It's 3:15 on a Thursday. The buses are pulling out, and a fourth-grade teacher finally finishes the weekly family newsletter. The field trip date is in bold. The purple header took her twenty minutes. On her laptop it looks great, so she hits send and starts on tomorrow's copies.
Monday at drop-off, a dad stops her at the door. "Is the field trip this week?" He holds up his phone. On his screen the newsletter is a dark purple block, and the words on it are so dark he gave up reading.
She did everything right. She just never saw it from his side.
Two weeks ago, I was that teacher, and the newsletter was this one.
What happened to me
A reader opened a forwarded copy of Issue 15 in Gmail and wrote back that she could barely read it: dark words on a dark purple background. On my screen it looked fine, with white words on purple. Her email program had stripped out part of the design on the way through. I had checked that issue several times. Every check was from my side.
So I rebuilt the look of this newsletter. Every issue now uses dark words on a plain white background, so even when an email program strips out the design, the words stay easy to read. You are reading that version now.
It happened twice that week. The AI summary I get every morning spent eleven days telling me to send an email I had already dealt with. It checked my to-do list but never looked in my Sent folder. From its side, the job was still open.
The idea
A change isn't done when it looks right to you. It's done when it looks right to the person on the other end: the family, the student, the sub, the teacher down the hall.
The same goes for the Google Classroom link a student can't open, or the sub plan that only makes sense to the person who wrote it.
Worth Your Time
NYC's AI ban confusion: what's allowed and what's banned in city schools by Alex Zimmerman and Michael Elsen-Rooney, Chalkbeat
New York flagged 38 products under its new student AI limits, including reading and math curriculums and the department's own chatbot. Several companies said their tools don't use generative AI at all and weren't sure why they were on the list. A rule can look clear from the office that wrote it and still confuse the people who have to follow it. Before your district publishes a tool list, have one teacher and one vendor read it first.
Google Launches New AI Tools Purpose-Built for Education by Adam Stone, EdTech Magazine
Read it for the student side. Students see a banner telling them their teacher can see their activity, and teachers can open a student's chat to see how the session went. That's the other-side check built into the tool. If your district turns these features on, try one activity from a student account before you assign it.
Schools get another year to comply with web accessibility deadlines by Kara Arundel, K-12 Dive
This one is from April, and it still matters. Districts in cities or counties of 50,000 or more now have until April 26, 2027, and smaller ones until April 26, 2028. The rule covers websites, apps, social media, and digital textbooks. A 2025 survey found only 14% of districts had finished or nearly finished the work. The other-side check is a good first step.
Try this week: the other-side check (10 minutes)
Pick one thing you sent or changed this month. Then look at it the way the other person will.
A family message. Send a test to your personal email and open it on your phone. Then forward it to yourself and open it again. Forwarding is what broke mine.
A link or assignment for students. Open it from a student account or student view, if your school gives you one, before the class tries it.
Saved instructions in ChatGPT, Gemini, or Copilot. If you have told the tool how you want it to write, open a brand new chat and paste this:
Before we start, list the standing instructions you have from me. If you do not have any standing instructions saved, say exactly that instead of guessing.
If the answer doesn't match what you set up, the tool is not using your instructions, no matter what the settings page says.
Write down what you found in one line. That line is your proof the check happened.
The thought to bring to your next meeting
Before a new tool or message goes out to the whole building, ask who has seen it from the other side. If nobody has, how do you know it works?
If your school is trying out an AI tool this year, my District AI Pilot Checklist walks through that check before the tool reaches every classroom.
If you try the other-side check, hit reply and tell me what you found. I read every reply.
On the podcast
EP 08: Ground It In Your Documents (12 minutes)
The fastest way to lose your staff's trust in AI is to let it make something up about your own policies. I walk through grounding, which means giving AI your own documents so it answers from your source of truth, and the five steps to build one with a person checking the answers. Listen here.
That's it for this one. If something here was useful, share it with someone who'd get something out of it. If it didn't, that's part of the deal too. You can find more of what I'm working on at evalveconsulting.com, or book a call if you want to talk through what you're dealing with.
Talk soon,
Chris