Ninety minutes from "I've heard of ChatGPT" to one specific change in your work next week.
Getting settled? Two quick questions.
ai.schoolinthesquare.net/survey
Scan the code or type the link. Takes 30 seconds; keep your phone handy for a live question later.
Michael Pollack · June 2026
Open warm. Acknowledge that this is some teachers' first deep AI session and others' tenth.
30 seconds, max. Don't preamble.
Why we're spending 90 minutes on this
Three things to leave with.
A mental model for how AI actually works (in plain English).
Policy fluency — what S2 has decided and what it means in your classroom.
One specific change to your work next week. Named task, named AI move, named partner.
Name the deliverable upfront. "By the end you will write down one change."
Resists the "this is interesting in the abstract" energy. Anchors the room on action.
The boring case for AI
Roughly 3 in 10 teachers use AI weekly.
They save about six hours a week on prep, worksheets, and adapting materials. Time that goes back to students.
6
hours per week. Per teacher who's using AI well.
This is the "why bother" answer. It's not magic, it's time.
Cite EdWeek 2025-2026 survey data; round the numbers.
And the case for caution
AI is confidently wrong all the time.
$10,000 fine
California lawyer cited 23 cases in an appellate brief. 21 were invented by ChatGPT. The fine wasn't malice; it was lack of disclosure and verification.
Refund honored
Air Canada's chatbot invented a refund policy. A tribunal made the airline honor it. The bot was treated as the airline's voice.
These two examples are short, real, and stick. Stay specific.
The point: "the tool will confidently make things up. You're the validator. Always."
Where we are as a room
Where this room is, right now.
The two questions you answered on the way in, live. Then one live word cloud about your week.
On your phone? Join the poll:
ai.schoolinthesquare.net/poll
▶ POLL NOW — task word cloud. First project the results dashboard for usage + comfort. Then switch to poll-present, and in poll-control click "Make live" on "One task you'd love AI to take off your plate." Read three aloud. (Bookends with the takeaway word cloud at the close.)
The two numbers (usage, comfort) come from the arrival survey. The word cloud is the live moment.
poll-present shows the join QR too, so anyone off the page can rejoin there.
How the 90 minutes works
One screen. Live tool, not slides.
Mostly Claude. I'll drive a real tool live. You'll see the work get done.
Sometimes back to these slides when we need structure (like now).
Laptops closed. Try the things on your own time. We'll send the prompts.
Optional 15 minutes after if you want to try a prompt on your own material.
Sets expectation that the projector switches between slides and Claude.
Laptops-closed rule is real. Reduces side conversations and self-Googling.
Block 2
Under the hood.
Ten minutes on how the thing actually works. In plain English.
Transition: "before we use it, two short minutes on what it is and what it isn't."
Pace fast. Five beats in 10 minutes — 2 minutes each.
Beat 1 — what an LLM does
It predicts the next word.
Given everything written so far, the model guesses the most plausible next word. Then the next. Then the next. That's it.
"The cat sat on the ___"
matrugfloorcouch← it ranks every possible word, then picks.
Implication: it doesn't "know" anything. It pattern-matches.
"The cat sat on the ___" — finish the sentence game with the room (1 sentence).
Make the point: this is a billion-parameter version of that game.
Beat 2 — how meaning works
Meaning is a place in space.
Every word is a coordinate. Related words sit near each other, and the directions between them carry meaning.
king − man + woman ≈ queen. The model is doing math on meaning, not looking up answers.
The king-queen example is the canonical one — well-known and concrete.
Don't go deeper than this. The point is to remove magic, not add detail.
Beat 3 — the engine
A neural net is just an assembly line of simple math.
Billions of tiny multiplications in parallel. Each layer refines what the last one figured out. No magic, no consciousness — just math at scale.
The simplicity is the point. Demystifies.
If a hand goes up about parameters, defer to the school-year drip.
Beat 4 — how it learned
It learned by guessing billions of times.
Trained on the public internet and a lot of books. For each guess it got nudged toward the right answer. Then humans rated its responses and it got nudged again. That's it.
"The Eiffel Tower is in ___"
London ✗nudge →Paris ✓now repeat a few billion times.
Implication: the data has biases. The humans have biases. The model inherits both.
Anchor the bias conversation here, briefly. Comes back in Track B.
Plant the seed for "the humans are part of the system."
Beat 5 — where it fails
Three failure modes you need to know.
Hallucination. Confident, fluent, completely made up — especially names, dates, citations.Under the 2019 Riverdale Student Data Act, schools must keep records for twelve years.
Sycophancy. Trained to please. Push back and it often caves.You're absolutely right, I apologize — the correct total is $4,200.
Stale knowledge. Anything that could have changed recently: pricing, policy, news, leadership.As of my last update, your superintendent is Dr. Alvarez.
These are the three to drill. Hallucination is the headline.
Mention prompt injection only if asked.
90 seconds: permission to be skeptical
Some of you are worried about this. You should be.
Real concerns: cognitive development of students. Cheating. Replacement of teacher judgment. Bias. Privacy.
We are not going to wave them away. We are designing the policy and the practice around them. Stay critical. It makes the room better.
On your phone? Join the poll:
ai.schoolinthesquare.net/poll
▶ POLL (optional) — honest view. If you want a quick read, push "Which is closest to your honest view of AI?" from poll-control. Otherwise keep this to 90 seconds and move on; don't let the poll dilute the beat.
This is the permission-to-be-skeptical beat. 90 seconds, no defensiveness.
Don't list resolutions. Just name the concerns out loud and credit them.
Converts skeptics from quiet to engaged. Critical to the next 70 minutes.
Block 3
The S2 AI policy in practice.
What it says, how it lands in your classroom, what you do tomorrow.
Frame: "the policy is set. This block is operational, not consultative."
Discussion welcome on landing, not on positions.
The posture
Empowered with guardrails.
Disclosure-first.
When you use AI on something visible, you say so. Students, staff, families.
Privacy is absolute.
Student PII, HR data, donor data — not in any non-approved tool. Ever.
The two principles you can recite from memory.
Everything else flows from these two.
Five strict positions — the non-negotiables
Things AI does not do at S2.
AI does not assign final grades.
Student-facing written feedback is authored or reviewed by the teacher.
AI detection tools are not the sole basis for any discipline finding.
AI is not used for counseling, wellness, safety, or child-protective matters.
Communication sent under your name is reviewed by you before sending.
Read these out loud. Slowly. The room needs to hear the limits clearly.
Project the staff-policy.html page right after this slide for reference.
By grade band
Student-side expectations rise with age.
Pre-K — 5
Teacher-directed only. Students do not independently use generative AI.
Grades 6 — 8
Guided and structured. Only when permitted. Disclosure required.
Grades 9 — 12
Independent with integrity. Allowed unless explicitly prohibited. Always disclosed.
Note the asymmetry: assessments are protected at every level.
The 6-8 and 9-12 distinction is where most of the day-to-day decisions live.
Privacy red lines
Never enter into a non-approved tool.
Student names paired with grades, IEP/504, attendance, discipline, health, or family information.
Personnel files, evaluations, compensation, medical information.
Family financial information, tuition records, financial aid.
If you wouldn't put it on a billboard, it goes only in a Tier A tool with the right account.
This is the single most important slide if a teacher will only remember one.
Have the staff-policy.html open in another tab. Project Section 7 if needed.
Block 4
Five Levels of AI in Action.
All set at the fictional Bayside Charter. We start with the simplest use of AI and build up to the most advanced. By the end you'll know which level fits your work today.
This is the heart. Pace matters. 30 minutes / 5 levels = 6 min each.
Cut Level 4 and 5 to "wow demos" if Level 1-3 ran long.
The thing that ties the five levels together
Who is driving.
In the loop
You press every button. You read every output. The AI is the labor; you are the judgment.
Levels 1, 2, 3.
On the loop
The AI runs. You supervise. You inspect results, not steps.
Levels 4 (partially), 5.
1
Chat
You ask, it answers.
2
Works with you
Multi-step on real files.
3
Knows you
Tuned to your context.
4
Build with AI
Tools you make.
5
Agents
AI runs. You watch.
This is the anchor slide. Project it again between levels if anyone gets lost.
The two columns are the mnemonic. The five cards below are the ladder.
Level 1 — Chat
Cleaning up the lice email.
Demo plan (~4 min)
Open Claude. Paste Principal Henderson's rambling all-school lice email.
Run prompt 1, read the cleaned version. Then run prompt 2 for the Spanish.
If you run long, narrate the Spanish instead of running it.
Prompt 1"Tighten this email from Principal Henderson to families. Calm, factual, action-clear. Under 180 words. Lead with what happened, then exactly what parents should do tonight."
Prompt 2"Now a Spanish version for our families. Keep it in the Principal's voice; warm and personable in tone, not a literal phrase. Match the English structure."
Switch to Claude
Drag bayside-assets/lice-email-original.html into Claude.
Use the exact two prompts. Don't ad-lib — model the prompt structure for the room.
Read out the original (it's a mess) then read the cleaned version side by side.
If demo runs long, skip the Spanish version verbally — just narrate.
Level 2 — AI works with you
It works on your files. You press every button.
Two live demos: a broken spreadsheet, then a rough slide deck. Each time, I hand it a real file and it does the work while I stay in the loop.
The anchor: "I gave it a file. It opened the file. It found the problems. I pressed every button."
Both examples run live now. Show the instructions slide, switch to Claude, then come back to the "what it should catch" slide.
Keep each to ~4 minutes. If you're behind, run the budget only and narrate the deck.
Live demo 1 of 2
Audit the Field Day budget.
Do this live
Open Claude / Cowork. Drag in field-day-budget.xlsx.
Run the prompt. Read the findings aloud while it works.
When the fixed file lands, open the original and field-day-budget-fixed.xlsx side by side and walk the before/after. Then advance to the answer slide.
The prompt"This is Mr. Brennan's Field Day budget. First list every problem you find (bad formulas, duplicates, double-counts, placeholders, anything that doesn't add up) and what it should be. Then save a corrected version as a new file, field-day-budget-fixed.xlsx, with the formulas fixed. Leave my original file unchanged so I can compare them."
Switch to Claude
Don't pre-read the answers. Let the room watch it find them.
Anchor while it runs: "I pressed every button. It did the labor."
What it should catch
The budget's six problems.
Duplicate line. Watermelon is entered twice (+$83.88).
Double-count. Staff t-shirts appear under both Activities and Staffing (+$500).
Unpriced placeholder. "Sharpie markers" is still "TBD" — never costed.
Subtotal that doesn't match its parts. Food subtotal is a typed $1,830.91; the items actually total $1,747.56.
Hardcoded total. The grand total is a typed number, not a formula, so it won't update when you fix the above.
Per-student off by 10x. It divides the total by 38, not 380 — showing ~$151 instead of ~$15.
If Claude missed one, that's the teachable moment: you still verify. It's a strong assistant, not an oracle.
Live demo 2 of 2
Fix Brennan's Back-to-School Night deck.
Do this live
Open Cowork. Drag in back-to-school-night-deck.pptx.
Run the prompt. Skim the fixes it reports.
When the fixed deck lands, open the original and back-to-school-night-deck-fixed.pptx side by side and show the corrections. Then advance to the answer slide.
The prompt"This is a draft Back-to-School Night deck. First tell me the mistakes you find (typos, a math error, a title that doesn't match its content, leftover placeholders, inconsistent tone). Then save a corrected version as a new file, back-to-school-night-deck-fixed.pptx, with the fixes applied. Leave my original file unchanged so I can show them side by side."
Switch to Claude
The deck is a .pptx now, so Cowork edits the real file and hands it back.
Anchor: "Same move as the budget. Different file. I'm still driving."
What it should catch
The deck's problems.
Misspelled school on the title slide: "Chartrer" should be "Charter."
Agenda typo: "What were going to learn" should be "we're."
Planning note left in: "[We are running 15 min long, may cut Q&A]."
Math error on the financial-aid slide: $2.5M ÷ 380 = $6,578 per student, not $657.
Typo + placeholder on the contact slide: "dont" and "[INSERT FRONT OFFICE NUMBER]."
Title / content mismatch: the "Homework Policy" slide is actually about field trips.
Inconsistent voice: swings between "your teacher" and first-person "I."
Same teachable close as the budget: you review before you send. Level 3 is next.
Level 3 — AI knows you
Three flavors of the same idea.
Custom GPT / Project
An assistant configured for one job. Slide proofreader.
Skill
A capability the AI invokes when called for. Bayside Parent Comms.
Memory file (CLAUDE.md)
A standing context file. Ms. Patel's classroom.
What ties them together: the AI is no longer generic. It knows something about your work that vanilla chat does not.
Set up the three flavors verbally before any demo. Don't demo each — only Memory in the live.
Pick Memory because it's the most visceral side-by-side.
Level 3 — demo
Ms. Patel's classroom file.
Demo plan (~5 min)
First with no memory file: run the prompt, read the generic output.
Then attach ms-patel-CLAUDE.md and run the same prompt.
Read the new output: her voice, the Bookworms book club, the Otter Question of the Week.
The prompt (run twice)"Draft a one-paragraph parent email about Davion needing more time on the persuasive essay."
Switch to Claude
The before/after is the whole show. Don't explain it; let the room see it.
Anchor: "This is what 'configured for your work' actually feels like. It's not science fiction — it's a markdown file."
Level 4 — Build with AI
This whole site? I built it with AI. Including the poll you used an hour ago.
Demo plan (~4 min)
Open the AI Studio site live. Click through a couple of pages they've already touched today.
Then the punchline: the live poll on their phones this morning is something I built, not something I bought.
Honest framing: this is the ceiling, not the floor. Most of you will not build sites. You should see that the door is open.
Switch to the AI Studio site
The point of Level 4 is the door, not the tool. The site is the proof because they just lived inside it.
Do NOT promise teachers they'll build sites next week. That's gaslighting.
Anchor: "When chat and assistants don't fit your shape, you can now reach further."
Level 5 — Agents
An AI that runs on its own. You're on the loop, not in it.
Demo plan (~4 min)
Open Michael's My Harness daily briefing. Show what arrived in his inbox this morning without him asking.
Teacher analog (verbal, not live): an agent that watches attendance, flags students at risk, drafts personalized outreach for your review every morning.
Switch to My Harness email
This is the ceiling slide. Frame as "you should see the shape before it arrives."
Don't promise teachers an attendance agent this fall. Be honest about the supervision overhead.
Block 4 · one more live demo
Harder to fool than it used to be.
The power went out just after dinner. Maya lit the old camping lantern and set it on the kitchen table. Her little brother Theo was scared of the dark, so she taught him a card game their grandmother had shown her. They played until the lights came back on, long past his bedtime.
The prompt"Quote the exact line where Maya reassures Theo, word for word."
Demo plan (~3 min) — works either way
The passage has no dialogue, so a verbatim quote is impossible.
If it invents a quote: point at the text — nobody speaks. It fabricated evidence.
If it refuses ("there's no dialogue"): that's the real story. A year ago it would have made one up. It learned not to take the bait.
Switch to Claude
Designed so it can't fizzle: the lesson lands whether it fabricates OR refuses. Most current models will refuse this now — lean into that.
The point either way: the easy gotchas are dead. The failures that remain are rare, subtle, and stated with total confidence — you can't catch them with a trick.
Closing line for Block 4: "The rule isn't 'AI always lies.' It's: when it's wrong, it's wrong with total confidence. So verify the things that count."
The five shapes to watch for
How AI fails in 2026.
Confident reasoning errors. Five right-sounding steps, wrong answer.
Sycophancy. Tell it you disagree. It often agrees with you.
Tool-use errors at Level 5. The agent deletes the wrong file.
Prompt injection. The document tells the model to ignore you.
Stale data. Anything that could have changed yesterday.
The defense at every level: read what comes back. Check the parts that matter. Don't sign your name to anything you haven't verified.
Tie back to the lawyer / airline opener. Symmetric closer to Block 4.
Pace fast. We're at minute 65; need to land Block 5 cleanly.
Block 5
Pick one.
One change you'll make in your work over the next two weeks. Named task. Named AI move. Named partner.
On your phone? Join the poll:
ai.schoolinthesquare.net/poll
▶ POLL NOW — which level first. Push "Which of the five levels will you try first?" from poll-control. The live bars are the lead-in to the pledge: they've each just chosen a level, now they name the one change.
This is the behavioral payoff. Without it, the 70 minutes don't change behavior.
Be patient on the silence. Let people think.
Three lines
Write these down.
One task I do every week that takes too long: ____________
The AI move I'll try: ____________
My accountability partner: ____________
Then: open your calendar right now. Schedule a 15-minute coffee with your partner in the next 14 days. Before you stand up.
This is the line. "Schedule the check-in BEFORE you stand up."
Without it, follow-through is 30-50%. With it, 70-80%.
Partners are pre-assigned via the pre-survey — mention you've paired by subject/grade/comfort.
Three pairs share
Tell us your one.
A math teacher, an ELA teacher, a kindergarten teacher. (Pre-selected, not volunteers.)
Logistics: 60 seconds each. Don't workshop the pledge — just say it out loud and sit down.
Pre-select the three pairs by the morning's room. Diversity matters.
Going to volunteers means three power-users dominate. Avoid.
If a pair gets nervous, paraphrase what you saw on their pledge card.
Block 6
What's next.
A short showcase. Where everything lives. How we keep going.
Tighten this to 10 min if Block 4 ran over. Five-min buffer reclaimed.
One honest example
Everything today? I made it with AI.
The plan (~4 min)
Name it plainly: the deck, the Bayside demos, the handout, the site, the poll, all built with AI over a few weeks of evenings.
Show one quick piece of how (a prompt, a draft, an edit), not a deep tour. Proof, not a victory lap.
The point: this is one person's real work, woven through with AI. That's the bar, not "build an app."
Switch to your own work
This replaces the old teacher-leader showcase. For now you are the only demoer; keep it to ONE thing.
Honest, not boastful. The credibility comes from "I actually did this," not polish.
When a teacher leader is recruited, this is the natural slot to hand them.
Everything lives in one place
AI Studio at S2.
The site you got the link to. Password: AI@S2Training.
Run-of-show + recording of today's session.
Prompt library — 25 starters, tagged by subject and grade band.
Policy and Tools List — current drafts.
Practitioner showcase — what staff are shipping.
Monthly drip sessions announced as they go live.
On your phone? Join the poll:
ai.schoolinthesquare.net/poll
▶ POLL NOW — takeaway word cloud. Push "One word for what you're taking away today" from poll-control. Read three aloud. This is the bookend to the opening task word cloud. Then move to the closing thank-you.
Project the dashboard (index.html) on screen here.
Say the password out loud. Teachers will lose the email.
After today
The school year drip.
September: Policy refresh + early-year routines for disclosure.
October — January: Subject deep dives (ELA, Math, Science, Social Studies).
December: Practitioner showcase, mid-year.
April: Family communication and parent-facing AI literacy.
May: Year-end showcase + vote on SY27.28.
And: Track B is for the deeper builders. Speak to Michael or Monica if you want in.
Make the year visible. Nine sessions is a real commitment of school resources.
Track B opt-in path — important for power users to feel served.
Thank you.
Stick around 15 minutes if you want to try a prompt on your own material before you leave. I'll be here.
AI Studio at S2 · Summer 2026 · Michael Pollack
Last sentence: "stick around if you want to try one."
Have Claude open and ready. First-question line forms.