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The Enneagram in Business

10 min

Harnessing the Power of Personality Type to Build Great Teams

Introduction

Narrator: Imagine it’s your first day as the new General Manager of a high-profile hotel. You’re stepping into a role with a seasoned team, and you need to establish your leadership immediately. Two of your senior team members walk in for their first meeting with you. Instead of taking the visitor chairs in front of your desk, they deliberately sit at the large conference table in the room, a subtle but unmistakable power play. What do you do? Ignore it and risk looking weak? Overreact and start a war on day one? The new GM in this situation didn't hesitate. He looked at them and said, “Gentlemen, this is a fine example of positional power that you’re demonstrating. However, I’m not playing. Get over here and sit down.” The power dynamic shifted instantly.

This decisive moment wasn't just a lucky guess; it was the result of deep self-awareness. In the book The Enneagram in Business, the author uses this story to introduce a powerful framework for understanding the hidden motivations that drive our actions, especially under pressure. The book argues that effective leadership isn’t about memorizing management theories; it’s about understanding the internal patterns that shape how you and your team think, feel, and act. The Enneagram becomes the map for navigating this complex human terrain.

True Leadership Begins with Getting Your Hands Dirty

Key Insight 1

Narrator: Before you can lead, you must understand. The book makes a powerful case that leadership credibility isn't earned in a corner office but on the front lines, by demonstrating empathy and a willingness to understand the work of those you lead. This principle is vividly illustrated by a story from early in the author's career at the Walt Disney Company. A young, confident hotel school graduate, the author was assigned to work under Maxcine Bell, the legendary executive housekeeper.

Believing his education had prepared him for anything, the author was shocked when Maxcine’s first assignment was for him to clean hotel rooms for thirty days, inspecting every single one himself. After that grueling month, he was moved to the pool area to clean public restrooms in the sweltering Florida heat. The author initially resented the work, but the lesson became clear over time. Maxcine told him, "You cannot effectively lead others unless they know you’ve walked in their shoes." This experience fundamentally changed his approach to leadership. From that point on, in every job he held, he began his day with his housekeepers. This wasn't a symbolic gesture; it was about connection, respect, and a deep understanding that built unshakable loyalty and trust.

Your Three Brains Must Work in Harmony

Key Insight 2

Narrator: The Enneagram proposes that humans operate from three distinct centers of intelligence: the Head for logic, the Heart for emotions, and the Gut for action and instinct. We all have a dominant center, but true growth and effectiveness come from balancing all three. When these centers are out of sync, conflict is almost inevitable.

Consider the case of Tim, a high-achieving Type 3 Vice President of Sales, and his detail-oriented Type 1 colleague, Janice. They clashed while planning a major client event. Tim, driven by his Gut (action) and Head (logic), just wanted to get the seating chart done and move on. Janice, operating from her Heart (emotion) and Head (logic), was concerned about following protocol and making people feel valued. Their argument escalated because Tim ignored the emotional component, while Janice was stuck in feeling and logic without moving to action. The author intervened, pointing out their imbalances. By recognizing that Tim was over-relying on action and Janice was stuck in emotion, they were able to pause, apologize, and find a solution that honored both the need for efficiency and the need for thoughtful execution. This illustrates a core lesson: most workplace conflicts arise not from malice, but from an imbalance in how people process the world.

Self-Awareness Transforms Feedback from a Weapon to a Tool

Key Insight 3

Narrator: Few activities in the corporate world cause more anxiety than giving and receiving feedback. The book argues that most feedback fails because it’s delivered without self-awareness. When we don't understand our own triggers and patterns, we can't deliver a message that can be truly heard. To solve this, the author presents a simple, four-step model: Observe, Interpret, Feel, and Need. First, state a neutral observation of the behavior. Second, share how you interpreted it. Third, express how that interpretation made you feel. Finally, state what you need.

This model is brought to life through the story of Mim Flynn, a senior manager at Disney who had to give the author some very tough feedback early in his career. The author, frustrated with his role, had developed a poor attitude. Mim called him into her office and, with remarkable self-control and care, told him directly: "I have a hard time understanding why you are currently such an egregious disappointment." The feedback was brutal, but it was delivered from a place of genuine concern for his potential. She didn't yell or attack; she observed his behavior, interpreted its negative impact, and stated what she needed from him to succeed. This direct, self-aware feedback was a turning point in the author's career, proving that when delivered correctly, even the hardest truths can be a gift.

Failure Isn't an Endpoint, It's a Turning Point

Key Insight 4

Narrator: Our greatest fear is often failure, but the book reframes it as "triumphant failure"—an event that, while painful, can be the catalyst for profound growth. The most powerful story of this is the author's own. After years of success, he was unexpectedly fired from his job as a general manager. In that moment, his lifelong fear of failure became a reality.

Instead of collapsing, he tapped into his three centers of intelligence. His Gut took action, packing his office. His Heart processed the shock and sadness, and he reached out to his partner for support. His Head began to analyze the situation, not with blame, but with curiosity. Walking away from the hotel, he realized the firing wasn't just an end; it was a liberation. It forced him to confront the fact that he wasn't on his true path. This "failure" gave him the push he needed to start his own consulting business centered on the Enneagram, a career that brought him far more fulfillment. The experience teaches that failure only defines you if you let it. With self-awareness, it can be the very thing that redefines your path for the better.

Collaboration Thrives on Understanding, Not Agreement

Key Insight 5

Narrator: In any team, you will have a mix of personalities, motivations, and fears. The book argues that successful collaboration doesn't come from everyone thinking alike, but from everyone understanding and respecting their different patterns. This was put to the test when the author was tasked with building the executive team for the W Hollywood hotel. He intentionally assembled a diverse group of Enneagram types, including driven Type 3s, visionary Type 7s, and perfectionistic Type 1s.

Their meetings were loud, argumentative, and filled with laughter. They learned each other's patterns—who would get anxious, who would get optimistic, and who would focus on the details. This mutual understanding became their superpower. When the hotel, nightclub, and restaurant partners inevitably came into conflict after opening, the team was able to navigate the tension. They didn't always agree, but they understood each other's pressures and points of view. This allowed them to create solutions that worked for everyone, ultimately leading to massive success. The lesson is that you don't need a team of clones; you need a team that has the self-awareness to see and leverage its differences as strengths.

Conclusion

Narrator: The single most important takeaway from The Enneagram in Business is that the Enneagram is not a system for labeling or boxing people in. Instead, it’s a tool for liberation. It shows you the invisible box you may have unconsciously built around yourself through years of repeated patterns, and then it hands you the key to unlock it. It reveals that your greatest strengths, when overused, become your greatest weaknesses, and that growth comes from consciously choosing your responses rather than defaulting to your programming.

Ultimately, the book challenges the very definition of leadership. It’s not about being the loudest person in the room or having the most authority. It is about the quiet, consistent work of self-observation. The real challenge is to begin watching your own patterns without judgment. Ask yourself: Why did I react that way? What fear was driving that decision? The moment you start asking those questions, you are no longer being driven by your patterns. You are driving them. And that, the book makes clear, is the beginning of true leadership.

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