic novel or a blockbuster film?
- Spend a day with no technology or a day with nonstop notifications?
- Shop for vintage treasures or the latest fashion trends?
- Binge-watch a documentary series or a reality competition?
- Swim with dolphins or hike with llamas?
- Try a new sport or learn a new instrument?
- Paint a giant mural or write a short story?
- Escape to a secluded cabin or explore a bustling city?
- Judge a baking contest or compete in one?
- Remember every dream or never dream at all?
- Speak in rhymes for a day or sing every sentence for a day?
- Experience life 100 years in the past or 100 years in the future?
- Design your dream home or invent your dream gadget?
- Play an outdoor laser tag match or an indoor virtual reality game?
- Learn a traditional dance or a modern street dance style?
- Own a pet bird or a pet reptile?
- Host a podcast or record a music album?
- Be known for your cooking skills or your storytelling abilities?
- Have a famous face but an anonymous name, or a famous name but an ordinary face?
Plan Your Next Team Building Event with TeamOut
When it comes to sparking great conversation and building stronger teams, “this or that” questions are a fun and interesting way to get people talking, laughing, and learning about each other. If you’re currently looking for conversation starters, questions to help your group open up, or a simple question to break the ice, these 200 fun questions are an excellent approach to pass the time and get to know someone at any gathering, meeting, or fun game night.
If you want to take your team building to the next level, TeamOut can help. With over 1,000 corporate retreats and events organized and a satisfaction rate of 95%, TeamOut partners with more than 4,000 venues worldwide, saving you up to 30 hours of research. Our team specializes in planning everything from logistics and meals to activities like “would you rather” and game sessions that help everyone connect, whether you’re trying to help new members know someone or re-engage seasoned colleagues.
TeamOut’s services include:
- Venue sourcing in settings designed for meetings, seminars, team-building experiences, and great conversation that get people talking
- Tailored activity planning, including fun game questions, icebreakers for groups of any size, and outdoor activities
- Comprehensive logistics coordination for a smooth retreat experience
- Professional facilitation to make sure the whole team is engaged and that the event's goals are reached
TeamOut’s specialists will help you design a variety of activities tailored to your team and goals.
Ready to boost team connection? Start planning your retreat with TeamOut today and discover how team-building experiences can build real connections.
FAQ
How many questions should we use per session?
Icebreaker sessions: 8-12 questions over 30 minutes
Deeper discussions: 5-7 questions over 45 minutes
Quick energizers: 15-20 rapid-fire questions over 15 minutes
Focus on quality conversations rather than covering many questions quickly. It's better to have rich discussions around fewer questions than to rush through a long list.
What if someone doesn't want to participate?
Make participation completely optional. Promote alternative roles like timekeeper, question selector, or conversation observer. Most reluctant participants might join in once they see others enjoying the conversations. Never force participation because it defeats the purpose of creating comfortable connections.
Can these work for remote teams?
Absolutely. Use breakout rooms for small group discussions and return to the main room to share highlights. Consider these virtual adaptations:
- Use virtual backgrounds that show preferences (beach vs. mountains)
- Create polls for rapid-fire questions
- Use chat for shy participants to share answers
- Record favorite questions for future team meetings
How do we avoid awkward silences?
Prepare follow-up prompts: "Tell us more about that," "When did you discover that you prefer this to that?" or "Has that always been true for you?" Train facilitators to jump in with these when conversations stall. Also have backup questions ready and don't be afraid to move on if a particular question doesn't resonate with the group.
What's the ideal group size for different formats?
4-6 people for intimate discussions and deeper sharing
8-12 people for energetic exchanges and varied perspectives
20+ people should break into smaller circles with facilitators rotating between groups
Large groups (50+) work best with rapid-fire formats and physical movement
Should we prepare questions in advance or improvise?
Always prepare questions in advance. Have a structured list organized by session type, but remain flexible to adapt based on group energy and interests. Prepare 20% more questions than you think you'll need to account for varying discussion lengths.
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