One of the weird paradoxes of corporate life, when I think back to my time in an airborne unit, is that culturally, as a paratrooper, I understood every directive or plan to be subject to my own situational awareness. I show up at work with a presumption that I have room to judge, apply creative thinking to directives, and think in terms of accomplishing “commander’s intent,” not “stick to the plan even if it means the commander’s intent won’t be realized.”

Corporate leaders who know my biography have said things like, “compared to normal startup people your background probably means you understand the importance of strict control and compliance.”

No, my background means that I operated in a culture where we were given careful plans for operations, but focused on what the plans were for and how any one of us might, at any given moment, end up needing to toss the plan to accomplish the mission.

And that wasn’t just paratrooping. My first assignment out of jump school was a conventional signal unit in South Korea, providing FM retransmission over the southern half of the peninsula. Things were always going wrong, and it was always left to teams of three or four operating in isolation on a series of mountaintops to “adapt and overcome,” regardless of the original plan or what the field manual said. My very first radio watch in the field, something went wrong, I reached for the troubleshooting flow chart, and my team lead sighed, and said, “that’s going to take an hour. Forget what those instructors said. Use your common sense. What do you think is wrong? Fix that.”

Micromanagement, strict alignment, and deep discomfort with creative interpretation and execution are way more common in the businesses I’ve worked in than they ever were in either a conventional Signal platoon, or an airborne unit.

The challenge for me, as a leader in a corporation, has been to understand I have that formative experience and am just stubborn and naive enough to believe it was a good operating model that left me feeling empowered even if I had to keep my uniform pressed and hair short. Out in the civilian world, not everyone had that experience and often will interpret “here’s a rough plan, improvise as needed” as “execute in this manner, don’t deviate.” Or rather, it’s a mindset that appears at some frequency above “uncommon.”

In that retransmission platoon, and in that airborne unit, we all knew better than to think like that. We knew we needed to just get the shot and keep comms flowing.