Winning writing critic

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)
• 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?"