Actual AI: Build Your Context Portfolio!

In my first blog post I promised the more advanced readers a follow-up, and this is it.

The fifteen minute self-interview I described last time gives your AI a standing profile of you. A context portfolio goes further and teaches it about your district and your work. Once it knows all three, the answers you get back read like they came from a colleague who works in your district and knows your internal culture.

Three Layers of a Context Portfolio

I build the portfolio in three layers, in this order:

The first layer is your identity, and if you did the self-interview you already have it. Your role, district size, state, what you care about most, and how you like output formatted all sit in your tool's global settings, so every new chat starts with that information.

The second layer is a district knowledge base, and it made the biggest difference for me. I built ours in Gemini Notebook (formerly NotebookLM) with about thirty documents, including our strategic plan, both master schedules, the curriculum guide, school report cards, the staff handbook, our collective bargaining agreement, board policy, and our school improvement plans.

When I ask it a question now, the answer comes from our own documents and cites the page it pulled from. If a Board member asks me about graduation requirements at 8:40 on a Tuesday night, I can answer from the source instead of digging for a binder.

You do not need to use Google Gemini to do this. Most AI tools now let you attach a set of files to a workspace and keep them there, whether they call it a project, a space, or a custom agent. Look for that feature. You want documents that stay attached and get referenced every time, so you are not uploading the same PDF to every new conversation.

The third layer is a smaller portfolio built around one task you do over and over. For me, that is my Board Update memo. I keep every past update in a single archive document, and I gave that archive its own notebook, separate from the district knowledge base. When it is time to write the next one, I give it the topics and my rough notes, and the draft comes back in the format my board is used to reading, with the same structure and tone as the dozens of updates before it. I still edit every item, but I am editing a solid draft instead of staring at a blank page, and the whole thing takes me 45 minutes now instead of 3 hours.

Pick your own version of this.

It might be your monthly community newsletter, your cabinet meeting agenda, your monthly board metrics update, or the weekly note you send to your leadership team. Gather your last ten or twelve examples, add anything the task always pulls from, like a template or a calendar, and keep them together in one notebook or project. The next time that task comes due, ask for a first draft based on your past work and see how close it gets.

Before you upload a single file, decide where your line is.

I use a simple test: if the document is already public or already available to every employee, it can go in. Board policy, handbooks, strategic plans, master schedules, and published report cards all pass. Student records do not, and neither do personnel files, investigation materials, anything privileged, or anything under a FOIA request or litigation hold. Talk to your board attorney before loading your collective bargaining agreement or other documents about employment terms, since the answer can depend on your state and on the agreement your district signed with the vendor. Use the enterprise version of the tool inside your district account so your data stays covered by that agreement. I would much rather build slowly than explain a data incident to my Board.

You can feel the difference in a district knowledge base with ten documents. Start with your strategic plan, Board metrics, Board policy manual, staff handbook, school improvement plans, and your latest report card data. Put them in one notebook or project and ask a question you already know the answer to. If it gets the answer right and shows you the page, it is working.

After that, share it with your leadership team, and eventually your whole staff. A knowledge base in the superintendent's account only helps the superintendent. Once it is shared, anyone on your staff can attach it to a conversation, including your assistant principal writing a parent letter at 9 p.m.

Every hour I stop spending hunting down documents or re-explaining my district to a blank chat window goes back into being present in our schools, and that is why I force myself to nerd out and figure this stuff out! Build your ten document notebook this week, then email me at [email protected] and tell me what surprised you!

In my next post, I will show you how to take these portfolios one step further and build role specific agents that start doing some of this work for you.

• Post I: Actual AI: Two Challenges to Kick Off a Year of Actual AI