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.
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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:
| Mode | Cuts | Use when |
|---|---|---|
| target-count | throat-clearing, hedges, weak sentences, anything between the draft and the word target | User has a length to hit (200 for cold email, 500 for op-ed, 6 for product summary) |
| redundancy | phrases 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:
- Cut to 1.5× the target — easy passes only
- Cut to 1.2× the target — harder; remove subordinate clauses
- Cut to 1.0× the target — surgical; every word earns its place
- 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:
- What's the single most important thing about this?
- Who is the protagonist?
- What changed?
- 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
- First pass — read aloud. Cross out any sentence you stumble over. Stumbles are usually sentences not earning their place.
- 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.
| Redundant | Fixed |
|---|---|
| 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.
| Redundant | Fixed |
|---|---|
| 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.
| Redundant | Fixed |
|---|---|
| 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.
| Redundant | Fixed |
|---|---|
| 9am in the morning | 9am |
| Free gift | Gift |
| New innovation | Innovation |
| Past history | History |
| Future plans | Plans |
| End result | Result |
| Final outcome | Outcome |
| Unexpected surprise | Surprise |
| Personal opinion | Opinion |
| Each individual person | Each person |
| Advance planning | Planning |
| Joint collaboration | Collaboration |
| Period of time | Period |
Pattern 5 — Doubled qualification
If the noun or verb is absolute, the intensifier is redundant.
| Redundant | Fixed |
|---|---|
| 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
| Redundant | Fixed |
|---|---|
| Free of charge | Free |
| At a price of $100 | $100 |
| In the month of November | In November |
| The country of Greece | Greece |
| Despite the fact that | Although |
| In light of the fact that | Because |
| For the purpose of | To |
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 words | One strong word |
|---|---|
| Incredibly important | Vital / crucial |
| Dramatically cut | Slashed |
| Mitigating the impact | Cushioning / softening |
| Grown up significantly | Matured |
| Make better | Improve |
| Make sure | Ensure |
| Walk fast | Stride / hurry / dash |
| Impact significantly | Reshape / overhaul |
| Extremely smart | Brilliant |
| Especially unusual | Singular / unique |
| Negatively affect | Harm / hurt |
| Look carefully at | Examine / inspect |
| Think hard about | Reckon with / weigh |
| Get bigger | Grow / swell |
| Get smaller | Shrink |
| Get worse | Decline / worsen |
| Get better | Improve / mend |
| Very angry | Furious |
| Very tired | Exhausted |
| Very happy | Thrilled |
| Very sad | Bereft / devastated |
| Very surprised | Astonished |
| Very scared | Terrified |
| Very small | Tiny / minute |
| Very big | Enormous / vast |
| Very fast | Rapid / sudden |
| Very slow | Glacial |
| Very old | Ancient |
| Very new | Novel / fresh |
| Looked at quickly | Glanced |
| Spoke loudly | Shouted / boomed |
| Spoke softly | Murmured / whispered |
| Held tightly | Gripped / clutched |
| I'll be able to do this | I can do this |
| Action item | Task / to-do |
| Make a decision | Decide |
| Reach a conclusion | Conclude |
| Conduct an investigation | Investigate |
| Give consideration to | Consider |
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)
- Does this phrase add information not already implied by the verb, the subject, or the surrounding sentence?
- 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.