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Automation Squad
You run thisWritten for Claude or ChatGPT (file upload)

Turn a messy folder of documents into one briefing

Robert MacKelfresh

By Robert MacKelfresh

Founder, Automation Squad

Asking for a summary of many files gets you a blended average that quietly buries the one thing you needed to notice — that two documents disagree. This forces the contradictions to the surface with both sources named, which is the only part of the output a person genuinely cannot produce faster themselves.

The prompt

I'm attaching [HOW MANY] files about [WHAT THEY'RE ABOUT]. They were written by different people, at different times, for different reasons. Some of them contradict each other. Some are out of date.

Read all of them before you answer anything.

Then give me:

1. THE PICTURE — what's actually going on here, in under 150 words, written for someone who has read none of these files.

2. THE FACTS THAT HOLD — things stated consistently across more than one document. Note which documents each one comes from.

3. THE CONTRADICTIONS — anywhere two documents disagree. Quote both, name both files, and tell me which one is more likely to be current and why. Do not resolve a contradiction by picking one silently.

4. WHAT'S MISSING — the questions someone would obviously ask that none of these files answer.

5. WHAT I SHOULD DO ABOUT IT — no more than five actions, each tied to something specific in the documents.

Rules: never merge two sources into one confident statement. If only one document says something important, mark it "single source." If a document has a date, use it — an old file and a new file disagreeing is a fact about the timeline, not a mistake to average away.

One more thing: use anything you already know about me from our past chats and anything you're connected to. If you can find it yourself, don't make me look it up.

Copy it, paste it, run it. Nothing here is gated.

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Written for Claude or ChatGPT (file upload) as of August 2026. Models change — if this stops working the way it should, that is worth telling us about.