For General Administrative Assistants ·
What you'll accomplish
By the end of this guide, you'll be using Claude Pro to read, compare, and summarize multiple documents — contracts, reports, meeting files, policy documents — and produce a concise executive briefing that your manager can read in 2 minutes instead of you spending 2 hours reading everything yourself.
What you'll need
Go to claude.ai → sign up or log in → click your profile icon (top right) → "Upgrade to Pro" → enter payment details. You'll see "Claude Pro" in your account badge after subscribing.
What you should see: The standard Claude interface — the difference is you can now paste or upload much longer documents and run many more conversations per day.
Claude Pro accepts text you paste directly into the message. For PDFs, you can drag and drop them into the chat window (there's a paperclip icon in the message bar for file uploads).
Paste or upload your documents one at a time, labeling each one:
Document 1 — Vendor Proposal from Acme Corp:
[paste text here]
Document 2 — Vendor Proposal from XYZ Services:
[paste text here]
What you should see: Claude acknowledges each document and is ready for your question.
Troubleshooting: If a PDF won't paste cleanly (formatting breaks), copy-paste just the text sections you care most about, or use the file upload button (paperclip icon) if the PDF is under 10MB.
Type your question after pasting the documents. Be specific about what your executive cares about:
My director needs to choose between these two vendor proposals before Thursday's meeting. She cares most about: (1) total cost, (2) implementation timeline, and (3) references/proven track record.
Please summarize each proposal on those three dimensions and give a clear recommendation with one-sentence reasoning.
What you should see: A structured comparison — a table or numbered list with each vendor scored on the dimensions you specified, followed by a recommendation.
After the comparison, ask Claude to format it as a briefing document:
Format the comparison as a one-page executive briefing that [Director's name] can read in 2 minutes before the vendor meeting. Include: meeting purpose, the two options with pros/cons, your recommendation, and 3 questions she should ask in the meeting.
What you should see: A clean, scannable one-page document with clear headers and a recommendation that your director can reference during the meeting.
Read the briefing before sending it. Add any context Claude couldn't know — internal politics, relationship history, budget constraints. Remove anything confidential you didn't intend to surface (Claude only knows what you told it).