The Enneagram + Leadership Development
Exceptional Leadership Through the Enneagram
Monthly training, live coaching, and a practitioner community — built around one thing: using the Enneagram for professional development to change how you work and lead.
- Live monthly training
- Group coaching
- VIP community access
Trusted by leaders and teams at
The real problem
Assessment Alone Isn't the Answer
Most teams treat personality frameworks as a one-time event. A workshop. A report. A type. The Enneagram at Work is built for what comes after the assessment. The Enneagram at Work gives you a playbook to go from insight to action.
72%
of teams who've taken a personality assessment say it didn't change how they actually work together.
What usually happens
You take an assessment. You get a type. Nothing changes.
- A report you skim once and never revisit
- A label that sits on your Slack profile
- Two days of team excitement, then nothing
- The same conflicts, the same frustrations
What enneagram at work does
You gain insight. You apply it. Your team’s performance improves.
- Monthly training that builds on itself
- Real-time community support
- Conversations that land the first time
- Group coaching to learn from others
Who should join
Built for people who want to create lasting change
If you're a leader, manager, or HR professional dealing with communication breakdowns, team friction, or the challenge of leading people through change — this is for you.
You've probably tried the workshops. Maybe even the retreats. They're fine for a week. Then the old patterns come back.
“We've done the offsites and assessments. This is the first thing that actually changed how my team shows up on week after week.”
Laura S.
Chief People Officer
This membership program is for
01
Executives & Senior Leaders
You set the culture — intentionally or by default. Learn how your type shapes your leadership shadow, and how to bring out the best in the full range of people around you.
02
HR & People Operations
Equip yourself with a practical framework for leadership development, conflict mediation, and team design. One that actually accounts for human complexity.
03
Managers & Team Members
You're in the work every day. Understand why certain dynamics keep repeating — and get a concrete language for improving them, starting this week.
What's Inside
Coaching, training, and community. Working together.
One membership.
This isn't a course you buy and forget. It's a membership built around consistent practice, real application, and a community that keeps you moving forward.
Pick the level that’s the best fit.
Monthly Training
One deep-dive session each month. Includes practical takeaways you can apply right away. Live, recorded, and added to your library.
Group Coaching + Hot Seat
Live group coaching every month. Hot seat participants get hands-on coaching with a real life practitioner.
Foundation Course
A standalone course on Enneagram fundamentals for professional application. Start here and return any time you need a refresher.
Resource Library
Type guides, workbooks, session replays, and training decks — all in one place. The library grows every month. It’s yours to access 24/7 as long as you’re a member.
Resource Library
Type guides, workbooks, session replays, and training decks — all in one place. The library grows every month. It’s yours to access 24/7 as long as you’re a member.
Over 1000 Trained
By the numbers
Monthly Training
One deep-dive session per topic — live, recorded, and added to your library.
$2,997
Group Coaching + Hot Seat
Live group coaching sessions. Hot seat opportunities.
$4,997
Resource Library
Grows every month. New tools and techniques to add to your personal playbook.
$997
Enneagram Quick Start Guide
A comprehensive reference guide for applying the Enneagram at work.
$79
Foundation Course
Enneagram fundamentals course.
$297
Total Value
$9,367
Your Price
Memberships starting at just
$79
/mo
What people are saying
This will transform your team forever
“My team's dynamic shifted in ways I didn't think were possible without a full culture overhaul. We communicate differently now — and it stuck."
Matthew W.
CTO
"I've sat through a lot of leadership training. This is the first time I've seen my managers actually change how they show up — not just for a week, but months later."
Vivek P.
VP Engineering
"We reduced friction on my senior team that had been there for years. I didn't expect that kind of shift from a membership program."
Amy W.
Chief People Officer
Who is behind the Enneagram at Work
Hello, I'm Todd
A former leadership executive at Twitter/X, Cisco, and Workday. I know how to turn organizations around, develop leaders, and build high-performing teams.
I've taken personality assessments, done countless team-building exercises, and been through day long workshops. Nothing ever changed.
That’s why I built The Enneagram at Work — to turn insights into action that actually changes how you lead, communicate, and show up for your team.
If that sounds like what you've been looking for, you're in the right place.
Over the past 25 years, I’ve coached and trained 1000+ leaders.
Choose your membership level
Three levels. Pick the one that’s right for you.
Whether you're just getting started or ready to go all in, there's a level built for where you are right now.
Explorer
For professionals who want to learn at their own pace
$79
/Month
- Monthly live training
- 30-day session replays
- Resource library
- Enneagram quick start guide
- Community group
Most Popular
Growth
For practitioners ready to grow and do the work
$169
/Month
- Everything in Explorer
- Lifetime replays
- Foundation Course
- Extended resource library
- Monthly live group coaching
- Upgraded community group
VIP Inner Circle
Reserved for leaders who want the fastest path forward
$299
/Month
- Everything in Growth
- Priority group coaching hot seat
- Quarterly 1:1 coaching
- Early access to new courses
- Certification fast track
Access to resource library and replays remain as long as your membership is active. Cancel anytime.
Got Questions
FAQs
How is this different from a one-day workshop or certification?
Workshops give you a framework. This gives you ongoing practice, coaching, and a community that holds the work between sessions — which is where real change actually happens.
Do I need to be an Enneagram expert to join?
Not at all. If you know your type and you're curious about putting it to actual use at work, you're ready. The training starts with application, not theory — so whether you took a test last week or you've been studying for years, you'll find your footing quickly.
How is this different from just taking an Enneagram course?
A course gives you information. This gives you ongoing practice. The training, coaching, and community are all built around one question: how do you actually use this in the room, in the meeting, in the hard conversation? That's the gap most Enneagram content leaves open. This is designed to close it.
Is this for individual contributors or leaders and teams?
Both. Individual professionals use it to understand themselves better and navigate their work relationships. Managers and HR leaders use it to coach their teams, run better conversations, and build cultures that actually stick. The Enneagram is one of the few tools that works at every level of an org.
How can I expect this to impact my team's performance?
Members typically report reduced interpersonal friction, stronger executive communication, and leaders who are more self-aware under pressure. The shift isn't overnight — but it compounds month over month.
How much time does this require each month?
Plan for roughly two to three hours per month for live sessions and coaching. The resource library and community are available whenever you need them.
Can I switch tiers or cancel?
Yes to both. You can upgrade to a higher tier anytime. And if life changes, you can cancel before your next billing cycle — no hoops to jump through. This is meant to be a membership you stay in because it's working, not because you forgot to cancel.
Can I expense this or bring it to my organization?
Yes — most companies have a budget for professional development. If you're interested in a team or organizational membership, reach out directly and we'll work something out.
Which membership level is right for me?
Explorer is great if you're just getting started. Growth is the most popular for leaders who want live coaching and community. VIP Inner Circle is for those who want direct access and personalized support.