AI is transforming legal work. But not all AI is created equal — and using the wrong tool for contract review could cost you more than your billable hour.
The Experiment
Last week, I ran a simple test. I took a standard mutual NDA — the kind that crosses a solo lawyer’s desk three times a week — and uploaded it to ChatGPT (GPT-4o) and ContractPilot AI. Same document. Same questions. No tricks.
The results weren’t even close.
What ChatGPT Got Right
Let’s be fair. ChatGPT identified the basic structure correctly. It spotted the parties, the effective date, the definition of confidential information, and the term. It gave a reasonable plain-English summary of what the NDA does.
For someone who’s never seen an NDA before, ChatGPT’s summary would be helpful. But you’re not “someone who’s never seen an NDA.” You’re a lawyer. And your client is paying you to catch what they can’t.
Where ChatGPT Failed — And Why It Matters
1. It Hallucinated a Mutual Obligation That Didn’t Exist
The NDA we tested was technically labeled “mutual,” but the operative clause only imposed confidentiality obligations on the receiving party. ChatGPT read the title, assumed reciprocity, and told us both parties had equal obligations.
They didn’t.
If you relied on ChatGPT’s analysis and advised your client that they were equally protected, you’d be wrong. And “my AI told me so” isn’t a defense your malpractice insurer will accept.
ContractPilot flagged this immediately. The risk report highlighted a “Mismatch: Title vs. Operative Clauses” warning, noting that despite the “mutual” label, only Section 3(a) imposed obligations — and only on the receiving party. It recommended adding a mirror clause or renegotiating the title.
2. It Missed a Carve-Out That Gutted the IP Protection
Buried in Section 5(c) was a carve-out that excluded “independently developed” information from the definition of Confidential Information. The clause used language broad enough to drive a truck through — any information the receiving party could claim was “independently conceived” was excluded.
ChatGPT didn’t mention it. At all.
ContractPilot scored this clause as HIGH RISK, explaining that the “independently developed” carve-out lacked a documentation requirement, a burden-of-proof allocation, or a temporal limitation. It suggested three alternative formulations with tighter guardrails.
3. It Gave Confidence Without Jurisdiction Awareness
ChatGPT analyzed the NDA as if contract law were universal. It didn’t mention that the governing law clause specified Delaware, that the forum selection clause was non-exclusive (meaning litigation could happen anywhere), or that the injunctive relief provision might not be enforceable as written under Delaware Chancery Court rules.
ContractPilot analyzed these clauses with Delaware-specific context, noting that the non-exclusive forum selection undermined the choice of Delaware as governing law and flagged that the liquidated damages clause might face enforceability challenges under Delaware’s penalty doctrine.
4. It Couldn’t Distinguish “Fine” from “Dangerous”
When I asked ChatGPT “Is this NDA safe to sign?”, it said: “This NDA appears to be a standard mutual non-disclosure agreement. The terms are generally reasonable, though you may want to have a lawyer review the specifics.”
Helpful.
When I asked ContractPilot the same question, it returned a risk score of 67/100 with four specific flags: the one-sided obligation masked by a mutual title, the broad IP carve-out, the non-exclusive jurisdiction clause, and a missing return-or-destroy provision for confidential materials upon termination.
One answer gives you comfort. The other gives you leverage.
Why This Happens
ChatGPT is a general-purpose language model. It’s brilliant at many things — writing emails, explaining concepts, brainstorming ideas. But contract review isn’t a language task. It’s a legal analysis task.
The difference matters because:
General AI reads words. Legal AI reads risk.
ChatGPT processes the text of your contract the same way it processes a recipe or a poem. It understands what the words mean. It doesn’t understand what the words do — how they interact with governing law, how they compare to market standards, where the asymmetries hide, or what a court would actually enforce.
ContractPilot is purpose-built for this. Every clause is analyzed against:
- Market standard benchmarks — Is this indemnity clause typical for this contract type, or is it unusually broad?
- Jurisdiction-specific rules — Will this non-compete hold up in California? (Spoiler: probably not.)
- Internal consistency — Does the termination clause actually work with the term clause?
- Risk scoring — Not just “is this clause here” but “how dangerous is this clause for YOUR position?”
The Real Cost of Using the Wrong Tool
Let’s do the math.
You’re a solo practitioner billing $250/hour. A client sends you an NDA to review. You paste it into ChatGPT, get a summary, spend 20 minutes checking it, and send it back with a few notes. Bill: $83.
Except ChatGPT missed the one-sided obligation. Your client signs. Six months later, they share confidential information assuming mutual protection. The other party claims no obligation to keep it confidential — because they had none. Your client’s trade secrets are out. The lawsuit costs $150,000. Your E&O claim costs more.
Or: You upload the same NDA to ContractPilot. In 90 seconds, you have a risk report that catches all four issues. You send the client a redline with specific fixes. Bill: $250 (one hour, because you added real value). Client is protected. You look like a star.
The $49/month for ContractPilot paid for itself before your first cup of coffee.
“But I Use ChatGPT Carefully…”
I hear this a lot. Smart lawyers who say they use ChatGPT as a “starting point” and always verify. But here’s the problem with that approach:
You can only verify what you know to look for.
ChatGPT’s hallucinations aren’t obvious. It doesn’t say “I’m guessing here.” It states incorrect conclusions with the same confidence as correct ones. If it tells you a clause is mutual and you don’t independently read every operative section to verify, you’ll miss it. And the whole point of using AI was to save you that time.
A tool that requires you to double-check everything isn’t saving you time. It’s adding a step.
What ContractPilot Does Differently
ContractPilot isn’t ChatGPT with a legal prompt. It’s a fundamentally different approach:
Structured risk analysis, not chat. You don’t have a conversation with your contract. You get a structured risk report — clause by clause, scored and explained. Every flag comes with a “why it matters” and a “what to do about it.”
Jurisdiction-aware. ContractPilot knows that non-competes are treated differently in California vs. Texas vs. New York. It doesn’t give you generic advice — it gives you advice that accounts for the governing law in your contract.
Benchmarked against market standards. When ContractPilot says an indemnity clause is “unusually broad,” it means it’s compared that clause against thousands of similar contracts and found it outside the norm. ChatGPT has no basis for comparison.
Designed for lawyers. The output is a risk report you can hand to a partner or attach to a client communication. Not a chatbot conversation you have to screenshot.
Try It Yourself
Upload your next NDA to ContractPilot. Your first three contracts are free — no login required for the first one. See the difference between “AI that reads” and “AI that reviews.”
In 90 seconds, you’ll know exactly what ChatGPT would have missed.
Upload Your First Contract Free →
ContractPilot AI is purpose-built contract review for solo practitioners and small firms. Risk reports in 90 seconds. $49/month. No enterprise sales call.