The "Regular" Advantage: Context Files for AI Agents
Why giving your AI a file about *you* is the fastest way to better results, without the repetitive prompt engineering.
2026-06-25
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Why giving your AI a file about *you* is the fastest way to better results, without the repetitive prompt engineering.
We spend a lot of time telling AI what it should be, but rarely tell it who we are. By dragging a few simple context files into a chat, you can skip the tedious prompt engineering and get straight to the work.
I spend a lot of time telling people they need better prompts to get better results from AI. Usually, that means one of four things: writing better prompts (which takes a long time), going back and forth with the AI before asking it to "do" anything (slow and repetitive), feeding one AI's output into another, or adding more context.
But there's a missing piece here. When an AI talks to me, it should talk to me differently than it talks to my wife. The things I care about are different from what she cares about. We often prompt AI by telling it what it is, but not who we are. Telling the AI who they're talking to really helps focus their outputs. AI is perfectly capable of addressing each of us uniquely, and we should benefit from that.
There's a place near our house called "The Post." I have celiac disease and need to eat gluten-free (cross-contact is a problem). I have three kids. We order chicken tenders and fries. When we walk into The Post, the waitstaff know our names, they know our order, and they know what we want.
That is, except my wife. When she walks in, she has to look at the menu. If it's happy hour, she'll look at the happy hour menu; if it's a weekday, she'll look at the specials. Meanwhile, I'm joking with the kids, we're coloring in coloring books, and my Coke Zero is delivered to the table before my wife even knows what cocktail she's having. We're ten minutes into being there before her order has been taken and she can engage with the family restaurant experience.
You want to be a regular with your AI.
At a high level, you almost never need AI to do your job for you. What you need is for AI to help you accomplish your job. Letting the AI agent know more about you is the first step.
When I crack open Claude to work on a task, I don't start with a massive prompt. Instead, I drag a job description in for the "hat" I'm wearing that day. I drag in a markdown file describing the type of task I'm trying to get done. Then, I pull in a ticket, crash report, stacktrace, error log, or whatever specific context for the problem I'm trying to solve.
Suddenly, I have three documents with a huge amount of context that amplify the efficacy of every other part of the prompt I type. My actual text prompts might end up being only a few sentences long, but Claude "gets me" and has my order ready with very little prompting.
These files are incredibly powerful because they are entirely portable to any other AI agent on any platform. They're not platform-locked skills. They're just text files easily synced via Google Drive, GitHub, Dropbox, or iCloud. I can share task descriptions with teammates and colleagues. I even have files that describe different people I work with and people in my family.
This context helps get the most out of an AI agent with the least amount of effort in the moment.
The best part? I have never written one of these files myself, and I don't plan on it. Sometimes, I'll generate the task files after an especially arduous task that I worked through with an AI for a while. It's not something I have to plan in advance. I can go back to old chats and have the AI generate these documents for me.
These documents are tiny—usually around 1 KB. Even if I dropped 100 of them into a chat, I'd still be under 25k tokens of context used. I barely spend time organizing them (sometimes I'll ask Cowork or Obsidian to find them for me and put together the prompt).
If you want better results from AI, stop writing longer prompts from scratch. Write a file about who you are, what your job is, and what you care about. Hand it to the AI when you walk in, and let it have your order ready.