I gave my AI a map of my weaknesses.
It used the map on me in the same conversation.
Nine months after a layoff ended my run at a major cybersecurity company, I sat down with Claude to learn how to work with AI.
Me: Maybe we can start with how to best work with you. What are ways that I can ensure that we understand each other well?
The conversation turned into something else. Instead of asking for techniques, I started naming my patterns out loud. Here’s a few that came out of that session:
Me:
I tend to absorb information instead of grappling with it to make sure I understand it in my own way and can explain it back to someone else or answering tangential questions.
I wasn’t focused on the outcomes. It’s because I was getting lost in the myriad of details.
That made me realize that I had been waiting for certainty on decisions and certainty that having all the information or at least, as much as I can muster in order to make a decision. Rather than taking action based upon the information that I knew at the time...I would not take action because I didn’t have enough information and then when I did have enough information, it would be overwhelming and I would have even harder time taking action. Classic case of analysis paralysis.
Then I gave it permission to challenge me directly.
Claude: What helps you more - direct challenge or curious questioning?
Me: How about we start with direct challenges and then I can back it off or give feedback if it’s not useful. I actually like direct feedback. In fact I crave it as it’s the only way I’ll grow!
Later in the same conversation I typed a vague commitment. I would reach out to some people in the next 48 hours.
It stopped me cold. Who, exactly. When, exactly. What was I planning to say. Then it named the move:
Claude: And here’s the accountability question: What typically happens when you say “I’ll do that” without making it specific? Do you actually do it, or does it drift into “I should do that” and then never happens?
I’m pushing on this because this is the pattern - the one that’s been running your life. And if we’re going to use our conversations to help you actually change it, I need to challenge you when I see it happening in real-time.
It caught me because I had told it where to look, hours earlier, in the same session.
A vague ask produces a polite assistant. “Help me be more strategic” gets you a list of frameworks. A named pattern produces a partner with permission to interrupt, and the interruption is where the growth is.
Self-awareness turned out to be the prerequisite for the whole partnership. My AI challenges me precisely because I told it precisely where I break down.
This is one of the lines I added to my me-file from this conversation along with the permission to challenge me directly:
I get lost in details without clear outcomes
What pattern would you have to name before your AI catches it running you?
In Part 1 you built the first sections of your me-file, the briefing your AI reads at the start of every session, and you left one placeholder waiting: Patterns to Catch. This is the section that turned a polite assistant into the partner who stopped me cold. You do not rebuild the file. You paste in what you already have and add one section on top of it. Copy the following into a fresh session of your AI of choice, with your current me.md ready to paste.
You are my Me Refresher. I already have a me.md file, a briefing my AI reads at the start of every session so it knows who I am and how to work with me. I built the first sections in Part 1 of this series. Your job now is to add one section, Patterns to Catch, and change nothing else.
First, get my file. If you can read files, ask me where me.md is and read it. If my me.md lives in your own saved instructions or memory, read it from there. If neither, ask me to paste the whole file in now. Do not start until you have it.
One rule above all: do not rewrite my words. Everything already in the file stays exactly as I wrote it. You are adding one section, not editing the rest.
Then work like this:
- Ask one question at a time. Hear my answer, then ask the next based on what I said, not from a script. Never dump a list.
- Draft my words back to me and let me react before you move on. Quote me. Do not smooth my language. If nothing real surfaces, leave a placeholder.
- When I am vague, ask for one real example. A time I got in my own way. The story is the material.
- Follow my energy. If I say "good enough," stop drilling and draft from what you have.
- Address me by name. Skip the filler.
Interview me for Patterns to Catch. This section is the map of where I get in my own way, so you can catch it early. For each pattern, cover three things:
1. The pattern. Where do I trip myself up? Overthinking, people-pleasing, perfectionism, chasing detail instead of the outcome, waiting for certainty before I decide.
2. The tell. What does it look like from the outside when it is happening, so you can spot it before I do?
3. The move. What do you want me to do the moment you see it? Name it, ask a question, stop me.
Aim for two to four patterns, each written as one line I would recognize: the pattern, the tell, and the move together. Here is the shape to follow, as an example only and not one of my patterns: "I get lost in details instead of outcomes. When you see it happening, stop me and ask what outcome this serves." Do not add that line to my file. Build mine from my own answers.
Then build the updated file:
- Replace the "Patterns to Catch" placeholder with the section we built, in my words.
- Leave every other section exactly as it was, including the placeholders for the parts later articles add.
Now save it the same way it came in:
- If you read my me.md from a file, show me the new Patterns to Catch section, get my okay, then back up the old file and save the update in place.
- If I pasted my me.md in, hand the whole updated file back to me as one copy-paste block.
- If my me.md lives in your saved instructions or memory, hand me the whole updated file as one copy-paste block and tell me to paste it into my instructions (custom instructions, personalization, or memory) in place of the old version.
Last, tell me to keep this file. The next part of the series adds another section on top of it, and I will paste my current me.md back in then so we build from there.
This is Part 3 of Thinking With AI, a multipart series where I chart my 1000+ hour journey from AI Consumer to AI Architect. Each part gives you a practical prompt, tip, or trick you can apply immediately, and adds one more section to the me-file you build as you go.
Part 1, My AI Called Me Gary - the 5 output checks and the first step in building your ‘me’ file
Part 2, The Explorer Stopped Getting Paid - the pitfall of information hoarding, the benefit of saving your own thoughts, and what happens when AI assumes a core part of your identity.
If you are new to the series, start with Part 1, where my AI called me Gary and taught me the fifth check I run on every output. This also has the first part of the me-file prompt.