
It was the second non-IP request of the week from a longtime client, made through their new in-house counsel. The first of the two requests was easy enough to dispatch, even though it involved an already-filed litigation. The client and I had gotten a similar case dismissed a few years back, even before answering the complaint. All I needed to do was go back through my emails around that dispute. Once I refreshed my recollection on the investigation we had done in that earlier case, I was able to guide my client’s new in-house person as to what information he needed from the business unit and a relevant outside vendor. With that info in hand, it was then a simple matter of presenting it to opposing counsel and securing their agreement to drop the case. This time, we didn’t even need to engage Biglaw co-counsel with specific expertise in this type of litigation, as we did the first time around. Score one for the value of long-term client-attorney relationships and institutional knowledge.
The second matter that arose, however, was a bit more challenging. To start, the client had received a notice of the potential claim a while back, with a limited time remaining to reply. Complicating matters, the likelihood of the client getting indemnified by its supplier was nonexistent, since the product had been discontinued and recent sales were just an attempt to clear out remaining inventory. Moreover, the plaintiff’s attorney was threatening to file a lawsuit in state court, across the country from where my client is located, which would necessitate me helping the client identify competent local counsel in an area of law I was unfamiliar with. Gulping down this witches’ brew was an unattractive proposition on my part, especially because the client was asking for immediate help preparing for a last-ditch effort to get the matter resolved prelawsuit via a scheduled call with plaintiff’s counsel. Because the matter was time-sensitive, I did a quick read of opposing counsel’s demand letter and followed up with my client to confirm a factual point the letter raised. Because of my unfamiliarity with the type of claim, my plan was to suggest to the client that they ask around for recommendations to a firm based in the state where the dispute was centered.
Keeping Law School Accessible When Federal Loans Fall Short
As federal borrowing caps tighten financing options for law students, one organization is stepping in to negotiate the terms they can't secure alone.
In fact, that was my initial recommendation to the client by email. To the client’s credit, they pressed for more guidance, which prompted me to see what AI could do to help direct me to next steps. So I fired up one of my trusty AI tools and started by asking for a primer on the type of claim being raised against my client. To say it was nowhere as complex as an IP dispute would be an understatement. My next step was to ask the AI what would be the best approach to “head off” a filing against my client. The AI returned a few different strategies, including some that my client could not execute on, (e.g., qualifying for a safe harbor based on the size of the business, as one example). I knew all along that I would need to upload the demand letter my client had received to get more tailored advice — but I felt that it was important to get some more general guidance from the AI first, so that I could double check that it was giving me consistent responses.
As a next step, I uploaded the demand letter from opposing counsel. The AI analyzed it in seconds — and even pulled the underlying notice that opposing counsel had filed with the state authority — before returning a detailed, step-by-step approach to counseling the client on their legal options. For step one, I needed to confirm how many units had been sold in the relevant period. A quick email exchange with the client later, and I had the information. Armed with that data, the AI was able to prepare a more detailed approach for my client to take on the call with opposing counsel. It even suggested an opening settlement offer, large enough to force opposing counsel’s hand toward a reasonable response, but low enough to reflect the limited exposure my client faced even if a case was filed. I then switched gears, prompting the AI to give me my client’s maximum exposure under the law, taking all facts in the favor of opposing counsel as set forth in their letter. It confirmed that the biggest risk to my client was getting entangled in an expensive legal proceeding, where even a narrow loss on the merits could result in a stinging attorney’s fees award.
With all that analysis in hand, coupled with my own verification of everything the AI had suggested, I then felt comfortable advising the client on how to approach the initial settlement discussion. I reckoned that even were that talk proven unsuccessful, we would have learned something about the other side by virtue of the discussion, with the ability to pivot to the original strategy of hiring competent local defense counsel as needed. And if our AI-assisted approach proves to work, then the client — even after paying me for my counsel — would have saved significant money in outside counsel fees, while avoiding an ongoing business distraction with nothing to gain. Moreover, because the client has traditionally worked with me on a flat fee per project basis, I didn’t have to worry too much about how much time using AI may (or may not) have saved me. Instead, both the client and I would have benefited by the research capabilities of the AI, as well as the speed with which it suggested different approaches that I was allowed to pressure test. Only on that foundation, as well as my confirmation with independent research of everything it pointed me to, did my legal judgment kick in to allow me to advise the client in the way I felt best.
Ultimately, I would couch this experience as a successful use of AI, irrespective of whether this dispute resolved on a faster or slower track. Perhaps what is most interesting to me about the experience is the fact that this was not a project that I would have felt comfortable delegating to an associate, whether or not they used AI. If they didn’t use AI, I wouldn’t expect an IP associate to give me accurate guidance on an area of law unfamiliar to us both. And if they did use AI, having them regurgitate for me the AI’s output would have been of little additional help — and likely more inefficient with a higher chance of error. Put another way, just as I would not substitute an associate’s judgment for my own, neither would I outsource my judgment to any AI tool. Going forward, I will look for an example from my practice where handing off an AI-assisted assignment an associate’s way would prove to have been a better approach. In the meantime, using AI on this one project was all I could ask for.
AI Is Reshaping Legal Practice—But Tools Aren’t The Real Differentiator.
Explore the mindset, cultural shifts, and training strategies that define the AI‑savvy lawyer, revealing why human judgment, standardized competence, and integrated learning—not technology alone—will shape the future of the profession.
Please feel free to send comments or questions to me at [email protected] or via Twitter: @gkroub. Any topic suggestions or thoughts are most welcome.
Gaston Kroub lives in Brooklyn and is a founding partner of K2K IP Law, an intellectual property litigation boutique that also serves as a leading consultancy on patent issues for the investment community. Gaston’s practice focuses on intellectual property litigation and related counseling, with a strong focus on patent matters. You can reach him at [email protected] or follow him on Twitter: @gkroub.