But AI says…

How to use AI effectively when working with your lawyer.

We're seeing it more and more. We send a client an email or a contract we've drafted. A day or two later, we get a reply with a list of comments, questions, or suggested edits clearly generated by ChatGPT, Claude or another AI tool. Sometimes the feedback is genuinely useful and sparks a good conversation. More often, it isn't - and we spend time explaining why a "suggestion" doesn't apply, is legally incorrect, or misses the point of a provision we carefully crafted on the client's behalf.

We're not writing this to discourage you from using AI. It's here to stay, and we use it ourselves for certain tasks. We're writing this because we'd rather have an honest conversation about what AI can and can't do in the context of your legal work so you can spend your money and our time on things that actually move the ball.

A Quick Note on Privilege

Attorney-client privilege protects confidential communications with your lawyer. The law is still catching up, but sharing our advice with an AI tool can waive that protection, and once it's waived, it's usually gone for good.

Before you paste our advice or a sensitive document into an AI tool, pause. When in doubt, call us first.

What AI doesn't know about your matter

When you paste a contract or legal advice into an AI tool and ask "is this good?" or "what should I change?", the tool is working with almost none of the context that shaped the document. It doesn't know:

• The history of your negotiations with the other side, including what you gave up to get something else

• Your risk tolerance, your industry, or the specifics of your business

• The legal issues that matter most to you, which often meaningly differ from the "general" law the AI draws on

• Prior drafts, prior deals, or the relationship between the parties

• What we already considered and deliberately chose not to include

So when AI flags a clause as "unusual" or "missing," that's often because the clause is tailored, not because something is wrong. A thoughtfully drafted contract frequently looks different from a generic template, and "different" is what AI is trained to notice.

Where AI gets things wrong

AI tools:

Make things up. This is known as "hallucination." AI can confidently cite cases, statutes, or legal standards that don't exist, or misstate what a real law says. Courts across the country have sanctioned lawyers for filing AI-generated briefs with fake citations. If it can happen to lawyers paying attention, it can happen when a non-lawyer asks AI to review a contract.

Default to generic. AI tends to suggest what a "typical" contract looks like. For many of our clients, typical is not the goal - tailored is. Suggestions to add boilerplate provisions, soften negotiated language, or "standardize" a clause can undo work that was done on purpose.

Don't know what they don't know. AI won't tell you, "I'm not sure about Florida's current noncompete rules." It will give you an answer, and the answer will sound authoritative whether or not it's right.

Can't weigh trade-offs. Much of what we do is judgment: balancing risk, cost, relationships, leverage, and timing. AI doesn't weigh; it describes. A suggestion to "add an indemnification provision" sounds prudent in isolation and may be exactly wrong in your deal.

Where AI can genuinely help

We want to be fair here. AI can be a useful starting point for some things:

• Catching typos or inconsistent defined terms

• Generating questions to ask your lawyer

• Helping you understand general concepts or unfamiliar vocabulary in a document

• Summarizing a long agreement at a high level so you know where to focus

  
  

The common thread: AI is most useful when it helps you ask better questions, not when it gives you answers to act on.

A suggestion for working with us

We'd rather spend our time on your actual matter than on explaining, point by point, why a general-purpose AI tool gave you incomplete (or wrong) advice. You hired us because contracts and employment law are full of judgment calls, local nuance, and trade-offs that don't live on the face of the document. That's where we shine.

If something in a contract we've drafted doesn't make sense to you - whether AI raised the question or you did - call us. That's what we're here for.