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New AI and the Law course explores the capacity and limits of technology in the legal profession

by Sarah Bello,
Student sitting in a classroom

In just a short time, with a well-written prompt, AI tools can produce documents with credible legal arguments.

The briefs appear polished — but are their claims sound and supported by the law?

Terry O'Reilly HeadshotA new course, “AI and the Law,” taught at Willamette Law by Associate Professor Terry O’Reilly aimed to find out last spring, as students examined AI legal tools and their potential applications.

When the dean’s office asked for proposals from faculty on a course about AI, O’Reilly thought that preparing an outline would be effective motivation for him to learn more about the subject, which was drawing intense interest since the release of ChatGPT 3.5 at the end of November 2022.

O’Reilly reviewed news articles, reports by law firms and accounting firms, entertainment industry bargaining agreements with AI clauses, technical reports and legal filings in cases involving AI. He also experimented with AI tools to prepare simple handouts for topics he understood well, assessing the current strengths and weaknesses of the tools.

Given the subject’s novelty, he was able to organize enough material for a course in about a week, in collaboration with the dean’s office. He made considerable adjustments before and during the course to keep pace with rapid developments in AI and in the AI tools for lawyers.

During the course, O’Reilly gave an overview of the technology of large-language models and the legal issues surrounding the development and applications of AI.

To evaluate the quality of AI legal output, students first reviewed the format and style of law firm work products: internal memos, client memos, legal opinions and legal briefs. They then surveyed AI tools designed for or adaptable to legal applications and experimented with methods of allocating tasks, structuring queries, and reviewing and refining AI output for proper formatting.

Their assignments simulated law firms using AI to draft documents on firm policies, a memo to clients identifying potential environmental law issues in acquiring industrial properties, and documents addressing legal issues arising out of the use of AI.

“The emphasis of the course was to obtain sound legal analysis using existing artificial intelligence tools. It is challenging for students — for anyone — to achieve this,” O’Reilly says. “The capacity of a particular AI tool to produce reliable legal documents sometimes varies even from session to session in the same week, plus new versions of a tool might respond differently to instructions than a prior version.”

Despite occasional setbacks with some of the tools, students appreciated their progress and exchanged ideas and discoveries about AI.

The course is scheduled to be offered again next year, but O’Reilly says he would be surprised if, in five years, it was still being offered without changes. The course could be obsolete if AI developments stall, or, if progress continues, it could be too much content for a single class.

Regardless, he recognizes the attention that AI requires. It’s prudent to appreciate its capacity and limits, he says.

“Even using sophisticated techniques in formulating AI instructions does not guarantee satisfactory output,” O’Reilly says. “In any event, each claim and cited authority still must be reviewed and confirmed — that’s nothing new and may never change. But with care and experience using a particular AI platform, it is often possible to obtain useful legal analyses or drafts — sometimes quickly, and of impressive quality. So, for better or worse, heads up.”

A Q&A with student Ja’Terra Scott JD’26

What were your overall thoughts about the AI and the Law class?

“Overall, AI and the Law was an eye-opening class. I didn’t enter law school with a strong background in the legal system (outside of TV), and AI was completely foreign, so signing up for the class was an opportunity I saw to familiarize myself with emerging technology. All too often, the Black community is underrepresented in high-growth tech fields and are sometimes the first to face job displacement due to automation. I wanted to set myself up for success as I prepare for a legal career, especially as AI and technological advancements continue to grow. I went into the class with no specific expectations, only to learn.”

Was there anything interesting or insightful that you discussed that you hadn't thought of before or that was especially memorable?

“I was really shocked by how quickly AI transformed and essentially got smarter throughout the semester. I think the entire class can admit it seemed like every couple of weeks a new model emerged, [with] new features we could explore and more capabilities. It was fun to see the limitations of the large language model (LLM) in January when we first walked in, compared to the end of the semester. 

“I’ll be honest, I used to think AI was the be-all and end-all, but very quickly you realize it's not. There was so much still needed, like verifying that all cited quotes were 100% accurate (which they almost never were), and making sure the inference it relied on was also valid. Since the class existed on a continuum and the memos were just demos, we didn’t always have a solid baseline of knowledge about the information we were asking AI to figure out for us. However, once you understand the question you’re trying to answer, it becomes much easier to see that the answers AI provides are not always spot on. 

“Some of the reasoning was extremely generic and missed the mark. That’s why it’s so important not to rely entirely on the LLM, because doing your own research is still crucial. It made researching much easier — it could help point you in the right direction if you got stuck or needed help finishing a sentence, but it’s nowhere near something I would recommend to a novice as their problem solver. We’re close, but we’re just not there yet.”


Do you feel the class was beneficial to you on your law school journey, and if yes, in what way?

“Absolutely, I have already begun incorporating it into my research methods for my summer internship. However, without this class, I would have never recognized the weaknesses of the LLM. 

“I think everyone has their own way of researching a particular topic or shepherding a case. AI is really good at finding what you may need, but it just doesn’t replace the secondary sources and due diligence of reading the material and having a solid background of knowledge. Without that, you’re doomed to fail. 

“The class was great and a total eye-opener for me, but that is nothing without a great teacher. Professor O’Reilly was extremely knowledgeable about the technology (even though he's humble about it) and took the time to explain not only what AI is, but how it works. That’s so pivotal to understanding the system you’re using. So now, as I look forward to practicing law in this new digital age, I’m comfortable employing these emerging technologies to streamline my research and writing, but even more equipped with the understanding that it should be used carefully and relied on about 35% of the time.”

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