For most assistant principals (APs), the best AI tools are the ones the district already licenses: Gemini and Gemini Notebook in a Google district, Microsoft Copilot in a Microsoft 365 district, and ChatGPT for Teachers where the district has claimed it. Add MagicSchool if you run the building's AI rollout, and Otter.ai for meeting notes where everyone agrees to be recorded. None of them should touch a discipline decision or a teacher's evaluation, and two major school systems now say so in writing.
What Do the New AI Rules Mean for Assistant Principals?
They take AI away from the two jobs that define the role and leave it the logistics. On September 1, 2026, Washington, DC's education agency put "student discipline decisions, evaluations of teacher performance" in the red, prohibited band of its model staff policy, and "supporting logistical operations" in green (OSSE). New York City then barred AI for "grading, behavior monitoring, counseling, or developing special education plans" (Chalkbeat). That red list reads like an AP's job description: Tennessee data reviewed for the Wallace Foundation found APs "spend more time on discipline and less time on observing teachers" than principals (Wallace).
How This List Was Built
I started from the 26 tools in the school administration and safety category. None is sold for deciding a student consequence, and seven are built around UK or Australian systems, so the picks lean on enterprise assistants a district can cover with a data agreement. Nobody pays for placement. I left out SLT AI, built for England, and StaffDraft, hosted in the UK. Pricing checked September 11, 2026.
| Tool | Best use for an AP | Limitation | Price / free tier | Privacy (vendor says) |
|---|---|---|---|---|
| Gemini | Rosters, testing logistics | Knows only your rules | Free with Workspace for Education | Not used for training |
| Gemini Notebook | Code of conduct lookups | Only as current as your files | Free with Workspace for Education | Not used for training |
| Microsoft Copilot | Same jobs, Microsoft districts | In-app help costs extra | Chat free; $18 per user per month in-app | Not used to train models |
| ChatGPT for Teachers | Master schedule stress tests | Staff only | Free through June 2028 | Student data privacy agreement |
| MagicSchool | Leading teacher AI use | Built for teachers | Free; Plus $12.99 per month | iKeepSafe FERPA and COPPA programs |
| Otter.ai | Staff meeting notes | Consent is on you | 300 free minutes a month | Trains on de-identified audio |
Best for Duty Rosters and Logistics: Gemini
Gemini is the best fit for the rosters an AP rebuilds every fall because it is free in every Google Workspace for Education edition. Give it staff free periods, duty posts and your rules, then ask for a draft plus every conflict it could not solve.
Watch out for: a tidy roster that breaks your contract's duty-minutes clause. Paste the clause into the prompt.
Pricing: free in all Workspace for Education editions (Google); checked September 11, 2026.
Safety: Google says school-account data "is not human reviewed or used to train AI models." Use your school login, never a personal Gmail.
Best for Code of Conduct Questions: Gemini Notebook
Gemini Notebook, formerly NotebookLM, is the best fit for "what does the code actually say?" because it answers from documents you upload and shows the passage. The lookup is green; choosing the consequence stays red.
Watch out for: stale files once the board amends the code. Keep incident reports and names out.
Pricing: free in all Workspace for Education editions; checked September 11, 2026.
Safety: the same terms as Gemini. Google says its tools "support compliance" with COPPA and FERPA.
Best for Microsoft 365 Districts: Microsoft Copilot
Microsoft Copilot is the best fit for districts on Outlook and Teams because Copilot Chat comes with a school account. Use it for the same rosters, logistics and first drafts of attendance letters.
Watch out for: help inside Word and Excel is a paid add-on.
Pricing: chat at no additional cost; Microsoft 365 Copilot $18 per user per month (Microsoft); checked September 11, 2026.
Safety: Microsoft says data is "never used to train foundation models." Student access starts at 13.
Best for the Master Schedule: ChatGPT for Teachers
ChatGPT for Teachers is the best fit for stress-testing a master schedule because it is free for verified K-12 staff, school leaders included. Use layered prompts to expose trade-offs, never "make my schedule" (SAI). OpenAI's help center now says the free period runs through June 2028; several third-party guides still say 2027.
Watch out for: constraints that live only in people's heads.
Pricing: free through June 2028 (OpenAI); checked September 11, 2026.
Safety: OpenAI offers "a student data privacy agreement"; your district must claim the workspace. Claude for Teachers is the alternative.
Best for Leading Teacher AI Use: MagicSchool
MagicSchool is the best fit for the AP running the rollout because its site admin role shows school-level usage reports (MagicSchool).
Watch out for: coaching notes sit in DC's yellow band; evaluation ratings are red.
Pricing: free; Plus $12.99 per month; Enterprise by quote (MagicSchool); checked September 11, 2026.
Safety: MagicSchool says it is in the iKeepSafe FERPA and COPPA programs and bars AI providers from training on student data. Check for a signed district agreement.
Best for Meeting Notes: Otter.ai
Otter.ai is the best fit for staff meeting and professional learning community (PLC) notes, with 300 free minutes a month.
Watch out for: consent. Otter trains on "de-identified audio" (Otter), and a 2025 class action alleges recording without consent. Never use it in a discipline, IEP or 504 meeting.
Pricing: free tier; Pro $8.33 per month billed annually (Otter); checked September 11, 2026.
Safety: not for children under 13. Ask whether your district approves it.
Khanmigo, Quizlet and Diffit are classroom tools, not AP tools; SchoolAI is a district decision.
How Should an Assistant Principal Decide?
- Is it a decision about a student or a teacher? Red. AI stays out.
- Does it identify a student? Only a district-approved enterprise account.
- Will a person check it first? Then it is green.
Outsource the doing, not the thinking. The roster is doing; what happens after the referral is thinking.
Worked Example: The Fall Duty Roster
For 42 staff: export free periods (no student data), paste them into Gemini or Copilot with your rules, ask for a table plus unmet constraints, and settle the conflicts yourself. Measure the time saved and the swap requests.
Dan Fitzpatrick is a Forbes contributor, three-time bestselling author and founder of The AI Educator.
