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Writing & Content

Free Outlining & Research Prompts

Prompts for upstream writing work - outlining, researching, interviewing, organizing notes. Use them before drafting to save hours later, or to dig out of an over-researched mess.

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Narrow my topic

Cut a broad topic down to a writable thesis.

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My broad topic: [PASTE]. Help me narrow it. Output: 1) 5 narrower angles, 2) the angle most under-served in the existing conversation, 3) the angle I'm best-positioned to write, 4) the specific question my piece would answer, 5) the one-sentence thesis. End with the working title.
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Research questions, ordered

Know what I'm trying to learn.

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My topic and thesis: [PASTE]. Generate the 10 questions my research needs to answer, in dependency order. For each: 1) the question, 2) the type of source likely to answer it, 3) the failure mode if I skip it. End with the 3 to research first and the 2 to defer until I have a draft.
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Build a starter source list

5 sources, not 50.

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My topic: [PASTE]. Build a starter source list: 5 sources that, if I read them well, would give me 80% of the argument material. Mix: 1 foundational text, 1 contrarian voice, 1 recent data series, 1 firsthand practitioner, 1 cross-domain analog. End with the order to read them and the time-box per source.
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Section-by-section outline

Outline that reads like a draft skeleton.

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My thesis: [PASTE]. Length target: [PASTE]. Build a section-by-section outline. For each section: H2, the one point it makes, the 2-3 sub-beats, the example or evidence anchoring it, the transition to the next. End with the section to draft first because it unlocks the rest.
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Match evidence to claims

Place the right evidence under the right claim.

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My claims: [PASTE]. My collected research notes: [PASTE]. Match evidence to claims. For each claim: 1) the strongest piece of evidence I have, 2) the weakest claim that's still under-supported, 3) the evidence I have that doesn't fit any claim (and whether to find a home or discard).
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Interview question set

10 questions that earn real answers.

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I'm interviewing [PERSON] for [PIECE]. What I know about them: [PASTE]. Generate 10 questions in order: 2 warm-ups, 5 substantive, 2 contrarian, 1 unexpected. For each: the angle and the follow-up if the answer is short. End with the question to save for last because it surprises them.
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Pre-interview prep

30 minutes before the call.

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I'm interviewing [PERSON] in 30 minutes. Topic: [PASTE]. Help me prep: 1) the 3 things I know about them I should mention, 2) the 2 things I should NOT bring up, 3) the question to lead with, 4) the rabbit hole to avoid, 5) the soft landing for the close. End with the 1 quote I'd love to leave with.
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Notes to outline

Turn 6,000 words of notes into 1 outline.

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My research notes: [PASTE]. Convert to an outline. 1) Cluster notes by theme. 2) For each cluster, the one claim emerging. 3) The order of claims that builds an argument. 4) The notes that don't fit (and whether they're a different piece). 5) The outline. End with the gap between what I have and what I still need to research.
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Escape the rabbit hole

When I've over-researched and can't start.

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I've been researching [TOPIC] for [TIME]. I can't start writing. Help me escape. 1) The diagnosis (perfectionism, fear, or actual gap). 2) The single question I have enough to answer right now. 3) The draft to start in the next 30 minutes (even if rough). 4) The rule for when to research more vs draft more. End with the deadline to ship a v1.
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Mini literature review

Map the existing conversation in one page.

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My topic: [PASTE]. Walk me through a one-page literature review: 1) the 3-5 dominant voices in this conversation, 2) where they agree, 3) where they disagree, 4) what's missing, 5) where my piece enters the conversation. End with the angle that gives me something to say.
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Stress-test my outline

Catch a wobbly outline before drafting.

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My outline: [PASTE]. Stress-test. 1) Does each section earn its place? 2) Is the order load-bearing or just chronological? 3) Where will I get bored writing? 4) Where will the reader get bored? 5) The cut that would make the piece sharper. End with the strongest single sentence I should write into the outline now so I don't lose it.
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Clean up my second brain

Process backlogged notes into something usable.

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My notes inbox: [PASTE titles or excerpts]. Process them in batches: 1) cluster by latent theme, 2) flag the 3 themes worth writing about, 3) flag the 2 worth keeping but not writing about now, 4) flag the rest to delete or archive. End with the 1 cluster ready to draft this week.
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Outline from a conversation

Turn a great conversation into a structure.

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Transcript of a conversation I want to turn into a piece: [PASTE]. Extract: 1) the central claim, 2) the supporting beats, 3) the strongest quote, 4) the surprising tangent, 5) the missing piece I should add in writing. End with the outline that uses the conversation as scaffolding without quoting too much.
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Primary vs secondary sources

Decide where my sources fall and what I need more of.

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My current sources: [PASTE list]. Classify each as primary or secondary. Then: 1) am I leaning too hard on secondary, 2) the primary sources I'm missing, 3) the secondary source I should drop because it's just repackaging primary I already have. End with the 1 primary source to chase this week.
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Set a research time-box

Stop researching forever.

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My piece: [PASTE topic + length]. Set a research time-box: 1) the total hours of research that's appropriate, 2) the split across reading / interviews / data, 3) the stop-loss signal (when more research = less marginal value), 4) the date by which research stops and drafting starts no matter what. End with the calendar block to put it in.
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