What I Learned from Coaching a CEO and Her Brother

When I first started coaching, one of my earliest referrals was a small, family-owned business. The CEO had brought in her brother to serve as the CFO. On paper, it looked like a good decision because he cared deeply about her and the business, and she trusted him. But below the surface, old family patterns were about to collide with the day-to-day realities of running a company.

In their family, money was emotionally charged. His role as CFO, where he was tasked with making financial decisions and advising on risk, activated deep fear. As CEO, she was driven, visionary, and ready to leap, ways of being that activated his anxiety. She was wired for possibility. He was wired for protection. The dynamic was volatile.

At the time, I didn’t have the tools I have now. I could see the tension, I could feel the reactivity between them, but I didn’t know how to help them name or navigate it. I had no framework for helping them understand how their personal histories and patterns were bleeding into the business.

Now, years later, I look back and know: That was a pivotal moment for me.

Today, I know how profoundly family systems show up in family businesses. That experience sparked a deep curiosity in me. I wanted to understand what made those dynamics so sticky, and more importantly, how to help people work through them in a way that preserved relationships and protected the business.

If I could go back now, I’d bring the Enneagram into the room. I’d help them see how their personality types shaped their responses to risk, money, and conflict. I’d help them build compassion—for themselves and for each other. I’d bring in the tools of systems coaching, which are all about revealing the system to itself, without blame, and helping it move forward with more awareness and choice.

What I’ve come to see is that family business is rarely just about strategy. It’s about legacy, identity, loyalty, and often unspoken rules about love, duty, and success. The very things that make families strong can also make it incredibly hard to run a business together, especially when conflict avoidance or caretaking patterns from childhood get reinforced in professional roles.

In that first engagement, the brother eventually made the painful decision to step out of the business. It was harming his relationship with his sister and with her kids, his nieces and nephews. And at their core, they were a close family. Once the business was no longer between them, healing could begin. They’re in a good place now. 

That experience shaped the work I do today. I help families in business see that what they’re experiencing isn’t just personal—it’s patterned. And that awareness opens the door to choice. You can learn to lead each other differently. You can set clearer boundaries. You can decide how you want to be in business and in relationship with each other.

What I love most is helping family businesses have the right conversations: ones that honor both their humanity and the structure of the work. Ones that ask:

And if someone’s in the wrong role? That’s not failure. That’s information. Let’s get honest about it—and make a plan. Because leadership is about being at choice. Not just going along out of obligation or fear.

So much of my passion for systems coaching, for the Enneagram, for helping teams and leaders bring awareness to their blind spots, started with that family business. That “failure” changed the way I coach. And it’s why I love the work I do now.