Sailing Leadership Lessons
As a natural servant leader, I had lots to learn by taking the helm as captain.
As a professional program manager in the technical realm, I’m comfortable in my wheelhouse when I’m facilitating the work of others, assisting teams with managing their process and meeting goals, communicating, prioritizing, developing timelines, reporting on status, and creating order from chaos. I generally work with multidisciplinary teams or teams with special skills. I solicit their expertise and opinions to help articulate their dependencies, challenges, milestones, and requirements. It’s my job to help them remove obstacles to their success. My comfort zone is being of service and leading the team from behind.
I also spent some years as a professional sailing captain, where I was asked to step up, take the helm and manage teams differently. It turns out this experience was invaluable to my role as a program manager.
I love sailing. I grew up boating on the east coast and had many adventures on the water. After I made my way out to the San Francisco Bay area, I connected to a sailing school in Sausalito. Originally, I reached out to them to get some local knowledge about this world-renowned sailing bay, and eventually, they invited me to teach and captain for them.
The woman who ran the school was passionate about promoting her program “Women on the Water” and encouraged me to teach. I was reluctant at first, but she pressed me into service, and for that, I will be forever grateful. Even though I had a lifetime of experience on the water, I assumed I was not qualified. I had a classic case of the Confidence Gap. Fortunately, she saw potential in me and managed to overcome all my objections. Her partner in running the marina, the sailing instruction program director, took me under his wing and became my mentor. I went through a rigorous US Sailing training and credentialing program and eventually got my US Coast Guard captain’s license. All because of their confidence in me and their unwavering encouragement.
Lesson 1: Mentors Matter
For me, it was profound to have mentors who saw my potential, encouraged me to step into a new role, gently pushed me through my discomfort, and stayed by my side to support me as I gained confidence in my new role.
Lesson 2: Act as If
A lot has been written about imposter syndrome, a cause of suffering for many professionals. It’s the state in which a person in a role secretly does not feel deserving of the position they’re in.
I had an amazing lesson in this from another female captain. Our first adventure together was a sailing trip in Greece. We had a full crew of newbie female sailing students on a 56-foot sloop. It was a big boat and a lot to handle in unfamiliar waters. To make matters more interesting, we were required to ‘Med moor’ in every port. This complicated maneuver requires the boat to tie up backward to a stone wall, first dropping anchor, backing up perfectly between existing moored boats and their anchor lines, and then heaving docking lines to awaiting helpers on land. Very stressful, to say the least. She instructed the crew with aplomb, handled the boat with precision, and got us safely and securely tied up for the night, each and every time. Wow, what a role model.
What I didn’t realize at the time is that she was also insecure at times and wondered if she had the skills or leadership to manage the boat and the crew. She clearly did. But in her moments of self-doubt, she acted as if she was confident and that she knew what she was doing. She wasn’t faking it; she did have the skills. But she wasn’t sure herself. But those of us on the boat and the docks had no idea her confidence was wavering. She acted as if she was the captain. And she was.
Lesson 3: Respect Rank
In the world of software and product development, there’s an emphasis on empowering self-directed teams. It’s been an evolution since the old-school factory models of a manager lording over the workers from behind a glass wall up above the floor where the workers toiled, with direction and information coming from on high, without input from the workers themselves. In the more modern approach of empowered teams, the skilled experts doing the work can often be in a better position to make important decisions about the best ways to accomplish their goals, and they learn, evaluate, and modify their methods as needed, not waiting for direction from ‘the boss.’
Self-managed teams can be highly effective, and still, there’s an appropriate place for hierarchy and rank. I learned this very clearly as I stepped into my role as sailing captain.
There are times when situations come up on a boat, and there’s not enough time to take a poll about what everyone thinks. There are safety and communications issues that cannot wait until the team discusses and approves. As a captain, I can’t wait to take opinions or have a debate in those critical situations. Something has to be done NOW, exactly as I say. I can explain later. Don’t argue. Just do it.
This is when rank matters and the team needs to understand and act accordingly. This took me some time to get used to. What helped me fully step into the role of captain and sometimes barking orders was that it was ultimately about the safety of my crew, even if they didn’t fully understand at the time. Lives can truly be at stake, and the captain’s direction needs to be clear and crisp and acted upon immediately.
In the corporate setting, lives may not be directly at risk, but certain situations can impact multitudes. The team may not have all the information for one reason or another. Leaders may have to issue commands, and for that to work, the team will need to have trust and act accordingly.
Lesson 4: The Captain Can Call the Shots and Still Consider the
Crew’s Input
Early on in my sailing career, I had the opportunity to crew on a 50-foot sailboat on a trip from Connecticut to Bermuda. The owner/captain was clearly in charge and had the expertise and position to call the shots. What impressed me was that whenever he needed to make an important decision, and there were time and opportunity, he huddled the crew and, one by one, asked each of us our opinion and recommendation. He thoughtfully asked questions, heard all of our points of view, considered all the input, and then decided. Of course, he could not do this in the heat of the moment when something intense was going down on the boat, but when he could, he did. This style made a big impression on me. What I learned: even when you are in charge, ask your team about what they think, and you’ll all be better off. You will benefit from various points of view, and the crew will feel involved and heard when it is important, especially when lives depend on the decision.
Lesson 5: The Right Tool for the Job
What I’ve taken away from my roles as program manager and sailing captain is that there are many styles of leadership: collaborator, coach, commander; delegator, expert, facilitator; pioneer, relationship builder, visionary — the list continues. You can lead from the front or the back. Or you can coach from the sidelines. There’s an appropriate time and place for each, depending on the circumstances, the environment, and the goals and culture of the team and the broader organization.
Do you have leadership lessons you’ve acquired outside of the office? I’d love to hear about them.
Wishing you fair winds and following seas.
