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The Least Productive Week in America
If you are reading this right now, congratulations. You are part of a very elite group – specifically, the approximately dozen or so people not currently hunched over a double-overtime thriller or frantically refreshing a bracket that was busted by noon yesterday (thanks Wisconsin – I thought High Point was a beverage).
Statistically, today and yesterday are some of the lowest productivity days of the year. So, to the few of you reading this (and our families), welcome. Since you’ve clearly decided to actually work today, we figured we’d reward that diligence with some news about how your AI assistant is a narc and New York City has once again moved the goalposts on sick (…et al) leave.
Let’s dive in!
Your Chatbot is a Snitch
Right now, everyone and their mother is just yapping their unedited thoughts into a chatbot – in both their personal and professional lives. Whether it’s summarizing a meeting, making an email less (or more) snarky, or – our personal favorite – vibe coding, AI has gone from a tech curiosity to a permanent fixture in the workplace. So what does this mean and how can we possibly fearmonger this story? Glad you asked. While we are clearly still in the early innings of this whole AI-thing, a few recent federal decisions have given us a sneak peek at how this fight is going to unfold . . . and for anyone in HR or running a business, it’s a massive reality check that the AI “assistant” you or your employees are chatting with might just become the star witness for the opposing party. NBD.
The two cases are United States v. Heppner and Warner v. Gilbarco, Inc., and the contrast between the two tells the whole story. In Heppner, a defendant decided to play lawyer and used a public AI platform to draft defense strategies on his own whim (what could possibly go wrong?). The other side requested these so-called strategies during discovery, the defendant opposed on the grounds of privilege, and yada yada yada the Judge ruled that these documents weren’t protected by attorney-client privilege. And the reasoning is one that . . . makes sense? According to the Terms of Service, most public AI tools (the free versions of ChatGPT or Claude, for example) explicitly tell you they are using your inputs to train their models. By clicking “agree,” you’ve essentially invited the general public – or an adversary – into your conference room. The court found the defendant had zero “reasonable expectation of confidentiality,” and since he wasn’t acting under a lawyer’s direction (foreshadowing alert), the AI was just another third party blabbing his secrets.
On the flip side, the Warner court actually protected the AI-related materials. Why the different result? Because there, the AI was used within an attorney-supervised workflow. The judge shut down a “fishing expedition” into the prompts, noting that the tech is a tool, not a person. It shouldn’t automatically blow up work-product protections just because a computer helped draft the memo, provided a human lawyer (for now) is actually the one steering the ship.
This is also a good spot to point out that AI hasn’t actually changed the law; it has just changed the facts. To protect yourself, be intentional. AI-assisted work is only likely to stay privileged if it’s done at the specific direction of your attorney. Stop using “free” public tools for real work; if you aren’t using enterprise versions with contractual data isolation and “zero-training” guarantees, you’re making our job more difficult essentially broadcasting your secrets. Most importantly, update your handbook, your employment agreements, etc. You should have clear policies on what can and cannot be fed into a chatbot. If you wouldn’t want it attached as Exhibit 1 to the complaint, proceed with caution.
Maybe Leave for March Madness Is Protected Now?
As a reminder, NYC’s amended Safe and Sick Time Act went into effect on February 22, 2026, with the highlight likely being the new requirement for 32 hours of unpaid protected time off . . . in addition to the 40 or 56 hours of paid leave you’re already providing. And unlike the “paid” component, this 32-hour bank doesn’t accrue over time; it hits the books immediately upon hire and at the start of every calendar year. So, if you haven’t touched your handbook since our last update, maybe turn off March Madness, pause Tell Me Lies, and get to steppin’.
But wait, there’s more!
NYC recently came out with some amendments and updated guidance that move the goalposts even further. First, they’ve officially rebranded the whole thing as the “Protected Time Off Law” (PTOL). It’s the same law we’ve lived with for a decade, just with a shiny new name (and more ways to get sued).
The biggest shift – beyond the 32 unpaid hours – is in what counts as a “protected” reason to miss work. The list now includes: “public disasters”, workplace violence, babysitter cancellations, the Monday following Super Bowl Sunday, and school holidays to the list.
(by the way – we only made up one of those reasons)
You also have to distribute and post an updated “Notice of Employee Rights” immediately. More importantly, your pay stubs now need to track every separate bucket, not just the original 40 or 56 hours. Yes, that means: paid leave, this new 32-hour unpaid bank, and the 20 hours of paid prenatal leave that’s now set in stone.
And finally, Department of Consumer and Workplace Protection (DCWP) – the City agency that oversees this law – is getting in on this AI-thing and moving toward a “data-driven” enforcement model. The DCWP will literally benchmark your company’s leave usage against national averages. If your records look too “healthy” (couldn’t resist), the DCWP may decide you have an unofficial policy of discouraging leave and penalize you. And if you’re still reading this and not picking up the phone to contact us . . .
That’s all for this one. Have a great weekend everyone and good luck on your brackets! As always, if you’ve got questions, you know we’ve got answers (except if you have questions about what to do with the snow, then you’re on your own).
~ The W + K Team
ABOUT WEINSTEIN + KLEIN P.C.
Founded in 2019, Weinstein + Klein is a modern boutique law firm that serves as outside general counsel to businesses across industries. Weinstein + Klein provides strategic, day-to-day legal support with a focus on labor and employment law, corporate and transactional matters, and business litigation. Weinstein + Klein works closely with business owners, executives, and entrepreneurs to proactively manage risk, navigate complex employment issues, and handle key transactions – from formation to funding to exit.