How Lawyers Are Using AI and Where They Draw the Line

Kyle McEntee:

For the past couple of months, we've been asking our guests a bonus question:

Katya Valasek:

How has AI affected your practice?

Kyle McEntee:

The answers vary widely. Some lawyers are skeptical, some enthusiastic, and a lot fall somewhere in between.

Katya Valasek:

I definitely land more on the skeptical side. I tend to avoid using AI, if at all possible, for many reasons. But included in them are the impact on the environment and the fact that it very often gets things wrong.

Kyle McEntee:

So I've been pretty open about my frequent use of AI, perhaps even love of AI. Just this past weekend, I used it to help me with some recipes based on food that was going to spoil soon. I used it to help with some personal finance questions. And even started to forecast what retirement might look like, even though that is a really long time away.

And when it comes to the law, I think it does have the potential for positive impact too. And in a field where sorting through mountains and mountains of documents is a day-to-day reality, having that extra set of eyes, even digital ones, can help.

Venetia Mayhew:

AI has just started affecting me because I'm always resistant to new things.

Katya Valasek:

That's Venetia Mayhew, one of Oregon's most well-known clemency and post-conviction lawyers, talking about her relationship to the technology.

Venetia Mayhew:

I've just started realizing how it's helping me research legal issues much quicker than I would otherwise do myself fumbling through Westlaw for days at a time. So it's really helping me streamline that part of my practice, which is making me quicker and more efficient at things I need to be. So I'm really benefiting from it in that way.

Michael Kohagen:

AI is still sort of coming into its own in terms of M&A. I think the biggest place where we see it being used is in the diligence process.

Katya Valasek:

And that's Mergers and Acquisitions lawyer, Michael Kohagen.

Michael Kohagen:

So it's really good at sifting through massive amounts of information and trying to pare that down a little bit to whatever the individual wants to actually review. And you know, in M&A, there's a lot of diligence review and you can have a company that has a thousand contracts and there's various provisions that in every deal you're going to be looking for in each one of those contracts. Can't 100% trust it, but that's the best use case we've got so far.

Kyle McEntee:

For trial consultant and public defender Joe Stephens, AI has also proven incredibly useful.

Joe Stephens:

AI has been like the invention, the creation of fire to humanity when it comes to the way public defenders can work. The trope, the cliche, the sort of idea of what a public defender is, is overworked, underpaid, massive caseload, more than you can handle. AI is fundamentally, from a public defender point of view, about access to justice in a way that I think is just beautiful.

Katya Valasek:

As Joe puts it, AI lets you do more with the resources you have. That's why, in addition to his public defense work, he works with lawyers and AI to streamline their litigation strategies and case preparation. It's something lawyers across the country are experimenting with, including international trade lawyer, Audi Syarief.

Audi Syarief:

In the past, we've done a lot of our research manually, but now, you know, we have access to databases that are able to kind of identify the sources that we need to review very quickly and organize them in a way that's quite helpful.

Kyle McEntee:

For land use and real estate lawyer Eric Bernheim, AI has been especially useful when it comes to parsing through long hearings.

Eric Bernheim:

You know, to summarize, six hours of nothing but commissioned comment and questions and concerns would be a huge task. But now we're using AI to upload that audio file and to provide a more workable summary that then we could utilize for what we need to utilize it for.

Katya Valasek:

And for Asha Sharma, a social security disability lawyer, AI has become a helpful sorting device.

Asha Sharma:

We use medical records quite a bit to prove social security disability, and hardly a month goes by that we don't have a case with a thousand pages of medical records. So we've tried out some AI summaries of medical records, and they definitely show promise but still have a long way to go.

Katya Valasek:

Like many lawyers experimenting with AI, Asha is quick to point out the limitations. When it comes to the law, AI is far from a perfect tool.

Asha Sharma:

They miss critical things. I can't wait for the day when AI does a great job summarizing medical records, because we spend days and days sometimes reading through medical records, trying to cull the most critical facts that'll help prove the case. And sometimes you'll find something buried in there, which AI is not going to find.

A couple of weeks ago, a case, and I found a mention of the client having had some kind of a court hearing. And so I asked him, what kind of a hearing was this for? Anyway, long story short, he had been pulled over for driving and the charges had been dismissed. I said, why? And it turned out he had been deemed incompetent to stand trial. We got those records. I'm convinced that helped win the case. I'm not sure AI would have found that, at least not AI as it currently exists.

Audi Syarief:

Is it spitting at legal advice? No. Are we taking whatever it spits out and handing it over to the client? No.

Katya Valasek:

Audi Syarief again.

Audi Syarief:

But it's getting faster and smarter, and it's going to be a bigger and bigger part of my practice for sure, as I think will be true for really anyone practicing law.

Kyle McEntee:

M&A lawyer Michael Kohagen agrees.

Michael Kohagen:

As of now, it's not quite there in terms of drafting and things like that. It'll probably get there, and it can be helpful for idea generation and things like that. But really, I think the struggle now is to figure out what it helps me be more efficient at and what it's really just kind of adding more time to your bilIables.

Kyle McEntee:

One of the biggest dangers we've seen already is hallucinated cases, lawyers citing cases that literally don't exist. According to one study conducted through Thompson Reuters Westlaw of cases between June 30th and August 1st of 2025, in that small timeframe, they found 22 cases where courts or opposing parties found hallucinated cases in filings.

Eric Bernheim:

It can be a useful tool to point you in the right direction to get you started, but it should never be the end point, right? You always have to do more than just accept what they give you and think that that's worthy of sending out and putting your name on it.

Kyle McEntee:

That's Eric Bernheim again. And appellate litigator Rachel Frank agrees. While she sees the promise of AI, hallucinations keep her cautious.

Rachel Frank:

I never use AI for legal research because the hallucinated cases are so real. I see them all the time and, you know, I never want to be putting that into my brief. So I would never use it for that alone. And site checking has just become ever more important because of AI.

Kyle McEntee:

The true promise of the technology, she says, a kind of thinking partner.

Rachel Frank:

I sort of talk to the AI sometimes to work through a difficult issue. And it's often wrong, right? It often is misleading, but a lot of the time it's helpful to just have someone who sort of quote unquote knows, you know, the background of your case and can talk through things in a way that, you know, your colleagues aren't always available at the drop of a hat to, you know, have a chat about something.

Katya Valasek:

But brainstorming with AI raises another issue, confidentiality. For that reason, many lawyers are restricted to firm approved tools and platforms.

Molly Henry:

There are so many conversations going on in the legal field right now about the implications of AI and the ethical use of AI.

Katya Valasek:

That's Molly Henry, a lawyer in the world of admiralty, aka maritime law.

Molly Henry:

So in addition to my regular practice as a maritime attorney, I also serve as associate general counsel to my law firm. And, you know, we're watching this issue really closely because we have seen a number of cases coming out where lawyers have relied on AI to write briefs and submitted them to the court without checking them. And of course, you know, AI is great for a lot of things. It is not yet great for legal writing. And it makes up case law. And we've seen some sanctions coming out of courts around that.

So we're watching it. You know, there's certainly a lot of potential out there to change the practice of law and to assist us and to make us better lawyers. But it's not there yet. So it's definitely something that we talk about all the time.

Katya Valasek:

For Molly, these risks are enough to warrant limitations.

Molly Henry:

Yeah, as of right now, we have pretty strict rules around when we can use AI and when we can't. And, you know, largely for client practice, we do not use it because there just aren't the safety controls around it in terms of maintaining confidentiality and things like that.

Kyle McEntee:

For environmental protection lawyer, Elise Bennett, the decision to use AI isn't just about efficiency. It's also about impact.

Elise Bennett:

You know, we have a really complicated relationship with AI in the environmental sphere because of the intense environmental impacts. AI uses huge amounts of energy. It impacts landscapes, rural and natural communities. And so, you know, I think that's something that a lot of environmental practitioners are really trying to find a balance with.

Katya Valasek:

As artificial intelligence becomes more integrated in our daily tools, it can be a real challenge to avoid.

Elise Bennett:

I think the relationship is thoughtful, you know, and not overusing. But in the end, it is a tool and we recognize that attorneys on the other side of the V are using it. You know, I think it's something we're navigating thoughtfully and carefully, particularly given the mission of the clients that we have.

Kyle McEntee:

Another major worry, thinking about how the next generation of lawyers will fare. Will new lawyers, reliant on AI, lose core research skills?

Elise Bennett:

It kind of reminds me of in law school where we learned to go to the library and use the books and it seemed kind of silly, right, because we had these virtual databases. But in the end, I think it's important not to lose those basic skills of research.

Kyle McEntee:

For commercial litigator Alexis Taitel, it's the potential loss of the human side of lawyering that gives her pause.

Alexis Taitel:

We recently started using some AI research tools at our firm and so far, I'm not very impressed. I think AI is definitely a growing and changing area, but I'm not sure that at this point it's, it has a very strong application in the law because so much of what we do is really nuanced and needs that human element.

Katya Valasek:

Kyle, I think that these clips show that the differences between you and I with our attitudes towards AI is not uncommon across different practice areas, different practice settings. Lawyers seem to have the same conflicts that you and I have when it comes to talking about using AI.

Kyle McEntee:

And it's really not surprising. We're still really early with this technology. Yes, we've had machine learning for a decade or more, maybe two decades at this point, but AI has crossed this threshold where now it is just part of our everyday life in a way that it just wasn't, or at least it wasn't obvious previously.

And what you said earlier about integration is completely right. You really can't avoid it at this point in time. And that means we just kind of have to learn to deal with it no matter what. You really can't opt out.

Katya Valasek:

Believe me, I have tried in many, many spaces. If I have the opportunity to opt out, I will. But every time I google something, the very first response I see is the AI response. And I will admit, sometimes it does save me needing to look further if the answer is right there.

Kyle McEntee:

I did learn last night that you can be selected for the Super Bowl according to Google AI summary, which is very obviously not correct.

Katya Valasek:

Well, it hallucinates sports facts too, it seems. And I think that that is still the one piece of AI in the legal context that really troubles me the most. Lawyers are representing clients whose, whatever the area, the issue at hand is really important to them.

And they are relying on their lawyer to be their counselor, to be their advocate. And they're often paying a lot of money for this support. So the hallucinated cases are really the thing that just gives me the most heartache when I think about how AI can negatively impact a lawyer's work that they're doing on behalf of their clients.

So all the examples we just heard about where it's really helping, they are using it in an ethical way, they aren't relying on it completely. That does give me a little bit of hope.

Kyle McEntee:

Yeah, I really do love AI as a thinking partner. And I think what gives me the most pause is wondering about non-experts using AI. When I look at my uses of AI, I make the most of it when I have expertise that I'm already bringing to the table. That's really what I think having a thinking partner is, because you can go back and forth and you know enough to be like, eh, that's not right. Or you didn't quite get what I meant. Let me revise my prompt and get somewhere better.

My concern is when non-lawyers start using it and thinking that it substitutes for that expert's judgment, or when new lawyers go through law school and come out, don't have that expertise and aren't able to identify what's wrong with what's being displayed. And until you have that expertise, it can be really difficult to identify that. And therefore, it makes it really tough to see how you transition from someone who is going through school today into the expert who can make the most use of AI, compared to the person who is already a lawyer, already a professional, already some kind of expert, and is just increasing their productivity and making themselves better thinkers. And I don't really know how this plays out yet.

Katya Valasek:

Well, I think one of the first places we'll see it play out is law schools as they tackle how to educate up-and-coming lawyers on how AI could and should be a part of their practice. Law firms are already using it. So my hope is that law schools learn how to partner in the process of preparing new lawyers to integrate AI in many different capacities into the work that they'll be doing on behalf of clients.

I know one thing people worry about is non-lawyers using AI to get their legal answers, maybe representing themselves in court, maybe creating a legal document. Kyle, I don't know what you think, but I sort of flip-flopped back and forth whether this is going to actually be something that empowers people to more accurately understand their issues when they are representing themselves on a legal matter, or if they're more at risk of falling into the trap of just accepting whatever misinformation they may be presented with.

Kyle McEntee:

I mean, I think it's yes, yes, and... this is also going to be an opportunity. There is a substantial part of the United States and the world that is not having their legal needs met. And it's not being met because it's expensive to go get expertise and find someone who has that context. And so if a chatbot can give someone adequate context and knows to look for non-experts and identify someone who maybe isn't likely to understand it on the first go, then maybe that kind of trained chatbot will do a good job of helping a self-represented litigant do a little bit better than they would have otherwise.

And we really don't get into advice on this show, and that's very intentional. But I do have some advice for listeners, especially those of you very early in your career or considering law school: develop that expertise without AI so that way you can make better use of AI. It can complement you, but if you use it as a substitute, you're not going to get where you need to go.

All right, thanks for listening today, everyone. If you want to hear more from the guests you heard from today in this episode, check out the description.