When things go sideways

Add one specific personal detail and re-run it — their business name, a real date, something they actually said. If it is still flat, tell the AI plainly: "Rewrite this the way a person would say it out loud. Cut anything that sounds like a form letter."

Vague tone instructions get vague tone back. Name it in ordinary words — warm, direct, firm but kind, like I'd say it to a mate who's also a customer. You can also give it a rule: "No corporate phrases. No 'I trust this finds you well'."

Put a number in. Under 100 words works; keep it short does not. If it still runs long, reply in the same chat: "Half that length. Keep the ask, cut the throat-clearing."

Say one clear action explicitly, and make sure the goal you wrote has a single verb in it. Multiple asks in a business email reliably get you no reply at all, because choosing is work and the reader is busy.

AI will invent a date, a figure or a commitment if the prompt implies one should be there. That is why the pre-send check starts with everything in it is true. If it keeps happening, add a line to the prompt: "Do not invent any dates, prices or commitments. If something is missing, leave it in brackets for me to fill in."

Refine in the same chat rather than opening a new one. Keep the structure, change the tone. Same email, but assume they've already paid. Iteration gets you there in two moves; regeneration gets you a fresh draft with a fresh set of problems.