Artificial Intelligence and the Courage to Rethink Educational Leadership

After more than 30 years in education, I recently found myself considering a return to senior school administration. It is work I know well and loved deeply.

After reflection from a recent school visit and a long drive home filled with honest conversation, I reached clarity.

Education is approaching a marketplace disruption, and many systems are not yet ready to respond.

This realization does not come from theory or trend watching. It comes from lived experience.

I’ve Seen This Kind of Disruption Before

Early in my career, I served as a teacher, technology coordinator, and later as a director of educational technology and innovation during the rise of mobile computing. I was there when laptops entered classrooms, when iPads promised new forms of engagement, and when smartphones, particularly iPhones, became nearly ubiquitous in students’ lives.

At the time, many of us worked carefully to integrate these tools with sound pedagogy. Phones were calculators, cameras, organizers, research devices and tools to inspire and use creativity to design projects that deepened learning. The intention was thoughtful and student centered.

But technology evolves, and so do its consequences.

Over time, it became increasingly clear that constant connectivity and the forward facing camera embedded in smartphones were shaping student behavior in ways we did not fully anticipate. These changes included attention fragmentation, social comparison, rising anxiety, and diminished presence.

Leadership required a shift.

About four years ago, I was part of leading the decision to remove phones from classrooms. This decision was not made because technology is inherently harmful, but because discernment matters. We listened to teachers, observed students closely, and responded to emerging research on adolescent well being and the crisis unfolding before our eyes.

That experience reinforced a lesson I had learned before.

Progress is not just about adoption. It is also about reassessment.

Disruption Under Pressure Lessons From COVID

That lesson became even clearer during COVID.

Like many technology leaders and educators, I spent that period working alongside teachers, schools, and families as learning shifted almost overnight into hybrid and remote environments. There were no playbooks, only principles.

The work was not about platforms or tools. It was about helping adults ask important questions. What truly matters for student learning right now. How do we maintain connection when we are physically apart. What expectations are humane, and what can we let go?

Some of what we tried worked. Some did not. What carried us through was a shared commitment to sound pedagogy, flexibility, and care for students, teachers, and families alike.

That period reminded me that technology can support learning, but it cannot replace relationships or tools and pedagogy that were needed to support students’ various learning styles, strengths, and weaknesses.

Artificial Intelligence Is the Next Inflection Point

Artificial intelligence feels new, but the pattern is familiar.

AI is a disruptor much like mobile computing was 25 years ago. Entire industries did not change because leaders were reckless. They changed because leaders were responsive.

The taxi industry offers a useful analogy. Before Uber and Lyft, the experience had stagnated. When disruption arrived, it was not just about technology. It was about reimagining service, including cleaner cars, respectful drivers, transparency, and ease. Consumers did not need persuasion. The market responded.

Education is now at a similar moment.

What AI Makes Possible and What It Requires

Used wisely, artificial intelligence can assess and personalize learning at scale. It can identify skill gaps in real time. It can reduce administrative burden so teachers can focus on mentorship and feedback. It can shift learning from time based to mastery based models. It can create space for curiosity, creativity, and purpose.

If we have learned anything from smartphones, it is this.

Tools shape culture.

How we integrate artificial intelligence, or rush to deploy it, will matter just as much as whether we adopt it at all.

The Readiness Gap

What concerns me is not resistance, but delay.

Many schools talk about innovation, yet struggle to take instructional risks. Innovation spaces remain underused. Classrooms remain largely didactic. Students are overloaded with schedules packed with Advanced Placement courses aimed at standardized tests that reveal little about adaptability, wisdom, or flourishing in an AI shaped world.

Meanwhile, new schools are emerging thoughtfully and responsibly. They are rethinking instruction, assessment, and time. Early data from these models is promising when compared to traditional outcomes.

The difference is not resources.

It is posture.

Why I’m Choosing a Different Path

I recently wrote The Virtue Code: A Guide to Flourish for the AI Generation, a book about human virtues in the age of artificial intelligence. That work was shaped by decades of walking alongside educators with students and their familiies through moments of disruption, including mobile computing, smartphones, COVID, and now AI.

At this stage of my life, I no longer feel called to return to systems that resist both sides of leadership. The courage to innovate matters. The courage to pause when harm emerges matters just as much.

Instead, I want to support educators and institutions already preparing for what comes next. These are the schools and leaders willing to redesign learning with wisdom, humility, and care.

This is not burnout.

It is discernment.

The Constant That Has Never Changed

Across every technological shift, one truth remains.

The students are extraordinary.

They are perceptive, adaptable, and deeply affected by the systems we design around them. They deserve adults who are willing to learn, unlearn, and relearn in service of their growth.

A Hopeful Invitation

Education is not failing. It is being invited to evolve.

Artificial intelligence, like every disruption before it, will reward leaders who pair curiosity with humility, innovation with virtue, and progress with care.

I am choosing to spend this next chapter helping build what comes next by supporting schools and leaders ready to shape the future of learning wisely and humanely.

The future of education is not something to fear.

It is something to build together.

References

Jonathan Haidt (2024). The Anxious Generation.

Twenge, Jean M. (2017). iGen.

Organisation for Economic Co operation and Development. (2021 to 2023).

Darling Hammond, Linda, et al. (2020). Restarting and Reinventing School: Learning in the Time of COVID and Beyond.