Enneagram Workshops for Teams
Make your next team retreat more than just a great day together.
An engaging, insightful Enneagram workshop that helps colleagues understand what makes each other tick, appreciate their differences and find better ways of working together.
For team retreats, leadership off-sites and away days where you want something enjoyable, meaningful and genuinely useful to take back to work.
When you get your team together, you want it to count.
Getting everyone together away from the demands of everyday work is a valuable opportunity. You want people to relax, have a laugh and connect beyond the usual meetings and deadlines.
But you also want them to leave with something more than a few good memories: a better understanding of the people they work with, and something useful they can take back into their everyday interactions.
An Enneagram workshop, delivered in person or virtually, works especially well when you’re:
Planning a team retreat, team-building day or away day and want to combine genuine connection with meaningful insight.
Bringing a leadership team together to strengthen relationships and understand each other’s different ways of working.
Running a strategy off-site where you’re exploring what you want to achieve and also want to consider how you’ll work together to make it happen.
It gives your team time to focus on the people and relationships behind the plans.
“Jessica was a pleasure to work with! She was super responsive, informative, and professional in setting up a workshop that matched our team’s unique needs. We all had a great time learning about ourselves and each other in her workshop. Jessica is knowledgeable and personable and an excellent facilitator. The workshop was engaging and interactive and the hours flew by. Thanks for your expertise!”
Lauren Drake - Spring Health
There’s a difference between knowing someone and really understanding them
We all have colleagues whose behaviour we find a little puzzling. The one who needs every detail before making a decision. The one who’s always challenging the plan. The one who avoids difficult conversations, or the one who wants everything done yesterday.
We might know exactly how someone behaves, without really understanding why.
That’s where the Enneagram offers something different. It helps us look beneath behaviour to understand the motivations, fears and perspectives that shape how people see the world.
When we begin to understand what’s driving someone, rather than simply reacting to what they’re doing, things can shift. What once felt frustrating starts to make sense. Differences become something to appreciate rather than work around.
It makes for a workshop filled with moments of recognition, laughter and surprise, alongside conversations that can change how colleagues see and respond to each other.
What you’ll get from the Enneagram workshop:
Drawing on insights into their own Enneagram styles and those of their colleagues, participants have an opportunity to:
Recognise their strengths, motivations and habitual patterns, including how they tend to respond when under pressure.
Understand what drives other people, and why colleagues can approach the same situation so differently.
Appreciate the different strengths and perspectives in the team, rather than getting caught up in the frustrations those differences can create.
Explore better ways to communicate and work together, with a shared language they can continue using back at work.
The aim isn’t to turn everyone into Enneagram experts. It’s to give them insights they can keep drawing on in their working relationships.
“Our team of 15 hosted an Enneagram Workshop led by Jessica, during our annual retreat. The 4-hour, Zoom-based session exceeded our expectations and gave our team plenty of food for thought to consider long after the session. Highly recommend for teams with diverse personality types looking to work more cohesively!”
Sean Hoff - Moniker Partners
What to expect:
Before the workshop:
Each participant completes an Enneagram assessment and receives a personalised report. I recommend a confidential 1:1 debrief beforehand, so everyone has the chance to explore their results, confirm their type and feel comfortable with their own style before coming together as a team.
During the workshop:
Through relatable examples, reflection and conversation, we explore the nine Enneagram styles, what drives different people and how those differences show up in everyday working relationships. The session is engaging and interactive, with space to share experiences and learnings. Both in-person and virtual workshops available.
After the workshop:
People leave with a better understanding of themselves and their colleagues, and practical insights they can draw on in how they work together.
Optional 21-day “insight into action” Habit Builder to embed behaviour change.
Frequently Asked Questions:
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3.5-4 hours. Long enough to go beneath the surface, short enough to fit into a retreat or off-site agenda alongside everything else you have planned.
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Yes. I run workshops in person and live online, and online works far better than most people expect. I’ve Zoomed into a living room with six people gathered on the couch, and onto a big screen in front of 25 people in a conference room. Either way, it’s interactive and personal, never a webinar.
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Anything from a small team of six to a group of around 25. If your group is bigger, get in touch and we’ll find the format that works best.
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For a team of 10, the full workshop, including an Enneagram assessment, personal report and confidential 1:1 debrief for each person, is around US$8,000. That’s where much of the deeper insight happens. If budget is tight, a workshop-only option starts at around US$3,600. Get in touch for a quote based on your group and format.
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Ideally, yes. Everyone completes an assessment and has a confidential 1:1 debrief before the workshop, so they arrive knowing their type and what it means for them. If that’s not possible, we can explore the nine types together in the session.
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Yes. The Enneagram gives people a shared language for what drives behaviour, their own and each other’s. Used well, it opens up understanding rather than putting people in boxes. I’m an accredited Enneagram professional and ICF coach, and I keep the focus firmly on how your team works together.
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Yes. Most of my clients are in the US and Canada, including teams at Spring Health, Moniker Partners & Partners in Health Canada. I schedule sessions to accommodate both our time zones.
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The workshop is a single session, ideal for a retreat or off-site. The Team INsight Programme goes further over 2 full days or 3 separate virtual sessions, building self, relational and team awareness for teams that want lasting change.
Planning a team retreat or off-site?
If you’re looking for something that will bring your team together, spark interesting conversations and give people a fresh appreciation for the colleagues they work with, I’d love to hear what you have in mind.
Let’s talk about your team and how an Enneagram workshop could fit into your plans.
“Jessica was warm, engaging and interesting. In taking the Grade 11’s through the Enneagram, her explanations were clear and she kept them captive. She is incredibly knowledgeable and has the ability to share this knowledge in an easy-to-understand way. I personally learned so much and have used these learned skills in my professional and personal life”
Sheryl Gordon - Grade 12 Head, St Mary’s DSG
Looking for something more in-depth?
Hi, I’m Jessica
I'm a former Consumer Insights Director at Unilever, Certified Narrative Enneagram Teacher, IEA Accredited Enneagram Professional and ICF Professional Certified Coach. I've spent more than 10 years working with the Enneagram, driven by a fascination with human behaviour - why we do what we do, the patterns we keep repeating, and what happens when our patterns bump up against someone else's.
I bring this curiosity, along with years of corporate leadership experience, into my work with teams.
My workshops are engaging, insightful and practical, helping people make sense of themselves and each other in ways that are useful long after the workshop ends.
If you’d like to find out more about me, including my experience & credentials, click the button below.