February 26, 2025

How Do Captains Lead?: A Snake in the Garden


The quick response marine assistance industry in the United States was born from a policy shift in the 1980s. When the Reagan Administration instructed the U.S. Coast Guard to step back from non-life-threatening rescues in 1985, the private sector stepped in to fill the void. The result was an industry not unlike the AAA of […]


The quick response marine assistance industry in the United States was born from a policy shift in the 1980s. When the Reagan Administration instructed the U.S. Coast Guard to step back from non-life-threatening rescues in 1985, the private sector stepped in to fill the void. The result was an industry not unlike the AAA of the highways but on the water. Originally, in many areas the launch and growth of the industry was very dynamic. Companies competed fiercely, sometimes ruthlessly, in an untamed and rapidly developing business landscape. I was there from the beginning, working for one of the founding companies in New England in 1989. It was the Wild West: aggressive competition, the constant threat of regulatory overreach, and an ever-present battle between the “duty to render aid at sea” culture and the more sensible approach and logistical need to charge for rescue services because the resources used in that rescue required significant investment and risk on the part of the company owners. 

As marine assistance grew into an industry, best practices and regulatory structures attempted to shape its evolution. Membership plans ensured boaters received help when needed, and salvage law provided fair and ethical compensation for the work of saving vessels and livelihoods at the risk of the private towing company’s investment in people and equipment. But the realities on the water were often much messier. When a boat owner is standing knee-deep in water, watching their investment sink, they aren’t thinking about admiralty law or the nuances of fair market compensation. They see a captain with a pump and a bill.

Company and industry growth wasn’t just about technical skills or marketing strategy. There were ethical dilemmas, risk management considerations, and leadership challenges that no training manual or regulation could fully prepare us for. Like many new industries, risk was not something we proactively addressed. It was simply part of the job. Risk equated to reward, and the cowboys of the sea rode aluminum and rubber horses, jet-driven and high-powered, chasing that reward. We managed risk, of course, albeit informally. We needed to in order to get home safely. Eventually, as the industry grew, its need for more formalized risk management inevitably percolated.  

Fast forward to the early 2000s, when my career had evolved from driving boats into training and consulting about them. I was tasked with developing a risk management curriculum for the marine assistance industry as a whole. It was effective. It raised a lot of great awareness, and it helped many captains nationwide develop professionally. Still, I witnessed firsthand how theory and practice can be hard to reconcile. Even as I trained others in risk mitigation, I continued to work as a per diem captain for the same company where I had started years before. Convincing the captains I had grown up alongside to adopt formalized risk policies and even following them myself (as opposed to just trusting my skills and my gut as I had always done) was new, and it was not always comfortable, to say the least. Especially when we were staring money in the eye. We knew our limits. We pushed envelopes. We didn’t like the new rules of the game we started. Marine assistance captains, by nature, resist constraint. We live for speed, power, the immediacy and rush of the job, and especially for the money. However, it was because we, as a company, were the very best in the business that most risk management practices eventually stuck. We and a handful of others knew that it was us who had started the industry. We were the industry leaders, and other operators looked to us to set the standard. So we did the right thing. Those policies and self-regulation have served the industry very well. 

In their essay titled Principled Leadership: A Framework for Action by MaryAnn Glynn and Heather Jamerson. The authors explore the idea that principled leadership is not just about possessing the right values but about being able to act on them, especially in environments where pressures push leaders away from their ethical foundations (Glynn & Jamerson, 2010). They reference the well-known Stanford Prison Experiment, where participants unknowingly crossed ethical lines, believing they were simply fulfilling assigned roles. The experiment demonstrated how environmental pressures and authority structures can lead individuals to act in ways they might not recognize as problematic until viewed from an outside perspective (Glynn & Jamerson, 2010). The study demonstrated that even when individuals are trained in proper protocols, instinct, situational urgency, and environmental pressures can override those teachings. The implication is clear. You can write about values, preach about safe behavior, and structure leadership models around steadfast integrity, but when faced with a dynamic and often chaotic environment, aggressive competition, financial pressures, and cultural norms that resist change - principles and policies alone may not be enough.

In the early days of marine assistance, the industry saw a culture where it was easy to get caught up in environmental pressures. Those pressures mirror the experience of those in the Stanford Prison Experiment, who did not recognize they were crossing lines until external observers pointed it out. Just as the participants in that study acted according to the pressures around them, we in the marine assistance industry sometimes only saw our mistakes in hindsight when after-action scrutiny forced us to look at them constructively. The best practices I taught in risk management had clear, rational justifications. But when the call came in, when a boat was in distress, and when time and money were on the line, captains still reverted to instinct and experience. They did what worked, not what was written in a policy manual. Leadership, as Glynn and Jamerson argue, is relational. It exists in the interplay between leaders, followers, and their environment. It is shaped by cultural schemas and organizational structures, not just individual character (Glynn & Jamerson, 2010).

One method I used to evaluate decisions while running my response vessel was asking myself, "How would this sound out loud?" Understanding that "out loud" meant coming from the mouth of a reporter or, worse, an attorney. This simple mental exercise helped me gauge the sensibility and optics of an action before committing to it. If a decision sounded like a bad idea out loud, I didn’t do it. If it sounded like a bad idea but had a strong justification, such as saving a sinking boat but risking my own, I ensured the narrative was bulletproof. That meant identifying ways to mitigate risk, bolstering my operational or decision-making stance, and ensuring that the decision aligned with the principles of leadership and responsibility.

The lesson? You can document ideal behaviors, develop robust training, and enforce policies, but the snake never truly leaves the garden. There is always temptation. There is always the lure of cutting corners, pushing limits, and chasing the highest reward with the least resistance. Principled leadership is not just about crafting the proper framework. It is about understanding the reality that leadership exists in tension. The best leadership is not about eliminating the snake but recognizing its presence and navigating around it, constantly, imperfectly, but intentionally. It’s about putting protections in place for our followers' weakest moments and worst decisions. It’s about enabling followers to thrive by doing the right thing.

We solved the early concerns of the early days in the industry very effectively. Although I do not do much work in that industry anymore, I still have good friends and great memories from it. I still ponder on ways to create resilience in the culture of risk management and good leadership within it.  One approach is through virtuous leadership, where leaders epitomize and cultivate character excellence in themselves and those they lead. This means fostering an industry-wide culture of accountability, reinforcing best practices through clear expectations, and leading by example. Another strategy is embedding thoughtful decision-making into the organizational structure, ensuring that reward systems and operational procedures align with principled leadership. Regular training, mentorship programs, and fostering an open dialogue about decision-making or operational challenges can also help keep the snake in check. Ultimately, the key is not to assume virtue and risk management will prevail naturally but to create an environment where it is continuously nurtured and reinforced.

Just as we learn on the water to respect risk rather than eliminate it, leadership must acknowledge human nature. It must bridge the gap between individuals and culture, always mindful that the snake is cunning, arrives unexpectedly, and is ever present in the garden.