Kickstart Your Company Offsite with the Enneagram: The Secret to Stronger Teams and Better Collaboration

There was a buzz of anticipation as twelve members of the marketing team from a global dating app trickled into the sunlit conference room. Laptops in hand and coffees in tow, they greeted each other with a mix of familiarity and curiosity. While they worked together throughout the year, their collaborations were mostly virtual. This annual offsite was their chance to reconnect in person—to bond beyond the boundaries of Slack channels and video calls.

At the front of the room stood Eric Enders, an Enneagram workshop facilitator with a calm presence and a twinkle in his eye. He greeted the group warmly. “If you haven’t already, grab a cup of coffee,” he said. “You’ll need it. We’re going to have some lively conversation today.”

What followed was a two-and-a-half hour session that didn’t just break the ice—it melted it. The session was engaging, energizing and deeply insightful. By the end, the participants were buzzing with conversation, reluctant to leave. And what was the secret ingredient? The Enneagram.

Why the Enneagram Works for Team Bonding

When it comes to understanding human behavior, few tools are as dynamic or revealing as the Enneagram. Unlike other personality systems that focus primarily on behavior, the Enneagram goes a level deeper, uncovering the motivations, fears and desires that drive our actions. It offers a lens through which people can understand themselves and each other more clearly, which is why it’s especially powerful in the context of team building.

Says Suzanne Bell, PhD, an associate professor of industrial/organizational psychology at DePaul University in Chicago, “The studies suggest it's the "deep-level" factors you can't see at a glance, such as the members' personality traits, values and abilities, that tend to have a much bigger impact on work teams.” These attitudes, behaviors and motivations collectively influence how a team works together and whether a team achieves its goals. 

At a company offsite, especially with distributed teams, there’s often a need to establish connection, build trust and align communication. The Enneagram offers a structured-yet-flexible way to do just that while also revealing the “deep-level” factors. And when the session is done right, you can expect laughter and fun–a great way to start a workplace retreat.

Creating Instant Connection

Enders began the session by introducing the nine Enneagram types in simple, accessible language. No jargon, no psychobabble—just plain speak. Each type came to life with relatable examples, humor and stories from the workplace.

Then came the game-changer. Before the session, each participant had completed an online assessment to identify their likely Enneagram type.  After his introduction, Enders asked participants to stand and rearrange their seats around a U-shaped table based on their Enneagram number. Suddenly, people were no longer sitting next to their closest coworkers—they were sitting next to their Enneagram type twins. This reorganization subtly shifted the group dynamic and created instant camaraderie.

“It felt like we were all speaking the same language,” said Maria, a Type 3 Achiever from the London office. “I didn’t even know some of the others were Type 3s, and yet it made so much sense once we started talking. Our energy was just synced.”

The room filled with laughter, recognition and the occasional "Ohhh, now I get why you do that!" The conversation flowed naturally and, with each round of discussion, the group grew closer. The Enneagram types didn’t just help people understand themselves—they gave language to long-held perceptions and smoothed over previous misunderstandings.

Bridging Communication Gaps

After the initial connection exercise, Enders guided the group through a deeper exploration of communication styles by type. Type 1 Perfectionists prefer clarity and order. Type 5 Investigators might need time to process before responding. Type 9 Peacemakers avoid conflict and may be indirect about their opinions. With each insight, the team began to understand not just what their colleagues did, but why they did it.

This shift in awareness fostered a deeper level of empathy and understanding. The result? Less frustration, more patience. Miscommunications that might have once caused tension were now seen through the lens of personality and style differences. Strengths that had previously been felt only intuitively suddenly had language and structure. This kind of awareness lies at the core of emotional intelligence—and it's a gift the Enneagram continues to offer, time and again.

Building Trust Without Forced Vulnerability

Many team-building exercises push people toward quick vulnerability—which can feel forced or even uncomfortable. The Enneagram, however, invites vulnerability in a more natural and self-directed way. When people recognize their own patterns and hear them reflected in others, walls come down organically. People share what they want, staying within their own personal boundaries. The Enneagram makes this easy as it offers a non-personal way to talk about differences.  

For example, when Martin, a Type 6 Skeptic from Berlin, shared how he often prepares for worst-case scenarios because it helps him feel safe, his Type 7 Enthusiast colleague across the table nodded in understanding. “I do the opposite,” she laughed. “I look for the silver lining in everything. It drives people nuts.”

Moments like these allowed for honest, productive conversation—and laid the groundwork for deeper trust moving forward.  

Enneagram facilitator Pieter Polhuijs agrees, “After more than 20 years developing teams, I always come back to the Enneagram—it's simply the most powerful tool I’ve found. Nothing else opens people up like this personality system. People share things they normally might not because they are given a non-personal way to talk about their internal experience.”

A Tool That Keeps Giving

The beauty of starting your company offsite with the Enneagram is that it doesn’t end when the session is over. The insights gained become a common language that teams can continue to use long after they return to their regular workday.

By the end of Ender’s session, the group had created type-specific communication agreements. For example, the Type 8 Challengers  requested direct, no-nonsense communication. The Type 2 Helpers asked for more acknowledgment of their efforts and for appreciation to be expressed more regularly. These agreements became a living document—a user manual for each team member.

Making It Work for Your Team

If you're considering using the Enneagram as a workshop to your next offsite, here are a few best practices:

• Keep it experiential. People learn better when they’re engaged. Include interactive exercises, group discussions, and plenty of real-life examples. Lecture and theory have a place in the workshop, but the participants should do most of the talking.
• Make it safe. Emphasize that there are no "good" or "bad" types—just different perspectives. And set clear expectations and boundaries about the confidentiality of anything that is shared in the session.
• Use a skilled facilitator. A great Enneagram session depends on the person leading it. Look for someone who knows the system well and can create a warm, inclusive environment.
• Follow up. Don’t let the insights fade. Encourage ongoing use of Enneagram language in meetings, one-on-ones, and project planning.

Final Thoughts

A strong team starts with self-awareness, trust, and mutual understanding. The Enneagram offers all this and more in a format that’s fun, memorable, and surprisingly profound. For the marketing team at the dating app, those two and a half hours laid a foundation that would strengthen their collaboration for months to come.

So if you’re planning your next company offsite, consider leading with an introduction to the Enneagram. It may just be the workshop that transforms your team dynamic—one personality at a time.