Everything I Know About Leadership I Learned on My Sailboat

Yes, I founded and ran a successful company. I went to Harvard Business School and worked as a management consultant with Arthur D. Little, Inc., to senior private company and government agency leaders. I also wrote my leadership guidebook, Create the Future, about how to be more creative and make difficult decisions for your company when you have an exciting opportunity or face a major threat.

I race my J 130 sailboat, CHARIAD, from Marblehead, Massachusetts. We sailed the Newport to Bermuda race in 2024. Preparing for a challenging sailboat race requires mastery of the full range of leadership and management skills needed to run a successful business. The boat’s crew members help prepare the boat for our racing season and train for the high-performance racing we do. They are all volunteers who come together to race and to win. I learn about leadership every time I go racing.

To be successful as a company’s leader, you must have a compelling vision of success for the company that you communicate to your team, investors, and customers. You must have a business strategy to compete and win and a business model that delivers a competitive product or service to your customers while making a profit. Racing a competitive sailboat collapses all of these requirements for business and leadership success into one sailing season and into every on-the-water race.

Little kids sail on Optimists. Men and women cruise and race sailboats worldwide. Professional sailors are celebrities racing high-tech boats in the America’s Cup and other regattas. Sailing is fun and rewarding as recreation and as a competitive sport for young and old.

Some sailors excel as individuals on a one-person boat such as a Laser. For them, the challenge is personal – the physical mastery of the boat by yourself while competing in the complexity of changing wind and waves. Others race on boats such as J 24s with two or three other crew members trimming the sails. A talented skipper can do well directing the crew on sail trim as the wind changes. The skills required for racing success in a smaller boat are the same as those of an entrepreneur or the CEO of a startup or small company.

My recent sailboat racing has been on larger boats with eight to ten crew members. As skipper, I cannot tell nine team members what they should do every minute of the race. Success requires specialized skills, collaboration, communication, and a leadership structure within the team. We practice and perform as a team, and each crew member has a specific job on the boat. Crew handling sails on the bow of the boat and those trimming sails in the cockpit operate as largely independent sub-teams.

My role as skipper is to provide overall team leadership. I communicate goals and am the orchestra leader signaling when we will tack and jibe. Each team member must know their role when we launch a spinnaker or tack the boat from port to starboard.

Every other year, sailboats from around the world come to Newport, RI, to race 636 miles to Bermuda. (www.BermudaRace.com) 176 boats raced three to five days across the turbulent Gulf Stream and the Atlantic Ocean. Bermuda is wonderful once you are there, but it is a small island far from Europe or America.

Boats racing to Bermuda must be ready to compete in whatever conditions we could experience at sea, and the crew must train to work together as a team in all conditions. To prepare for the race, I divided up responsibilities for getting us to the starting line. Individual crew members were responsible for provisioning, logistics, boat preparation, and safety. We had a Compliance Officer who dealt with the race organizer’s requirements and international travel documentation.

Most of us took a full-day Safety at Sea training course that included jumping into the water, staying afloat, and getting into a life raft. Each crew member was responsible for training the rest of the crew on specific safety at sea procedures, such as what to do if a team member fell overboard.

During the race, we divided into two watches responsible for sailing the boat four hours at a time, each with a watch captain. The navigator designed our race strategy, monitored progress, and got us to Bermuda. The navigator and I, as captain, floated between the watches.

We needed a strategic plan for the race given the course, the weather, and our competitor’s capabilities. Before the Friday afternoon race start, we used Expedition routing software to find the fastest course to Bermuda, considering the expected wind and current and our boat’s performance potential. Crossing the Gulf Stream at the right place with three or four knots of current, either with us or against us, is an early navigation challenge. Using the information we had about the Gulf Stream, the weather over the next several days, and our boat’s performance characteristics, we charted a course above and below the straight line path from Newport to Bermuda, the layline. During the race, we adjusted our race strategy as conditions changed.

Every boat must prepare for high wind and no wind and for survival with only what is on the boat. Much of the race is outside of Coast Guard’s rescue range. Two boats sank during our race to Bermuda, and another sank while returning. Fortunately, other racers rescued the crews. We did not experience storm conditions, but the constant high winds and high, banging waves eventually damaged the boats. The rod rigging running from our boat’s stern to the top of the mast failed 100 miles short of Bermuda, and we stopped racing to keep the mast from falling into the water.

Racing a sailboat is a combination of optimizing complex technologies and performance art. During the race, we are maximizing our speed to the next mark of the course. We are not heading directly towards the mark on a typical race leg. Our compass heading is 20 or 30 off the direct heading to the mark, and we are working hard to maximize our projected speed towards the mark. We closely monitor the boat’s speed through the water and its angle to the wind. We try to match these values to the optimized values predicted by computer modeling. We adjust the sail combination, sail trim, and angle of the boat to the wind to get to the boat’s projected speed potential towards the next mark.

Steering the boat at 3 AM in a deep, cold fog or driving over high waves calls on different skills. As the skipper, I face two challenges. The first is my personal challenge – how to keep the boat driving fast in these challenging conditions. The second is how to share what I know with the team while giving them space to master these skills themselves. I am a good helmsman, but I can only be at the helm for short time periods. The only way we could get to Bermuda and be competitive in the race was for the crew to drive us there at top speed while I was sleeping below.

Lots of data are on display: boat speed; wind speed; wind direction; heading; etc. When racing, I monitor this data to optimize the boat’s performance. The lights and swirling data can distract me while I am driving the boat at night in difficult conditions. I do better relying on what I am experiencing and sensing – the heel, the wind on my face, the sound of the waves, and the dim line between the fog and the water. Yes, I glance at the illuminated compass to be sure we were on course, but being in touch with my senses is far more important than obsessing with the distracting lights and data. I sometimes turn them off.

Two crew members were skilled helmsmen when we raced to Bermuda. We spelled each other during the particularly difficult conditions. Their initial instincts were to focus on the instruments. I coached and encouraged them to get in touch with their senses. “May the force be with you,” was the message. Our best performance against competitors was when we had a general sense of what the instruments said and danced with the waves and wind.

Preparation, teamwork, strategy, tactics, and performance are the requirements for success for every race, as they are for every business. Once the race is underway, we must execute our strategic plan, sail the boat to its highest potential, and tactically compete against the other boats.

Every time we race, I let the force be with me, and I grow as a leader.

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