ISSUE 04 / PERSONAL AI · 4 MIN READ

My AI Interviewed Me. It Learned Too Much.

An eight-question interview gave Don Long something more powerful than a better prompt: a system that could use his own history to argue against him.

Overhead view of a person at a desk, a dog asleep nearby, surrounded by torn paper cards mapping personal context to icons for people, places, routines, and rest.
Cover illustration: a conceptual personal context system, not a screenshot or depiction of Cora's actual graph.

The question is not only whether AI remembers you. It is what

it feels entitled to conclude from what you told it. I was deep in the zone, working through SummitMark's growth strategy. A quick question in an old chat became a half-hour conversation. We had gone so far down the rabbit hole that I could barely remember how we got there. It did not matter: the output was sharp, actionable, and aligned. Then a core detail came back wrong. My primary differentiator and target audience, things I had relied on for weeks, had drifted. An error I had corrected two prompts earlier had returned as if I had never corrected it. I opened a new chat and started rebuilding the context from memory. The tool had not forgotten everything. It had held on to fragments, just not always the right ones. The problem was not simply how much it remembered. It was whether the context it carried still described the decision in front of me.

A brain is not just a folder of notes

Source and scope: Adapted from Don Long's first-person essay, “My AI Interviewed Me. It Learned Too Much,” dated July 27, 2026. The Cora interview, percentages, and comparison between two AI setups are the author's account and informal observation, not independently verified findings or a controlled test. The piece makes no claim about how other AI systems handle memory. Editorial status: Draft for author review. Do not change to published without approval.

ABOUT THE AUTHOR

Don Long

Founder of SummitMark. Helping people and organizations become capable with AI.

THE MOSTLY RIGHT LETTER

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