winning-writing

Drafts and critiques business pitches, investor decks, mission statements, and personal pitches using the 7-part pitch framework, S.H.I.T., and the six-word test. Use when the user is writing a VC pitch, a deck narrative, a "tell me about yourself," a LinkedIn bio, a one-pager, a founding story, or any pitch about themselves or their company. Triggers on "pitch," "deck," "investor," "mission statement," "tell me about yourself," "founding story," "LinkedIn bio," "elevator pitch."

Drafts and critiques speeches, talks, keynotes, lightning talks, demo-day pitches, all-hands updates, conference presentations, wedding toasts, and any spoken-delivery piece using Glenn Kramon's 12 wowing-the-crowd rules from Stanford GSB's Winning Writing. Use when the user is preparing a talk, presentation, keynote, panel opener, board presentation, all-hands, town hall, demo-day pitch, toast, eulogy, commencement address, or any piece that will be delivered aloud. Triggers on phrases like "I'm giving a talk," "preparing a speech," "keynote," "all-hands," "demo day pitch," "wedding toast," "panel opener," "TED-style," "deliver this aloud," "speaking at," "presentation script."

Reorganizes a memo, email, status update, or report so the bottom line is up front. Implements Kramon's BLUF (Bottom Line Up Front) rule. Use when a draft buries the lede, opens with context instead of conclusion, or builds up to the point with "organ music." Triggers on "BLUF," "lede," "buried," "memo," "status update," "exec summary," "TL;DR."

Cuts a draft to a target word count without losing substance. Two modes behind one skill. target-count hits a specific number (200 for a cold email, 500 for an op-ed, 6 for a product summary). redundancy catches the specific failure where a phrase says what the verb or context already implied — "going forward" after a future-tense verb, "as I mentioned earlier," "reduce so they are smaller." Implements Kramon's "rewrite this in less than 100 words" exercise, the six-word summary drill, and the in-class redundancy exercise. Use when the user says "shorten this," "cut this," "tighten," "make it concise," "too many words," "going forward," "say it twice," "redundant." Pass --mode target-count|redundancy|both (default both) and --target-words N for target-count.

Mode-aware writing critic. Distilled from Rachel Konrad's Stanford GSB "Winning Writing" course (spring 2026), the 10 rules of cold outreach, Heidi Roizen's mailing rules, and live class critiques. Loads a rule catalog (rules/catalog.json) and a mode definition (rules/modes.json) at invocation. Use whenever drafting or critiquing a cold email, outreach message, LinkedIn intro, exec memo, personal essay, bio, README, or LinkedIn post. Pass a mode argument to filter which rules apply.

Fixes two sentence-rhythm tells that mark prose as AI-generated. Two targets behind one skill, picked via the --target arg. fragment-chain (three or more short sentences back-to-back) and uniform-length (two or more consecutive sentences within ~2 words of each other, especially with parallel structure). Use when the user says "reads like AI," "too choppy," "same length sentences back to back," "staccato," "fragments piled up," "rhythm is off," "uniform pacing." Pass --target fragment-chain|uniform-length|all (default all).

Rewrites blunt downward or peer feedback as "what I like plus what I would like," focused on the work rather than the person, ideally phrased as a question. Use whenever the user is drafting a performance review, a Slack message to a report, a 1:1 talking point, an HR conversation script, a peer-review comment, or any line where they're tempted to criticize a colleague directly. Triggers on "give feedback to," "tell my report," "perf review line," "stop doing X," "you don't / you're not / you should stop," "smile more," "speak up more," "interrupt less," "less blunt," "burning out," "running late."

Finds the unexpected, dry, or self-deprecating angle that makes an email memorable. Turns "professional and polite" into "this person sounds like a real human." Use when a draft is technically correct but forgettable, when the user wants humor without slapstick, or when they need a subject line or sign-off with personality. Triggers on "make it funny," "more personality," "less corporate," "humor," "memorable subject line," "sign-off ideas."

Rewrites section titles, slide titles, op-ed headlines, email subject lines, and chapter headings from category labels into bold arguable claims. Implements Constine's "punchy slide titles that tell the story" rule and Kingsbury's NYT Opinion guidance that headlines should make a bold claim, not a neutral description. Use when the user has titles like "Product," "Market," "Background," "Why this matters" — labels that waste the reader's eye. Triggers on "slide titles," "section headings," "op-ed headline," "subject line," "chapter title," "punchy title," "scannable."

Cuts cinematic details that don't serve the main point. The opposite move from vividness. Vividness adds sensory detail; this skill removes detail that's vivid but distracts from the argument. Use when a narrative paragraph has impressive sensory texture (sounds, colors, weather, mechanics of an unrelated scene) that the reader has to push past to get to the point. Triggers on "eliminate irrelevant detail," "tighten the narrative," "the details are great but distract," "this paragraph wanders," "too much texture."

Diagnoses drafts that tell three half-stories instead of one full story, and rewrites them around the single strongest narrative thread. Implements Konrad's rule 7 and Adam Bryant's "stay in your lane" advice — distinct from compression (which cuts words) because pick-a-lane cuts whole stories. Use when a bio, cold email, op-ed, or pitch reads as a resume regurgitation, when the writer is dumping multiple accomplishments instead of telling one fully, or when a paragraph keeps turning corners. Triggers on "pick a lane," "stay in your lane," "too many stories," "resume dump," "before/after rewrite," "compress the narrative," "feels like a CV."

Scrubs the three surface tells that make prose feel AI-generated, padded, or jargon-heavy. Three targets behind one skill, picked via the --target arg. em-dashes (default off in cold email / memo / Slack, max one per page in op-eds), adverbs (the -ly and intensifier pile), jargon (the Silicon Valley / consultant kill-list plus AI-tell phrases). Use when the user says "kill the AI tells," "scrub jargon," "remove em-dashes," "cut the adverbs," "make this sound human," "less corporate," "sounds like ChatGPT," "—," "very," "really," "leverage," "synergy," "delve," "tapestry." Pass --target em-dashes|adverbs|jargon|all (default all).

Cuts opening sentences that recap what the recipient already knows about themselves, their company, or their own work. Implements Konrad's rule 2 ("begin with something they don't know — tell me a secret about the future") and Kramon's rule 4. Use when a draft opens with flattery, a summary of the reader's accomplishments, restating their stated thesis, or reciting biographical facts they already have. Triggers on "they already know," "rewrite the opener," "stop with the flattery," "first sentence is weak," "secret about the future," "tell them something new."

Pushes a draft from abstract toward concrete at two scales. Noun-level (replaces "dog" with "German shepherd," "customer" with "Sarah at JPMorgan's options-trading desk," "many" with "47 of 100") and scene-level (turns "I was angry" into the body signal, room, and dialogue). Implements Kramon's "specific over abstract" rule, Kristof's "real names, real numbers, real interviews," and Lauren Weinstein's "could a director recreate this scene?" test. Use when a draft is technically correct but flat, when category nouns leak through, when stories tell instead of show, or when the user says "be specific," "show don't tell," "more vivid," "less abstract," "make it concrete," "find the colors." Pass --mode noun-level|scene-level|both (default both).

Audits a draft on Susan Fiske's two-axis model of social judgment — warmth (do I like and trust this person?) and competence (do I respect this person?) — and rewrites the lines that signal the wrong thing on either axis. Implements Kramon's hardest rule: "show competence AND warmth in a single sentence." Use when a draft reads cold-but-impressive (high competence, low warmth — the "consultant trap"), warm-but-unserious (high warmth, low competence — the "intern trap"), or flat on both. Triggers on "warmth," "competence," "too cold," "too eager," "not serious enough," "I sound like a consultant," "I sound like an intern," "first impression."

Drafts and reviews answers to reporter questions, on-the-record statements, crisis-comms responses, and press-inquiry replies. Implements Andrew Ross Sorkin's 11 rules (taught with Kramon at Stanford GSB) plus AP attribution definitions for off-the-record / background / deep background conversations. Use when a journalist is calling, when a story is about to break, when a competitor has just been hacked and you want to get ahead of inquiry, or when a class assignment asks you to play CEO under fire. Triggers on "reporter," "journalist," "press inquiry," "PR statement," "no comment," "on background," "off the record," "crisis comms," "media interview," "quote me."

Drafts and critiques a text-first investor pitch memo for pre-seed and seed founders, structured around the 15 questions every investor asks. Use as an alternative or complement to a pitch deck — memos are faster to iterate, harder to hide weak thinking inside, and serve as the script for walking through a deck in a meeting. Triggers on "pitch memo," "investment memo," "fundraise memo," "memo for investors," "pitch document," "alternative to deck," "memo not deck."

Read the user's recent cold-outreach sent mail, look up which messages got replies, classify reply sentiment, and produce an outcome report that surfaces what the responders had in common. Use when the user says "did my cold emails get replies," "what's my reply rate," "sent-mail outcomes," "track outcomes," or "/sent-mail-outcome-tracker." Requires a connected Gmail MCP. Read-only. Never contacts recipients.

Update `context/voice-and-style.md` or `context/about-me.md` from one of three sources. Manual (user dictates a single new rule, sample, or career fact). Memory (batch pull from Claude Code's auto-memory in `~/.claude/projects/<slug>/memory/`). Sent-mail (analyze the last 20-50 sent Gmail messages and propose updates from observed patterns). Always proposes diffs and requires per-file approval; never auto-writes. Use when the user says "save this to my voice file," "remember this style," "consolidate my voice," "update from memory," "read my sent mail," "voice from sent mail," "what does my voice actually look like," "voice-update," or "/voice-update." Pass --source manual|memory|sent-mail.

Grades any draft against the full Winning Writing rubric (Kramon + Konrad + Kingsbury) and rewrites it. The orchestrator skill — invoke when you don't know which specialized skill applies, when the user just says "review this" or "make this better," or when the draft spans multiple forms (e.g., a pitch email that's also kind of an op-ed). Triggers on "review," "critique," "feedback," "make this better," "is this good," "grade this."

Drafts and critiques bios, LinkedIn About sections, intro slides, "tell me about yourself" interview answers, and personal-essay openers using Adam Bryant's 500-CEO research and Lauren Weinstein's warmth+competence frame. Different from pitch-coach (which is product-shaped) and cold-email-coach (which is recipient-shaped). This skill is for the format where you ARE the subject. Use when writing a bio for a website, a LinkedIn About paragraph, the first slide of a deck about yourself, the opening of an application essay, or rehearsing the "tell me about yourself" interview answer. Triggers on "tell me about yourself," "write my bio," "LinkedIn About," "about me page," "intro slide," "personal essay," "self-introduction."

Drafts and critiques performance reviews using Glenn Kramon's seven rules from Stanford GSB's Winning Writing course. Use when the user is writing an annual review, mid-year check-in, self-review, 360 feedback, peer review, or any written feedback for an employee, boss, partner, or themselves. Triggers on phrases like "performance review," "annual review," "self-review," "write up my feedback for," "review my report's performance," "evaluate my employee," "write feedback for [name]," "promotion packet," "calibration writeup."

Finds specific, genuine "like you" hooks between the writer and a cold-outreach target — the bridges that turn a generic email into one that feels hand-written. Takes the recipient dossier and the writer's profile (about-me.md) and surfaces ranked angles. Use after recipient-research is done, before drafting. Triggers on "like you," "find a connection," "what do we have in common," "common ground."

Drafts and critiques op-eds, opinion pieces, and LinkedIn long-form posts using Glenn Kramon's framework, Katie Kingsbury's NYT Opinion guidance, and Nicholas Kristof's storytelling rules. Use when the user is writing an op-ed, an opinion piece, a Substack essay, a LinkedIn long-form post, or pitching one to a publication. Triggers on "op-ed," "opinion piece," "essay," "column," "pitch to NYT," "Substack post," "LinkedIn article."

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."

Makes a draft read like a real human typed it — adds asymmetry, light contractions, and (rarely) one safe typo. Use only when a draft is technically correct but reads polished beyond plausibility, when the user wants to "rough it up," "make it more human," or "less AI-clean." Does NOT run on high-stakes writing (see "When NOT to humanize"). Triggers on "humanize," "rough it up," "less polished," "more casual," "sounds too clean."

Independent second-model gate for cold emails before send. Must run on a DIFFERENT model than the one that drafted (e.g., draft on Opus, review on Sonnet — or vice versa). Acts as a binary pass/fail gate, not a regrade or rewrite. Names the specific failure mode from a 14-mode catalog (strategy / personalization / posture). Always surfaces the most likely counter-question the recipient will reply with. Triggers on "second pass," "cross-model review," "independent review," "review before send," or as the final step after `cold-email-coach` and `winning-writing-critic`.

Finds the human bridges between the writer and a target — mutual contacts, alumni networks, ex-colleagues, podcast connections, board overlaps — and ranks them by how likely they are to make a useful introduction. Different from connection-finder (which finds "like you" content hooks). This one finds *people* who can vouch. Use whenever the user is about to send a cold email and hasn't checked who they know in common with the target. Triggers on "warm intro," "find a connection," "who do I know," "mutual contact," "do I have anyone," "who can introduce me."

When pitching an idea, researches the graveyard — companies that tried something similar in the past 5–25 years and failed, what specifically killed them, and which operators or investors lived through those failures and would be valuable to talk to. Use before pitching to a VC, a customer, or a hiring manager — the graveyard reframes the pitch from "this is a great idea" to "this is a great idea AND I know why every previous attempt died." Triggers on "research the graveyard," "who tried this before," "previous attempts," "failed companies in this space," "post-mortem," "why did X fail."

Builds a research dossier on a cold-outreach target before drafting. Pulls LinkedIn, podcasts, blog posts, news, portfolio (if VC), and any specific personal details that would let an email feel hand-written rather than templated. Use when the user says "I want to email X" or "research Y before I write to them" or "build a dossier on Z." Triggers on "research," "dossier," "before I email," "background on," "find out about."

Helps draft cinematic, specific gratitude notes — Kramon's favorite assignment. Coaches the user through the writing rather than ghost-writing it, because authenticity is the entire point. Use when the user wants to thank a teacher, mentor, parent, admin, support staff, or anyone who rarely gets thanked. Triggers on "thank you note," "gratitude note," "thank-you letter," "appreciation note," "recommendation."