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Sample chapter 2 of 4

The Monday Morning Problem (Ch. 12, pp. 93–94)

Leading Change at the Speed of AI

It’s 7:18 a.m.

A principal opens an email from a parent: “Are you using AI on our kids?”

At 8:06 a.m., a teacher asks whether it’s okay to use AI to draft feedback for student writing.

At 9:40 a.m., the technology director flags a vendor update: a new “AI assistant” feature is now turned on inside a core platform. No one reviewed it.

By lunch, a board member has forwarded a screenshot from social media claiming the district is “uploading student data to AI.”


None of these moments are rare anymore. They are the new cadence of leadership. AI changes fast — and it shows up everywhere: inside platforms you already pay for, inside workflows staff are trying to streamline, and inside student behavior you didn’t initiate but still must govern.

This is where districts lose control — not because leaders are careless, but because they don’t have a repeatable change routine. Without one, governance becomes reactive: a burst of attention after a headline, a rushed memo after an incident, a temporary ban after confusion.

Staff experience whiplash. Families experience uncertainty. Trust erodes. Shadow use grows because people stop asking and start improvising.


What Evolve Really Means

In districts that handle this well, governance has three properties:

  • Versioned: Guidance changes are tracked — what changed, when, why, and by whom.
  • Triggered: Updates occur for specific reasons, not because someone panicked.
  • Routinized: Oversight happens on a cadence — so leaders process change through practice, not personality.

If your governance isn’t versioned, triggered, and routinized — it will drift. And drift is the quiet enemy of trust.

Evolve work isn’t about chasing tools. It’s about building a system that absorbs change without losing the mission.

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