Navigating Leadership and Humanity in a Digital Age

There is a specific kind of exhaustion that only exists at 8:15 on a Sunday morning when you are standing in front of a room of local association presidents or interested members. We are the ones who usually carry the weight of everyone else’s worries, yet there we were, caffeinated and ready to lead. My presentation at the NEA Leadership Summit was a whirlwind of heartfelt connection and pedagogical strategy, but the universe clearly decided I hadn’t quite finished my lesson for the weekend.

The transition from presenting to racing toward O’Hare for a 12:45 flight would have been a blur, but before I left I received a dreaded text alert.  Flight cancelled. A blizzard in Iowa had decided that I was to remain in Chicago for an additional two days. 

By Tuesday morning, I found myself in that strange, liminal space of the airport gate, sitting with a group of strangers. We were a motley crew: workers from Ohio heading to Iowa, a traveler returning from the ancient sun of Greece, and another still carrying the spirit of Italy. We were all bound by a common, frustrating situation, yet something shifted. We weren’t just passengers.  Instead, we became a temporary community.

We talked about the simple, visceral joys of the world. We shared stories of eating pheasant without all the greasy residue and the unmistakable taste of a fresh salad in Greece. One of our group members laughed about his failed grand plan to rent a car for the four-and-a-half-hour drive home, only to find the rental lots as empty as a school hallway on the first day of summer break.

I even ended up sitting next to one of these new friends on the plane, a statistical anomaly that felt like a little gift from the travel gods.

As I sat there, I couldn’t help but think about the students I work with who increasingly prefer the predictable, low-stress interaction of an AI chatbot over a living, breathing human. I get it. An AI doesn’t challenge your bad mood, it doesn’t have an unpredictable opinion, and it certainly doesn’t require the emotional labor of small talk.

But an AI also can’t feel the shared camaraderie of being stuck at an airport for another short delay. It can’t randomly pivot a conversation from weather patterns to the specific texture of European food. It lacks the heart-to-heart spark that occurs when two people realize they are living the same moment from completely different lives.

These moments are the bedrock of our humanity. In our rush to implement the next great tool or find the most efficient way to communicate, we risk losing the beautiful, messy, unplanned connections that happen in the now.

My weekend was about leadership, associations, and connections.  However, it reminded me of the most important part of existence which is our humanity and our desire to serve one another.. Let’s be honest, we can bridge any gap with a shared story and a little empathy, whether we’re in a classroom, a boardroom, or Gate B12.

I’m back home in Iowa now, but I’m carrying those stories of Greece, Italy, and Ohio with me. It’s a reminder that while AI can mimic a lot of things, it can never replace the soul of a shared journey.If you would like to continue this conversation about the human side of technology or how we can lead with heart in our schools, I would love to connect with you. You can find a time that works for you on my calendar here.