Launch offer — $50 off with code HEADSTART50 at checkout
A Field Guide for School Leaders

The Head of School Field Guide to AI

The whole-school view from the head's chair — what AI changes about strategy, governance, people leadership, and crisis readiness in a private school, and what to do about it, in what order.

$149  · includes the current edition and the next quarterly edition, free

14-day no-questions refund · read on any device · nothing to install

Updated quarterly
A Field Guide for School Leaders
The Head of School Field Guide to AI
Linda Haitani
Q3 2026 Edition
Why this guide exists

Written for a seat nobody was writing for

— Linda Haitani, founder of Ravenna Solutions

The general AI advice out there is written for corporations or for classrooms. The person who actually runs the school sits somewhere else entirely — where deeply human judgment meets real operational responsibility, and where every AI decision touches families, faculty, and mission at once.

So I wrote for that seat. This guide is a complete map for the head of school: what AI genuinely changes about your work, what it doesn't, where the boundaries belong, and what to do in what order. It is honest about limits — it will not tell you AI fixes everything, because it doesn't.

If your questions sound like the four below, this was written for you.

i.

"What do I tell the board?"

ii.

"What is my team already doing with AI?"

iii.

"Where are the real risks — and which are mine to own?"

iv.

"What should we do first, and what can wait?"

What's inside

Fifteen chapters, two appendices —
organized by altitude

Enter at your own level. Every section carries a reading-level tag, so a first pass and board-prep work follow different paths through the same guide.

Table of Contents

Foundations Practitioner Advanced Governance
00If AI Makes You Uneasy, Read This First
01The AI Moment in Private K-12 Education
02How AI Actually Works and Behaves
03The Data Line — Privacy, Security, and Trust
04Working with AI — The Personal Disciplines
05The Leadership Layer and Workflow Redesign
06AI in the Head's Work — Strategy, Board, and Communications
07AI and People Leadership
08Enrollment, Advancement, and the Financial Picture
09Crisis and Incidents in the AI Era
10Governing AI — Posture, Policy, and the Board Conversation
11Agents — Understanding, Buying, and Overseeing Them
12Leading the Team — Adoption, Enablement, and Measurement
13Different Schools, Different Playbooks
14The Head and Classroom AI
15Glossary
AAppendix A — The Vendor Landscape (refreshed quarterly)
BAppendix B — Board Materials: The TRE-to-NIST Crosswalk

The opening chapter meets the skeptical reader honestly — because skepticism, in this seat, is a professional asset.

A book about AI is out of date before it ships. This is built differently.

A year ago, every school was teaching its people to write the perfect prompt. Today, no one mentions it. That's the real challenge of leading here — not just that the tools change, but that the advice changes: what's suddenly possible, what's now simply expected, what deserves your attention this year and didn't last. Every edition is re-thought against what genuinely shifted, so the map in your hands reflects the ground as it is now — not as it was the day the book was written.

So every section in the guide carries one of three markers — telling you at a glance how fast its ground is moving, and which parts a new edition is most likely to have changed:

Holds steadyEvergreen

The judgment, boundaries, and leadership principles that hold as the technology moves.

🌊

Shifts by quarterFast-moving

Practices and patterns that drift over quarters — reviewed and updated each edition.

Changes by monthVolatile

Tools, vendors, and rules in constant motion — re-verified every single edition.

You buy once — $149

Today's edition right in your web browser, plus the next quarterly edition free. Your access code arrives by email within minutes.

"What's changed since I last read?"

Every edition opens with a short What's New synthesis that answers exactly that — the quarter's real developments in one sitting. Skip an edition or three; one chapter catches you up.

Come back when it matters — $39

No subscription, nothing recurring. Return whenever you like: the new edition is the complete, current book — every update since you left already folded in — plus a fresh read on what just changed. Wait a season or a year; you're never behind.

Free — no purchase needed

The guide is the map.
The shelf holds the tools.

Every guide pairs with a free companion shelf on this site — the tactical, rubber-meets-road material the chapters point into. The guide tells you what matters and in what order; the shelf shows the work being done. It grows every quarter.

a.

Screen-recorded demonstrations

The real work, shown end to end.

b.

Downloadable templates

Ready to adapt to your school.

c.

Case studies from schools

What this looks like in practice.

d.

New material every quarter

The shelf grows between editions.

Pricing

One guide, one price. No subscription.

Launch offer — HEADSTART50 takes $50 off at checkout

Updated editions

$39 / edition
for returning readers · come back any time
  • Opens with a What's New summary of everything that changed
  • You decide, edition by edition
  • No auto-renewal
How updates work

Questions? linda@haitani.org

Questions

Frequently asked

How do I read the guide?
Right in your web browser — Chrome, Safari, whatever you already use — on any device. After purchase you'll receive an access code by email within a few minutes. No app to install, nothing to download.
What does "includes the next edition" mean?
Your $149 covers the edition you buy today and the next quarterly edition when it ships. You'll get the new access code automatically, and that edition opens with a What's New summary up front. After that, whenever you'd like a refresh of the content, you can pick up an updated edition for $39 — only when you choose to, never automatically.
Is this the same content as the free Library on this site?
No. The Library holds my essays, videos, and exercises — it's the thinking. The guide is the complete, organized, role-specific map, kept current quarterly. The free companion shelf links the two.
What if it isn't for me?
Full refund within 14 days of purchase, no questions asked.
I lost my access code.
Email linda@haitani.org and I'll resend it.
The Head of School Field Guide to AI

Lead the AI conversation at your school —
instead of reacting to it.

The current edition plus the next quarterly edition, for $149. Reading within minutes.

Get the guide — $149 $50 off with code HEADSTART50 · 14-day no-questions refund · secure checkout by Stripe