Exploring the Enneagram: My Personal and Professional Journey in Sales

Life has a way of presenting crossroads, moments where we question who we are and where we’re headed. For me, one of those moments came during a business trip to Singapore. I found myself alone, frightened, confused about my career trajectory. Rather than ignoring the crisis I leaned into it, for reasons I still can’t explain and spent the next couple of years intensely reflecting and discerning. Looking for clarity and direction. I turned to the works of Richard Rohr, including a book he authored about the Enneagram. I was captivated. It changed the course of my career and my life.

A New Perspective on Self-Awareness

Learning about the Enneagram was like a lifeline. Without it I didn’t have the tools to discern and find clarity. With it many things steadily began to make sense. I began understanding who I truly was. Of the nine Enneagram types, I am a type 3, The Achiever.

The insights were profound. I came face-to-face with the realization that much of my life had been driven by an insatiable hunger for achievement, particularly in my career. That focus left little room for relationships or community, and candidly, I wasn’t interested in things that didn’t directly serve my goals. This self-awareness, while humbling, was liberating.

A Game Changer for Relationships

As I began to understand and accept my type 3 tendencies, everything changed—my personal relationships, my business relationships, how I showed up in my role as a coach, sales trainer and consultant. I changed how I approached sales.

Connecting the Enneagram to Sales

I first applied what I was learning to my coaching practice. I helped clients learn which of the nine Enneagram types they are, and set them on their journey to higher self-awareness and leadership effectiveness. Later, I applied my Enneagram knowledge to the sales profession and created the program Blindspots in Sales.

Real Change, Real Results

I’ve witnessed firsthand how understanding the Enneagram can transform a salesperson’s approach. I’ve seen clients completely change how they “show up” for customers.

One client of mine struggled to engage a customer during contract negotiations. His emails to the main stakeholder were obsessively business-focused, and his rigid stance in the negotiation wasn’t fostering collaboration. Often his emails to her went unanswered for days or weeks. I encouraged him to try a simple gesture—show genuine interest in the stakeholder. One Friday late afternoon he emailed the client, solely wishing her and her family a good weekend. He was shocked when she responded within 30 minutes, thanking him.

To some, this might seem like a cute victory. To me, it’s a breakthrough. My client experienced something magical - he elicited a response by doing something he’d never imagined doing. He’ll build on this with this client and others. These small moments can pivot the direction of a sale or negotiation, often creating the opportunity for success where failure seemed imminent.

Applying the Enneagram to Leadership

For managers, the Enneagram opens doors to better understanding and motivating their teams. By weaving the language of Enneagram and Blindspots into daily conversations, managers can challenge their salespeople to reflect and grow. Questions like, “How will you prevent Blindspots from affecting this sales call?” or “How are you incorporating these insights into your plans and execution this week?” become tools for transformative growth.

My Advice to Sales Professionals

If you’re new to the Enneagram, my advice is simple: Start the journey. The Enneagram offers unparalleled insights into yourself and others. And if you’re curious about how it could revolutionize your sales or leadership approach, I’d be happy to help you explore its potential.

If you’d like to learn more, give me a call. This might just be the breakthrough you’ve been looking for.