How Do I Load an AI Agent's Instructions From a File?

You have a prepared instructions file and you'd rather upload it than speak or type your way to the same place. My materials have two routes. On the recording I dictated, and later told the AI agent to update its instructions (40:49). The session page offers the file.

Which route do I take, dictation or the file?

Either one. On October 7, 2026 I described the dictation route with the instructions box open:

From the recording, 24:07. So the information that we provided in the first screen and then the questions that we've answered, it will create instructions for us.

Just before that, at 23:51, I told the group that if you're familiar with setting up AI agents you can type in your own instructions. The file route is the prepared version of that. For the dictation route, see How Do You Dictate Goals to an AI Agent?.

Should I read the file before I upload it?

Yes. I said this about skills at 34:47: I'm very hesitant to copy someone's skill offline if I don't have access to read it before I download it, because people can write any set of instructions in a skill. A file of instructions is the same kind of thing, pages somebody wrote for your AI agent to follow. Open it first, and read it top to bottom.

The session page lists the file at 5 KB, so it's quick to read. It opens with the role:

From the file on the session page. Turn my calendar and inbox, or a pasted list of open items, into a short daily brief plus drafted replies.

What are the steps?

The steps below follow Step 3 on the session page, as listed there:

1. 01

   Read the file.

2. 02

   In Gumloop, open Agents and create a new one. Name it Chief of Staff. You should see the new AI agent's own page, with its name at the top and a chat box.

3. 03

   In the chat box, find the plus button in the bottom-left corner. Use it to upload chief-of-staff-agent.md.

4. 04

   Send one message: "Use this file as your instructions."

5. 05

   Ask: "what do you do?" You should see an answer that mentions a daily brief, drafted replies and never sending on its own.

6. 06

   Open the AI agent's settings, next to its instructions, and find the toggle that lets it sharpen its own instructions. Switch it on, or leave it on if it already is.

For step 5, the file has a line to match the answer against:

From the file on the session page. You never send an email.

That line, and the rest of the never list, are written rules in the file. A file isn't a lock. What the AI agent can actually send is set in the connector's tool settings, which I showed for Gmail at 44:19.

Three names, one toggle: the session page calls it Self-Improving Instructions, I said edit own instructions on the recording (24:18), and Gumloop's documentation calls it Edit Own Instructions and says it's on by default. Gumloop's documentation also shows a plus button at the bottom left of the message bar, with an option to add photos and files, which is the same spot the session page points to. Checked on 2026-11-05 against Gumloop's Agents documentation.

On my relationship to Gumloop, I said this:

From the recording, 33:22. I don't work for Gumloop. I found this tool over the summer through Lenny's podcast, and I started using it and have since made myself an ambassador for them. I've created a relationship with Gumloop. I am not an employee.

More on that answer: Do you work for Gumloop? (the answer from the session).

What goes wrong

Uploading a file nobody read. I said it about skills: you can inadvertently give away access to data you don't feel comfortable with.

Letting the instructions change with nobody watching. With the toggle on, the AI agent updates them as you work with it. At 25:36 I asked the group to put a calendar reminder in to come back and check. How Often Should You Review an AI Agent's Instructions? has the cadence.

What the recording doesn't show: the upload itself, because I dictated. The session page doesn't say whether the file's text then appears in the instructions box, so open that box after step 4 and look.

Where this comes from

This article grows from the session I taught live with Women Applying AI on October 7, 2026. The quoted passages from the recording are my own words, taken verbatim. The passages marked as from the file on the session page come from the files published with that session. The tables, steps and checklists around them were drafted by my team's AI agents from those words and my published pages, and checked against the recording before publishing. The file and its steps are on the session page. Platform facts that have a public source carry the dated line above, and screens change.

Build Your First AI Agent in One Hour: the full session with the clips, the prompts and the transcript.

Related reading: How Do You Dictate Goals to an AI Agent?, What Are AI Operating Rules?, How Often Should You Review an AI Agent's Instructions?.