The Flannel CEO:
A Real-World Guide to Purposeful Leadership
Intro
Leadership can be exhilarating. When the team is winning, it feels incredible. When team members express their excitement for the mission, it is deeply satisfying. When customers are sending accolades, you are overwhelmingly proud.
At its foundation, however, leadership is about accepting responsibility. It’s about being ultimately accountable for the productivity of a group creating much more than you could alone.
If you are in a leadership role, this series is intended for you.
Knowing Why We Lead
The reason we lead becomes the foundation for how we lead, ultimately determining what will come from our leadership. While our real motivations may be deep, nuanced, and even hidden, the business goals of leadership tend to be pretty straightforward.
There are many times, however, when we need to push through hard work. Ultimately, our reason for doing the work needs to come from something deeper.
Knowing our own personal motivation to lead is imperative.
Setting a Vision
To lead, you need to point your people in a common direction. Your team is undoubtedly a group of problem-solvers who fundamentally want to do a good job, and the best thing you can do is name the problem you want them to solve. Declare the vision. Tell them where you need them to go. By starting with a declaration of where you want to end up, you tap the power of multiple great brains figuring out how to get there.
Why "The Flannel CEO"?
My team started calling me “The Flannel CEO” partly in jest, I am sure, but it was true that collared flannel shirts had become my daily wardrobe.
I grew up in a rural area, and flannel felt practical, grounded, and approachable. As a small-town guy who once talked a lot about “those pinstripe bankers,” I felt more authentic in flannel.
When I think of leading people, I feel the same way. I wanted our team to have grounded, practical methods of achieving real-world results.
Yes, we were fighting hackers using a cloud technology, data platforms, ML, and AI, but we weren’t doing it for the hype. We were mission-driven to defend critical infrastructure. I even once worked for a bank, and we all recognize that finance is of the utmost importance—I now hold the Chartered Financial Analyst designation. We also knew when to dress up. We keenly respected that healthcare management teams were more formal, and we all knew that an investor pitch in NY had better be done in a suit.
But for our daily work, we needed to roll up our sleeves and get the job done.
My wife once said I had a “flannel problem” when I brought home another two flannel shirts. They paid for themselves. My weekly dry-cleaning bill would cover those shirts in under a month!
Our style was maybe non-traditional, but only because we prioritized purpose and human connection over flash and jargon. Flannel fit the bill.
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