What Finding My Wife Taught Me About What Most Leadership Teams Never Do

Most executive teams are standout skilled at strategy and execution. And somehow embarrassingly unskilled at the one behavior that makes both possible: clarifying what they want early and acting in lieu of certainty.

“I’m based in Dallas. Would love to meet you,” I wrote while in New York on business. Rebecca replied, practical and curious: “Dallas is a great city! How would this work me being based in NY?”

I answered: “Step one, I visit. Step two, you fall for me. Step three, we take it from there.”

She said yes. At the time, I did not think of this as a leadership lesson.

On August 22, 2025, I stepped into Osteria La Baia in Midtown Manhattan. My favorite part of that first evening was simple: she smiled and said yes when I asked to sit next to her.

Five hours later, she declined another mocktail and said, “Let’s end on a high note.” Out on the streets of New York, I assumed I’d been let down easy.

I changed my flight anyway and asked her out again the next day. That night, I texted my mother: “If she’ll have me, she’s the one. I found my wife.”

Only months later I learned Rebecca had texted her brother that same night: “I didn’t know dating to find your husband could be this easy.” The next day was Central Park, coffee at Bluestone Lane, lunch on the Upper East Side, and the East River at sunset. I extended my stay five times that first weekend.

The following weekend, I returned. Rebecca introduced me to her family. Within three weeks of meeting her, I asked her father for his blessing. The next day, in front of Saint Patrick’s Cathedral, I proposed.

We met in August. We were married in January.

Since then, we’ve been building a life together: an Ecuadorian, Latina woman with Jewish roots and a Catholic Irish-American married in Manhattan, now building a home in Delray Beach.

Rebecca embraced the Catholic faith and, after a decade in educational leadership, joined my consulting practice. We move as one.

Rebecca Sullivan found a man who cherishes her, loves her, and challenges her. I found a woman of depth, loyalty, and a beauty I cannot fully take in. She is my true companion.

What This Says About Leadership Teams

That story is not really about romance. It is about the ability to name what you want clearly, commit to it publicly, and move before conditions feel safe.

I knew what I wanted. I said it. I moved on it before I had any guarantee it would work.

That is not how most leadership teams operate.

The Clarity Problem in Plain Sight

When I sit with executive teams, I consistently find one of two problems, sometimes both at once.

The first is strategic ambiguity: leaders who cannot name their top three non-negotiable priorities without qualifying them into meaninglessness.

In my experience, rarely is this an intelligence problem. Naming priorities means eliminating alternatives. The best definition of this is from Alex Hormozi: Commitment means “the elimination of alternatives.”

The second problem is behavioral ambiguity: leaders clearly see a problem, be it a misaligned peer, a floundering initiative, a lack of accountability. And they say nothing. Not because they do not care, but because they are unwilling to tolerate the discomfort of not only forcing clarity and closure but even of demanding debate.

What Confusion Costs

Execution can never surpass clarity. In the meantime, teams pursue conflicting objectives. And when results end up disappointing, no one can agree on why. Because no one bought in (or even weighed in) on commitment in the first place.

When behavioral ambiguity is tolerated, the most corrosive dynamic on any leadership team takes hold.

The real conversation happens after the meeting.

Decisions get relitigated in the hallway. Trust is lost. As both team leaders and team members learn to stay quiet.

Patrick Lencioni calls this artificial harmony: the illusion of alignment that forms when leaders settle for comfort over truth. While it is one of the most expensive line items on any executive team’s balance sheet, it never appears there.

What You Too Can Do Differently

When I wrote to Rebecca, I did not hedge. When I changed my flight, I did not wait for permission. When I asked her father for her hand three weeks after meeting her, I had no idea he would grant it.

Clarity of intent followed by imperfect action —massive imperfect action— is one of the most consistent traits of the successful leaders and teams I work with. Those leading the healthiest organizations are not the ones who have the most information before they decide.

It is no coincidence that when we measure a team’s commitment against The Five Dysfunctions of a Team, we assess the frequency with which: “The team is decisive, even when perfect information is not available.”

The Question To Ask During Your Next Leadership Meeting

What would happen if I were to ask every person on your executive team to write down, on paper, independently, right now, your organization’s top three priorities for the next 90 days? Would answers match?

If you are not certain they would, you have a clarity problem.

Solving that problem is central to the work we do at Sullivan Practice.

In the end, what clarity brings is the fulfillment and fruitfulness of bottom line success. Sometimes that looks like the risky pursuit of what you want in Midtown Manhattan.

Send me a note with the one place where ambiguity is costing your team the most right now.

If you lead or advise an executive team and recognize these patterns inside your organization, reach out. One focused 30-minute conversation often reveals what’s limiting an entire team.