Leadership Lessons from Under the Surface: Y is my favorite letter.

Note: This is part 3 of a series on leadership lessons I learned during my time serving on board nuclear submarines in the mid 80's and early 90's. And no, Hunt for Red October isn't all that realistic. Sorry. Das Boot is simply the greatest submarine movie ever made. Nothing else comes close.

Part One can be found here, Part Two here...

You'll always remember your first "real" job. The one where the government actually withheld taxes and you realized how little money you bring home. The one where considered how you could stand out against your competition, how you could advance into management, how you could grow in your career.

I usually tell people my first job was as a submariner. And this is a lie.

My first "real" job was as a Grunt, as an 11Bravo Infantryman. Those of you that know me have to find this extremely funny. I'm not exactly what you picture when you think of the U.S. Army, especially when I joined as a 5'7" 145 lbs 17 year old. But I did proudly qualify to wear the Infantry badge.

The most impactful life lesson I learned during my brief stint in the Army was two-fold. First, I don't enjoy being sweaty, dirty, tired, and yelled at for hours on end. Boot camp and Advanced Infantry Training for me took place in the summer of 1984 at Fort Benning, Georgia. The average July temperature in Fort Benning is 92 degrees Fahrenheit (thanks Google) and this doesn't include the humidity factor. I spent a wonderfully fun filled 13 weeks running around constantly in full battle dress twelve hours a day asking myself "What were you thinking?!?".

The second life lesson instilled from this experience was learning that Drill Sergeants really don't enjoy the word "Why" very much. I performed so many pushups during this time for asking "why" I gained 15 lbs of muscle. I remember Drill Sergeant Wa, the most patient antagonizer of my life, smiling at me as he told me to "drop and give him 20" and then saying "When will you ever learn to quit asking *&!* questions?".

My love of the simple phrase "why" is why I was cut out to be a submariner. Think about it. Everything about a sub goes against the grain of logic. A submarine is a ship built to purposely sink, a ship whose crew is more comfortable hundreds of feet underwater as opposed to cruising on the surface, a ship built to spend months running silent and deep on patrol. A ship composed of a crew who embraces the word "why".

Here's the thing. A submariner has to learn about every square inch of the boat. For a simple reason - everyone's life depends upon this. You don't carry a bench of people out on patrol. Every single person is a vital member of the team, is a contributor; and if not willing to learn and ask why, a liability. And liabilities aren't entertained in this environment. They are quickly weeded out. But that's a different story for a different time.

I'm a passionately curious person, one who likes to take things apart to see what makes them work the way they do. This is what made my experience onboard the boat so impactful throughout my civilian career. I spent years continuously learning about the boat beyond just my area of expertise as a Nav ET. I learned how a torpedo operates, how to split seawater into hydrogen and oxygen through electrolysis, the theory of nuclear energy, how a Trident missile adjusts its trajectory via the stars as it breaks through the surface of the ocean when launched, how sonar distinguishes between a whale and a surface ship; the list goes on and on. I haven't been at sea for almost 30 years now and yet these lessons still reside in the back of my brain. Curiosity and "why" is a must-have character trait for submariners.

I've learned another valuable lesson as I've matured (ok, gotten older) and throughout my career in Financial Services. The word "why" is powerful. The phrase "Why not?" is just as important. "Why" is essential in learning how a system operates. "Why not" is essential in disrupting an ecosystem. And it is a phrase not embraced near enough.

"Why" is essential in learning how a system operates. "Why not" is essential in disrupting an ecosystem.        

Around a decade ago I traveled to San Francisco for client meetings. I always reach out to friends of mine whenever planning a trip like this to try and catch up and also to meet new interesting people. On this occasion I gave the legendary Billy Robbins a call to let him know I was headed his way. At the time Billy was part of the Product Strategy Team at Wells Fargo and was (and still is) one of the most connected characters I know in the tech space. Billy didn't disappoint as he set up a meeting with well over a dozen techie folks at a dive bar in downtown San Francisco.

During the course of the evening, and after several beers, Billy introduced me to a new company co-founder, one whom Billy said I should talk to and provide product feedback based on my vast industry experience. I can still vividly remember this young tech entrepreneur walking me through the product offering and the market gap the company was focused on. I then proceeded to give my feedback and advised him to maybe pivot as this was a saturated space with well entrenched legacy solution providers. I wished him well and remember thinking "This company is DOA".

Fast forward to the Money2020 Conference in Las Vegas about eight years later. A good friend of mine, Jeff Tisjeen, and I, along with several thousand other conference attendees, were at the after party sponsored by Plaid, the fintech unicorn with a $13.4B valuation. The crowd grew quite as Zack Perret, the company co-founder, gave a brief welcome speech. I turned to my friend Jeff and said "Did I ever tell you about the time I told Zack his idea for Plaid was never going to work?".

Life lesson: Ask "why not".