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The Superintendent’s Field Guide

Practical systems thinking for superintendents and district leaders navigating the rising complexity in public education. Written by Byron Headrick.

superintendentsfieldguide.substack.comSource feed ↗10 posts

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The School Year Is Opening on Wrong Assumptions

Signals to Watch, August 17, 2026

Everyone’s AI Gives the Same Advice

Last week I introduced AI as your smartest new hire. This week I want to look under the hood: what that new hire actually learned, where its answers come from, and why that matters more than how smart

Your Smartest New Hire Has No Experience

What education leaders get wrong about working with AI

The Quiet Metrics Behind the Plan

Signals to Watch, August 3, 2026

The Forecast Was Wrong. The Warning Wasn't.

What the Oil Shock Teaches District Leaders About Risk That Moves Instead of Disappears

The Org Chart Is a Forecast

Your structure is a bet about enrollment, money, and work. This summer, a lot of those bets came due at once.

The Numbers Under the Budget Are Still Moving

Signals to Watch July 20, 2026

The Back Office Is Where AI Starts

While everyone argues about AI in the classroom, the safest and most certain returns are sitting untouched in finance, HR, and operations.

The Letters Have Dollar Amounts Now

Signals to Watch, July 6, 2026

Exhaustion Is Becoming the AI Strategy

The tool is not entering where districts are most innovative. It is entering where the work is least sustainable.