ClaudeLong-formLevel 2: Context

How Do You Get Claude to Outline Before It Writes?

Tell Claude to write an outline and to stop there. Give it the reader, your main point and your sources, then edit the outline yourself before any prose exists. Moving a line in an outline takes seconds, while moving an argument through 5,000 written words takes much longer.

Prompt to copy 
Source material is attached: [list the files and what each one is].

I'm writing [type of piece] for [reader]. After reading it, they should [decide or do what]. My main point is: [one sentence].

Give me an outline only, and stop there. Don't write any prose until I say to go ahead.

For each section, give:
- A heading
- One sentence stating what the section argues, written as a claim and not a topic
- Which source it draws on, or "no source" if none
- A rough word count

Then tell me: which section is weakest, what a reader in this position would expect that's missing, and any question you need answered before drafting.
  1. 1Ask for an outline, then stop
  2. 2You edit the outline
  3. 3You approve it
  4. 4Draft to that version
A rule of thumb, not an Anthropic chart: your main edit happens in the second step, where a change costs one line.

Try it now

  1. 1Click +, choose Add files or photos, and attach your sources. Then paste the prompt.
  2. 2Read just the one-sentence claims from top to bottom. They should read like an argument on their own.
  3. 3Reply with your changes, reorder as you see fit, and ask for the revised outline. When it's right, say "Go ahead with section 1 only".
  4. 4You'll know it worked when you changed something important, such as the order or a section's claim, before any drafting happened.

Use it when

Anything with an argument or a sequence that matters: reports, proposals, long articles, talks, grant applications and book chapters. It's most valuable when the piece draws on several sources, since the outline shows how each one is going to be used.

Skip it when

Very short pieces, where an outline would be almost as long as the piece. And early idea generation, when you don't yet know your point. Ask for several possible angles first, then outline the one you choose.

Why it works

The "stop" has to be explicit. Anthropic's guide to Sonnet 5.5 warns that on an open-ended request, the model can start building a report when you only wanted ideas. Its suggested fix is to say so in the request: give the plan and stop until told to go ahead.

An outline also shows you Claude's reading of the job before you've paid for a draft. You can see at a glance if it misunderstood the reader or missed a source. Put long source files above your request, since Anthropic says placing long documents near the top of a prompt, above the query and instructions, improves performance across all models. Claude Docs counts toward usage limits, with long multi-source drafts using more, so catching errors here saves your plan as well.

Example

Say you're proposing a four-day week trial to your leadership team, using a staff survey and a report on similar trials, both as PDFs. Claude's outline might open with the survey results. You know your CEO cares first about client coverage, so you move that section to the start and change its claim to say how coverage will work. "No source" next to the coverage section tells you to find some evidence before drafting.

Going further

Writing each section as a claim rather than a topic is the most useful part of this prompt. "Costs" hides a missing argument, while "The trial costs less than one hire" can be challenged. Check that the source column isn't quietly empty. Anthropic's docs suggest telling Claude to use only the provided documents when you need that restriction, and to say when information is missing.

To keep the outline, ask for it as a doc using /docs, or in a project add it to project knowledge. Then a later chat can draft from it, even though chats in a project don't otherwise share context.

Common mistakes

  • Asking for "an outline for a report on X" without the reader or main point. You'll get a generic table of contents that fits any report on X.
  • Approving the outline without editing it. If you changed nothing, you probably just skimmed it.
  • Leaving out "stop". Anthropic's Sonnet 5.5 guide says open-ended requests can lead it to build more than you asked for.
  • Drafting all sections from an outline written before you read the sources yourself. Claude can only flag the gaps it can see.

Sources

Checked 6 November 2026. Products change often, so confirm details with the vendor.

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Beyond the course

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