Stack
Email is where automation gets personal
Automating email is dangerous because the output goes straight to a human who will judge you by it. A clumsy automated email is worse than no email: it tells the recipient you did not care enough to write it. AutoMail was my attempt to automate the repetitive parts of email without losing the part that makes it feel human.
The human-in-the-loop step that saved me
My first version sent everything automatically. It was a mistake. The fix was to keep a human approval gate for anything the system was not sure about, so the automation drafts and the human nods. Over time, the categories that were reliably good got promoted to full auto, and the rest stayed under review.
- The system drafts; a human approves anything outside the known-safe categories.
- Templates handle the boring, identical cases; the LLM handles the ones that need nuance.
- Every send is logged so I can see exactly what went out and to whom.
What I learned about trust and tone
The big lesson was that automation earns trust gradually. You do not start by handing the keys to the machine; you start with the machine drafting and you approving, and you widen the autonomy only as each category proves itself. That graduated approach is the same pattern behind every safe automation I have built since: validate first, automate the validated, and keep a human watching the edges. Tone matters too. A few human touches in the templates kept the emails from sliding into that flat, generated register that makes people stop reading.
Lessons learned
- Automate email gradually. Start with draft-and-approve, promote categories to full auto only once they earn it.
- A human-in-the-loop gate is not a failure of automation. It is what makes automation safe to trust.
- Templates for the identical cases, an LLM for the nuanced ones. Do not make the model do work a template can.
- Tone is a feature. A few human touches keep automated email from reading like a bot wrote it.