Outline Before Prose Skill

Documents get rewritten in review because the structure was wrong — and structure feedback arrived after two days of prose polishing. The outline-first discipline moves that feedback to hour one: a skeleton where every section is a one-line claim (not a topic), a header naming the reader and the decision, and a five-minute outline review with the key stakeholder before any paragraphs exist. Prose expands an approved outline in one pass; prose written first defends itself against restructuring forever.

What This Skill Produces

• The header — reader, the decision/action the doc exists to produce, and the length budget
• The claim outline — each section as the sentence it will argue, in order, with the evidence it will carry noted
• The outline review step — who sees the skeleton, what question they're asked, before drafting starts
• The expansion rules — how the approved outline becomes prose without growing new sections in the dark

Required Inputs

Ask for these if not provided:

• The doc's job — what the reader should do after reading (approve, decide, follow, stop worrying); docs without a job become tours
• The reader, specifically — their context level and their likely objection; the outline argues to someone
• The material — what's known, what evidence exists, the conclusion if one is already honest — outlines organize material; they don't survive its absence
• The reviewer — whose restructuring would hurt most later; that's who reviews the outline now

Framework: The Skeleton Rules

1. Sections are claims, not topics: "Performance" is a topic; "The latency regression comes from the new retry logic" is a claim — a claim outline can be disagreed with at outline stage, which is the entire point. If a section's claim can't be written, the thinking isn't done, and prose would have hidden that for two more days.
2. The header is the contract: reader + the decision + length budget, written first. Every outline decision gets tested against it — a section that doesn't move the named reader toward the named decision is cut now, at one line of sunk cost.
3. Order is the argument: claims sequenced so each earns the next — context → the problem's cost → the proposal → the evidence → the risks conceded → the ask. Reordering at outline stage is drag-and-drop; at prose stage it's surgery with transitions.
4. The outline review asks one question: "if the sections argue these claims with this evidence, does the doc work for you?" — five minutes, the reviewer who'd otherwise restructure in review. Their edits land on one page, and the expensive rewrite dies unborn. (This is the executive-summary discipline applied one stage earlier.)
5. Expansion is faithful or renegotiated: drafting fills sections without spawning new ones; material that demands a new section goes back through the header test (and the reviewer, if it changes the shape). The outline travels at the doc's top during drafting — becoming the TOC, or the exec summary's skeleton, at ship time.

Output Format

Outline: doc] — for reader] to decision] · budget: length]

The Skeleton

1. Section claim, as a sentence] — evidence: what carries it]
2. …

Ordered as the argument · cuts noted: "considered and dropped: X (fails the header test)"]

The Review Step

Who · the one question · scheduled before drafting]

Expansion Rules

Fill-don't-spawn · the renegotiation trigger · the outline's afterlife as TOC/summary]

Quality Checks

• ] Every section is a disagreeable claim, not a topic word
• ] The header names reader, decision, and budget — and every section passed its test
• ] Order makes each claim set up the next
• ] The outline reviewer is the person whose late restructuring would cost most
• ] Drafting rules prevent silent new sections

Anti-Patterns

• ] Do not outline in topics — "Background / Analysis / Conclusion" postpones every real decision to prose
• ] Do not draft while outlining — pretty sentences at skeleton stage are premature attachment
• ] Do not skip the review because the outline "is obvious" — obvious outlines take five minutes to confirm and two days to rewrite
• ] Do not defend outline structure at prose review — that conversation was available cheaper earlier; have it earlier
• ] Do not outline without the material — a skeleton of unknowns is a research plan wearing a doc's clothes, and should be named as one