Most corporate team building falls flat. Trust falls, escape rooms, and forced icebreakers leave people drained, exposed, or simply uncomfortable. A better approach is simpler: this or that questions create real moments of discovery without the pressure. A binary choice cuts through small talk and gets to what matters, how people think, what they value, and how they work.
This format works because it removes the fear of being wrong. There is no right answer. Unlike "Tell us your biggest achievement," a preference question is personal without asking for too much. The real insight comes in the follow-up. Ask "Why?" and you learn more about priorities and decision-making than any survey can show.
Here are 15 questions organized by depth, from surface warmup to operational insight to deep dive, designed to build real connection on your team.
The core mechanism: why binary choice works for connection
Team connection depends on psychological safety. When activities feel competitive, complex, or emotionally demanding, people shut down. Binary choice works because the format is simple and there is no risk of getting it wrong.
The follow-up is where the value shows up. A preference reveals personality and priorities faster than any complicated framework.
The connection depth model for "this or that"
Match your questions to your team's current trust level:
- Surface Warm-Up: Lifestyle, media, basic personality. Best for new teams or meeting kickoffs.
- Operational Insight: Work environment, communication style, decision-making approach. Essential for better collaboration.
- Deep Dive: Values, ethics, long-term goals. Best for established teams or offsites.
The 15 questions below cover the full range.
1. urban energy or mountain retreat?
This shows how someone recharges. Some people need high-energy environments, while others need quiet solitude. The choice tells you whether they rely on outside stimulation to feel productive or whether they need silence and space. Their answer, and especially the reason behind it, says a lot about how they will handle a hectic sprint versus deep work.
2. fiction novel or non-fiction documentary?
Fiction readers tend to value narrative and possibility. Non-fiction readers usually want data and practical use. That difference matters when you present information, because it tells you whether a case study or a strategic story is more likely to land.
3. planning ahead or spontaneous action?
Some people do their best work with clear plans and defined timelines. Others work faster when they can improvise. Knowing which one fits a person helps you assign work and use resources well.
4. immediate reply or thoughtful delay?
Do they prefer a quick response, even if it is incomplete? Or do they want time to think and send something polished? For remote teams, that answer helps set email and Slack norms.
5. comfort food or gourmet cuisine?
Comfort food points to reliability and familiar satisfaction. Gourmet points to risk and experimentation. In the workplace, that often predicts whether someone prefers established processes or wants to try new tools.
6. full autonomy or clear direction?
Some people do their best work with full control. Others need clear scope and benchmarks to stay on track. If you know which one you are dealing with, manager-team friction drops fast.
7. written documentation or verbal brainstorming?
Some teams sort ideas best on paper, while others need a live conversation to get anywhere. That choice decides whether your standup is async Slack updates or a real-time discussion.
8. solving technical flaws or streamlining people processes?
People who lean toward systems and logic usually fit technical problem-solving. Those who lean toward collaboration and culture are a better fit for people processes. Put the role where the work matches the person.
9. data-driven pivot or intuitive leap?
Some people want statistics before they move. Others trust accumulated experience and gut feel. When a decision stalls, this is usually where the disagreement starts.
10. iterative small wins or large, single milestones?
Frequent progress updates keep some people motivated. Others are fine working toward one big release with nothing visible in between. That difference shapes how you handle project updates.
11. absolute security or unlimited freedom?
Security stands for stability and predictability. Freedom stands for flexibility and self-determination. The answer tells you what someone wants from their career.
12. eliminate minor annoyances or solve one major global problem?
Some people want quick visible wins. Others are drawn to work that takes years. It usually comes down to whether they think in quarters or in decades.
13. perfect memory of the past or clear knowledge of the future?
Some people look to history for answers. Others focus on strategy and what comes next. That difference shapes how they handle uncertainty.
14. be known for kindness or be known for intelligence?
Some people value strong relationships and team morale. Others put results first and want to be known for sharp thinking. This tells you what they prize more.
15. the ability to fly or instantaneous teleportation?
Flying is about the journey and the process. Teleportation is about getting there fast and removing friction. It is a clean way to close the conversation.
Running your this or that session
Run this with a clear read on where your team stands.
Common facilitation mistakes
- Rushing the "Why": Treating this like a quiz misses the point. The choice takes five seconds, the discussion takes five minutes, and the why matters every time.
- Forcing participation: Silent observation is fine. Once people feel required to speak, the room gets less honest.
- Mismatching depth to trust: New teams need lighter questions first. Go too deep too soon, and the answers get guarded.
Scenario: Applying the connection depth model
A product team of nine people, including three recent hires, holds a half-day offsite. The goal is better cross-functional empathy and clearer decisions.
- Warm-Up (15 minutes): Questions 1 and 5, Urban Energy and Comfort Food, set an easy tone and get people talking.
- Operational Insight (30 minutes): Questions 6 and 9, Autonomy and Data-Driven, surface why engineers and designers keep clashing: they use different certainty thresholds. That gives the team something concrete to discuss.
- Deep Dive (30 minutes): Question 14, Kindness or Intelligence, closes the session. The group agrees kindness matters, but they also quietly judge colleagues who do not show strong intelligence in meetings. That leads to a needed conversation about how to challenge ideas without damaging relationships.
Move from casual to substantive and you get real operational insight. To explore more workplace insights and activity options, read more articles on the Naboo blog.
Measuring the outcome: beyond just participation
Since the goal is qualitative, look for behavior changes:
- Follow-up dialogue: Do team members reference the session later? ("Remember when Sarah said she prefers spontaneous action? We should loop her in.")
- Reduced communication friction: Fewer emails that miss context. Better Slack conversations. People know how to reach each other now.
- Faster conflict resolution: Disagreements move past blame faster. The personal context from these questions builds empathy, so people separate the idea from the person.
These conversations build the trust needed for complex collaboration. If you are looking for more event ideas for teams that focus on structured connection, Naboo provides practical solutions for modern workplaces.
Frequently asked questions
What is the ideal group size for a This or That session?
Keep groups to 4 to 6 people. That gives everyone room to speak and explain without the conversation turning chaotic.
How should we handle controversial or awkward answers?
Focus on the preference behind the answer, not the answer itself. The point is to understand what people mean, not to force agreement.
Can these questions be used during mandatory meetings?
Yes. Start with 1 or 2 light questions and use five minutes to move people out of individual contributor mode and into a group setting.
How often should we use a new this or that list?
Use 1 to 2 questions in weekly meetings. Save a full structured session for quarterly meetings or offsites when deeper relationship work is the stated goal.
Is it better to use "This or That" or "Would You Rather" questions?
"This or That" is faster and simpler because it stays focused on preference. "Would You Rather" adds trade-offs and usually leads to deeper discussion, but it takes more time to think through.