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Contract red flags prompt: a first read for ChatGPT or Claude

SOPs and operationsOperationsLawWorks in ChatGPT, Claude, Gemini and Copilot

Updated · By Robert Breen

To check a contract for red flags with AI, upload or paste the contract, copy the prompt below, and fill in who you are and which side you are on. It returns a plain-English summary, then the risky clauses with the exact words and clause numbers: auto-renewal, price increases, termination fees, liability limits and indemnity. Anything not in the contract is called out as "not in the contract."

This is a first read to help you ask better questions, not legal advice. A lawyer should review anything important before you sign, and you should only upload a contract your company allows you to share with an AI tool.

Have a professional review it. This prompt helps you draft, not decide. AI can get the law wrong and doesn’t know your jurisdiction or your facts, so have a licensed attorney review anything legal before you send or sign it.

The prompt

Copy it into ChatGPT (or Claude, Gemini or Copilot) and replace every [BLANK] with your own details. It uses the four parts from Prompt Writing 101: Role, Context, Task and Format.

Role: You are helping [YOUR ROLE] at [COMPANY] read a contract before signing. I am the [YOUR SIDE] and I am not a lawyer.
Context: The contract is attached or pasted below. Use only its words. Quote exact text and give the clause number for every point. If something is not in the contract, write "not in the contract." Do not give legal advice or say whether I should sign.
Task: First, summarize in plain English what I get, what I pay, how long I am locked in and how I can get out. Then list the clauses that look risky for me: auto-renewal, price increases, termination fees, limits on liability, indemnity and anything unusual. Then write three polite questions I can send the other side.
Format: Three headed sections. For each risky clause: clause number, exact quote, why it matters in one sentence. Plain words. Under 450 words.

Here is the contract:
[CONTRACT TEXT]

Fill in the blanks

[YOUR ROLE]
Your job, such as office manager.
[COMPANY]
Your company name.
[YOUR SIDE]
Customer, vendor, tenant, contractor, whichever you are in this deal.
[CONTRACT TEXT]
The contract text. If you upload a file instead, delete this line and the paste heading. Leave out signatures and personal details.

Example, filled in

A made-up example from the free lesson Check a Contract for Red Flags with Claude. Harbor Lane Accounting is the made-up accounting office in the contract lesson, with a three-year managed IT contract waiting for signature. The details below illustrate how the office manager might fill the prompt in.

Role: You are helping the office manager at Harbor Lane Accounting read a contract before signing. I am the customer and I am not a lawyer.
Context: The contract is attached or pasted below. Use only its words. Quote exact text and give the clause number for every point. If something is not in the contract, write "not in the contract." Do not give legal advice or say whether I should sign.
Task: First, summarize in plain English what I get, what I pay, how long I am locked in and how I can get out. Then list the clauses that look risky for me: auto-renewal, price increases, termination fees, limits on liability, indemnity and anything unusual. Then write three polite questions I can send the other side.
Format: Three headed sections. For each risky clause: clause number, exact quote, why it matters in one sentence. Plain words. Under 450 words.

Here is the contract:
The attached three-year managed IT services agreement.

What a good answer looks like

  • Each flagged clause has its number and the exact words, so you can find it yourself in a minute.
  • Missing items, such as no data return clause, are listed as "not in the contract" rather than guessed.
  • The three questions are polite and specific, for example asking what ends the auto-renewal and how much notice is required.
  • The summary never says "you should sign" or "this is fine."

How to check it before you use it

An AI draft can sound right and still say something you never told it. Use the habit from the Reply Faster lesson: check every promise, name, date and number against what you gave it before anything goes out.

  • Open the contract and read every quoted clause. If a quote does not match the page, throw it out.
  • Do not upload a contract unless your company allows it. Use a plan your company approved and check the privacy settings.
  • Take the list of risky clauses to a lawyer for anything that costs real money or runs a long time.
  • Remember a clause the AI did not flag may still matter. It is a first read, not a guarantee.

Why this prompt works

The hard part of a contract is knowing which paragraphs to slow down on. Asking for exact quotes with clause numbers keeps the AI honest, and turning findings into polite questions gives you something useful to do next.

Practice it in the free lesson

Check a Contract for Red Flags with Claude: Upload a vendor contract, get it in plain English, find the risky clauses with the exact words quoted, draft questions for the vendor, and save the review as a project for the next one. You do every step yourself in a practice copy of Claude, and nothing touches your real accounts.

Start the free lesson

Also useful: AI Contract Review in 10 Minutes using Foxit AI

Terms used here

Master services agreement (MSA)Non-disclosure agreement (NDA)Human in the loopHallucination

More sops and operations prompts

Frequently asked questions

Can ChatGPT or Claude review a contract?
They can give you a plain-English first read and point to risky clauses, but they can miss things and do not know your law. Have a lawyer review anything important.
What are contract red flags?
Common ones are auto-renewal, price increases, termination fees, limits on liability, broad indemnity and unclear ways to get out.
Is it safe to upload a contract to AI?
Only if your company allows it. Use an approved plan, check the training and privacy settings, and leave out confidential details that the review does not need.

All free prompt templates · AI glossary