Files and documents · AI Tools Field Guide

Five things to do with a file

Summarize"Summarize the attached instruction for a watch team in under 200 words; keep every deadline." Tell it what must survive the compression.
Extract"List every reporting requirement as a table: what, to whom, by when, paragraph." It reads forty pages faster than you can find the page.
CompareAttach the old and the new. "Show only what changed, as a two-column table." The fastest way to read a revised instruction.
Rewrite"Rewrite the attached SOP as numbered steps, one action per step, plain language; do not add steps that are not in the source."

And the fifth: draft from. "Using only the attached bullets and the attached memo as a format example, draft the memo. Mark anything you had to assume with [CONFIRM]."

What each tool accepts

All four take PDF, Word, PowerPoint, Excel, text and images. Exact size and count limits differ by tool and change as vendors update them; check the current help page before you plan around a specific number. Claude, for example, documents 500 MB per file and 20 files per chat, or 30 MB per file for a project.

A few relevant documents beat a dumped share drive, and if a many-file question fails, try fewer files or one merged PDF. Long files are queried rather than read whole, so ask a long document specific questions rather than "tell me about this".

You have	Attach it as	Then ask for
An instruction or directive	PDF	A checklist with the paragraph number beside each item
Last year's package	DOCX	A new draft with the changed names and dates marked
Message traffic	TXT or PDF	A one-page summary, newest first, with the DTG beside each line
A slide deck	PPTX	Speaker notes; a list of slides that mention the old logo
A scanned form or a whiteboard photo	Image	The text, typed out, in a table

Getting a file back

Text comes back as text in every tool; you paste it into your own document. Grok is the exception: its Skills (Word Documents, Presentations, Spreadsheets, PDFs) let it write a real .docx, .pptx, .xlsx or PDF file for you to download.

The Skills page in Grok with a New Skill button and six Personal skills: Word Documents (create, read and edit .docx), FFmpeg (video and audio), PDFs (create, merge, split and extract), Presentations (create, read and edit .pptx), Skill Creator (build new custom skills through conversation) and Spreadsheets (.xlsx and .csv). — Grok's built-in skills. Ask for "a Word document" or "a three-slide PowerPoint" and it loads the matching skill.

Grok working on a request to build a three-slide PowerPoint with the Presentations skill: the progress lines read Loaded 2 skills, Connected to computer, Running command List pptx skill directory contents, and Working for 11m 34s. — What a file job looks like in progress. Ours was still running at eleven minutes and past twenty-five when we stopped watching.

A file job runs for minutes, sometimes many, and what comes back is a starting file rather than a polished deck. Ask for the words and the structure, drop them into your own template, and you are usually faster.

Always ask for references

Add "with the page or paragraph reference beside each item" to whatever you ask. An item with no reference, or a reference that does not say what the model claims, is the item to fix. Checking output makes a method of it.

The one rule

Vendor facts checked 25 Sep 2026; re-verify before relying on them.