Offshore Sail Training: A Midshipman Skipper’s Perspective
It’s been months since I moored the Commitment (NA-32), a 44-foot sail training craft in the U.S. Naval Academy’s Santee Basin for the last time after my final cruise as a midshipman in the Offshore Sail Training Squadron (OSTS) program. I can no longer remember each distinct day of my voyages, what items needed to be fixed below decks, or even each of my crew members’ names. Come to think of it, I can’t even remember the exact names of all the equipment topside. The good news, however, is that the real value of the OSTS program isn’t found in an academic understanding of sailing, the number of miles sailed, or the speed of the boat. Instead, my three summers spent in the program as a crew member, executive officer (XO), and finally as skipper of an all-midshipman crew taught me invaluable lessons about a far more important topic—leadership—in a way no other training program had been able to replicate up to that point in my career.
This is because the OSTS program is a culmination of three fundamental leadership challenges: the charge to teach a complex art to inexperienced subordinates in a short amount of time; a demanding mission with the potential for real consequences; and the need to accomplish a mission without overbearing directives or formal job descriptions. Simply put, I’ve found no other program at the Academy that is more rewarding, and it deserves greater recognition and appreciation for the fundamental leadership challenges it creates.
Basic Training
When I entered the Academy, I had no sailing experience whatsoever. Then, like every midshipman during plebe summer, I was placed on a 26-foot sailboat for an hour of basic sailing several times over the course of two months. This initial exposure created more questions than answers about this complex art. However, I would not answer these questions until a full year later, when out of a desire to try something different for summer training, I asked for OSTS as my third-class Professional Development Summer Cruise. That was when my sailing career truly began.
Over the course of four weeks as a crew member on the first large sailboat I’d ever been on board, I did my very best to learn what to do, the vocabulary to describe what I was doing, and finally why I was doing what I was doing. I remember reaching only this tier of understanding about basic tasks during the first summer as crew.
What still amazes me is exactly how much I have come to know about sailing and how much more I have yet to fully grasp, despite XO and skipper tours during subsequent summers. It seems every time I reach a desired level of understanding, I find more to learn, and I am sure this will always define my relationship with sailing.
Herein lies the challenge: It took me eight weeks of dedicated training over two summers as crew and then XO, along with additional work during the academic year, to reach some level of proficiency in sailing. How was I to teach an inexperienced crew the art of sailing in less than two weeks to a level where we could safely sail offshore from Annapolis, Maryland, to Newport, Rhode Island, and back?
Heading Offshore
The answer is that it took organization, dedication, and a grounded understanding of what I was teaching, all of which are coincidentally the backbone of good leadership. Specifically, I needed to create a training plan, diligently execute the plan, and then demonstrate my technical proficiency to develop a positive and professional mentor/student relationship on board. Simply put, these same leadership skill sets could not be learned nearly as well in an environment that wasn’t as complex or nuanced as sailing. However, beyond the complexity of the art of sailing, another element in this leadership equation further emphasizes its value as leadership training: the potential for very real consequences.
Other training programs at the Academy often culminate in graded evolutions that incorporate lessons intended during the course of instruction. While this is an accurate way to gauge how effectively information was taught, most final graded evolutions have no direct negative consequences except the possibly of a failing grade. OSTS training, on the other hand, culminates in passage over open ocean. This experience comes with no guarantees—especially when it comes to rudder cables.
All good sea stories start at three in the morning. As skipper, my crew and I were sailing 50 miles off the New Jersey coast during the third day after departing Annapolis, headed for Newport. About 0300 (no moon, full darkness), a sudden squall line moved through our area. Then—because of incorrect execution of a common evolution (maneuvering from starboard tack to port tack) followed by cascading/complicating events—the rudder cable was snapped; the boat now had no steering in difficult winds and seas. Thus, a challenging leadership scenario was created almost instantly and at the worst possible time. After quick assessment, we implemented casualty procedures thatsuccessfully prevented the situation from becoming much worse. Alternate steering was rigged, control of the boat regained, and the Commitment diverted to Freeport, Long Island, for repairs.
There was nothing contrived about snapping a rudder cable. No one could call a “training timeout,” nor were we guaranteed to sail away from the incident without damage to the vessel or serious injury. Thankfully, everyone is able to look back on the casualty and appreciate its excitement and drama because of the exemplary performance of those involved.
This was a scenario that demanded immediate action and had tangible consequences for all on board. As a result, I will likely never forget the lessons I learned about leadership that night, or in the ensuing months of review and reflection. And no, such a meaningful scenario cannot be mimicked without the genuine challenge and risks associated with the realities of skippering a sailboat on the open ocean.
Leadership Autonomy
Finally, and most important, I can proudly say that I was never told how to do my job as XO or skipper. This does not mean I was not given pointers, suggestions, and excellent role models on which to base my leadership style. However, I could skipper my crew as I saw fit, as long as the mission was accomplished safely and completely. Compare this with common leadership training, and the importance of this autonomy becomes obvious.
For example, during the academic year at the Naval Academy, there are many leadership billets, each with their own challenges. However, large amounts of instruction are usually given on how best to accomplish the mission, and, because of this, it is sometimes hard to gain the broader leadership experience from these training evolutions. If one is not granted the leeway to fail, one cannot possibly learn the lessons that are best learned by falling short. Thus, the fundamental difference between OSTS and other leadership training environments is defined. Failure is possible and not unexpected in the OSTS program, and such failure is always accompanied by genuine consequences that are inherent to sailing on the open ocean. These failures are always used as a teaching tool, and so the full experience of leadership can be realized.
All training is what one makes of it. However, the OSTS program’s willingness to expose midshipmen to the naturally complicated art of sailing, genuine consequences, all with the freedom to fail and learn from one’s mistakes, are what make the OSTS program so rewarding. I will always maintain that no other leadership development environment at the Naval Academy is inherently more enriching than the OSTS program; it is leadership training at its finest.