Most corporate team building falls flat. Trust falls, escape rooms, forced icebreakers—they leave people drained, exposed, or just uncomfortable. The better approach is simpler: team building this or that questions create moments of genuine discovery without the pressure. A binary choice between two options cuts through small talk and gets straight to what matters: how people actually think, what they value, and how they work.
This format works because it removes the fear of failure. There's no right answer. Unlike "Tell us your biggest achievement," a preference question is personal without being vulnerable. The real insight comes in the follow-up: asking "Why?" reveals more about priorities and decision-making than any survey.
Here are 15 questions organized by depth—surface warmup, operational insight, and deep dive—designed to build genuine connection on your team.
The Core Mechanism: Why Binary Choice Excels at Connection
Team connection requires psychological safety. When activities are competitive, complex, or emotionally demanding, people shut down. Binary choice works because the format is simple and there's no risk of getting it wrong.
The magic is in the follow-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 spectrum.
1. Urban Energy or Mountain Retreat?
This reveals how someone recharges. High-energy environments or quiet solitude. The choice shows whether they need external stimulation to feel productive or whether they need silence and space. Why they chose one tells you a lot about how they'll approach a hectic sprint versus deep work.
2. Fiction Novel or Non-Fiction Documentary?
Fiction readers value narrative and possibility. Non-fiction readers want data and practical application. This matters for how you present information—whether a case study or a strategic story will actually land.
3. Planning Ahead or Spontaneous Action?
Some people thrive with comprehensive plans and defined timelines. Others excel when moving fast and improvising. Understanding this preference shapes how you delegate and allocate resources.
4. Immediate Reply or Thoughtful Delay?
Do they prefer quick communication, even if incomplete? Or slower, polished responses? This matters for remote teams figuring out email and Slack norms.
5. Comfort Food or Gourmet Cuisine?
Comfort food = reliability and proven satisfaction. Gourmet = risk and experimentation. At work, this predicts whether someone prefers established processes or wants to try new tools.
6. Full Autonomy or Clear Direction?
Some people need maximum control over their work. Others feel lost without explicit scope and benchmarks. Knowing this prevents friction between managers and their team.
7. Written Documentation or Verbal Brainstorming?
Do they consolidate ideas best on paper or in real-time conversation? This determines whether your standup should be async Slack updates or live discussion.
8. Solving Technical Flaws or Streamlining People Processes?
Some lean toward systems and logic. Others toward collaboration and culture. This helps you assign roles that actually fit.
9. Data-Driven Pivot or Intuitive Leap?
Do they anchor decisions in statistics? Or in accumulated experience and gut feel? This shows where the disagreement really comes from when you're stuck on a decision.
10. Iterative Small Wins or Large, Single Milestones?
Some people need frequent progress updates to stay motivated. Others can work toward one big release without visible movement. This shapes how you structure project updates.
11. Absolute Security or Unlimited Freedom?
Security means stability and predictability. Freedom means flexibility and self-determination. The conversation here reveals what someone actually wants from their career.
12. Eliminate Minor Annoyances or Solve One Major Global Problem?
Quick visible wins or decades-long systemic work. This shows whether someone thinks in quarters or in decades.
13. Perfect Memory of the Past or Clear Knowledge of the Future?
Do they believe all answers are in history? Or are they focused on strategy and what's ahead? This shapes how they approach uncertainty.
14. Be Known for Kindness or Be Known for Intelligence?
Relational success or intellectual success. This identifies who prioritizes team morale and who prioritizes results.
15. The Ability to Fly or Instantaneous Teleportation?
Journey versus destination. Flying is about experience and process. Teleportation is about efficiency and cutting friction. A good way to wrap up the conversation.
Operationalizing Your "This or That" Session
Running this well requires sensitivity to where your team actually is.
Common Facilitation Missteps
- Rushing the "Why": Don't treat this like a quiz. The choice takes five seconds. The discussion takes five minutes. Always ask why.
- Forcing Participation: Silent observation is fine. The moment someone feels required to share, the safety is gone.
- Mismatching depth to trust: Don't ask deep questions on a brand-new team. You'll get cautious, dishonest answers.
Scenario: Applying the Connection Depth Model
A product team of nine people, three recent hires, does a half-day offsite. Goal: improve cross-functional empathy and decision clarity.
- Warm-Up (15 minutes): Start with questions 1 and 5 (Urban Energy, Comfort Food). Gets laughs and establishes safety.
- Operational Insight (30 minutes): Move to questions 6 and 9 (Autonomy, Data-Driven). You discover why engineers and designers keep clashing—they have different certainty thresholds. Now you can talk about it.
- Deep Dive (30 minutes): End with question 14 (Kindness or Intelligence). The conversation reveals they all value kindness but subconsciously judge colleagues who don't demonstrate high intelligence in meetings. This opens a necessary discussion about how to challenge ideas without damaging relationships.
By progressing naturally from casual to substantive, you get actual operational insight. To explore more workplace insights and activity options, you can read more articles on the Naboo blog.
Measuring the Outcome: Beyond Just Participation
Since the goal is qualitative, look for behavioral 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 tailored solutions for modern workplaces.
Frequently Asked Questions
What is the ideal group size for a This or That session?
Divide into groups of 4 to 6. Everyone gets time to share and explain without chaos.
How should we handle controversial or awkward answers?
Steer toward the underlying preference rather than the surface answer. The goal is understanding, not alignment.
Can these questions be used during mandatory meetings?
Yes. Use 1 or 2 surface questions as a five-minute opener to shift people from individual contributor mode to collaborative mode.
How often should we use a new this or that list?
Add 1 to 2 questions to weekly meetings. Run a full structured session quarterly or during offsites when deeper relational work is the explicit goal.
Is it better to use "This or That" or "Would You Rather" questions?
"This or That" is simpler and faster, focused on preference. "Would You Rather" introduces complex trade-offs and generates deeper discussion but takes more time to process.