Standard corporate team building often relies on cringe-inducing activities: forced trust falls, escape rooms in central Manchester, or elaborate challenges designed to push collaboration. While meant well, these activities often fall flat, leaving introverted or newer team members feeling exposed, judged, or simply drained.
The most effective team building isn't about manufactured drama; it's about engineering moments of genuine, low-stakes discovery. This is where the simple elegance of binary choice questions—the classic “This or That” structure—becomes a powerful, low-cost method for team managers. By posing a choice between two non-threatening options, teams bypass superficial pleasantries and dive straight into personal preferences, values, and working styles.
This article provides a refined, curated selection of 15 essential questions, grouped by their intended depth, designed not just to entertain, but to uncover deep insights that translate directly into better collaboration.
The Core Mechanism: Why Binary Choice Excels at Connection
Effective team connection relies on people feeling psychologically safe. When an activity is too complex, competitive, or emotionally demanding, participants shut down. The power of a quality ‘This or That’ list lies in its simplicity. There is no right or wrong answer, removing the fear of failure.
Unlike icebreakers that demand facts (e.g., "What is your biggest professional achievement?"), the binary choice format asks for preference, which is inherently personal yet non-vulnerable. The magic happens in the follow-up: asking "Why?" after a team member chooses an option reveals more about their personality, priorities, and decision-making process than any complex questionnaire ever could.
The Connection Depth Model for "This or That"
To get the most from any list of ‘This or That’ questions, we’ve grouped them into three distinct stages of connection. Team leaders should select questions based on the team's current relationship maturity:
- Surface Warm-Up: Questions focused on basic lifestyle, media, and general personality traits. Ideal for brand new teams or short meeting kickoffs.
- Operational Insight: Questions focused on preferences in work environment, communication, and decision-making. Essential for improving collaboration efficiency.
- Deep Dive: Hypothetical or philosophical questions that reveal core values, ethical frameworks, and long-term goals. Best reserved for established teams or away days.
The following 15 essential questions are designed to cover this entire spectrum, ensuring your next session fosters substantial connection.
1. City Buzz or Country Calm?
This question gauges preferences regarding high-energy environments versus restorative solitude. The choice between the constant buzz of a place like Canary Wharf or Leeds City Centre (stimulation, noise, accessibility) versus the peace of a remote natural setting, perhaps the Scottish Highlands or the Peak District (calm, focus, immersion), often mirrors how an employee recharges and feels productive. Asking why they chose one reveals their need for external input versus internal reflection.
2. Fiction Novel or Non-Fiction Documentary?
This preference taps into learning style and how a person processes information. The fiction enthusiast likely values narrative, creative abstraction, and exploring possibilities. The non-fiction enthusiast tends toward verifiable data, practical application, and mastering reality. This helps management decide whether to present updates using technical case studies or through clear, strategic storytelling.
3. Planning Ahead or Spontaneous Action?
This reveals a fundamental approach to getting things done. Do they thrive in structure, preferring comprehensive project plans and defined timelines? Or do they excel in agile, reactive environments that prioritise speed and improvisation? Understanding this preference is key to effective task delegation and resource allocation within the team.
4. Immediate Reply or Thoughtful Delay?
How quickly we communicate is crucial in today's teams. This query addresses whether an employee prefers quick, high-frequency communication (even if incomplete) or slow, detailed, and polished responses. This is particularly insightful for remote teams navigating email, Slack, and video conferencing norms.
5. Comfort Food or Gourmet Cuisine?
This simple choice reveals their preference for what they know versus what is new. Comfort food represents reliability, security, and proven satisfaction. Gourmet cuisine implies risk, experimentation, and seeking new sensory experiences. Translated to work, this predicts whether they prefer established processes or new technologies.
6. Full Autonomy or Clear Direction?
Shifting into the operational phase, this question is a crucial way to assess the necessary management style. Some employees need maximum control over their domain, viewing micromanagement as counterproductive. Others feel overwhelmed without well-defined scopes and explicit benchmarks. Knowing this prevents friction between team leads and contributors.
7. Written Documentation or Verbal Brainstorming?
This is a core operational indicator. Do they consolidate ideas best by seeing concepts mapped out in writing, relying on clear communication that doesn't need an immediate reply? Or do they flourish in dynamic, real-time verbal exchanges that generate energy and immediate feedback? This choice helps determine the format of weekly stand-ups and project kickoffs.
8. Fixing Technical Glitches or Improving How People Work Together?
This question reveals whether a team member's passion leans toward systems and code (logic, structure, precision) or toward organizational design and interpersonal dynamics (empathy, collaboration, culture). Identifying this inclination helps leaders assign roles that align with innate strengths, especially in cross-functional projects.
9. Data-led Change or a Gut Feeling?
For high-stakes decisions, knowing where a colleague anchors their certainty is vital. Do they trust empirical evidence and statistical confidence above all else? Or do they rely on accumulated experience, market feel, or strong gut instinct? The discussion around this choice reveals how risk is perceived and justified.
10. Frequent Small Wins or One Big Milestone?
This concerns how motivation is sustained throughout a project. Some derive energy from frequent, measurable progress updates, preferring continuous delivery. Others are motivated by working toward one significant, high-impact release, tolerating longer stretches without visible progress. This helps define the rhythm of project updates.
11. Absolute Job Security or Total Career Freedom?
Moving into the deep dive section of this ‘This or That’ list, this touches on foundational values. Absolute security implies prioritising stability, predictability, and safety (career, financial, personal). Total freedom implies prioritising flexibility, exploration, and self-determination. The resulting conversation offers profound insight into career aspirations and personal boundaries.
12. Sort Out Minor Daily Frustrations or Tackle One Massive Global Issue?
This is a question about the scope and scale of impact. Does the person prefer quick, visible wins that improve daily life (e.g., fixing bad software interfaces) or committing to decades-long, potentially unseen work toward massive, systemic change? This provides clues about their long-term vision and patience.
13. Perfect Memory of the Past or Clear Knowledge of the Future?
This hypothetical choice explores how a person approaches uncertainty and regret. Do they prioritise learning from history, believing all necessary answers reside in previous data? Or do they prioritise strategic advantage and forward planning, believing the past is irrelevant compared to optimising the road ahead?
14. Be Known for Your Empathy or Your Technical Brilliance?
This taps directly into personal legacy and identity within a group. It asks whether they value relational success (being supportive, empathetic, and well-liked) or intellectual success (being innovative, technically brilliant, and authoritative). It helps identify team members who prioritise morale versus those who prioritise results.
15. The Ability to Fly or Instantaneous Teleportation?
A classic hypothetical that, when treated seriously, reveals preference for the journey versus the destination. Flying is about the experience, the perspective, and the slow process of movement. Teleportation is purely about efficiency, immediate outcome, and minimising friction. This is an engaging way to conclude a high-value ‘This or That’ session.
Operationalising Your "This or That" Session
Running a successful binary choice session requires more than just reading questions from a complete ‘This or That’ list. Facilitation must be sensitive to the team’s dynamics and the intended depth of connection.
Common Mistakes When Running It
- Rushing the "Why": The most common error is treating the exercise like a rapid-fire quiz. The choice itself takes five seconds; the follow-up discussion should take five minutes. Always enforce the rule that the choice is followed by a brief, voluntary explanation—the 'why' is the key part.
- Forcing Participation: Never call out non-participants. Make it clear that silent observation is acceptable. The low-pressure environment is instantly ruined if a team member feels required to expose themselves.
- Ignoring Context: Asking Deep Dive questions (like 11-15) to a brand-new team can make people uncomfortable or lead to overly careful, less honest answers. Always match the question type to the existing team trust level.
Scenario: Applying the Connection Depth Model
A product team of nine people based in Birmingham, including three recent hires, is meeting for a half-day away day. The goal is to improve cross-functional empathy and decision-making clarity. The facilitator uses the Connection Depth Model:
- Warm-Up (15 minutes): The team starts with questions 1 and 5 (City Buzz/Comfort Food) to get laughs and basic context. This establishes psychological safety.
- Operational Insight (30 minutes): The team moves to questions 6 and 9 (Autonomy/Data-led). This immediately identifies friction points between engineers (often Autonomous/Data-led) and designers (often Direction/Gut Feeling). They discover that their conflicts stem from differing certainty thresholds.
- Deep Dive (30 minutes): The team concludes with question 14 (Empathy/Brilliance). The conversation reveals that while everyone values empathy, they admit they subconsciously judge colleagues who don't demonstrate high technical brilliance in meetings. This opens a necessary discussion about how to respectfully challenge ideas without damaging relationships.
By structuring the session this way, the team progresses naturally from casual exchange to highly valuable operational insights. 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 of this approach is qualitative (better relationships), measurement shifts from typical HR metrics to observable behavioural changes:
- Increased Follow-Up Dialogue: Do team members reference choices made during the session in later work? ("Remember when Sarah said she prefers spontaneous action? Let’s loop her in on this urgent pivot.")
- Reduced Communication Friction: Is there a noticeable decrease in communication misunderstandings (e.g., fewer emails that miss context, more effective Slack conversations)? The understanding gained from a good ‘This or That’ session helps colleagues choose the right way to communicate with one another, often before a problem even arises.
- Faster Conflict Resolution: When disagreements arise, are teams able to move past them more quickly? The personal context revealed by these questions builds a foundation of empathy, allowing individuals to separate the idea from the person.
These conversations are crucial for building the foundational 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?
The best approach is to divide larger groups into breakout circles of 4 to 6 people. This size ensures that everyone has enough time to share their choice and explain the "why" without the conversation becoming chaotic or impersonal.
How should we handle controversial or awkward answers?
The facilitator should gently steer the conversation back to the underlying preference or value, rather than the surface-level answer. Emphasise that the goal is understanding, not alignment, and remind the team that all preferences in this type of question are valid.
Can these questions be used during mandatory meetings?
Yes, but treat the first 5 questions (Surface Warm-Up) as optional five-minute warm-ups. Using a binary choice question to kick off a status meeting is an excellent way to transition from individual contributor mode to collaborative team mindset without requiring heavy emotional labour.
How often should we use a new this or that list?
For maximum impact, integrate 1 to 2 questions from a comprehensive ‘This or That’ list into weekly meetings. Reserve a more extended, structured session (using the Connection Depth Model) for quarterly team away days or retreats when deeper relational work is the explicit goal.
Which works better: 'This or That' or 'Would You Rather'?
While similar, 'This or That' is often simpler and faster, focusing on preference (e.g., Coffee or Tea). 'Would You Rather' often introduces complex hypothetical trade-offs (e.g., Would you rather fly or teleport?), which are better for generating deep philosophical discussions but take more time to process and explain.