Leadership and teamwork are fundamental drivers of organizational performance and long-term value creation. While executives often draw on mentorship and their formal education, some of the most profound insights about leadership and teaming come from real-world experiences beyond the boardroom. These experiences can offer valuable insights on how to rally individuals around a common purpose, help them adapt under pressure, and collaborate effectively to support organizational success.
James Jackman and Lori Heffelfinger are long-time sailing partners who have spent countless hours navigating the waters around Southern California. Their shared passion for sailing has offered unforgettable adventures, deepened friendships, and added depth to their perspectives on leadership and teamwork. Both seasoned coaches, James and Lori often draw from their sailing experiences to help leaders and teams discover new ways to collaborate, adapt, and grow in the face of uncertainty and inevitable change. In this conversation, James and Lori share how lessons learned on the water have directly influenced their approach to leadership and teaming in organizations.
Leadership Is Like Sailing
Much like leadership, sailing is about setting a course, working together as a team, and adapting when conditions inevitably change. When asked about the parallels between sailing and leadership, Lori noted: “Sailing and leading, or sailing and teaming are essentially the same. They kind of go hand in hand. On a sailboat, the skipper sets the direction, but success depends on the crew. Everyone must fulfill their role while also being ready to step in and adapt when conditions change.” Lori explained, “This requires a lot of trust—between the crew members and skipper, and between employees and leaders. It’s really about being able to lead and follow as needed.”
James added another important layer: “One of the key parallels between leadership and sailing is changing roles. There are times when either one of us is in the lead on the sailboat, and the other person steps in and changes up roles, because they would be better at doing it. The same can be true in an organization.”
Building Trust and Collaboration
In both sailing and business, teams achieve success when each member performs their role reliably and behaves in a way that builds trust. Sailing has influenced how James and Lori think about trust within teams. Lori shared: “Honest, open communication and sharing of vulnerabilities is what builds trust. For both sailing crews and employees, trust grows when they are honest about their abilities, limitations, and readiness to contribute.” Not sharing vulnerabilities that could be supported by fellow crew members can be damaging to the team and create safety issues while sailing.
James expounded, “Being an effective leader is about being authentically confident, and then acting on that confidence… knowing who’s going to do what, and when does someone else have to step in and help them get that done.”
Click this link Honest Communication Video to listen and watch Lori and James talk about what's important to be an effective leader.
