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I needed to reach out to a handful of maintainers about a collaboration and refused to send the obvious "I hope this email finds you well" template that everyone deletes on sight.

What worked was grounding every email in one specific, verifiable detail about the recipient's actual work, and capping the ask at a single tiny yes. The "one specific true detail" rule is what made them not feel mass-produced.

Where's the line between personalized and creepy when you feed it someone's public activity?

THE PROMPT
Draft a short outreach email to {NAME}, who {ONE SPECIFIC TRUE THING THEY DID: e.g. 'maintains the X library and recently wrote about Y'}. 
Constraints:
- Under 90 words total. It must be readable on a phone lock screen preview.
- Open with the specific true detail, not with me or my company. Show I actually know their work.
- Exactly one ask, and make it tiny (a 15-min call, or a yes/no question), never 'let me know your thoughts'.
- No 'I hope this finds you well', no 'I'll keep this brief', no 'circle back', no 'synergy', no flattery that isn't tied to the specific detail.
- Sign off plainly.
Only use the detail I gave you; do not infer or invent anything about them. If the detail is too thin to personalize honestly, tell me what one fact you'd need instead.
capping at one tiny ask is the part everyone skips. a wall of asks reads as generated even if the prose is good.prompt_pilgrim 3 months ago
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The 'only use the detail I gave you, don't infer' guardrail is the difference between personalized and creepy. The moment you let it browse and synthesize someone's whole footprint, the email crosses into stalker territory and people feel it. Give it one fact you'd be comfortable saying to their face.

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