How to Use ChatGPT for Contract Review: Complete Guide with Prompts

Contract review doesn't have to take hours. Learn how to use ChatGPT to quickly analyze contracts, identify risks, and prepare for negotiations—with ready-to-use prompts.

Important Disclaimer

ChatGPT is a powerful tool for initial contract review and understanding, but it should not replace legal counsel for important agreements. Always consult a qualified attorney for contracts with significant financial or legal implications.

Whether you're a small business owner reviewing vendor agreements, a freelancer checking client contracts, or just someone signing a lease, understanding what you're agreeing to matters. The problem? Legal language is dense, and lawyer fees add up quickly.

ChatGPT can serve as your first line of defense—helping you understand contract terms, spot potential issues, and prepare intelligent questions for legal counsel when needed.

Step 1: Uploading Your Contract to ChatGPT

Before ChatGPT can analyze your contract, you need to get the text into the chat. You have several options:

Option A: ChatGPT Plus Native Upload

If you have ChatGPT Plus ($20/month), you can directly upload PDFs up to 25MB:

  1. Click the paperclip icon in the chat input
  2. Select your contract PDF or DOCX
  3. Wait for upload confirmation
  4. Start asking questions

Option B: FileUploadGPT (Free)

For free ChatGPT users or contracts larger than 25MB, FileUploadGPT handles the upload automatically:

  1. Install the FileUploadGPT Chrome extension
  2. Open ChatGPT in your browser
  3. Click the extension icon and select your contract
  4. The extension splits and sends the document automatically

For detailed instructions, see our guide on uploading large PDFs to ChatGPT.

Option C: Copy and Paste

For shorter contracts (under 10 pages), you can copy the text directly into ChatGPT. This works but loses formatting and can be error-prone.

Step 2: Initial Review Prompts

Start every contract review with these foundational prompts to understand what you're dealing with:

Contract Overview Prompt

Please analyze this contract and provide:

1. **Contract Type**: What kind of agreement is this?
2. **Parties**: Who are the parties involved and their roles?
3. **Effective Date & Duration**: When does it start and end?
4. **Core Purpose**: What is the main purpose of this agreement?
5. **Key Obligations**: What are each party's main responsibilities?
6. **Payment Terms**: Summarize any financial terms
7. **Termination Conditions**: How can either party exit?

Present this as a structured summary I can reference.

Plain Language Summary

Explain this contract to me as if I have no legal background.
What am I actually agreeing to in plain, everyday language?
Highlight anything that might surprise a typical person signing this.

Obligations Checklist

Create a checklist of everything I would be required to do if I sign this contract.
Include:
- One-time actions
- Ongoing obligations
- Deadlines or time-sensitive requirements
- Restrictions on my behavior

Step 3: Contract-Specific Analysis Prompts

Different contract types have different risk areas. Use these targeted prompts based on your contract type:

Non-Disclosure Agreement (NDA)

Analyze this NDA and tell me:

1. **Scope of Confidential Information**: What exactly is considered confidential? Is it too broad?
2. **Duration**: How long must I keep information confidential?
3. **Permitted Disclosures**: When can I share the information (legal requirements, employees, etc.)?
4. **Return/Destruction**: What happens to confidential info when the agreement ends?
5. **Mutual vs One-Way**: Does this protect both parties or just one?
6. **Exceptions**: What information is excluded from confidentiality?
7. **Non-Compete/Non-Solicit**: Are there any hidden restrictions on my future work?

Flag anything that seems unusually restrictive or one-sided.

Freelance/Service Agreement

Review this service agreement from a contractor's perspective:

1. **Payment Terms**: When and how do I get paid? Are there conditions?
2. **Scope of Work**: Is the deliverable scope clearly defined?
3. **Revision Limits**: How many revisions are included?
4. **IP Ownership**: Who owns the work product? When does ownership transfer?
5. **Kill Fee**: What happens if the client cancels mid-project?
6. **Liability Cap**: What's my maximum financial exposure?
7. **Indemnification**: Am I required to cover the client's legal costs?
8. **Late Payment**: Are there penalties for late client payment?
9. **Non-Compete**: Am I restricted from working with competitors?

Highlight any terms that are unfavorable to the contractor.

Employment Contract

Analyze this employment contract:

1. **Compensation**: Base salary, bonuses, equity - what's guaranteed vs conditional?
2. **Benefits**: What benefits are mentioned? Any that start after a waiting period?
3. **At-Will Status**: Can I be terminated without cause?
4. **Non-Compete**: What restrictions apply if I leave? Duration and geographic scope?
5. **IP Assignment**: Do they own everything I create, even outside work hours?
6. **Invention Assignment**: Does this cover prior inventions I've already created?
7. **Severance**: What do I get if terminated?
8. **PTO Policy**: How does vacation/sick time work?
9. **Arbitration Clause**: Am I giving up the right to sue in court?
10. **Clawback Provisions**: Can they take back bonuses or equity?

What should I try to negotiate before signing?

Lease Agreement

Review this lease agreement as a tenant:

1. **Monthly Rent**: Amount, due date, late fees?
2. **Lease Duration**: Length and renewal terms?
3. **Security Deposit**: Amount, conditions for return, deduction rules?
4. **Maintenance Responsibilities**: What am I responsible for fixing?
5. **Early Termination**: Can I break the lease? What's the penalty?
6. **Rent Increases**: How and when can rent be raised?
7. **Guest/Subletting Policy**: Any restrictions?
8. **Pet Policy**: Fees, deposits, restrictions?
9. **Entry Rights**: When can the landlord enter my unit?
10. **Move-Out Requirements**: What condition must I leave the unit in?

What clauses are unusual or particularly restrictive?

Software/SaaS Agreement

Analyze this software agreement:

1. **License Type**: What am I actually licensing? Any usage limits?
2. **Subscription Terms**: Auto-renewal? Price increase provisions?
3. **Data Ownership**: Who owns the data I put in the system?
4. **Data Portability**: Can I export my data? In what format?
5. **SLA/Uptime Guarantee**: Any service level commitments?
6. **Security Provisions**: Data protection, encryption, breach notification?
7. **Termination**: What happens to my data if I cancel?
8. **Limitation of Liability**: What's their max liability if things go wrong?
9. **Indemnification**: Who's responsible for IP infringement claims?
10. **Changes to Terms**: Can they change the agreement unilaterally?

Identify any particularly concerning terms.

Step 4: Identifying Red Flags

After the initial review, use these prompts to dig deeper into potential problems:

Red Flag Detection

Review this contract for red flags and concerning clauses:

1. **One-Sided Terms**: Anything that benefits only one party?
2. **Unlimited Liability**: Am I exposed to uncapped damages?
3. **Automatic Renewals**: Any auto-renewal with difficult cancellation?
4. **Unilateral Changes**: Can they modify terms without my consent?
5. **Broad Indemnification**: Am I required to cover excessive legal costs?
6. **Unreasonable Non-Competes**: Overly broad restrictions on future work?
7. **Hidden Fees**: Charges not obvious in the main payment terms?
8. **Unfair Termination**: Can they terminate more easily than I can?
9. **Vague Language**: Terms that could be interpreted against me?
10. **Missing Protections**: Important protections that are absent?

Explain each red flag you find and why it's concerning.

Comparison to Standard Terms

Compare this contract to what would be considered standard or fair market terms for this type of agreement.

Specifically:
- What terms are better than typical?
- What terms are worse than typical?
- What important provisions are missing that are usually included?

Focus on substantive differences, not just formatting.

Common Contract Red Flags

Red Flag What It Means Risk Level
Unlimited indemnification You could be liable for all their legal costs High
No liability cap Your potential damages exposure is unlimited High
Unilateral termination rights They can exit easily; you cannot Medium
Broad non-compete (2+ years) Severe restriction on future employment High
IP assignment of "all work" They may own your personal projects Medium
Mandatory arbitration You give up right to sue in court Medium
Auto-renewal with 60+ day notice Easy to miss cancellation window Low

Step 5: Preparing for Negotiation

ChatGPT can help you prepare counter-proposals and negotiation points:

Negotiation Points

Based on your analysis of this contract, suggest:

1. **Must-Change Items**: Terms that are unacceptable and must be modified
2. **Should-Negotiate Items**: Terms I should try to improve but could accept
3. **Nice-to-Have Changes**: Minor improvements worth asking for

For each item, explain:
- The current term and why it's problematic
- What a fair alternative would look like
- Suggested language for the modification

Counter-Proposal Language

For [specific clause], draft alternative contract language that:
- Protects my interests better
- Is reasonable and likely to be accepted
- Uses standard legal phrasing

Provide 2-3 alternative versions from most to least aggressive.

Questions to Ask

What clarifying questions should I ask the other party about this contract before signing?

Focus on:
- Ambiguous terms that need definition
- Processes that aren't clearly explained
- Scenarios the contract doesn't address
- Past disputes that might inform concerns

Understanding ChatGPT's Limitations for Legal Review

While ChatGPT is useful for contract review, be aware of its limitations:

What ChatGPT Can Do

  • Summarize and explain contract terms in plain language
  • Identify common red flags and one-sided terms
  • Compare terms to general industry standards
  • Help you prepare questions and negotiation points
  • Draft alternative language suggestions

What ChatGPT Cannot Do

  • Provide actual legal advice (it's not a lawyer)
  • Know your specific jurisdiction's laws
  • Understand your unique business situation
  • Guarantee accuracy of its analysis
  • Replace professional legal counsel for important agreements

When to Involve a Lawyer

Always consult a real attorney when:

  • The contract involves significant money (your threshold may vary)
  • You're dealing with employment contracts at senior levels
  • The agreement involves equity, investment, or ownership
  • You're signing a long-term commitment (2+ years)
  • The other party has significantly more power/resources
  • You're entering an unfamiliar industry or agreement type
  • ChatGPT identifies multiple significant red flags

Start Your Contract Review

Ready to analyze a contract with ChatGPT? Upload your document using FileUploadGPT and start with the prompts in this guide.

Get FileUploadGPT Free

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