What an Enneagram Workshop Actually Looks Like: Inside a Team Session

When a leader tells you she’s answering emails at 11:04pm because her team is pinging her at 11:01pm, you don’t need another “team‑building activity” — you need an Enneagram workshop that actually cuts through the corporate speak. Boundary issues, burnout, and constant stress aren’t solved by another forgettable training. They’re solved when a team finally sees why they’re stuck and what’s driving their behavior, opening up conversation and compassion for themselves and others.

The Boundary Problem That Sparked an Enneagram Workshop

“If I email her at 11:01pm, she replies at 11:04 pm.” she told me.

“You could say our boundaries kinda suck.”

YES.

Yes, you could say that, Sarah…

And look, I’m not claiming the moral high ground here. As I write this, it’s 10:45 pm when I should absolutely be in bed with a sci-fi novel and a cup of tea.

A few months ago, I was hired to lead an Enneagram workshop for a leadership team. During our first discovery call, the team lead (we’ll call her Sarah) explained why she was bringing me in.

Why Sarah Wanted a Better Enneagram Workshop

They’d already done an Enneagram workshop with another facilitator.

“He talked the entire time,” she said. “And we learned nothing.”

As someone with a little squirrel brain, I GET IT. When you are forced to tune into a Zoom team-building exercise, it’s easy to get distracted, nod along, and then go right back to your same dysfunctional habits.

Sarah was NOT interested in just throwing more information at her team.

(And let’s be real, ChatGPT can vomit that up to you in a heartbeat.)

She wanted transformation — the kind that actually shifts behavior.

What I Learned in the Discovery Call

From our first discovery call, I knew she was deeply invested in her team. (She’s a self-preservation Six.) She rattled off everyone’s names and problems:

• Arthur shuts down the second criticism enters the picture.
• Lily is emailing me at midnight… and I’m emailing her back.
• And a Type One who’s been at the company 10 years is arguing with this Type Three like 40 times a day, and I am sick of it!

And don’t worry, I’m not airing out this team’s dirty laundry. All names and details have been changed for anonymity!

Why a Basic Enneagram Workshop Wouldn’t Work

This was not a team that needed a cute “Here are the 9 types!” workshop.

They needed an in-depth conversation facilitated by an expert that actually changed things.

Everyone’s usual unhealthy patterns were running the show. Which is exactly where the Enneagram for teams becomes a powerful tool.

Inside the Enneagram Workshop: Naomi, the Type One

For example, one team member (let’s call her Naomi) was a Type One.

They had just had a major event, and she was STRESSED.

“No one is doing what they’re supposed to do!!”

Naomi, as a One, tends to move toward people by trying to improve, correct, and fix. Which sounds helpful… until the One is stomping around angry at everyone without SAYING why she’s upset.

So I asked her:

“Where did perfectionism show up today?”

And suddenly, the conversation got interesting. Because we were finally getting to the root of the problem:

Naomi felt constant frustration with herself and others that things were not matching up with her high internal standards.

Guiding Questions That Shifted the Room

For the Twos, I asked: “Where did you give beyond your actual capacity?”

For the Sixes: “What are you assuming… versus what do you actually know?”

We took the time and space to really talk it out.

Takeaway: The right questions unlock the real conversation.

Why Leaders Choose an Enneagram Workshop

And that’s exactly why the Sarahs of the world bring me in.

To get real with their people.

To help explain why two (very competent) leaders can feel like one is speaking Klingon and the other Elvish.

(Guys, I said I was reading sci-fi in bed earlier in this email. If it wasn’t already clear that I’m a super big nerd.🤓)

To uncover the patterns creating conflict, burnout, and miscommunication so teams leave with practical tools to work better together.

What Teams Walk Away With

• Clearer communication patterns
• Tools for navigating stress
• Language for conflict resolution
• Personal insights for each team member

Takeaway: Teams don’t just learn about the Enneagram — they learn how to use it so that it actually makes a difference in their lives.

Examples of Customized Enneagram Workshops

Every workshop is customized to your team’s specific dynamics and challenges.

For example, I led an in-person workshop for a group of burned-out school counselors. We focused on self-care and burnout prevention through the lens of their Enneagram types.

Then, for a group of go-getter real estate agents who wanted to 10x their sales volume, I facilitated a one-hour virtual workshop focused on Enneagram-based goal setting and productivity strategies.

My workshops are interactive, story‑driven, and built around the actual situations you and your employees are dealing with at work.

Book Upgrade: My Enneagram Guided Journal

If your team wants to take the work even deeper after the Enneagram workshop, you can add on discounted copies of my guided visual journal, My Enneagram. It’s a practical, take‑home resource that helps people integrate what they learned in the session — especially the coping stances, stress patterns, and communication habits we uncover together.

Teams often use it for ongoing reflection, 1:1 conversations, or monthly check‑ins to keep the momentum going.

My Enneagram is an approachable & playful guided journal designed to help you find your personality type and embark on an empowering journey of self-discovery. 

Both the Enneagram curious and longtime Enneagram fans can use this book to delve into the Enneagram types and put that knowledge into practice, all with an eye toward busting burnout, taming stress, and crushing life goals.

What’s Included:

• How to find your Enneagram type—including 2 quizzes that go way deeper than any cookie-cutter online quiz will go
• How to use the Enneagram to identify your biggest areas of growth
• Tips, tricks, and exercises to setting your goals—and achieving them!
• How the Enneagram can improve communication between you and the closest people in your life

Book Your Enneagram Workshop

If your team is stuck in stress, burnout, or frustrating (or nonexistent) communication habits, an Enneagram workshop can help. Book a discovery call and we’ll design a session that actually moves your team forward.