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You Already Signed This Off (In the Simulation)
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You Already Signed This Off (In the Simulation)

I made AI clones of my boss, a GitHub exec, and my CEO. They knew every rule the real people follow but never knew when to break one.

Oct 9, 2026 · 10 min read

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“Don’t freak out, I cloned you.”

That’s what I told Natalia Quintero, my boss at the time, after I distilled a year of her Slack messages into a file called natalia.md and used it to simulate whether she’d sign off on an email I was about to send a client. She didn’t freak out—in fact, she said it was her favorite call of the day.

I had just started in a consulting role reporting to Natalia, and I was worried I didn’t know how to communicate with corporate clients. Our clients were large enterprises, but I had only ever had experience working with startups. Natalia, meanwhile, had years of corporate and banking experience. I knew my tendency to write emails like I write tweets might not be professional enough for this context, but I didn’t want to be asking Natalia to check my emails multiple times a day. She had better things to do, and when she did give me advice, she was often repeating herself.

AI can produce more drafts, proposals, and emails than anyone has time to read, so the scarce thing at work is the time of a person with judgment who can say, “Yes, send it,” or “Try it another way.” Those people spend a lot of their day telling different people the same things, when they could instead be spending their time doing something more productive. Since AI is good at role-play, I figured it could help take some of that burden off my colleagues by capturing their judgment without me having to bother them.

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