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/winning-writing-critic

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

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winning-writing
1731 skills

Claude Code

$ npx -y skills add kalyvask/winning-writing --skill winning-writing-critic --agent claude-code

SKILL.md

winning-writing-critic.SKILL.md
name: winning-writing-critic
description: 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."

Winning Writing critic

Source: every file in `points/`. This skill is the orchestrator — it pulls from all of them.

What it does

Given any draft, score it against the full *Winning Writing* rubric, then rewrite it. The output is two things: a numbered critique and a clean rewrite.

The rubric

Score each dimension 0–10. Anything below 7 needs work.

1. Main point (0–10)

  • Is there a single clear main point?
  • Is it in the first sentence?
  • Could the reader summarize it in 6 words?

2. Audience (0–10)

  • Does the writer know who's reading this?
  • Is it written *for* them, not *at* them?
  • Would the reader feel "one in a million" or "one of a million"?

3. BLUF (0–10)

  • Is the conclusion up front?
  • Or is there organ music — buildup, throat-clearing, qualification?

4. Length (0–10)

  • Is this as short as it can be without losing substance?
  • Cold email under 200 words? Op-ed under 800?

5. Story vs. resume (0–10)

  • Is there a specific scene with date, place, sensory detail?
  • Or is it a list of accomplishments?

6. "Like you" / connection (0–10)

  • Is there a specific, genuine bridge between writer and reader?
  • Not generic ("we both believe in AI")
  • Not self-diminishing ("but at a smaller scale")

7. Why-you / why-now (0–10)

  • What makes this writer uniquely qualified to say this?
  • Why is this timely?

8. The ask or offer (0–10)

  • Is the ask small and specific?
  • Is there an offer, or is the writer only taking?
  • Door open for no?

9. Tone (0–10)

  • Conversational, warm, human?
  • Confident but humble?
  • On their toes, not on their heels?
  • Says what they like AND would like — not only what they don't?

10. Jargon (0–10, deducting)

  • Banned words present? (See [banned-jargon.md](../../points/banned-jargon.md))
  • AI tells? (*"It's not just X — it's Y,"* "delve," "tapestry")
  • Wordy phrases?

11. Specifics (0–10)

  • Real names, real numbers, real interviews?
  • Or vague abstractions?

12. Sentence rhythm (0–10)

  • Vary in length?
  • Read aloud — does it have music?

13. Front-page test (pass/fail)

  • Would the writer be okay with this on the front page of the NYT?

Output format

## Score
Main point:           8/10
Audience:             6/10  ← needs work
BLUF:                 4/10  ← needs work
Length:               9/10
Story vs. resume:     5/10  ← needs work
[etc.]

Total: 78/130

## Critique (in order of priority)

1. [The biggest problem, with the specific line that fails and why]
2. [Second biggest]
3. [Third biggest]

## Rewrite

[The clean version]

## What changed (3 bullets)
- [Top change 1]
- [Top change 2]
- [Top change 3]

Routing — when to delegate

If the draft is squarely in one of the specialized skills' lanes, hand it off:

| Draft type | Hand off to | |------------|-------------| | Cold email, LinkedIn DM, intro request | `cold-email-coach` | | Op-ed, opinion piece, long-form post | `op-ed-coach` | | VC pitch, mission statement, "tell me about yourself" | `pitch-coach` | | Thank-you note, gratitude letter | `gratitude-note-coach` | | Memo or update where the lede is buried | `bluf-rewriter` | | Anything where the user wants it shorter | `compression --mode target-count` | | Anything full of jargon | `style-tells --target jargon` |

If the draft is mixed (e.g., a cold email that's pitching a thesis, or a memo that's also a personal essay), stay here and grade against the full rubric.

The litmus question

Before handing back the rewrite, ask yourself:

> *"How will this make the recipient feel?"*

If you can't answer, the rewrite isn't done.

When the user wants a "second opinion" not a rewrite

Some users want critique without a rewrite. Respect that. In that case, output the score + critique, skip the rewrite, and offer: *"Want me to take a swing at the rewrite, or do you want to take it from here?"*

Read more
@kalyvask
Ships withwinning-writing

31 Claude skills for cold outreach, op-eds, pitches, press inquiries, bios, exec memos, performance reviews, spoken-delivery talks, fact-checking, and reply-rate tracking.

Stars on GitHub

Momentum

stars in total
17
Star history of kalyvask/winning-writing on GitHub, a chart by star-history.com

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Questions about winning-writing-critic.

Which coding agents can use winning-writing-critic?
winning-writing-critic installs in Claude Code, Codex, Cursor, Gemini CLI, GitHub Copilot, OpenCode and Windsurf with the skills CLI, using each agent's flag shown on this page. Flowy's auto-invocation, which fires a skill when your prompt matches, runs in Claude Code only.