Lock the Outline Before Writing a Word

A sequencing rule for long-form: get the outline right and explicitly approve it before asking ChatGPT to write any prose, so you're not restructuring a finished draft.

Structure is the expensive thing to change late — reordering a written 2,000-word piece means rewriting transitions, intros, and callbacks throughout. Nailing the outline first is cheap and high-leverage: you catch a missing section or a wrong order while it's one line, not three paragraphs. Prose written onto a sound skeleton needs far less surgery.

Any substantial piece — articles, reports, chapters, proposals — where the order of ideas matters and a wrong structure is costly to unwind.

Short pieces or free-writing where structure is trivial or emerges as you go, and outlining first would just stall momentum.

Before any prose, give me an outline for <piece>: section headings with a one-line purpose each, in order. Audience: <who>. Goal: <what it should achieve>. We'll refine the outline together; don't write the body until I approve it.

Reviewing the outline reveals the 'objections' section should come before 'pricing', not after — a one-line reorder now instead of untangling two written sections later.

Under each heading, have it note the single key point and the evidence or example that section will rest on — so you catch a thin, unsupported section before you've written 300 words defending it.

• Letting it draft the whole piece, then fighting to restructure prose.
• Approving a vague outline that hides gaps until they're written.
• Outlining but not stating audience and goal, so the structure serves neither.