Legal IT Insider spoke with Sheppard Mullin’s chief knowledge and innovation officer Kate Cain about the selection of Legora and how it fits within the Am Law 100 law firm’s wider generative AI strategy and roadmap.
In November, Am Law 100 law firm Sheppard Mullin announced a key milestone in its multi-year innovation roadmap – a partnership with European-founded GenAI provider Legora.
An early adopter of CoCounsel back in its pre-Thomson Reuters Casetext days, Sheppard Mullin is not a stranger to GenAI technology and has been keeping an eye on the legal AI assistant market, with chief knowledge and innovation officer Kate Cain observing: “Earlier this year, we were starting to hear from more and more clients expressing an interest in the kinds of projects that Legora and tools like it are really well suited for and decided that the technology itself had matured enough that it made sense for us to take a look at.”
While the Legora partnership is the firm’s newest milestone, it is part of a broader effort to modernise how its lawyers work, evaluate AI tools, and embed innovation across practice groups.
The selection process
There are lots of different ways to run a pilot, but in order to move quickly in selecting a legal AI assistant, Sheppard Mullin ran an intensive two-horse, head-to-head process led by eight partners. Each partner had an associate buddy and the selection team also included the head of legal training for Sheppard Mullin’s transactional practices, a dedicated diligence team, and Cain’s knowledge and innovation team, who all worked with both platforms.
Cain describes weekly huddles with the partner cohort and the associate cohort plus weekly office hour sessions with each vendor. “It was a pretty significant time commitment from these folks. So we kicked that off in August, ran through the course of it, and by mid-October, we had made our decision that Legora was the best fit for us,” she says.
Cain describes the outcomes as “a really close race”, but what differentiated Legora were three factors. Firstly, users found the language to be more nuanced and sophisticated. Secondly, the validation gave them more confidence. Cain says: “That’s the part that keeps lawyers nervous about using generative AI: how do we make sure that it’s correct and coherent and relevant? And so we want to make sure that any platform we put in front of our lawyers has really, really solid validation functionality so that they can check things with confidence. The thing that stood out to us from Legora was that it was one click to be able to see what the source information was, but they went a step farther. When, for example, the lawyers were using the drafting tools to suggest making the language of a provision more pro-seller or more pro-buyer or whatever the scenario was, Legora would give you the example language or the recommended language, but then it would explain its rationale, it would explain the analysis. That that stood out for us because we could understand and become more confident that the application was behaving the way we would want it to and also, because we see that as a terrific training opportunity as associates start to be introduced to the platform.”
The third thing that jumped out was the training, support, implementation planning framework and resources from Legora, with Cain observing, “They came to us with really great collateral.”
The use cases
Sheppard Mullin is rolling out Legora across all practice groups and offices, enabling more than 1,200 attorneys to use it for the likes of research and diligence, drafting and negotiations, and analysing trends. The firm is creating practice-specific playbooks and ongoing certification to ensure attorneys and business services professionals are getting the most from it.
Cain says that some of the early use cases revolve around analysing markups in transactional departments and rewriting provisions to be more in line with their client (pro-seller or pro-buyer, for example.)
“Where we have found a lot of utility is in what I would refer to as ‘ad hoc diligence’” she says. “So not the official formal due diligence for an M&A, but more of a, ‘hey, take a look at this set of contracts and quickly identify where there are certain issues or whether X, Y, Z, circumstance will be an issue’. If we take a look at these more ad hoc questions, it was really powerful,” she says.
A particular project that Cain says “we got really excited about” was where a team gave an old diligence report and work product together with a new set of diligence documents to Legora and said ‘create a tabular review that is going to look like this.’
“And it did!” she says. “It wasn’t perfect but it was really, really close. So it’s just one more step in jumpstarting things. It drafted all of those prompts and that table based on the work product we fed it, which was pretty cool.”
Cain says that the really powerful opportunity for lawyers is less time hunting and gathering and organising and more time analysing and digging into the details and doing the strategy of matters – “the more nuanced stuff that requires lawyers’ expertise and knowledge and experience and the things they went to law school for.”
Adoption
Sheppard Mullin executed the agreement with Legora in November and it’s too soon to talk about adoption but Cain observes that one of the early learnings is that this isn’t software that you learn what the button does and push it, it’s far more iterative.
There is a learning curve for partners in terms of how to interact with and instruct Legora, with Cain advising them: “If you were to give the same instruction to a summer associate, would you just say, ‘give me X?’ What would you tell them?’ We need to think through what the instruction is and that’s about building those prompts and workflows.”
Building prompts and workflows is a big part of Sheppard Mullin’s planning and implementation process and Cain says: “We’ve got a whole discovery work stream. The way we’re approaching the rollout is two concurrent rollouts. One is a firm-wide launch. So a 101: everybody who wants in the pool can get in the pool. We’ll give everybody that baseline training and start to build up those muscles and that awareness.
“At the same time, we’ll do practice-specific and team-specific rollouts where that’s the sort of 200 level, 300 level to use an American university analogy. For each of those practice groups we’ve got a whole discovery process where we’re identifying what are the two or three starting workflows or templates or applications or things that we want to have at the ready for day one for those practice rollouts.”
Guardrails
In terms of ensuring that people are using Legora appropriately, training is key. But Cain says that responsible use of AI is just part of every conversation.
“We work really closely with our office of general counsel to make sure this is all incorporated into the ethics training and compliance training that all lawyers are part of. Our general counsel team is fantastic and do a really great job of centering ethical, responsible use around the client and ensuring that we’re serving the client appropriately and effectively and really making it quite real for our lawyers.
“It’s a theme with everything that we do. So, it’s not just like a disclaimer that pops up or a disclaimer at the beginning of a training, it’s something that we talk about in lots of different channels so that it’s not a check the box kind of exercise.”
Wider AI strategy
Cain joined Sheppard Mullin in April 2024 in a brand-new role that spans both knowledge and innovation. She says: “A big piece of that remit is how do we look at innovation as a strategic priority for the firm, and how do we interweave it into everything that we do at the practice level, with the business service teams and such?”
Cain is building out the practice innovation team – a group of knowledge and innovation attorneys who have technology expertise and can help to ‘be the voice of lawyers’ in software evaluations.
“The goal for us is not to deliver software,” Cain says. “The goal for us is to help our lawyers transform the way they work today and tomorrow. And so having our practice innovation team is a big part of that. So there’s that investment. And we’ve spent the last year building that team, building relationships, and achieving smaller wins with products that we already had in our toolkit.
“What we learned very quickly as a team was that the firm has invested in some terrific software over the years. But not enough people knew about it, not enough people were using it, not enough people were getting value out of it. Just raising awareness around AI-enabled tools that were already in the firm’s toolkit and making better use of them, raising awareness around them, highlighting wins is really valuable. We’ll say, ‘Look, we used this for this particular real estate deal and here’s how it made an impact.’ Now I’ve got folks showing up in the doorways of my K&I attorneys saying, ‘Can I have what they were having?’, which is fantastic. That’s a dream come true for someone in my role.
“I want to be clear, Legora isn’t the start. Legora is an addition to an existing toolkit. We’ve already had wins across the firm. Our goal now is to institutionalize that. We’ve had pockets of successes. We want to make that consistent across the organization. And I think Legora is the next chapter of that journey.”
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