The Tool Is New. The Leadership Challenge Isn’t.

Everyone keeps asking the same question: “What AI tool should we use?”

I think that’s the wrong question. The better question is: Do our people trust us enough to learn alongside us? Because the tool does not fail first. The trust does. I learned that lesson during COVID.

The Lesson We Learned During COVID

Like many districts, we suddenly found ourselves trying to recreate school from kitchen tables, living rooms, and makeshift home offices. Every day seemed to bring a new challenge. Every vendor had a solution. Every social media thread offered another “must-have” tool. For a few days, it felt like we were being asked to rebuild education while standing on shifting sand.

I remember recommending something that felt almost counterintuitive at the time.

Instead of trying to maximize instructional days, I recommended that we intentionally reserve two days each week for teacher learning and professional development. Three days would focus on student learning. Two days would focus on helping educators learn how to teach effectively in a completely new environment. We used that time to cover what we were all figuring out in real time: best practices for learning from home and new ways to stay connected to students.

At the same time, I advocated for something else that felt unpopular: This was not the time to introduce a bunch of new technology. We had been leveraging virtual learning for years for inclement weather for years, so we had tools in place…we just always assumed they would be used for just a few days in the worst of northeast Indiana snowstorms.

Teachers were overwhelmed.

Students were overwhelmed.

Parents were overwhelmed.

The last thing anyone needed was another login, another platform, another workflow, or another thing to figure out. What people needed was stability.

So we doubled down on familiar tools, familiar routines, and familiar expectations. We spent our energy helping people become more confident with what they already had instead of constantly chasing what was new.

Looking back, I don’t think that decision was about technology at all. It was about trust.

The Trust Triangle

I’ve come to picture trust in leadership as a triangle with three sides: consistency, care, and competence. That COVID decision touched all three.

Consistency: because we protected familiar tools and routines while everything else was shifting.

Care: because we made room for people to learn instead of demanding they perform.

Competence: because we helped educators get genuinely good at teaching in a world none of us had trained for.

Take away any one side, and the triangle collapses. And notice what isn’t on it: the platform. The product. The tool.

The Leadership Challenge Hasn’t Changed

That’s why I worry when conversations about AI start with product comparisons. The question isn’t whether a platform can generate lesson plans or grade exist tickets. The question is whether teachers trust the process enough to experiment. Whether leaders have created a culture where people feel safe asking questions. Whether the people using it believe they’ll be supported while they learn.

Too many AI initiatives are being treated as implementation projects when they’re actually change management projects.More specifically, they’re trust-building projects.

And here’s what I’ve learned, what I ended up writing an entire book around. The cape is optional. The communication is essential. Trust doesn’t get built in the rollout. It gets built in every honest conversation that comes before it, and every honest one that comes after.

Districts that succeed with AI won’t be the ones with the biggest budgets or the newest platforms. They’ll be the ones that built trust first. The ones that created the conditions for curiosity and let people learn out loud, fear and excitement in the same room. Readiness was never measured by device counts, licenses, or training hours.

It’s measured by trust. When trust exists, people will figure out the tool. When trust doesn’t exist, no tool can save the initiative.

The tool does not fail first; the trust does.

So no, AI readiness isn’t primarily a technology problem. It’s a trust problem. And trust is built, or broken, by leaders, in how they communicate long before the first login. That’s the conversation I’m most looking forward to having with education leaders at ISTE this summer.