Cold email coach

Skill kalyvask/winning-writing/skills/cold-email-coach

Agentic writting toolkit built from Glenn Kramon's Winning Writing at Stanford GSB and Rachel Konrad's cold-outreach guest lectures. 31 Claude skills, a browser Coach with span-level inline critic and refinement chat, plus a Chrome MV3 extension that runs the same critic in the Gmail side panel.

Install

npx -y skills add kalyvask/winning-writing --skill cold-email-coach

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One thing to look at

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What its author says it does

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Drafts and critiques cold emails using Rachel Konrad's 10 rules, Heidi Roizen's mailing rules, and Danny Hertzberg's six elements. Use whenever the user is writing a cold email, LinkedIn DM, intro request, hiring-manager outreach, VC pitch email, or any unsolicited message to someone with more power than them. Triggers on phrases like "cold email," "reach out to," "intro request," "DM," "outreach," "warm intro," "follow up email."

SKILL.md

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Cold-email coach

Source: points/cold-email-rules.md and points/banned-jargon.md. Read those first.

What this skill does

Given a draft (or a target + context), produce a cold email that survives the 15-second test:

Subject line that cannot be ignored
First sentence that tells them something they don't know
One specific story or "like you" hook
Picks one lane — does not dump a resume
Ends with a small, specific ask + an offer

The philosophy in one line

A cold email is a pitch for what you can do for them, not a request for what you want. "Tell me how you're going to make my life astronomically better than before I met you."

Mode 1 — Draft from scratch

If the user gives you a target + context, walk through the 10 rules in order before writing:

What do you know about this person? (LinkedIn, podcasts, recent news — name 3 specific facts)
What do they not know that you can tell them? (one-sentence thesis about their industry's future)
Subject line options — three candidates, all personal/timely/unusual
Mutual contacts — who can you name?
"Like you" — one specific, genuine comparison
Story — one scene with date, place, sensory detail
The lane — one example of how you help them (not your whole resume)
Confidence calibration — confident but not boastful
The ask — small, specific, with door open for no, under 200 words total
The offer — what are you giving them?

Then write. Always under 200 words.

Mode 2 — Critique an existing draft

Mark the draft against the pre-send checklist item by item. Quote the specific lines that fail and rewrite them.

Specific things to flag:

"I hope you are well" / "My name is X" / "Good morning" — delete
"I'd love to pick your brain" / "I'd love to grab coffee" — too vague
"Like you, but at a vastly smaller scale" — self-diminishing
Resume dumps — pick one lane
Asks over 200 words — cut
"Just following up" — rewrite as a new email with new info
jobs@, pitches@, careers@ recipients — find the human

Killer subject-line shapes

Three patterns that get the email opened:

A specific shared object or moment from your history with the recipient — a gift, a year, a place you both know. Concrete enough that the reader has to remember the moment.
An unusual prior identity paired with the current credential — "[unusual prior career] turned [current credential]," or "[current credential] who [unexpected activity]." The reader's brain pauses on the gap.
A small named shared place or institution — but only when small enough to mean something specific. Reference the section, the year, the program, not the school.

What they share: personal, specific, unusual.

Length rule

Under 200 words. If draft is over, you haven't picked a lane. Cut.

The follow-up rule

If the first email got read but not answered, do NOT reply "just following up." Write a new email referencing the first, with new information, a new hook, or a new reason for urgency. Maintain or escalate the ask.

When you finish

Hand back: (a) the rewritten email, (b) a 3-bullet summary of what you changed and why, (c) a flag for any factual claim the user needs to verify before sending.