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ChatGPT might be a handy AI assistant for legal brainstorming and internal drafts—but when it comes to high-stakes contract work, it falls short on precision, security, and redlining. This article explores where ChatGPT helps, where it fails, and why tools like Gavel Exec offer a smarter, more secure alternative for real-world legal workflows.
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If you’re a corporate, real estate, or transactional attorney, chances are you’ve either tried ChatGPT yourself or you’ve heard colleagues talk about it. It’s fast, and easy to use, but as legal professionals, we know that contracts, negotiations, and redlines don’t just need polished language—they need precision, precedent, and professional judgment.
So while ChatGPT might be a useful tool in your legal toolkit, it’s important to understand what it can do—and where it falls short. Especially when you're working with high-stakes contracts, client confidentiality, and firm standards, there’s a big difference between a general-purpose AI and something built specifically by lawyers and geared towards legal work.
Here’s a breakdown of the pros and cons, and how legal AI tools like Gavel Exec are solving the problems that ChatGPT presents.
One of the most obvious benefits of ChatGPT is speed. It can turn a rough outline into a memo, help junior associates reword a long clause or explain boilerplate in plain English, or even serve you when you just need a first draft on paper, so you can focus your time on editing rather than starting from scratch.
Lawyers have used ChatGPT to generate internal templates, summarize lease clauses, and even draft polite client responses. For those kinds of quick, low-risk tasks, ChatGPT can be a time-saver.
With ChatGPT, you do not need to set up IT, a license, or undergo complicated onboarding. It is in your browser and works right away. If you're using GPT-4, it costs around $20/month, which is a fraction of what most legal tech platforms charge.
You don’t need permission from anyone to try it, and it’s a low-cost way to see how generative AI could fit into your practice.
If you’ve ever needed to explain the difference between an indemnification clause and a limitation of liability provision to a non-legal client, ChatGPT can help you translate legalese into plain English for clients to easily understand. It’s also handy for brainstorming how to phrase a clause or get inspiration when you’re stuck.
It won’t give you a legally binding analysis—but it can point you in the right direction when thinking through structure or tone.
This is the biggest issue. ChatGPT wasn’t trained on contract precedent, jurisdiction-specific statutes, or the deal logic we use every day. It doesn’t “understand” the difference between a Delaware LLC and a California S-Corp, or how a change to a “reasonable efforts” clause might affect risk allocation in an M&A deal.
It can generate something that sounds legally accurate. But often, that confidence is just surface-level polish. And if you’re not careful, you may end up with a clause that’s legally meaningless—or worse, legally dangerous.
Even though OpenAI has made improvements, hallucinations still happen. ChatGPT will confidently cite cases that don’t exist or make up regulations out of thin air. This has led to real-world problems, like attorneys being sanctioned for submitting briefs full of fake citations.
If you’re reviewing outputs closely and fact-checking everything, that’s one thing. But if you’re under time pressure or trusting it too much? That’s where the risks of hallucinations begin to rise.
For transactional attorneys, this is a deal-breaker. You can’t redline a Word doc directly in ChatGPT. You have to copy and paste, lose formatting, and then somehow transfer edits back into the document. There's no context-aware redlining, clause-by-clause approval flow, or version control.
This might be fine for blog writing—but it’s unacceptable for contracts worth seven or eight figures. Redlining is where the real work happens. And ChatGPT just isn’t built for it.
Confidentiality is non-negotiable in our field. ChatGPT is a third-party system with limited transparency around how data is stored, processed, or retained. Even OpenAI’s terms discourage sending sensitive client data through the platform.
If you’re in-house or at a firm that handles regulated data, using ChatGPT could pose a real compliance problem. Many IT departments are already restricting their use, and for good reason.
Most of us live in Word. We collaborate through comments, track changes, share drafts, enforce internal standards, and review edits clause by clause. ChatGPT doesn’t do any of that. It’s a separate tool that exists outside of our workflow.
There’s no playbook enforcement, no way to track how clauses evolve over time, and no visibility into team reviews. ChatGPT won't know if your team has a preferred fallback position or negotiation threshold.
What Gavel Exec Does Differently
This is where Gavel Exec comes in. It’s AI built specifically for legal professionals, especially corporate, real estate, and transactional teams that work in Word.
Gavel Exec operates directly inside Word, so you don’t have to leave your existing environment. Chat with it and run playbooks to review contracts using AI. It tracks changes, adds comments, and performs clause-specific redlining. Since it’s trained on legal language and workflows by corporate and real estate attorneys, it understands what a fallback clause looks like, when a term deviates from firm policy that you upload, and where approval is needed.
It also supports internal playbooks, so your team stays aligned across reviews. That means less reinventing the wheel, and more consistent outcomes—without needing to search for that one perfect clause from a deal you closed two years ago.
You get team collaboration and the ability to train the AI to perform like your firm does by uploading documents and providing instructions, complete with enterprise-grade security. Since you can draft and redline with Gavel Exec directly inside Word, your edits stay where they belong—in the document, not pasted across tabs.
Here’s the simple way to think about it:
That’s where purpose-built tools like Gavel Exec can make all the difference.
If you’ve been using ChatGPT and wishing it could just... do more—track edits, follow your playbook, keep everything in Word—Gavel Exec was made for you.
You can try it for free or schedule a demo to see how your team can redline faster, more consistently, and with less friction.
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