Fine-Tuning a Personal Executive Assistant: Lessons from My Management Notes

After successfully fine-tuning ChefBot on cooking recipes, I wondered: Could I fine-tune an AI on my own management experience to create a personalized executive assistant? Imagine asking your AI: “Summarize last week’s 1:1 with Sarah and suggest coaching points”, and getting a response in your voice, drawing from years of team dynamics and decision patterns. All running locally, with complete privacy and no API costs. This is the story of how I built exactly that. Spoiler: I failed three times before succeeding, and the lesson wasn’t about hyperparameters. ...

October 5, 2025 · 8 min · Brian Hengen

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