I’ve never been a big believer in “team building.”

At least not the awkward kind.

You know the drill: a conference room, a forced icebreaker, two people pretending to enjoy a trust fall, and someone from accounting wondering if this counts as billable time.

But team playing? That’s different.

Team playing is not a one-time event. It is a rhythm. A league. A monthly game night. A recurring tournament. A ridiculous holiday competition where people are laughing, plotting, negotiating, teaming up, losing gracefully, and occasionally accusing someone of “creative rule interpretation.”

That kind of play does something a slide deck cannot.

It lets people practice being a team before the pressure hits.

I learned this firsthand over many years of leading technology organizations, building products, scaling teams, and trying to create cultures that could handle both growth and stress. I’ve spent my career in environments where execution mattered: SaaS platforms, cloud modernization, security, compliance, AI-enabled products, enterprise customers, and aggressive growth targets. My résumé says “CTO” and “President & CTO,” but a big part of the job has always been simpler than that: help smart people trust each other enough to do hard things together.

And yes, sometimes that started with a game.

Over the years, I designed more than 25 custom gaming holiday parties. Every year had a new game. New rules. New teams. New surprises. Some were strategic. Some were silly. Some were probably a little too competitive for a room full of professionals holding plastic cups and tiny dessert plates.

But the impact was noticeable.

People who barely worked together suddenly had a shared story.
Quiet team members found a different kind of voice.
Departments that usually met only through tickets or escalations started seeing each other as people.
And when the real battles came later — deadlines, customer commitments, outages, audits, pivots — the team had more than org-chart relationships. They had reps together.

That matters.

Research supports the idea that shared rituals, even silly ones, help employees bond and add meaning to work. Harvard Business School summarized research showing that group rituals can strengthen connection and increase how meaningful people perceive their work to be. The magic is not that the ritual is serious. In fact, part of the magic may be that it is not. ()

There is also research specifically around play and performance. In one controlled experiment, newly formed teams that played collaborative video games together for 45 minutes improved productivity on later team tasks more than control teams. Another version of the study found about a 20% productivity improvement after team video gaming compared with traditional team-building activities.

And a broader systematic review of team performance research found that strong teams rely heavily on supportive behavior, communication, performance feedback, and leadership — exactly the kinds of muscles people rehearse when they play together in a low-stakes environment. ()

That is why I think companies should stop asking, “Should we do a team-building event?”

The better question is:

Where do our people get to practice being a team when nothing is on fire?

A monthly game night.
A company trivia league.
Murder Mysteries
A board-game lunch.
A fantasy innovation draft.
A scavenger hunt.
A custom-built holiday competition with suspiciously elaborate rules.

It does not have to be expensive. It does not have to be perfect. It should not feel like mandatory fun in a blazer.

But it should be ongoing.

Because one event creates a memory.
A repeated game creates culture.

When teams play together, they learn who takes risks, who reads the room, who encourages others, who spots patterns, who keeps score a little too carefully, and who somehow always finds the loophole.

Then, when the real work gets hard, they already know something important:

We have battled together before.

Even if the battlefield had dice, snacks, a leaderboard, and someone yelling, “Wait, that was not in the rules!”

The Team That Plays Together Battles Together Better