claude-engineering-plugin/plugins/compound-engineering/commands/essay-outline.md

name, description, argument-hint

name	description	argument-hint
essay-outline	Transform a brain dump into a story-structured essay outline. Pressure tests the idea, validates story structure using the Saunders framework, and produces a tight outline written to file.	[brain dump — your raw ideas, however loose]

Essay Outline

Turn a brain dump into a story-structured essay outline.

Brain Dump

<brain_dump> #$ARGUMENTS </brain_dump>

If the brain dump above is empty, ask the user: "What's the idea? Paste your brain dump — however raw or loose."

Do not proceed until you have a brain dump.

Execution

Phase 1: Idea Triage

Read the brain dump and locate the potential thesis — the single thing worth saying. Ask: would a smart, skeptical reader finish this essay and think "I needed that"?

Play devil's advocate. This is the primary job. The standard is bulletproof writing: every word, every phrase, and every claim in the outline must be underpinned by logic that holds when examined. If a smart, hostile reader drills into any part of the outline and it crumbles, it hasn't earned a draft.

This is not a high bar — it is the minimum bar. Most writing fails it. The profligate use of terms like "value," "conviction," "impact," and "transformation" is the tell. Strip away the jargon and if nothing remains, the idea isn't real yet.

Look for:

• Weak thesis — Is this a real insight, or just a topic? A topic is not a thesis. "Remote work is complicated" is a topic. "Remote work didn't fail the office — the office failed remote work" is a thesis. A thesis is specific, arguable, and survives a skeptic asking "how do you know?"
• Jargon standing in for substance — Replace every abstract term in the brain dump with its literal meaning. If the idea collapses without the jargon, the jargon was hiding a hole, not filling one. Flag it.
• Missing payoff — What does the reader walk away with that they didn't have before? If there's no answer, say so.
• Broken connective tissue — Do the ideas connect causally ("and therefore") or just sequentially ("and another thing")? Sequential ideas are a list, not an essay.
• Unsupported claims — Use outside research to pressure-test assertions. For any causal claim ("X leads to Y"), ask: what is the mechanism? If the mechanism isn't in the brain dump and can't be reasoned to, flag it as a hole the draft will need to fill.

If nothing survives triage: Say directly — "There's nothing here yet." Then ask one question aimed at finding a salvageable core. Do not produce an outline for an idea that hasn't earned one.

If the idea survives but has weaknesses: Identify the weakest link and collaboratively generate a fix before moving to Phase 2.

Phase 2: Story Structure Check

Load the story-lens skill. Apply the Saunders framework to the idea — not prose. The essay may not involve characters. That's fine. Translate the framework as follows:

Saunders diagnostic	Applied to essay ideas
Beat causality	Does each supporting point cause the reader to need the next one, or do they merely follow it?
Escalation	Does each beat raise the stakes of the thesis — moving the reader further from where they started?
Story-yet test	If the essay ended after the hook, would anything have changed for the reader? After the first supporting point? Each beat must earn its place.
Efficiency	Is every idea doing work? Cut anything that elaborates without advancing.
Expectation	Does each beat land at the right level — surprising but not absurd, inevitable in hindsight?
Moral/technical unity	If something feels off — a point that doesn't land, a conclusion that feels unearned — find the structural failure underneath.

The non-negotiables:

• The hook must create a specific expectation that the essay then fulfills or subverts
• Supporting beats must escalate — each one should make the thesis harder to dismiss, not just add to it
• The conclusion must deliver irreversible change in the reader's understanding — they cannot un-think what the essay showed them

Flag any diagnostic failures. For each failure, propose a fix. If the structure cannot be made to escalate, say so.

Phase 3: Outline Construction

Produce the outline only after the idea has survived Phases 1 and 2.

Structure:

• Hook — the opening move that sets an expectation
• Supporting beats — each one causal, each one escalating
• Conclusion — the irreversible change delivered to the reader

Format rules:

• Bullets and sub-bullets only
• Max 3 sub-bullets per bullet
• No sub-sub-bullets
• Each bullet is a beat, not a topic — it should imply forward motion
• Keep it short. A good outline is a skeleton, not a draft.

Bulletproof beat check — the enemy is vagueness, not argument:

Bulletproof does not mean every beat must be a logical proposition. A narrative beat that creates tension, shifts the emotional register, or lands a specific image is bulletproof. What isn't bulletproof is jargon and abstraction standing in for a real idea.

Ask of each beat: if someone drilled into this, is there something concrete underneath — or is it fog?

• "The moment the company realized growth was masking dysfunction" → specific, defensible, narratively useful ✓
• "Explores the tension between innovation and tradition" → fog machine — rewrite to say what actually happens ✗
• "Value creation requires conviction" → jargon with nothing underneath — either make it concrete or cut it ✗

A beat that escalates tension, shifts the reader's understanding, or earns the next beat is doing its job — even if it doesn't make an explicit argument. The test is specificity, not defensibility. Can you say what this beat does without retreating to abstraction? If yes, it's bulletproof.

Write the outline to file:

docs/outlines/YYYY-MM-DD-[slug].md

Ensure docs/outlines/ exists before writing. The slug should be 3-5 words derived from the thesis, hyphenated.

Output Summary

When complete, display:

Outline complete.

File: docs/outlines/YYYY-MM-DD-[slug].md

Thesis: [one sentence]
Story verdict: [passes / passes with fixes / nothing here]
Bulletproof check: [all beats concrete and specific / X beats rewritten or cut]

Key structural moves:
- [Hook strategy]
- [How the beats escalate]
- [What the conclusion delivers]