My understanding of leadership wasn’t shaped by a single moment. It was shaped over the course of a few short weeks. First at Recruit Training Command Orlando and then aboard the USS Vreeland (FF-1068). Those experiences became the foundation of the discipline-first, accountability-driven leadership philosophy that has guided me ever since.
I still remember standing in formation on my first morning in boot camp after getting our uniforms. Before then, I had never given much thought to how clothes fit. Then I put on my Navy uniform. It was tight where it should have been loose and loose where it should have been tight. I was an average-sized kid, yet somehow everything about it felt wrong. It was uncomfortable in every possible way.
As I looked around, I was convinced everyone else knew exactly what was happening. They seemed to understand where to stand, what to do, and what was expected of them. I felt utterly clueless.
Then came what everyone expects from boot camp: yelling, screaming, trash cans banging, and a pace that never seemed to slow down. I found the whole experience overwhelming and confusing. I honestly wondered whether I belonged there.
One of my Company Commanders noticed.
He pulled me aside. I braced myself, all this guy ever did was yell. He smiled and said, “You’re going to be okay. I believe in you. I’ve seen recruits far more screwed up than you make it through boot camp. You’re going to make it too.”
That was it.
15 seconds.
He didn’t lower the standards. He didn’t make boot camp easier. He simply gave me confidence that I could meet the challenge.
He was right, he made a difference, he got on my level and reached me with authenticity.
A few weeks later, somewhere in the middle of boot camp, we were told without warning that we were taking our swim qualification.
To my surprise, many of the recruits around me couldn’t swim. I remember quietly wondering if they fully appreciated that they had joined the Navy.
For me, it was the highlight of the day. I had worked as a lifeguard throughout high school and loved being in the water. Whether it’s a swimming pool, a lake, or the ocean, swimming has always been one of life’s great pleasures for me.
We marched to the pool, and the instructions were simple: walk off the diving board, don’t jump and don’t dive, surface, then swim to the opposite end of the pool.
That was all we were told.
I happened to be first in line. I stepped onto the board, walked off exactly as instructed, crossed my ankles, pointed my toes, and entered the water cleanly.
Almost immediately, before I reached the surface, I felt a hand grab me.
Then another.
Without thinking, years of lifeguard training took over. My first thought was that someone had fallen into the water and was in trouble. I secured both wrists, rolled the person into a controlled cross-chest rescue hold, and calmly said, “I’ve got you. You’re okay. I’m getting you to the side.”
That’s when I heard everyone yelling.
The entire recruit company was laughing. Both Company Commanders were shouting. As I reached the side of the pool, I finally realized I hadn’t rescued a recruit at all. I had “rescued” the Navy safety swimmer who had been stationed beneath the diving board in case one of us got into trouble.
No one had told us she was there.
One senior sailor standing nearby laughed and said, “I think the kid knows how to swim.”
But looking back, I took away something much more important than a funny story.
My Company Commanders were excellent leaders. If I had to do their job today, I’d probably make a hundred mistakes for every one they made. This wasn’t about criticizing them. It was about recognizing that even good leaders can miss something important.
One critical piece of information hadn’t been communicated: there was someone in the water who might make physical contact with us.
The order was clear.
The context wasn’t.
Because I lacked that context, I interpreted the situation based on the experience I already had. I wasn’t ignoring instructions. I was responding exactly as my training had taught me.
That experience taught me that leadership isn’t only about giving clear orders. It’s also about providing enough context so people can make good decisions when the unexpected happens.
A few weeks after graduating boot camp, I reported aboard the USS Vreeland (FF-1068), where I learned my third lesson.
After a long day of chipping paint, priming, and repainting sections of the ship, a few of us were assigned to sweep the flight deck before turning in for the night. The Vreeland had a small helicopter landing deck, but we didn’t even have a helicopter assigned to the ship at the time. It was late, I was tired, and all I wanted was to rack out.
As I swept, I noticed a small pile of debris tucked against the edge of the flight deck.
I remember thinking, It’s just a little bit. We don’t even have a helicopter. Nobody’s going to notice.
I started to walk past it.
“Stop.”
My petty officer had been watching.
“Go back and get every bit of it.”
After I finished, he explained why.
“That’s foreign object debris. Today we may not have a helicopter, but tomorrow one could land here. Rotor wash can turn that debris into a projectile. It can injure a sailor, damage an aircraft, or destroy an engine. Standards don’t change because the risk isn’t obvious.”
In that moment, discipline stopped feeling like punishment.
It became responsibility.
Looking back, those first months in the Navy taught me three lessons that have shaped every leadership role I’ve held since.
My Company Commander taught me that people perform better when someone genuinely believes in them.
The swim qualification taught me that leaders have a responsibility to communicate not only the task, but the context that allows people to execute it well.
My petty officer taught me that standards exist for a reason, and accountability cannot depend on whether someone is watching.
Together, those lessons became the foundation of my leadership philosophy: lead with empathy, communicate with clarity, maintain uncompromising standards, and hold yourself accountable before expecting it from anyone else. The Navy didn’t just teach me how to follow orders. It taught me how to lead, and I still find myself back on that flight deck, in that pool, or standing in formation in a uniform that didn’t fit, more often than I expect.
I didn’t carry a rank or a title into any of that. I was a nineteen-year-old recruit who was, at various points, terrified, confused, and completely unaware I’d just tackled a safety swimmer in front of my entire company. None of it looks like sales engineering leadership. But I’ve run technical sales teams for over fifteen years now, and those three moments are still the ones I return to.
When I hire an SE, my first job is the same as that Company Commander’s: find where they need someone to believe in them before they can believe it themselves. Some people need that on day one. Some need it in the middle of a technical deep dive that’s going sideways in front of a CISO. It doesn’t lower the standard. It just makes the standard reachable.
When I build a discovery framework or write a demo playbook, I think about that pool deck. An order without context isn’t really an order, it’s a guess dressed up as instruction. If I tell an SE to “handle objections” without telling them what’s actually at stake in the room, I’m setting them up to respond correctly to a situation that no longer exists, the same way I responded correctly to a rescue nobody needed.
And when I run a coaching cadence built around live role plays and assigned executive personas, I’m doing what my petty officer did with a broom and a pile of debris. We drill the boring parts until they’re automatic, not because anyone’s watching, but because the cost of skipping it only shows up later, when it’s expensive. Standards don’t get to depend on who’s in the room. Neither does practice.