One Moment With a Client That Made Me Pause

Recently, a client said something to me that almost made me lose my patience.
Why?
Because while working with a business owner on the sale of his company, part of what we do is bring together the right team to get the transaction done properly. The lawyer, accountant and/or tax lawyer, wealth advisor, and banker.
Transactions like these are rarely just about signing papers. They require coordination, judgment, negotiation, and strategy to protect the client’s interests and actually get the deal across the finish line.
So we were discussing the legal side of the transaction.
And the buyer says to me:

"Amiram, could we just use ChatGPT or something like that to draft the documents and then have the lawyer review them at the end? It might make things less complicated and speed up the process."

Oh boy. To me, it also sounded like he was also trying to save some legal fees, but for the wrong reasons. And this wasn’t a small transaction.

The lawyers I work with are not trying to complicate things. Quite the opposite. They have a very transactional and pragmatic approach to getting deals done. But they are also doing what good lawyers are supposed to do: protect the client.
For a moment, I felt my frustration rising. My first instinct was to react strongly and explain very bluntly why I thought that was a bad idea.
Instead, I paused.
And then we had a calm conversation.

AI can absolutely be a useful tool as long as people clearly understand what they are using it for, and just as importantly what it cannot do.

I use AI myself for many things. Researching industries, organizing notes, summarizing information, optimize processes and helping structure ideas before discussing them with clients. AI is also doing far more sophisticated work today. I recently came across an impressive example of AI-assisted medical record review software (see: parambil.com), which shows just how powerful these tools can be when applied in the right context.

Legal work in transactions, however, is rarely static. Situations evolve. Negotiations shift. Terms change. Issues surface that require judgment, adjustments, and strategy to properly protect the client’s interests.
Relying on the wrong tools or using them in the wrong context can lead to costly mistakes. And these are not the kinds of mistakes you want to make when millions of dollars and years of someone’s work are involved.

But AI cannot replace the experience, accountability, and professional responsibility that a human lawyer brings to a transaction.
Doing the right thing upfront and involving the right professionals early is often what prevents costly problems later.
And when things do become difficult or complex, who do you want on your side? A trusted lawyer… or an algorithm?
I think the answer speaks for itself.