AI Tools for Principals: 6 Picks for Walkthroughs, Messages, Coverage and Data

The best AI tools for principals depend on the job in front of you this week. Use Edthena Observation Copilot to turn walkthrough notes into feedback, MagicSchool for staff messages, Google Gemini or Microsoft Copilot for family letters and the coverage grid, Gemini Notebook for the data your leadership team will read, and Otter.ai for meeting notes. Each of the six is free to start or comes with a school account.

The job this week	Tool	Price (checked November 12, 2026)	Where your data goes (vendor says)	Choose something else when
Walkthrough notes into feedback	Edthena Observation Copilot	Free for individual users	Notes "never used to train or fine-tune third-party AI models"	Your district bars AI from any part of evaluation
Staff emails, PD plans, hard conversations	MagicSchool	Free; Plus $8.33 a month billed annually	Personal information not used to train models; no student names without a district agreement	You only need email help and already have Gemini or Copilot
Family letters and the coverage grid, Google districts	Google Gemini	Free in every Workspace for Education edition	Not human-reviewed, not used to train models	You want help inside Sheets or Meet, which is a paid add-on
The same two jobs, Microsoft 365 districts	Microsoft Copilot	Copilot Chat free with an A1, A3 or A5 license	Prompts and responses not used to train foundation models	You want help inside Excel or Outlook, which costs $18 a user a month
Data for the leadership meeting	Gemini Notebook	Free in every Workspace for Education edition	Uploads not human-reviewed, not used to improve models	Your district is on Microsoft, or the file needs joining to other systems
Notes from the meeting itself	Otter.ai	Free for 300 minutes a month	Trains its own models on de-identified recordings and on transcripts	Anyone in the room has not agreed to be recorded

What are principals using AI for right now?

Mostly for writing to people. In an Education Week Research Center survey of 852 educators, 262 of them district and school leaders, run between August 26 and October 6, 2026, communications came first among the operational uses leaders named, followed by translation, strategic planning, employee evaluation and class scheduling. Nearly one-third said they do not use AI for any operational purpose (Education Week, October 30, 2026). The survey does not separate principals from district leaders.

The older national figure points the same way. RAND surveyed US principals in spring 2024 and reported that "nearly 60 percent of U.S. principals reported using AI tools for their work" (RAND, February 2025). A year later, in a March and April 2025 survey of 3,668 principals, 45 percent told RAND that their school or district had policies or guidance on AI (RAND, September 2025). So a principal is more likely to be using AI than to have been told how.

Employee evaluation sitting fourth on that list is the item to watch, and it shapes the first pick below.

How this list was built

We started from the job, then looked for a tool, because the directory at aieducator.tools has almost nothing sold to principals by name. On November 12, 2026 we pulled all 138 listings from the directory's public API and searched each name, tagline, description and feature list.

• 25 tools sit in the school administration and safety category. Seven of the 25 declare FERPA alignment in their listing, five carry an independent 9ine security assessment, and nine state that they host data in the United States.
• No listing is built to arrange substitute coverage or a building schedule. Three mention scheduling in passing: a curriculum planner, a research agent and a tutoring service.
• One listing is built around observation by voice, and it records early years staff observing children, not a principal observing a teacher.

That is why one of the six picks, Edthena Observation Copilot, is not in the directory and links to its vendor. Every price and privacy statement below was read on the vendor's own page on November 12, 2026. No vendor paid to be included. Left out on purpose: TeachScribe, StaffDraft and SLT AI, which are priced and built for UK schools and covered in the school leadership shortlist. If you are an assistant principal, the assistant principals' list is organized around duty rosters and discipline paperwork instead.

Best for walkthrough feedback: Edthena Observation Copilot

Edthena Observation Copilot is the best fit for writing up a walkthrough because it does one thing: the vendor says it "turns classroom observation notes into framework-aligned teacher feedback in seconds" (Edthena). You type what you saw, pick the framework, and edit the draft. It supports the Danielson Framework for Teaching, T-TESS in Texas, the Marzano Focused Teacher Evaluation Model and custom rubrics. A general chatbot can do this too, but you would have to paste the rubric in every time.

Choose something else if your walkthroughs are informal and unscored. A short note in your own words, sent the same day, needs no tool.

Watch out for: the tool drafts feedback from your notes. It has not seen the lesson, so it cannot know what you failed to write down. Rob Weil of the National Academy for AI Instruction told GovTech that AI in evaluation "doesn't understand the relationships, it doesn't understand the context," and that "using it without transparency is a real problem" (GovTech, March 20, 2026). Tell teachers you use it, and keep the rating yours. The classroom observations post covers the research on that line.

Pricing: "free for individual users" (Observation Copilot FAQ); district partnerships are priced separately; checked November 12, 2026.

Safety: Edthena states that notes, transcripts and feedback drafts "are never used to train or fine-tune third-party AI models" (security page). That wording covers third-party models only. Observation notes are personnel records, so ask your district whether a free individual account is allowed to hold them. The tool has no directory listing, so there is no rating to quote.

Best for staff messages and PD planning: MagicSchool

MagicSchool is the best fit for the writing a principal does for staff because it groups that writing in one place. Its help center describes a Leadership Communication Suite of eight tools covering "professional emails, teacher observations, PD planning, and difficult conversations" (MagicSchool help center). It suits a principal whose teachers already use MagicSchool, since you will be reading the same outputs they do.

Choose Gemini or Copilot instead if all you want is a faster email. You already have them.

Watch out for: which plan includes the leadership suite is unverified. The help article does not say, and the tool page did not load when we checked.

Pricing: free plan at $0; Plus at $8.33 per user a month billed annually or $12.99 billed monthly; Enterprise by quote (MagicSchool pricing); checked November 12, 2026.

Safety: the privacy policy, effective March 19, 2026, says MagicSchool "does not use personal information to train artificial intelligence or machine learning models" (privacy policy). The terms ask users not to enter students' personally identifiable information unless a data protection addendum is in place (terms of service), so on a personal free account, leave student and staff names out. The directory lists a 4.74 rating from 19 reviews and an independent 9ine assessment.

Best for family letters and the coverage grid in a Google district: Google Gemini

Google Gemini is the best fit for a principal on Google Workspace because it comes with the account: Google says Gemini for Education "is also included in all Google Workspace for Education editions free of charge" (Google for Education). Use it for two jobs. Draft the family letter, then ask for a plainer version and a translation; the post on translating parent communication explains which letters still need a bilingual reader. And paste in tomorrow's period grid with the absences marked, then ask who is free to cover each class.

Choose a scheduling system instead if the problem is the master schedule, not one day's gaps. That is a different purchase, laid out in the master schedule post.

Watch out for: the assistant can propose coverage, but it does not know your contract's limits on lost planning periods. Check every proposal against them.

Pricing: the Gemini app is free in every edition. Help inside Sheets and note-taking in Meet need the Google AI Pro for Education add-on, listed at $20 per user a month on an annual plan or $24 monthly, for users 18 and over (Google Workspace admin help); checked November 12, 2026.

Safety: for education accounts Google states, "Your data is not human-reviewed or used to train AI models." Your district's administrator turns access on or off. That protection belongs to the school account, so do not do this work in a personal Gmail login. The directory lists a 4.59 rating from 41 reviews.

Best for the same jobs in a Microsoft 365 district: Microsoft Copilot

Microsoft Copilot is the best fit where staff live in Outlook and Teams because, in Microsoft's words, "Copilot Chat is available at no cost for users with a Microsoft 365 A1, A3, or A5 license" when they sign in with a school account (Microsoft Education). It handles the family letter and the coverage grid the same way Gemini does.

Choose something else only if your district is on Google.

Watch out for: the free chat sits beside your files, not inside them. Working in Word, Excel, Outlook and Teams is the paid license.

Pricing: Copilot Chat at no cost; Microsoft 365 Copilot "for $18 (USD) per user per month" as an academic offering, a price Microsoft's page dates to October 2025; checked November 12, 2026.

Safety: Microsoft states that "the prompts, responses, and data accessed through Microsoft Graph aren't used to train foundation models" (Microsoft Learn, updated November 4, 2026). As with Gemini, the protection applies to the school sign-in. The directory lists a 4.67 rating from 12 reviews.

Best for the leadership team's data: Gemini Notebook

Gemini Notebook, the tool Google renamed from NotebookLM, is the best fit for preparing a data meeting because it answers only from the files you give it. Google says it "answers questions based on the information provided in your uploaded sources" (Gemini Notebook help) and cites them, so a team member can click through and check a claim. Load the benchmark export, the attendance summary and last month's meeting notes, then ask which grade levels moved and where the two files disagree.

Choose a data platform instead if you need attendance, behavior and assessment joined across systems. The post on analyzing student data compares those.

Watch out for: it summarizes text better than it calculates. Ask it to find and quote figures, and do the arithmetic in the spreadsheet.

Pricing: free as a core service in all Workspace for Education editions (Google Workspace admin help, updated October 26, 2026). Google's help lists up to 50 sources per notebook for free users; the limit for each education edition is unverified. Checked November 12, 2026.

Safety: for Workspace accounts Google states that "uploaded files, chats and model outputs won't be reviewed by human reviewers or used to improve generative AI models" (Gemini Notebook help). Student-level files are still education records, so use the district account and remove names if a summary by grade will do. The directory lists a 4.84 rating from 90 reviews.

Best for meeting notes: Otter.ai

Otter.ai is the best fit for a record of the leadership meeting on a zero budget because the Basic plan is free for 300 minutes a month, 30 minutes a conversation (Otter pricing). A 45-minute meeting therefore needs the paid plan or two recordings.

Choose the note-taker built into Meet or Teams instead if your district licenses it; the school meeting note-takers post compares them and covers consent law.

Watch out for: Otter's privacy policy, effective June 16, 2026, lists "training our proprietary AI technology on de-identified audio recordings" and on transcriptions "which may contain Personal Information" (Otter privacy policy). We found no opt-out described. Keep it out of any meeting that names a student or discusses a staff member.

Pricing: Basic free; Pro $16.99 monthly or $8.33 a user a month billed annually; Business $30 monthly or $19.99 annually. Lower promotional prices were on the page when we looked; checked November 12, 2026.

Safety: Otter says users "must always ask for consent," and its Notetaker "joins as a named participant" visible to everyone in the meeting (Otter help). The directory lists a 4.20 rating from 5 reviews and an independent 9ine assessment.

What about ChatGPT, Khanmigo, SchoolAI, Brisk, Diffit and Quizlet?

• ChatGPT: a sound alternative to Gemini or Copilot. OpenAI says ChatGPT for Teachers "is free through June 2028 for verified U.S. K-12 educators," lists school leaders as eligible, and says content "is not used to train our models by default" (OpenAI help).
• Khanmigo: not a principal's tool. The teacher tools are free in the United States; for leaders Khan Academy lists only district tools with pricing on request (Khanmigo pricing).
• SchoolAI: a platform you approve for classrooms more than one you use yourself. Its school leaders page names no observation or feedback tool, and it publishes no prices (SchoolAI).
• Brisk Teaching and Diffit: built for teachers' classroom materials. We did not check either for leader features today.
• Quizlet: a student study tool with no job in a principal's week.

Which AI tool should a principal start with?

Four questions, in this order.

1. What does the district already license? Start there. Gemini or Copilot on a school account costs nothing and comes with the district's data terms.
2. Is a student or an employee named in what you are about to paste? If yes, use only a tool covered by a district agreement, or take the name out.
3. Will the output be read by the person it is about? Observation feedback and family letters are. Edit those line by line and say that AI helped draft them.
4. Is the job writing or arithmetic? These tools draft well and count badly. Keep totals and percentages in the spreadsheet.

Worked example: one week, planned

This is a plan for a 450-student middle school, written to show the sequence. It is not a report of results.

• Monday. Four ten-minute walkthroughs. Type notes on what students were doing. After school, run each set through Observation Copilot against your framework, cut anything you did not see, and send the feedback before Tuesday's first bell.
• Tuesday. A letter to families about the new pickup routine. Draft it in Gemini or Copilot, ask for a sixth-grade reading level, then ask for a Spanish version and have a bilingual colleague read it.
• Wednesday. Three teachers out. Paste the period grid and ask for a coverage proposal that spreads the load. Check it against the contract, then point each absent teacher to a sub plan tool.
• Thursday. Leadership team. The night before, load the benchmark export by grade, with names removed, into Gemini Notebook and ask for the three largest changes with the cell each came from.
• Friday. Draft the staff bulletin in MagicSchool from the week's notes.

One measure decides whether to keep going: did feedback reach teachers within 24 hours of each walkthrough?

What should a principal keep off AI?

The decision. The US Department of Education's July 2025 guidance says AI uses are allowable under existing federal programs and stresses "engaging affected stakeholders, especially parents, in decisions about the adoption and deployment of new technologies" (US Department of Education). One district has drawn the line more tightly for itself: Peninsula School District built an AI lesson coach for teachers and deliberately kept it voluntary and out of performance reviews (Education Week, June 1, 2026).

Our view: let these tools draft the letter, the feedback and the agenda. The rating, the discipline call and the staffing choice stay with the person whose name is on the door. District leaders weighing platforms will find that side in the superintendents' list.

Dan Fitzpatrick is a Forbes contributor, bestselling author and founder of The AI Educator.