Savvy’s Thoughts on ChatGPT in Law Firms
I was recently chatting with a lawyer friend of mine who was very proud of his accomplishments with ChatGPT. I asked what they were working on, and the response was that it was a simple demand letter for a real estate issue and that ChatGPT was very useful in helping craft the letter. Sounds good to me, I say, and asked what version of ChatGPT they were using? “What do you mean, what version? It’s just on my computer.” Oh goodness, and here we go again. Come to find out my friend was (but no longer) using the free version. Why is this bad?
Because not all ChatGPTs are created equal.
The free version of ChatGPT is useful, but it’s also limited. Very limited. It typically runs on an older model, lacks advanced reasoning, has weaker writing precision, and offers no access to tools like file uploads, document analysis, memory, or advanced data handling. In short: it can help you draft something, but not necessarily something you’d want to put on firm letterhead.
For lawyers especially, those limitations matter.
Legal writing depends on nuance, accuracy, tone, structure, and risk awareness. The free version may generate language that sounds fine on the surface but includes subtle issues: incorrect assumptions, overly aggressive phrasing, missing jurisdictional considerations, or boilerplate clauses that don’t quite fit. You may not notice the problem — until opposing counsel, or the judge, does.
More importantly, the free version does not allow you to:
- Upload and analyze contracts, leases, or exhibits
- Compare documents or redline changes
- Maintain context across longer matters
- Customize outputs consistently to your firm’s voice
- Work with current, more capable AI models
That’s the difference between “AI wrote me a letter” and “AI worked alongside me as a legal assistant.”
When attorneys say, “I tried ChatGPT and it wasn’t that impressive,” nine times out of ten, they were using the free version — unknowingly judging the entire technology based on the weakest offering.
The paid versions, especially the enterprise-grade and professional tiers, deliver dramatically better results: clearer logic, stronger drafting, improved formatting, better issue spotting, better security, and far more control over inputs and outputs. Used correctly, they don’t replace legal judgment; they amplify it.
And that’s the key point.
AI isn’t here to practice law.
It’s here to remove friction.
When lawyers use the right tools, in the right way, with the right training, tasks like first-draft demand letters, clause rewrites, summaries, timelines, and client communications can take minutes instead of hours — freeing attorneys to focus on strategy, analysis, and client service.
My friend upgraded shortly after our conversation.
Same prompt.
Same issue.
Completely different result.
And that’s when he finally said, “Okay… now I get it.”