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 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 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. 

We knew when to dress up. I have worked in banking and own the mandatory pinstripe suit. I know the importance of caring for financials—I now hold the Chartered Financial Analyst designation. At Critical Insight, we defended hospitals systems, and when we visited those organizations, we keenly respected that healthcare management teams dress more formally. We certainly knew that an investor pitch in New York had better be done in formal attire. 

But for our daily work, we needed to roll up our sleeves and get the job done.

Our style was maybe non-traditional, but only because we prioritized purpose and human connection over flash and jargon. 

Flannel fit the bill.