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Compression

Skill kalyvask/winning-writing/side-panel-coach/rules/skills/compression

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 compression

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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.

SKILL.md

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Compression

Source: points/core-rules.md rule 5 (be shorter), points/banned-jargon.md (wordy phrases), points/frameworks.md (six-word summary), and the Kramon in-class redundancy exercise.

"Be shorter. Always. Cut without losing substance." — Kramon

What this skill does

Two modes behind one skill. They cut different things:

ModeCutsUse when
target-countthroat-clearing, hedges, weak sentences, anything between the draft and the word targetUser has a length to hit (200 for cold email, 500 for op-ed, 6 for product summary)
redundancyphrases where one half is implied by the other (going forward, as I mentioned, reduce so they are smaller, free gift, definitely commit)Draft is wordy in a way that's hard to point at — long without obvious filler

Default --mode both runs redundancy first (it's surgical, every cut is defensible), then target-count (which may need to cut substantive material). The order matters: redundancy cuts free words first, so target-count doesn't have to.

How to invoke

/compression "draft text"
/compression --mode target-count --target-words 200 "draft text"
/compression --mode redundancy "draft text"
/compression --mode both --target-words 500 "draft text"

Without --mode, default to both. --target-words is required for target-count mode and optional for both (if omitted in both, run redundancy only).


Mode 1 — target-count

Most drafts can lose 30% with no loss of meaning. Many can lose 50%. Forced compression is what reveals which sentences were actually carrying weight.

Three drill levels

Level 1 — Cut 30% (standard pass)

Tactics:

  • Remove every -ly adverb that isn't doing real work
  • Replace wordy phrases (see banned-jargon.md)
  • Combine sentences that share a subject
  • Cut hedges: "I think," "perhaps," "it might be the case that"
  • Cut throat-clearing: "In this piece I'll argue that…" — just argue it
  • Replace passive with active

Level 2 — Hit a target word count

User gives a number (200 for cold email, 500 for op-ed, 100 for memo). Iterate:

  1. Cut to 1.5× the target — easy passes only
  2. Cut to 1.2× the target — harder; remove subordinate clauses
  3. Cut to 1.0× the target — surgical; every word earns its place
  4. Cut to 0.9× the target — leave room for one final addition

Level 3 — Six-word summary

The ultimate compression. One thing, six words, tells a story.

Run the user through:

  1. What's the single most important thing about this?
  2. Who is the protagonist?
  3. What changed?
  4. Draft. Score. Iterate.

Examples that work:

  • "For sale: baby shoes, never worn." (Hemingway)
  • "Edited Pulitzer winners. Now teaching business leaders." (Kramon)
  • "Immigrant's kid, chip on her shoulder." (student)
  • "Soldier first, engineer always, educator next." (student)

The rule: six words that tell a story — not six unrelated descriptors.

What not to cut

Compression is not amputation. Keep:

  • Specific sensory details (a date, a place, a sound, an image) — these make writing memorable
  • "Like you" lines and personal hooks
  • The one moment of warmth or humor
  • Names and numbers

Cut first:

  • Throat-clearing
  • Hedges
  • Adverbs
  • Synonyms used for variety ("she said… she explained… she argued…")
  • Unnecessary qualifiers
  • Background the reader can infer

The two-pass method

  1. First pass — read aloud. Cross out any sentence you stumble over. Stumbles are usually sentences not earning their place.
  2. Second pass — read again. For each surviving sentence, ask: what changes if I delete this? If nothing, delete.

Mode 2 — redundancy

A specific failure: a phrase that feels like it adds information when in fact it adds nothing. The verb or the surrounding context already implies it. Cut.

Pattern 1 — Verb-implied direction

"Going forward" and "moving forward" after a future-tense verb.

RedundantFixed
We promise better security going forward.We promise better security.
Moving forward, we'll offer encryption.We'll offer encryption.
In the future, all our hires will be technical.All our hires will be technical.
From this point onward, we'll improve.We'll improve.

The future tense already does the work. Add a tag only if you're contrasting with the past ("unlike last quarter, we'll publish monthly going forward" — fine).

Pattern 2 — Self-referential meta-commentary

The reader is reading it; they know.

RedundantFixed
I am currently writing this email to you.(cut entirely)
As I said earlier, X.X.
As I mentioned in my last email, X.X.
The purpose of this memo is to argue that X.X. (just argue it)
What I will demonstrate in this section is X.X. (then demonstrate it)

Pattern 3 — Verb-implied result

The verb names the action; the result is implied.

RedundantFixed
Reduce the size of teams so they are smaller.Reduce the team.
Increase headcount so we have more people.Increase headcount.
Lower the price so it costs less.Lower the price.
Shorten the meeting so it's not as long.Shorten the meeting.
Speed up the rollout so it's faster.Speed up the rollout.

Pattern 4 — Tautological qualifiers

The adjective and the noun say the same thing.

RedundantFixed
9am in the morning9am
Free giftGift
New innovationInnovation
Past historyHistory
Future plansPlans
End resultResult
Final outcomeOutcome
Unexpected surpriseSurprise
Personal opinionOpinion
Each individual personEach person
Advance planningPlanning
Joint collaborationCollaboration
Period of timePeriod

Pattern 5 — Doubled qualification

If the noun or verb is absolute, the intensifier is redundant.

RedundantFixed
I will definitely commit.I will commit.
It's absolutely critical.It's critical.
Completely unique.Unique.
Totally finished.Finished.
Fully comprehensive.Comprehensive.

Pattern 6 — Restating the obvious

RedundantFixed
Free of chargeFree
At a price of $100$100
In the month of NovemberIn November
The country of GreeceGreece
Despite the fact thatAlthough
In light of the fact thatBecause
For the purpose ofTo

Pattern 7 — Two weak words → one strong word

Kramon's Session 8 drill: nearly every adverb-plus-weak-verb pair has a single strong verb that does the work better. The strong verb is shorter, more vivid, and more memorable. Two weak words almost always lose to one strong one.

Two weak wordsOne strong word
Incredibly importantVital / crucial
Dramatically cutSlashed
Mitigating the impactCushioning / softening
Grown up significantlyMatured
Make betterImprove
Make sureEnsure
Walk fastStride / hurry / dash
Impact significantlyReshape / overhaul
Extremely smartBrilliant
Especially unusualSingular / unique
Negatively affectHarm / hurt
Look carefully atExamine / inspect
Think hard aboutReckon with / weigh
Get biggerGrow / swell
Get smallerShrink
Get worseDecline / worsen
Get betterImprove / mend
Very angryFurious
Very tiredExhausted
Very happyThrilled
Very sadBereft / devastated
Very surprisedAstonished
Very scaredTerrified
Very smallTiny / minute
Very bigEnormous / vast
Very fastRapid / sudden
Very slowGlacial
Very oldAncient
Very newNovel / fresh
Looked at quicklyGlanced
Spoke loudlyShouted / boomed
Spoke softlyMurmured / whispered
Held tightlyGripped / clutched
I'll be able to do thisI can do this
Action itemTask / to-do
Make a decisionDecide
Reach a conclusionConclude
Conduct an investigationInvestigate
Give consideration toConsider

Use the table as a sniff test, not gospel. If the strong word changes the meaning ("vital" and "important" are not exact synonyms — vital means "essential to survival"), keep the weaker pair. The point is to notice when two weak words are doing the job of one, not to forcibly substitute.

The two-question test (for any phrase)

  1. Does this phrase add information not already implied by the verb, the subject, or the surrounding sentence?
  2. If I cut this phrase, what changes?

If 1 is no and 2 is "nothing changes" — cut.


How to run the pass

Pass 1 — Redundancy scan

Search for direction tags (going forward, moving forward, in the future, currently, as I mentioned, as I said, as we discussed) — candidates to cut.

Pass 2 — Verb-result restatements

For each verb, check the next clause: does it merely describe the result? "Reduce X so Y is smaller" — cut the "so Y is smaller."

Pass 3 — Tautological adjectives and doubled qualifiers

free gift, new innovation, past history, end result, definitely commit, absolutely critical — cut the redundant half.

Pass 4 — Two-weak-words → one-strong-word

Scan for adverb-plus-weak-verb pairs and "very + adjective" pairs. Substitute the strong single word from the Pattern 7 table when the meaning holds. Skip when the strong word shifts the meaning.

Pass 5 — Target-count cuts (if a target is set)

Apply the three drill levels above. Stop when at target.

Pass 6 — Read aloud

Anything that lands twice in your ear lands twice in the reader's ear. Cut the second landing.

Output format

## Compression summary
Original: N words → Final: N words (X% reduction)
Target: N words [if set]

## Redundancy hits

| Line | Pattern | Original | Fixed |
|---|---|---|---|
| N | direction tag | "going forward, we'll improve" | "we'll improve" |
| N | self-referential | "as I said earlier, X" | "X" |
| N | verb-implied result | "reduce so they are smaller" | "reduce" |
| N | tautological | "free gift" | "gift" |

## Target-count cuts [if target set]

Categories of what was removed:
1. **Jargon and wordy substitutions:** [examples]
2. **Throat-clearing and hedges:** [examples]
3. **Substantive cuts:** [examples with one-line justification each]

## One flag
[If there's a sentence you might want to put back, with the tradeoff. Otherwise omit.]

## Clean draft
[The full text at the target length with all cuts applied.]

When the user resists cutting

Common pushback: "but that detail is important."

Response: "Then it should earn its place. Show me which other sentence we can cut to keep it. We can't keep both."

Compression is zero-sum.

When NOT to use

  • Legal writing where tag-alongs may be load-bearing for precision. "For the avoidance of doubt" sometimes does work "to be clear" doesn't.
  • Poetry, song lyrics, deliberate rhetoric. Repetition is the device.
  • Casual chat / Slack where small redundancy reads warmer than terse. "Just wanted to say" in a thank-you note may earn its place.

The Kramon rule

"Every sentence you write, ask yourself: am I being repetitive? That's the way to improve your writing."

Most drafts have two to five redundancy hits per paragraph. The most over-written drafts have one every sentence. Run this skill after style-tells for the cleanest result.

Keep looking

Skills are one crate of 328,083. Ordering is by how many stacks a row turns up in, so the top of any crate is what has actually been picked rather than what has the most stars.