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Lessons in Vision, Strategy, and Teamwork from Racing Across the Atlantic
I have founded and run a successful company, studied at Harvard Business School, advised senior leaders as a management consultant with Arthur D. Little, Inc., and authored Create the Future, a guidebook on creativity and decision-making in business. Yet, some of my most profound lessons in leadership didn’t come from boardrooms or books – they came from the deck of my J/130 racing sailboat, CHARIAD, on the open ocean.
In 2024, my crew and I competed in the storied Newport to Bermuda Race, a 636-mile test of seamanship, endurance, and leadership. Preparing for and competing in a race like this is a masterclass in management. Every season, every race, condenses what it takes to build and lead a successful business – vision, strategy, structure, execution, and trust.
Leadership at Sea and in Business
To succeed in business, a leader must present a compelling vision, build a winning strategy, and design a business model that can profitably deliver value. On the water, these principles compress into one racing season – and often into every race.
Whether it’s children sailing Optimists, solo sailors mastering Lasers, or professionals competing in the America’s Cup, sailing mirrors leadership. A skipper of a small J/24 may succeed with sharp direction to two or three crewmates. But on a larger racing boat with eight to ten crew, success demands delegation, specialized roles, and seamless teamwork.
As skipper of CHARIAD, my responsibility was not to micromanage, but to set the vision, provide clear communication, and empower sub-teams to act with autonomy. Like a CEO, my role was to orchestrate performance while others executed their jobs independently yet collaboratively.
Preparing for Bermuda: A Strategic and Human Endeavor
The Bermuda Race is no ordinary regatta. Boats and crews must be prepared for all conditions – storms, calms, and the unpredictable power of the Gulf Stream. Preparation required dividing responsibilities: logistics, provisioning, compliance, safety, and boat readiness.
We trained not just for speed but for survival. Crew members completed “Safety at Sea” training – jumping into the ocean, practicing man-overboard rescues, and boarding life rafts. Each sailor took responsibility for teaching others, reinforcing the leadership principle that the best teams are learning organizations where knowledge is shared, not hoarded.
During the race, our crew was divided into two watches, each led by a watch captain. Our navigator and I floated between groups, ensuring alignment with the race strategy. It mirrored business leadership: define the mission, empower team leaders, and maintain oversight without stifling initiative.
Strategy Meets Execution
Success in Bermuda begins before the starting line. Using Expedition routing software, we analyzed wind, current, and boat performance to chart a course that balanced speed and risk. Crossing the Gulf Stream at the right place – where a three-knot current could be an ally or an enemy – was a critical decision.
But as in business, no plan survives unchanged. Conditions shift. Competitors adapt. Strategy must evolve in real time. Each decision on sail trim, course adjustments, and watch rotations carried echoes of business strategy execution – balancing long-term objectives with immediate tactical responses.
Leading Through Uncertainty
The sea is an unforgiving teacher. Two boats sank during our race. Another on its return voyage. We faced constant winds and pounding seas that stressed equipment until our rigging failed 100 miles from Bermuda, forcing us to withdraw for safety.
Leadership under these conditions meant keeping the crew calm, focused, and motivated – despite setbacks. It required trust in the team’s ability to act without constant oversight. It also meant knowing when to prioritize safety over competition, a parallel to knowing when to pivot or pause in business.
Data vs. Intuition
Modern sailboats provide streams of performance data: speed, heading, wind angle, velocity. At night, in fog and rough seas, the data can overwhelm. I found myself relying less on instruments and more on instinct – the feel of the wind, the sound of the waves, the rhythm of the boat.
Two skilled helmsmen initially relied heavily on instruments. I encouraged them to trust their senses. “May the force be with you,” I told them – and when they blended instinct with data, our performance soared.
In business, too, leaders must balance analytics with intuition, using data as a guide but never allowing it to blind them to what their experience and instincts reveal.
Lessons for Leadership
Every race is a compressed lesson in leadership:
Vision – Define success and inspire others to chase it.
Strategy – Chart a course that balances ambition with reality.
Delegation – Trust your team to carry out their roles.
Adaptability – Adjust to changing conditions without losing sight of the goal.
Resilience – Lead with calm in moments of crisis.
Balance – Use data wisely, but don’t ignore intuition.
Racing to Bermuda is not just a sporting challenge – it is a crucible of leadership. Every mile sailed, every wave crested, is a lesson in how to build, lead, and inspire teams.
Every time I race, I grow not only as a sailor but as a leader. Out on the ocean, the lessons of leadership are distilled to their purest form. And each time, I let the force be with me.
