You receive a 60-page partnership contract. Reading it takes 3 hours. Understanding it takes longer.

Claude Sonnet 4.5 reads it in seconds and answers any question you have.

This guide shows you how to use Claude for analyzing contracts, reports, proposals, and any long document—saving hours of reading time.

Why Claude Wins for Long Documents

Claude vs. ChatGPT for Document Analysis

Feature	Claude Sonnet 4.5	ChatGPT (GPT-4o)
Context window	200,000 tokens (~150,000 words)	32,000 tokens (~24,000 words)
Document size	500-page PDFs easily	30-50 page limit
Analysis accuracy	Grounded in source material	Sometimes summarizes/skips details
Citations	References specific pages/sections	Less precise citations
Hallucinations	Low (more conservative)	Higher risk
Best for	Contracts, research, technical docs	Quick summaries, general questions
Speed	Fast	Faster

Bottom line: For analyzing important documents where accuracy matters (contracts, legal docs, financial reports), Claude is significantly better.

Claude can read:

• 750,000 words (entire Lord of the Rings trilogy)
• 75,000 lines of code
• 500-page PDFs
• Multiple documents simultaneously (up to 200K words total)

What You Can Do With Claude + Long Documents

Business Use Cases

1. Contract Review

• Identify key terms, payment conditions, termination clauses
• Flag risky language or unfavorable terms
• Compare two contracts side-by-side
• Check for missing provisions

2. Financial Report Analysis

• Summarize annual reports, 10-Ks, investor decks
• Extract key metrics and trends
• Identify risks and concerns
• Compare year-over-year performance

3. Proposal Evaluation

• Analyze vendor proposals (100+ pages)
• Compare multiple RFP responses
• Extract pricing and deliverables
• Identify gaps or unclear sections

4. Research Synthesis

• Combine multiple industry reports
• Extract insights from academic papers
• Identify trends across sources
• Create executive summaries

5. Due Diligence

• Analyze legal documents for acquisitions
• Review compliance documentation
• Identify potential liabilities
• Extract critical data points

Getting Started: Claude Pro vs. Free

Feature	Free	Pro ($20/month)
Daily messages	Limited (~10-20)	Much higher (~200+)
Document uploads	✅ Yes	✅ Yes
Context window	200K tokens	200K tokens
Priority access	❌ No	✅ Yes (during high demand)
Claude Projects	✅ Yes	✅ Yes

For CEOs analyzing documents regularly: Upgrade to Pro ($20/month). You'll exhaust the free tier quickly.

Sign up: claude.ai

Method 1: Quick Document Q&A

Best for: Single document, specific questions

Step 1: Upload Your Document

1. Open claude.ai
2. Start a new conversation
3. Click the paperclip icon (📎)
4. Upload your PDF, Word doc, or text file
5. Wait for Claude to confirm it's processed

Supported formats:

• PDF
• Word (.docx)
• Text (.txt)
• Markdown (.md)
• CSV
• Images (screenshots of documents)

Size limits:

• Single file: up to 32MB
• Total conversation: 200,000 tokens (~150,000 words)

Step 2: Ask Specific Questions

Template questions:

For Contracts:

Analyze this contract and provide:
1. Key terms summary (parties, duration, payment)
2. Obligations for each party
3. Termination clauses
4. Payment terms and schedule
5. Potential risks or unfavorable terms
6. Anything missing or unusual

Quote specific sections for each point.

For Partnership Agreements:

Review this partnership agreement focusing on:
1. Equity split and vesting
2. Decision-making authority (voting rights)
3. Exit scenarios (buyout, dissolution)
4. Non-compete and IP ownership
5. Dispute resolution process
6. Red flags or clauses requiring negotiation

Cite page numbers.

For Vendor Proposals:

Compare this proposal against these criteria:
- Pricing transparency and total cost
- Deliverables and timelines
- Team qualifications
- Risk mitigation strategies
- Flexibility and change management
- Support and maintenance terms

Rate each criterion 1-10 with reasoning.

For Financial Reports:

Analyze this annual report:
1. Revenue and profit trends (YoY comparison)
2. Key growth drivers mentioned
3. Risks and challenges disclosed
4. Strategic initiatives for next year
5. Management's tone (optimistic/cautious/realistic)
6. Concerning metrics or patterns

Summarize in 500 words.

Step 3: Drill Deeper

Claude remembers the conversation context. Ask follow-ups:

Example conversation:

You: [Upload 80-page partnership contract]

You: "What are the termination clauses?"

Claude: [Answers with page references]

You: "Are these clauses fair for both parties?"

Claude: [Analyzes fairness]

You: "What would happen if we wanted to exit in year 2?"

Claude: [Explains exit scenario based on contract]

You: "Draft an email to our lawyer asking about modifying section 7.3"

Claude: [Writes email draft]

Pro tip: Always ask Claude to cite page numbers or quote sections. This lets you verify critical claims.

Method 2: Claude Projects (For Ongoing Analysis)

Best for: Multiple related documents, ongoing work

What Are Claude Projects?

Projects are dedicated workspaces within Claude with:

• Their own 200K context window
• Persistent knowledge base (documents stay uploaded)
• Custom instructions that apply to all chats
• Separate conversation histories

Think of Projects as: Specialized assistants for specific topics.

How to Create a Project

1. Click "Projects" in the left sidebar
2. Click "Create Project"
3. Name it (e.g., "Q1 Partnership Contracts", "Vendor Due Diligence")
4. Add Project Instructions (how Claude should behave)

Example Project Instructions:

You are a legal analyst helping me review partnership contracts.

For every document I upload:
1. Summarize key terms in bullet points
2. Identify risks or unusual clauses
3. Compare against industry standards
4. Always cite page numbers
5. Use professional but clear language (avoid legalese)
6. Flag anything requiring lawyer review

When I ask about specific clauses:
- Quote the exact text
- Explain in plain English
- Note any ambiguities

Add Documents to Project

1. Click "Add content" (📎 icon)
2. Upload multiple documents (contracts, templates, reference materials)
3. Claude keeps them in the project context permanently

Example Project:

• Name: "2025 Vendor Contracts"
• Documents: Template contract, past agreements, vendor proposals
• Instructions: "Compare all proposals against our template. Highlight missing terms."

Now every conversation in this project has access to all uploaded docs.

Use Cases for Projects

Project 1: "Contract Templates Library"

• Upload: Your standard contracts, past agreements
• Use for: Quickly checking if new contracts match your standards

Project 2: "Competitor Research"

• Upload: Competitor annual reports, whitepapers, news articles
• Use for: Comparing strategies, tracking changes over time

Project 3: "Financial Due Diligence"

• Upload: Target company's financials, audit reports, tax docs
• Use for: Acquisition analysis, risk assessment

Project 4: "Board Meeting Prep"

• Upload: Last 6 months of board decks, financial reports
• Use for: Preparing presentations, answering anticipated questions

Pro tip: Create a new project every quarter and archive old ones. Keeps context fresh.

Advanced Document Analysis Techniques

1. Compare Two Documents Side-by-Side

Use case: Compare vendor proposals, contract versions, financial reports

Prompt:

I've uploaded two contracts:
1. [Vendor A Contract]
2. [Vendor B Contract]

Create a comparison table with these columns:
- Category (Pricing, Deliverables, Timeline, Support, etc.)
- Vendor A
- Vendor B
- Winner (which is better)
- Notes

Highlight the top 3 differentiators.

2. Extract Data Into Structured Format

Use case: Pull specific data points from multiple documents

Prompt:

Extract the following from this proposal and format as JSON:
{
  "vendor_name": "",
  "total_cost": "",
  "timeline": "",
  "key_deliverables": [],
  "team_size": "",
  "risks": [],
  "payment_schedule": []
}

3. Multi-Document Synthesis

Use case: Combine insights from 3-5 reports into one summary

Prompt:

I've uploaded 4 industry reports about [topic].

Synthesize them into a single 2-page executive summary covering:
1. Market size and growth trends (cite which report)
2. Key players and competitive dynamics
3. Emerging technologies or disruptions
4. Opportunities for companies like ours
5. Expert predictions for 2025-2026

Use bullet points. Cite sources: [Report 1], [Report 2], etc.

4. Risk Identification

Use case: Find potential problems in legal or financial docs

Prompt:

Act as a risk analyst reviewing this [contract/financial statement/proposal].

Identify potential risks in these categories:
1. Financial risks (cost overruns, payment issues)
2. Legal risks (liability, compliance)
3. Operational risks (delays, resource constraints)
4. Reputational risks

For each risk:
- Severity: Low/Medium/High
- Likelihood: Low/Medium/High
- Mitigation strategy
- Page reference

Prioritize top 5 risks.

5. Plain English Translation

Use case: Understand complex legal or technical language

Prompt:

Translate this contract section into plain English that a 12-year-old could understand. Explain:
- What it actually means
- Why it matters
- What could go wrong
- What I should negotiate

Original text: [paste section]

Real-World Examples

Example 1: Partnership Contract Review

Scenario: You're negotiating a partnership with another company. They send a 45-page contract.

Claude workflow:

Step 1: Upload & Initial Analysis

You: [Upload contract]

You: "Summarize this partnership agreement in 10 bullet points covering the most important terms."

Claude: [Provides summary with page references]

Step 2: Identify Concerns

You: "What are the top 3 most concerning clauses from my perspective as the smaller partner?"

Claude:
"1. Termination (p. 23): Partner A can terminate with 30 days notice, but you need 90 days. This asymmetry favors them.

2. IP Ownership (p. 31): Joint IP defaults to Partner A ownership unless explicitly documented otherwise. Risk of losing your innovations.

3. Indemnification (p. 38): You indemnify them for all claims, but their indemnification cap is $100K. Unlimited liability vs. capped."

Step 3: Negotiation Prep

You: "Draft an email to their team requesting modifications to these 3 clauses. Professional but firm tone."

Claude: [Writes diplomatic email]

Time saved: 3-4 hours of reading → 10 minutes with Claude

Example 2: Vendor Proposal Comparison

Scenario: You receive 3 proposals from agencies. Each is 80+ pages.

Claude workflow:

Step 1: Upload All Three

You: [Upload Proposal A, Proposal B, Proposal C]

You: "Create a comparison matrix for these 3 proposals. Compare: Total cost, timeline, team experience, deliverables, and value for money. Recommend which one to choose."

Claude output (abbreviated):

Category	Agency A	Agency B	Agency C	Winner
Total Cost	$50K	$65K	$45K	Agency C (lowest)
Timeline	12 weeks	8 weeks	10 weeks	Agency B (fastest)
Team Experience	5+ years avg	3 years avg	8+ years avg	Agency C
Deliverables	Standard	Premium (extras)	Standard +	Agency B
Value	Good	Best (worth premium)	Good	Agency B

Recommendation: Agency B offers the best value despite higher cost. Their timeline is 33% faster, and they include extras worth $15K at no charge.

Time saved: 6-8 hours of reading → 15 minutes

Example 3: Financial Report Analysis

Scenario: Analyzing a potential acquisition target's financials (200-page annual report).

Claude workflow:

You: [Upload 10-K report]

You: "Analyze this company as a potential acquisition target. Focus on:
1. Revenue trends and growth rate
2. Profitability and margins
3. Debt levels and financial health
4. Major risks disclosed
5. Strategic direction
6. Red flags or concerns

Provide 2-page summary for our board."

Claude output (summarized):

• Revenue growth: 25% YoY (pages 12, 45)
• Margins compressing: Gross margin down from 65% to 58% (page 47—concerning)
• Debt: $50M, manageable at 2.5x EBITDA (page 62)
• Risk: Customer concentration—top 3 customers = 60% revenue (page 89—red flag)
• Strategy: Expanding to new verticals (page 15)
• Concerns: Margin pressure, customer concentration, high employee turnover mentioned (page 102)

Recommendation: Promising growth but investigate margin pressure and customer concentration before proceeding.

Time saved: Full day of analysis → 30 minutes

Best Practices for Document Analysis

1. Clean Document Formatting

Claude handles messy PDFs, but clean documents = better results.

Before uploading:

• Remove unnecessary images, headers, footers
• Ensure text is selectable (not scanned images)
• Use proper heading hierarchy (H1, H2, H3)

If you have scanned PDFs: Use OCR first (Adobe, Google Drive, or online tools) to make text selectable.

2. Use Specific Questions

Bad:

"What's in this document?"

Good:

"Summarize section 5 (Payment Terms) and section 8 (Termination). Identify any unusual clauses compared to standard contracts."

Specific questions = specific answers.

3. Always Request Citations

Add to every prompt:

"Cite page numbers for every claim."
"Quote the exact text when referencing specific clauses."

This lets you verify critical information.

4. Break Large Tasks Into Steps

Instead of:

"Analyze this 300-page report and tell me everything important."

Do this:

Step 1: "Summarize the executive summary and key findings (pages 1-10)."
Step 2: "Analyze the financial section (pages 50-120). What are the trends?"
Step 3: "Review the risks section (pages 200-250). What are the top 5 risks?"

Sequential questions = better depth.

5. Use Projects for Recurring Work

If you analyze contracts monthly, create a "Contract Review" project with:

• Your standard contract template
• Checklist of must-have clauses
• Past contracts for reference

Every new contract review starts with this context.

6. Export and Save Analysis

Claude conversations disappear if you don't save them.

To save:

1. Click the share icon (top right)
2. Copy conversation URL (save in Notion, Google Docs, etc.)
3. Or: Copy-paste Claude's analysis into a document

Pro move: Create a Notion database of all contract analyses with links to Claude conversations.

Common Mistakes to Avoid

1. Trusting Blindly

Mistake: Accepting Claude's analysis without verification. Fix: Always verify critical claims by reading the cited pages yourself.

Claude is highly accurate but not perfect. For legal or financial decisions, use Claude to save time, but verify key points.

2. Asking Too Broad

Mistake: "What's important in this document?" Fix: "What are the payment terms, IP ownership clauses, and termination conditions?"

Broad questions = broad answers.

3. Not Using Projects

Mistake: Uploading the same reference docs repeatedly. Fix: Create a project, upload once, use forever.

4. Forgetting Context Limits

Mistake: Uploading 10 documents totaling 300,000 words (exceeds 200K limit). Fix: Break into 2 conversations or 2 projects.

5. Skipping Follow-Ups

Mistake: Accepting the first answer without drilling deeper. Fix: Ask follow-up questions. Claude's second or third answer is often better.

Claude Pricing (2025)

Plan	Price	Best For
Free	$0	Light usage (~10-20 messages/day)
Pro	$20/month	Regular document analysis, unlimited messages

For CEOs analyzing documents weekly: Pro is essential. The free tier runs out quickly.

ROI calculation:

• Pro: $20/month = $240/year
• If Claude saves 5 hours/month reading contracts/reports
• Your hourly value: $200/hour (conservative for CEO)
• Annual value: 60 hours × $200 = $12,000

Break-even: If Claude saves you 7 minutes per year, it pays for itself.

Claude vs. Other AI for Document Analysis

Use Case	Best Tool	Why
100+ page contracts	Claude	200K context, better accuracy
Quick email summarization	ChatGPT	Faster for short docs
Financial reports (50-200 pages)	Claude	Grounded analysis, cites sources
Code review (large codebases)	Claude	75,000 lines of code capacity
Multi-source research synthesis	Claude	Handles multiple docs simultaneously
Legal document comparison	Claude	More conservative, less hallucination
Meeting transcripts	ChatGPT or Claude	Both work well

Bottom line: For any document over 30 pages or where accuracy is critical, choose Claude.

Next Steps

1. This week: Sign up for Claude Pro ($20/month)
2. Upload one important document you've been meaning to read
3. Ask 3-5 specific questions using templates from this guide
4. Calculate time saved (reading time vs. Claude analysis time)
5. Create your first Project for recurring document types

Pro move: Create a "Document Analysis Prompts" note in your system with your favorite prompts from this guide. Copy-paste for consistency.

Want help implementing Claude for contract review and document analysis in your business? We help small companies build systematic document analysis workflows using Claude, including custom prompts, projects setups, and integration with your existing tools.