The On-Wing Isn’t Coming

By Keegan Evans

I had a shift in my perception of the world, one which was familiar with a different space and a different time and different people. It happened in the middle of a panel on AI during the Leadership Now Annual Summit this month, in a room full of business, government, and other pro-democracy leaders high above Central Park in Hearst Tower. As the panelists spoke, offering different views on business and policy responsibilities in the Age of AI, I felt the energy of the room rise with more collective discomfort compared to earlier topics. I realized that there wasn’t quite as much difference between me and those I had put on pedestals. This wasn’t a seminar with the sages telling the room the answers; it was all questions and hypotheses. Not only on the topic of AI (which I spend a lot of time thinking about), but in the space of good government, society, civics, and paths forward. 

In flight school, our first stage of training in the aircraft is with a single designated instructor, commonly called an “on-wing”.  When I was a brand-new student at Whiting Field, my on-wing was a former P-3 pilot who possessed an easy mastery of the systems, aircraft, and the sky. When I climbed into the cockpit with him, I knew he was going to be able to get me out of any situation I got us into. That feeling of an invincible instructor who could handle anything was useful while I was learning to fly. But over-indexing on it left me assuming that I wasn’t in the same class, or was better off taking a backseat while the experts took the lead on complex problems. That didn’t reflect reality – reality is that occasional mishaps crash planes and kill instructors – but it’s how I perceived the world.

Five years and three deployments later, my fellow combat tested senior Captains and I moved on from the squadron to our follow-on assignments. One of them was a friend I had flown with in some genuinely dicey situations in Iraq. He was calm under pressure, a solid pilot, and also, by any honest accounting, not invincible. And now he was going to be a flight instructor, just like my “invincible” on-wing had been. I had known intellectually that all flight instructors were human. But the personal connection of seeing my peer, with only five years more experience than when we had been brand new students, was different. My on-wing had not been an essentially different kind of person. He had been just like us: a calm, capable pilot who had shown up and committed to training a next generation of students.

Even though I learned this lesson in 2009, I’m still vulnerable to the pattern (and I suspect I’m not alone).

I read a great deal about AI. I follow the research, I work with the tools every day. At Euda we help leadership teams figure out how to transform their work in the age of AI. And I still feel the pull to defer to the people with greater technical expertise or professional pedigree to give the real answer. Their depth is real and informs the work I do, but if I were to wait and step back just because someone else has a deeper technical knowledge then I’m abdicating my responsibility to contribute to our clients’ ability to flourish.

I feel the same pull as I have jumped into the democracy space, where the obvious authorities are the issue-focused nonprofit leaders, the members of Congress, the lifelong policy wonks and party operatives who can name every committee chair and every margin in every swing district. They know more about the institutional plumbing than I will in this lifetime. But there is a lot of unknown space between what exists and what will work in this new, complex time, and that gap is one I can speak to with my experience and perspective as a veteran, business leader, and concerned American.

During the Summit, Leadership Now launched our Business Plan for America and hosted conversations on governance, institutions, the rule of law, and the next generation of public leadership. It was a roomful of people I had been thinking of as the invincible on-wings, the experts who already had the answers. But just like flight instructors, they were doing the best they could with the experience they had earned, and so was I, and so was every other person in the room.

The invincible on-wing isn't coming, especially for the complex challenges we face, because they never existed in the first place. We need good people to take the seat. My choice is to find a group with the common goal of a vision of America that serves the people, creates opportunity for all of humanity, and turns away from cruelty. Rising authoritarianism, corruption, and polarization threaten this vision. We’re only at the beginning of the Age of AI. This technology is changing at a pace which outstrips our human capacity to adapt to change. 

Solutions to these challenges won’t get handed to us fully formed. They are built by those of us willing to show up and try, knowing the work is imperfect and unfinished but lending our voices and credibility to it anyway. If you are a veteran who wants to know how to continue honoring your oath, a business leader who has not yet found where your voice fits, or a centrist who has been waiting to be invited, I’ve got some folks for you to meet.