At the beginning of this year, I bought a small, trailerable Com-Pac 16 sailboat. Cheap. Turns out there’s a reason for that — and it’s not that I’m a good negotiator or hunter of fabulous deals. It turns out it was in need of far more work than I expected — work amounting to structural and water ingress issues around the keel. I hadn’t sailed or worked on a boat in 23 years, since shortly after my daughter Sarah was born.
And I quickly found myself in over my head.
Hmmm. Kinda reminds one of leadership, doesn’t it? Things can look so simple from the shore but get way more complicated once you set sail.
Know the Real Condition
I assumed my two-plus-decades-old knowledge would serve me just fine as I inspected the boat I purchased. However, hidden problems in the hull and keel — lurking below the existing bottom paint — proved to be far more extensive and structural than I anticipated.
I find leadership to often be similar: We see the obvious, assume our past experiences are sufficient, and often lack the ability to see what is hidden. The result? Surprise discoveries in organizational challenges — sometimes structural in their nature and often lurking beneath the surface or under a thin façade.
Cultural gaps, trust issues, poor communication, accountability gaps, and unspoken assumptions are the keel cracks and water ingresses of a team that undermine their structural integrity. Ignoring them can cost trust, energy, and results.
Recognize Roles and Strengths
We have to remember as leaders that not everyone sees every opportunity the same. Take my girls for instance. My youngest, Leah, is eager to learn how to sail. She likes to figure out how things work. Sarah, not so much — but that doesn’t mean she brings no value or offers no contribution. Company, moral support, and fun are all assets on a boat, and she’s masterful at that. (And besides, someone has to be responsible for the snacks and beverages, and her boyfriend is a consummate foodie, so welcome aboard!)
Leaders must recognize capacities and preferences. Each team member has a natural role that can be nurtured and capitalized on. One of my core tools with leaders and teams, The Core Values Index™, helps with that by highlighting differences in unique contributions — Builder, Innovator, Merchant, Banker — and helping us align work with strengths that maximize performance. Forcing someone into the wrong role can create frustration and inefficiency, especially when there’s a “right” role that allows them to thrive.
Patience Over Quick Fixes
My instinct with the new boat was to launch immediately. Heck, I just wanted to get back on the water. But rushing would have meant missing critical repairs and causing even more water and structural damage.
Leaders, too, can fall into the “fix it fast” trap that brings short-term gain but painful long-term consequences. After all, spending my warm, perfect summer working on the boat rather than sailing was not the plan. But the resin and fiberglass work required strict temperature constraints — it couldn’t be put off until colder months when I’d be out in the rain on my driveway.
Slowing down allows for observation, diagnosis, and better long-term problem solving. It creates space for real support, higher-quality decisions, and sustainable growth.
The result? Teams that develop without burnout, perform longer, and operate with fewer structural weaknesses.
And remember, the leader is seldom in the trenches of the day-to-day emergencies that require immediate action. They usually have the luxury of time — to research, think, inquire, assess, verify, plan. As a leader, you are in a position to see the bigger picture. And in doing so, you can remove stress rather than add to it.
Leadership, like boat repair, requires keen observation, patience, diligence, mistakes, learning, flexibility, and intentional decision-making. Inspect the “hull.” Know your crew. Don’t be afraid of what you don’t know. Plan thoughtfully. When you do, the confidence you build into the ship can carry a team safely through rough waters and challenging crossings — successfully and for countless years to come, with confidence.
Photo by Jonathan Smith on Unsplash
