My wife, Alisha, and I recently found ourselves in a double kayak, paddling through the mangroves outside Miami. Full disclosure: neither one of us had any idea what we were doing. We had never been on that particular tour, we had no real plan, and somehow, we ended up at a place called Raccoon Island. I would never have chosen that destination in a million years. But Alisha wanted to go there, so we did. Which, if you know anything about our marriage, is pretty much how everything works.
Somewhere in the middle of the experience, we overheard someone nearby mention how good we looked out there. And here’s why: Kayaks were tangled up everywhere around us. Partners were barking at each other. Paddles were clashing. One couple drifted so deep into a mangrove cluster that a guide had to wade in and physically drag them out. No amount of practice seemed to help. The couples who were struggling at the beginning were still struggling at the end.
So, what were we doing differently?
Nothing. And everything.
I have a saying that I lean on hard: “Anything with two heads is a monster.” I have used it in business for years, but honestly, Alisha and I lived it long before I ever applied it to a boardroom. Early in our marriage, we just kind of fell into a dynamic that worked.
She picks the destination.
I steer.
And before anyone gives me credit for that arrangement, let me be clear: We go where she wants. I just drive. We have been operating that way for over 35 years, and I cannot imagine it any other way.
There was no power struggle in that kayak because there was never a power struggle to begin with. That was settled a long time ago.
But it was not just role clarity that made the difference. It was trust—real trust. The kind that only comes from shared experience. Alisha has watched me operate under pressure. I have watched her. We have been through things that tested both of us, and we came out the other side still choosing each other. Because of that, I don’t have to explain every move I make, and she is not second-guessing my direction. We have put in enough miles together that the communication is almost invisible.
I watch organizations try to manufacture that in a kickoff meeting, and it never works.
Leaders want a synchronized team but are not willing to invest in what synchronization actually costs. They hire talented people, point them toward a goal, and then wonder why the boat keeps drifting. The problem is almost never strategy. It’s the fact that trust has to exist before strategy can do its job. The hardest challenge is not getting your team in sync with you. It is getting them in sync with each other.
In a double kayak, you have one partner to manage. In most organizations, you have departments that have never really worked together, people operating on completely different assumptions about who is steering and why, and tensions that nobody has ever had the nerve to name out loud. And trust does not show up because you scheduled a team-building day. It shows up because you invested the time, had the hard conversations, and built enough shared experience that people actually know how each other move.
Your team is already telling you where they stand—not in what they say, but in how they look at each other when a hard decision lands on the table. They tell you by whether they instinctively know who steers when things get uncertain and in whether there is enough trust in the boat that nobody panics when the water gets rough.
You cannot build that in a crisis; you have to build it before you need it.
Have the conversations that feel unnecessary right now. Figure out who drives and who picks the destination. Put in enough shared miles that when things get hard, nobody has to stop and think.
The teams that skip that work end up stuck in the mangroves, waiting to be rescued by someone else. Raccoon Island is waiting for the teams that get it right.
Trust me. It is worth the trip.