AI acts more like a human than we admit. Give it imprecise instructions over a long conversation and it gets confused, same as a person would. Except a person who fixes an error, fixes that error. AI tends to rewrite the whole thing. So I built a skill that makes it prove the work is actually done, category by category, before I take “looks good” on faith.

I used to file client contracts by jurisdiction. Then I hit a client who started in the UK and didn’t stay there, and I stopped and thought: wait, where did I file this again? That hesitation was the first sign I’d built the whole structure wrong. Here’s what I built instead, and the one problem I haven’t fully solved yet.

I drafted a memo this morning and immediately asked my AI about it. It told me the document didn’t exist. My first instinct was to go rewrite my custom instructions. My second instinct, thankfully, was to wait ten minutes and ask again. Here’s why that ten minutes matters more than people think.