4 Ways to Use the Enneagram at Your Next Leadership Retreat or Team Offsite

There's something different about bringing a team together outside the office.

Whether it's a leadership retreat at a beautiful resort, a company-wide gathering, or a half-day offsite close to home, these events give colleagues something they don't always have during the workday: time to slow down, enjoy each other's company, and have conversations that go beyond their everyday responsibilities.

For some teams, it may even be one of the few times all year that everyone is together in person.

And while the change of scenery is wonderful, there's an opportunity to make that time together useful long after everyone returns to work.

At Enneagram MBA, we've facilitated Enneagram workshops as part of retreats and offsites for teams of all sizes. One thing I've learned is that the best approach isn't always the one with the most content. It's the one that fits the people, the setting, and the purpose of the gathering.

Here are four ways I've seen organizations incorporate the Enneagram into their retreats, along with a few ideas you might borrow for your own.

1. The Bring-Back: Build on What Your Team Already Knows

If your team has already been introduced to the Enneagram, your next retreat is a great opportunity to bring it back.

Maybe your original workshop happened virtually, and now everyone is meeting in person. Maybe it's been six months or a year since your team first learned their types.

Rather than starting from scratch, we can offer a brief refresher and introduce a new application of the framework.

For example, we might explore how different Enneagram types approach communication, conflict, stress, or growth.

But here's what I especially love about this format: we can dial back the teaching and dial up the conversation.

Since participants already have some familiarity with the Enneagram, we can spend more time in type-based breakouts, small-group discussions, and interactive exercises that help people understand one another.

I've had participants specifically request time to connect with colleagues who share their Enneagram type. Those conversations can be surprisingly validating, especially when people realize someone else experiences the same internal frustrations or motivations.

Why it works at a retreat: You're building on an existing shared language while giving people time to connect in a more relaxed environment.

2. The Cross-Department Collab: Bring Teams Together That Depend on Each Other

Some of the most valuable retreat experiences happen when two or more departments come together.

Think about the teams in your organization whose success depends on one another.

Maybe it's Sales and Operations. Marketing and Finance. Leadership and Human Resources.

They work together throughout the year, but how often do they have dedicated time to understand one another's perspectives?

I've worked with leaders who intentionally planned joint offsites so their departments could strengthen those relationships.

The Enneagram gives us a framework for exploring how different people approach priorities, communication, decision-making, and collaboration.

Rather than focusing only on individual personality types, we can facilitate cross-department discussions about what helps people work well together - and where misunderstandings tend to happen.

Depending on the size of the group, we might use breakout discussions, partner exercises, or larger facilitated conversations.

Why it works at a retreat: People get to connect with colleagues they rely on but may not work alongside every day. Those relationships can make a difference when everyone gets back to their regular responsibilities.

3. The 2-Parter: Take the Conversation Beyond the Workshop

This is one of my favorite examples because it shows that the Enneagram doesn't have to stay inside the meeting room.

We recently worked with a company that had already introduced the Enneagram to employees through internal learning cohorts.

When we joined their company retreat, we facilitated a shorter session focused on how the nine Enneagram types show up at work, including common workplace pet peeves and preferences.

It was interactive, but with a large audience and limited time, there was only so much room for conversation.

So we added a second part.

Later that evening, the organization arranged dinner seating by Enneagram type. We provided type-specific discussion prompts, and the internal event contact coordinated the activity.

Employees had an opportunity to sit with others who shared their type and explore the similarities and differences in how they experienced the world.

And I heard that the dinner conversations went over incredibly well!

What I love about this example is that we didn't need another formal training session. We simply created an opportunity for participants to continue exploring what they'd learned in a more relaxed setting.

Why it works at a retreat: The workshop becomes a starting point, with conversations naturally continuing into other parts of the agenda.

4. The Staycation: Create an Offsite Experience Close to Home

Not every team has the time or budget for a multi-day retreat at a destination resort.

And that's okay!

I've seen organizations create wonderful experiences without traveling very far.

They might book a bright, inviting conference room at a local hotel or coworking space, bring everyone together for coffee and breakfast, and spend the morning participating in an interactive Enneagram workshop.

Then they'll head out for lunch and a fun group activity.

I've seen teams incorporate everything from pickleball and Topgolf to escape rooms, axe throwing, and cocktail-making experiences.

Sometimes the order gets flipped because of the weather or venue logistics. The team might enjoy an outdoor activity in the morning, have lunch together, and finish with the Enneagram workshop in the afternoon.

The important thing isn't the exact agenda.

It's creating a different environment where people can step away from their routines and spend time together.

For a remote or hybrid team, this can be especially valuable if employees don't regularly see each other in person.

Why it works at a retreat: You can combine intentional team development with a fun day away from the office, without the expense or logistics of a destination retreat.

One More Thought: Let the Workshop Serve the Retreat

One thing I've learned through facilitating team retreats is that the Enneagram doesn't need to take over the entire agenda.

Sometimes a short kickoff session is exactly what the group needs.

Other times, a half-day workshop with deeper conversation and interactive activities is a better fit.

And sometimes the most valuable moments happen afterward - when teammates continue talking over dinner, during an activity, or on the ride home.

The goal isn't to turn everyone into an Enneagram expert.

It's to give people a shared language for better understanding themselves and each other, with practical insights they can use as they communicate, collaborate, navigate tension, and lead together.

And if people have a little fun along the way? Even better.

Because the time teams spend together away from work should make a difference in how they work together when they return.

Planning a Leadership Retreat or Team Offsite?

Enneagram MBA facilitates interactive leadership retreat workshops and corporate offsite experiences nationwide.

Whether you're planning a two-hour kickoff, half-day leadership session, or full-day team workshop, we'll help you create an experience that fits your group's goals and the larger purpose of your retreat.

Explore Our Leadership Retreat Facilitation & Team Offsite Experiences

This article was adapted from Episode 150 of the Enneagram at Work podcast, "Four Ways the Enneagram Can Enhance Your Annual Retreat." Listen to the full episode to hear more examples and ideas.