18 - How I Introduce Myself to Every New AI I Try
Most people open a new AI chat the same way they’d open a search bar — straight into a question, no context, no introduction. Then they wonder why the answers feel generic. In this episode, I walk through the three specific moves I make every time I start with a new AI (or reintroduce myself to one I’ve been using for a while), and why treating it like a relationship instead of a transaction changes what you get back.
Move One: Bring Your “AI Knows Me” Document
When I got locked out of my ChatGPT account, I didn’t start from zero — I had already asked it to summarize what it knew about me, and I imported that into a new AI. I walk through how to build this document and why it should never be treated as finished.
Move Two: Beyond Facts — Temperament, Not Just Biography
Facts are easy. What actually changes how AI talks to you is knowing your temperament — how you process things, what sets you off, what doesn’t. I share the specific instruction I gave AI about not treating me like an anxious person, and why that mattered.
Move Three: Give It a Story, Not Just a Bullet Point
I tell the story of driving a broken-down van through a Northwoods blizzard at eleven years old, and why sharing something like that tells an AI more about your temperament than any preference list could.
What You Put In Is What You Get Out
A generic answer isn’t a failure of the AI — sometimes it’s exactly what you wanted, and that’s fine as long as it’s on purpose. I talk through how to be intentional about when you want a robot answer versus something personalized.
Ask AI to Argue With You
Instead of using AI as an echo chamber, I use it as a pressure test — asking it to fact-check me and hand me the strongest counterarguments to my own position.
Standing Rules vs. One-Time Comments
The difference between a permanent instruction (“never suggest medical scenarios to my anxious friend”) and a temporary one (“don’t let me go down rabbit holes until after this test”), and why naming that distinction out loud actually works.
This isn’t a one-time setup. It’s a relationship that builds over time, the same way any relationship does. Next episode, we flip it around — how AI can introduce itself to you.
Jill’s Links
https://jillfromthenorthwoods.com/ - Find my podcasts, videos, downloads and ways to contact me
https://www.buymeacoffee.com/smallstepspod
Email the podcast at jill@startwithsmallsteps.com
By choosing to watch this video or listen to this podcast, you acknowledge that you are doing so of your own free will. The content shared here reflects personal experiences and opinions and is intended for informational and educational purposes only. I am not a software developer, data scientist, or AI professional. Any tips, tools, or suggestions offered should not be considered a substitute for professional technical advice. AI tools and platforms change frequently — always verify current features, pricing, and terms directly with the providers. You are solely responsible for any decisions or actions you take based on this content.
