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How Often Should You Review an AI Agent's Instructions?

As a best practice, I have a 15 minute meeting that reoccurs every three weeks on my calendar where I jump in and I review my agent instructions so that as it's auto updating, I am still fully aware of what's happening.

By Jacqueline V. TwillieNovember 5, 20262 min readGuide
Quick answer

If you're using your agent daily, you may want to check yours every two weeks. Most of my agents, I have them running a couple of times a week. So a three week cadence works for me.

The AI agent writes its own instructions

You'll notice here, there's a section that says add instructions for agents. So if you're familiar with setting up agents, you can type in your own instructions. However, one of the benefits of a system like Gumloop, it's really adaptive. So the information that we provided in the first screen and then the questions that we've answered, it will create instructions for us.

Hear this at 23:51 in the recording.

What the Edit Own Instructions toggle does

You'll notice there's something that says edit own instructions with a blue toggle button that is on. What that does is it allows the agent to learn from your interaction inside of the chat feature. And you can start multiple chats. For example, if you click new task that opens another chat inside of this agent, what this blue button does is it allows your agent to learn how you're interacting with it and it automates updates.

Hear this at 24:18 in the recording.

Pick a cadence and put it on the calendar

Please put a calendar reminder at some frequency for you to come back and check that.

Hear this at 25:36 in the recording.

Three words that write the instructions

The next thing that I'm going to do is I'm going to tell my agent to update agent instructions. So if you're paying attention to my screen, under the Kimi K3 model that I selected, there's no instructions for the agent yet. So just with three words, update agent instructions, it's going to start thinking again.

I told my agent a few moments ago to update the agent instructions. You'll now see, if you click into that box, my agent has operating rules. It has core jobs and it has a rhythm. So all of this is editable. The easiest way to edit would be inside of the chat bot. So inside of the chat feature, that's the easiest way to edit both skills and instructions. And I just want to reiterate here, put a reminder on your calendar at a frequent cadence to go in and read agent instructions if you give it access to auto update.

Hear this at 40:49 and 42:41 in the recording.

Where this comes from

Every sentence above is Jacqueline V. Twillie's own, spoken live with Women Applying AI on October 7, 2026. The headings, questions, timestamps and links are the only additions. Filler words are cut, and a passage that skips a few seconds starts at the timestamp shown.

Build Your First AI Agent in One Hour: the full build, with the clips, the prompts and the transcript. This article's clip is Edit Own Instructions, and the review you put on your calendar.

Related reading: What Does Edit Own Instructions Mean for an AI Agent?, What Are AI Operating Rules?, How a Chief of Staff AI Agent Audits 25 AI Agents Every Friday.

Frequently asked questions

What if the AI agent keeps asking for a tool I am not ready to connect?

I am actually going to give my agent access to my calendar. You'll notice I didn't connect it when I was in the connector section, but I was able to one-click log in here and I'm not going to connect mine to Slack now, so I'm also going to say I'll pause on connecting Slack. In my initial prompt, I said I'm going to use Slack, but now I'm pausing. I can now tell the agent I'll pause on that so it won't continue to prompt me to ask for that.

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