Why Team Building Activities Have to Stretch People a Little to Work at All

I will say something unpopular among people who sell comfort: if your team building activity feels entirely comfortable, it is probably entertainment, and you paid for it like it was development.

Entertainment is fine. It is just not the same thing. A bowling night will not change how your people collaborate under pressure, share information or trust each other’s judgment. Nothing about it asked them to do anything unfamiliar.

I am Jeremy Brooks, a corporate team building expert and co-founder and Chief Experience Officer of Strayboots. The core of everything I design, speak about and host comes down to one principle: to build any strong team, people have to step a little outside their comfort zone in a fun, competitive way. That stretch is what forces collaboration, trust and real communication.

Let me show you exactly how the stretch works, why it cannot be skipped and how to get the dose right.

The Comfortable Activity Problem

Picture a typical comfortable team activity. Everyone knows the rules, the most confident person takes charge, the same voices say the same things they always say and the group finishes roughly the way it started. People smile. Photos get taken. Monday arrives and the team communicates exactly as before.

Nothing failed, because nothing was asked. Comfortable activities let people practice being themselves in a new location. That is all.

Now picture the same group in an activity where the rules are unfamiliar, the clock is real and nobody quite knows how this ends. The confident person suddenly needs someone else’s idea. The quiet person has the piece nobody else saw. People have to decide together, commit together and sometimes fail together, in public, in a game frame that makes it safe to try.

The second version builds a team. The first one builds an afternoon.

Stretch, Defined by What It Is Not

Before going further, let me rule out the things stretch is not, because bad versions of this idea give the good ones a bad name.

• It is not humiliation. Nothing should single a person out, mock a weakness or trade somebody’s dignity for a laugh. The moment a design needs a victim, it is not stretch. It is bullying with a budget.
• It is not physical risk. Stretch can include movement, but nobody should be asked to do anything their body or their boundaries say no to. Good design offers roles, so the stretch is available in many forms.
• It is not a trust fall. Exercises that simulate risk without any real task attached produce awkwardness, not trust. Trust comes from doing real work together under real constraints, not from falling into someone’s arms.
• It is not chaos. Unstructured time with a ball pit is not a stretch zone. It is a playground, and adults know the difference.

Real stretch is structured, social and fun. The challenge lands on the team together. The game makes trying feel low-cost. The debrief makes the lesson stick.

The Three Things Stretch Forces Into Existence

1. Collaboration stops being optional

In a comfortable activity, the strongest personality can carry the group and call it teamwork. Stretch removes that option. A time limit, an unfamiliar format, limited information split across the team – any of these forces people to divide the work, share what they know and make decisions jointly. Nobody gets to be the hero alone, so the team has to function as a team.

Watch a stretched group and you will see the real org chart emerge: who organizes, who notices details, who speaks under pressure, who keeps morale alive. That information is priceless for a leader who wants to develop people honestly.

2. Trust gets built from evidence

Trust does not arrive by invitation. It accumulates through small, witnessed deposits: you said you would handle your part and you did; I depended on you and you came through; I admitted I was stuck and nobody made it a thing.

Stretch manufactures these moments at a pace normal office life cannot match. In an hour, a team can rack up a dozen trust deposits that would take a month of meetings to produce. The result is trust with receipts, which is the kind that holds when a real deadline hits.

3. Communication gets real

Comfortable rooms communicate in titles and agendas. Stretched rooms communicate like people. When the format is playful and everyone is slightly out of their depth, hierarchy loosens and curiosity takes over. People ask each other what they think, say “try my idea,” and laugh at their own mistakes.

I have watched this happen over and over: the moment the task is fun and the outcome uncertain, job titles fade and interests come forward. Human connection first – who someone is, not what their card says. That is not just nicer. It is more honest, and honesty is the raw material of good teamwork.

Calibrating the Dose: Enough to Matter, Not Enough to Hurt

The same activity can be the perfect stretch for one team and wrong for another. Calibration is the craft, and here is how I think about it.

Know the room. A newly formed team needs gentler stretch than a veteran team that already trusts each other. Senior leaders can handle more cognitive stretch and less silliness. A global room needs formats that do not depend on cultural references or perfect English.

Let people choose their edge. Roles are the secret weapon: strategist, builder, presenter, scout, timekeeper. An introvert’s stretch might be presenting the plan while an extrovert’s stretch is listening and building. Both are real. Neither requires being somebody you are not.

Watch the signals. Withdrawal, sarcasm and side conversations mean the stretch is too much or pointed the wrong way. Adjust early: shrink the group, change the constraint, swap a role. A skilled facilitator reads the room like weather and dresses the activity accordingly.

Debrief or it evaporates. The activity creates the raw experience. Five honest minutes of “what did we notice about how we worked” turn it into a lesson. Ask what surprised them, who stepped up, what they would do differently. Then connect it to real work, so the insight has somewhere to land.

What to Look for in a Team Building Partner

Since this is what I do, let me tell you plainly what separates good design from a box of props.

• Design for the outcome. A real partner starts with what you want the team to do differently and works backward. If the first question is about your budget instead of your goal, keep looking.
• Own the facilitation. Great materials run badly by a weak facilitator are just a raffle with steps. The person in the room is the product.
• Respect every size and budget. I have always believed strong team experiences should not require a huge budget or a huge group. Whether it is a leadership team of twenty or a conference floor of thousands, the design principles are the same: stretch, connection, fun, evidence.
• Prove it in the room. Ask to see conference activations and examples of programs for groups like yours. Results in case studies are useful, but the deeper question is whether the design philosophy is sound.

The Monday Test

Here is the test I would give every team building experience, including my own. On Monday morning, does the team talk about what they learned about each other, or just what they ate?

Stretch is the difference. Comfortable activities give you a shared memory. Stretched activities give you a shared reference point: “Remember when we cracked it by finally listening to each other?” That sentence gets quoted in meetings. It becomes part of the team’s story about itself. And teams, more than strategies, run on their stories.

You can see how these principles show up across different programs in my case studies.

Frequently Asked Questions

Does stretch work for remote or hybrid teams?

Yes, with translation. The stretch cannot be physical togetherness, so it becomes informational: limited clues distributed across the call, a problem no one person can see whole, a time box. The same mechanics apply – interdependence, evidence-based trust, honest communication – delivered through a different medium.

What about teams that resist “team building”?

They are usually resisting bad team building, and I do not blame them. Reframe honestly: this is not about forced fun, it is about working a hard problem together in a format that levels the room. Then deliver something genuinely good. Skeptics convert fast when the design respects them.

How do I justify the investment to my CFO?

Price is the wrong frame. Frame it against the cost of a team that does not collaborate, trust or communicate: slow decisions, duplicated work, talent quietly quitting. One day that genuinely changes how a team works is measured against that cost, not against the catering.