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Saturday, October 24, 2026

Your Chatbot Can’t Keep a Secret - CBIA

The following article was first published on Shipman & Goodwin attorney Dan Schwartz’ Connecticut Employment Law Blog. It is reposted here with permission.

Last week, we held our annual labor and employment seminar before a full house at Hotel Marcel in New Haven.

In my intro, I made an off-the-cuff joke about how we were thankful for those in attendance as we know that they had their AI chatbots they could always ask.

It got laughs, but as I was thinking about this (and how I will never be a stand up comic), it got me thinking: When do employers need attorneys anymore and why?

I’m not the first person to ask the question, and I won’t be the last. I’ve been poking at it on this blog for a while. Back in 2022, I asked an early version of ChatGPT to explain Title VII to a fifth grader and to tell me whether an employer could withhold pay from an employee who stole food.

The answers weren’t bad. My conclusion at the time was that AI may not replace attorneys yet, but its ability to provide basic information was clearly improving.

Four years later, “clearly improving” undersells it. So let’s try to answer the question honestly, without the reflexive defensiveness you might expect from a lawyer whose livelihood depends on a particular answer.

First, Some Credit Where It’s Due

Let’s start with what these tools do well, because they do quite a lot well.

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