“Starting With Why” Again: What Being a Fighter Pilot Taught Me About Digital Innovation

Twenty-eight years ago I left Brooklyn, New York, for the Air Force Academy. Why? Because I wanted to fly, fight, and serve.

In 20 years of active duty, I served and led the world’s greatest airmen. I flew history’s best attack aircraft in support of our bravest soldiers, sailors, and marines. I made amazing lifelong friendships, met the love of my life, had two beautiful children, and lived and traveled all over the United States, Asia, and Europe. At the core of all those experiences, my “why” never changed: fly, fight, and serve. It was a simple but powerful why that fueled four years at the Academy and twenty more in uniform.

Brendan O'Brien Solstice

In 2014 I made the toughest professional decision of my life when I retired from the Air Force to start a second career. I did the typical things many transitioning veterans do — attended workshops, updated my resume, bought a suit, networked, and filled out business school applications.  

The problem was that all those things were “whats,” not the why I needed to drive the next 20 years of my career. I had several great paths to consider: Should I continue in civil service? Should I do good for the planet by launching a career in renewable energy? Should I teach? Thankfully, I had an epiphany when I came up with my “cocktail party” test.

In that simple exercise, imagine yourself bouncing around conversations at a cocktail party. If there is a particular conversation you find yourself in most of the night, that’s likely a calling for you. For me, that was tech. More specifically, the application of technology to improve our lives. I found a new why: make the world better through technology or, to put it more dramatically, be a shepherd in digital transformation, not a sheep.  

Next was the “where,” which was just as important as the why. I needed a new squadron. I wanted to find a place where servant leadership comes first, where high-performing teams focus on outcomes, and morale is off the charts.


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As part of my search I attended a meetup at Solstice in late 2014. It was there that I heard our founder, J Schwan, talk not about tech but about servant leadership and innovation. I also met many wonderful Solsties who were passionate about their firm and their teams. I once had a commander tell me you can choose assignments based on a great location or a mission you love, but rarely do you get both. But in Solstice, I knew I’d found that rare combination — a world-class where to activate my why. So I joined in December 2014 in the best capacity I could at the time, as a scrum master serving our teams.

Making the transition from the military to a modern innovation firm has not been without its challenges. Perhaps the toughest has been the shift from 24 years of a vertical command and control hierarchy to a flat organization based on projects, circles, and networks. There are definitely times when I struggle with that. But the one thing I always come back to from my attack-aviation background is starting with the why in every decision. In my military days I called that the big picture — the BP. Then Simon Sinek taught us all to “Start With Why.” Starting with the why and thinking about the BP first is where veterans excel.

Veterans hate to waste resources because they know they are stewards of taxpayer dollars and, more practically, they operate in a resource-scarce reality. So veterans ensure every resource is applied toward the BP by starting with the why. They maintain a laser focus on outcomes and understand that activating strategy doesn’t happen in the command center (or the boardroom); it happens in the daily choices frontline airmen (or employees) make. In tactical aviation, you don’t find a target for your weapon (that’s what we call a self-licking ice cream cone), you choose the target first — the why for that moment. Then you take the time to understand the complete environment around that target (weather, orders of battle, terrain, threats) and then — and only then — do you select the right weapon and tactics to employ. Operationally, we start and end every briefing and debriefing with the mission’s objectives, the why for that sortie. 

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The same mentality has served well in digital innovation. In fact, I’d say it’s critical to successful innovation. At Solstice, we don’t help our clients find problems for emerging technology to solve. Rather — from the very first alignment conversation to the daily ceremonies throughout our partnership — we work to understand their big-business problems and challenges first. Then we employ the right technologies, teams, and methodologies to collaboratively solve them. Whether it’s a combat mission or an innovation challenge, it all starts and ends with your most critical objectives.

As a fighter pilot or a director in a global innovation firm, I always start with the why in every decision I make.