Navigating the new frontiers of Generative AI and legal tech innovation

With a background as an academic law librarian, Sarah Glassmeyer has developed a deep appreciation for taxonomies and data management.  Now Senior Analyst at LegalTechnology Hub, Sarah joins this episode to delve into her nuanced view of Generative AI and its impact on legal and legal tech: 

  • The preparatory work necessary to surmount challenges in implementing AI in legal contexts 
  • How Generative AI democratizes access to legal information, improving access to justice. 
  • Trends in law firms developing their own software products
  • The role of standardized legal taxonomies, like SALI, in facilitating true collaboration 
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Episode Guests

Sarah Glassmeyer

Senior Solutions Analyst | LegalTechnology Hub
Sarah has been solving problems across the legal industry for over 10 years. Currently a Senior Solutions Analyst at LegalTechnology Hub, Sarah produces content and analysis on legal tech solutions for law firm decision-makers.

Bill Bice

CEO | nQ Zebraworks
Recognized as a legal tech industry visionary, receiving Thomson’s innovator of the year award. Founder of ProLaw Software (acquired by Thomson Reuters), West km (used by 70% of the top 1000 law firms worldwide) and Exemplify (acquired by Bloomberg Law).


Bill Bice: Sarah, how are you?

Sarah Glassmeyer: Perfect. How are you doing?

Bill Bice: I am great. I’m so glad that we’re getting to do this together. I’ve been following you for a long time. I’ve been reading your content and your articles for a long time. I love your writing, so it is exciting for us to get to sit down and talk.

Sarah Glassmeyer: Thank you so much.

Bill Bice: So we were talking about, let’s start with the hot topic of the moment, which is which is our good friend generative AI.

Sarah Glassmeyer: Yes.

Bill Bice: I love how you put this of being kind of hot and cold on this. So, let’s pretend to be on the hot side for the moment.

Sarah Glassmeyer: OK. Yes.

Bill Bice: So, what are you excited about with, uh, with the potential of generative AI?

Sarah Glassmeyer: You know, so again, as I do, I run hot and cold out like some days I am this like this is going to change the world. This absolutely changes everything. How we like to interact with you is on par with web two-point. It’s on par with mobile technology. You know, it’ll be one of those things. Like it? It’ll just become so ingrained in how we interact with knowledge and information that we’ll forget what life was like beforehand. Umm. And then there’s, you know, some days are just like, sick of hearing about it. Especially cause, like so many, you know, a lot of the things coming out are like, oh, this will help you drop something or, you know, again, this is why initially really was not addressed in at any of that because I like staring up like page of a piece of paper and like brainstorming and writing and creating. I was absolutely not interested in the idea of editing something the computer wrote.
I’m not worried about being replaced by the technologies like I like doing it. I like to drive manual transmission. I am very much a control freak. But now you know some of the tools coming out like, OK, I get it. But I also like the things I’m excited about how it could do from the access to justice point of view because there are so many, you know, just taking like a crap load of content does not sound very professional. Still, you have all these regulations and laws that nonlegal professionals need to access. You think you’re a small business owner, and you just kind of want to know some regulations for your business, but you don’t like reading the CFR. It is not practical for anyone to understand what’s going on. But if you had like some way you could talk through it, you have you ask it questions, and if you provide an answer that seems cool and just the idea of like organizing and summarizing for and why I say access to justice. That’s also what many people think of, like a single mother getting kicked out of her apartment, and that’s access to justice. And it is, or you know, someone you know on death row trying to get, you know, their final appeal. And that is, but there are so many people who can’t afford an attorney, and they don’t need an attorney like it. It’d be dumb to pay $250 an hour for someone to summarize the CFR for you, but it’s vitally important for their small business.

Bill Bice: Right.

Sarah Glassmeyer: Or just there, you know, I want to put a fence in my backyard, but trying to access the zoning code is hard, you know? It’s just exciting stuff like that, but also because I’m a librarian and a data person, and otherwise, you know, I spend my life thinking about taxonomies and metadata. I know so much must be in place before these systems are used, and that’s, I think, like, oh, just going to be such a missed opportunity by legal if we don’t get our houses in order ahead of time.

Bill Bice: Well, now.

Sarah Glassmeyer: It’s like it can only do what you feed it.

Bill Bice: Right. You’re tackling an issue that I think is undervalued, which is the effort that needs to go into the data, the data hygiene like a create; it takes great data management for this stuff to work if it’s going to work.

Sarah Glassmeyer: Yeah. And I mean, I’m kind of, I don’t, I don’t know type A. Still, like I am very anal-retentive organizing as I like, doesn’t everyone have like 20 email folders that they file every email list in that they get it, and does everyone have like file folders and some files and they’re just personal document system? After 15 years of professional life, including in libraries, I’ve realized, no, you know, I always love it when I’m doing a Zoom call with someone I have to like. I mean, one of these faces that, like, completely says when I’m thinking. But you know, when doing a Zoom call and they’re sharing their screen and like, hey, if I see more than two rows of tabs, I’m just like, ohh get what are you doing with your life? But then, like they collapse their screen, you see their desktop, and it’s just, you know, files and icons and stuff. I like physical recoil. When I see that, and people are just living their life this way, it’s like, and then you multiply those times. How many thousands of attorneys and legal professionals are in the world? And it’s just like, ohh, we’re never going to get these tools to work. It’s a little distressing sometimes.

Bill Bice: Well, it makes KM professionals and firms much more valuable.

Sarah Glassmeyer: Yeah. Oh, yeah. They’re kind of, I mean, that’s the thing.
That’s I’ll be getting mean to you if I to do a list of exciting things about LLMs and umm, you know Jeremy I and then the that exciting the fact that it, you know, everyone’s saying like I mean for years it feels like librarians and knowledge management professionals have been not really appreciated and like and also like so many things like well everything on the Internet you don’t need a library at now.
It’s like, oh, no. Umm, just today, like literally 2 hours ago. I guess you know the case text integration for Westlaw is rolling out or Westlaw precision. I don’t know.
It’s either like Westlaw is homegrown LM or how they’re integrating Case Text is rolling out, but someone just like in the I don’t know. I’m in the private law libraries group on for as a member of the American Association of Law Libraries, and then, you know, that’s a real I mean, it’s such good information, and I it was nice, and it’s a private Lister because someone just said no, did I used it? I asked, you know, I worked with IT. They get me. I got some great cases, but I went back to my old Boolean searching, and I found three more cases and guess which ones the attorney cited. It was the one. Those were like the much better ones, you know?
So I think as part of all this base layer of work that must get done prep work, you’re very much like cooking the Nissan, plus you got to get all your, you know, stuff cut up and ready to throw into the pot. You know, there’s such work that must get done before we’re going to need people who understand management and how information is found and used. So, there’s going to be an implosion or explosion of need for librarians and Cam professionals, but also, you know, like there’s like, at some point, the work will be good enough for buy these tools. But right now, humans still provide a lot of great work that these tools have not met.

Bill Bice: No, it hasn’t. Now, of course, it’s very early, and in the big picture, you know, the big picture, I agree with you, and the idea that this is AI in general is as significant as the Internet.

Sarah Glassmeyer: Oh yeah, yeah.

Bill Bice: But short term, there’s a pretty big gap between how people talk about it and the reality of what the technology can do today and the problems that exist in that technology right now.

Sarah Glassmeyer: Right, yeah. Yeah. And even, you know, it was Nikki Schaefer who I worked with worked for. She just posted. I think it was on LinkedIn today. Just the idea that people are trying to nail down, you know, products and like internal tools made with these models. But the models keep changing and like how it’s so.
I mean, it’s really kind of shocking to remember how early days we really are because it seemed like suddenly it just like a light switch flipped, and everyone’s like, well, this is how the world is now. We’re going to be using these tools. Umm, but also, it’s funny because I am now old enough. Like, I feel like I’ve been feeling my middle age a lot lately that I do remember from even more so, you know, like the, you know, both like when web cheap would know kind of hit and 2006 and then again mobile technology 2009, 2008 how like everyone was coming up with an app or everyone was like coming up with some sort of tool using web toy .0 that people were adding content to or like a new social network or news that you know and it’s funny like every time I log into LinkedIn or use blue skies someone was like, hey, you know that opening eye has a developer toolset thing that’s available. Like, I made a chart GTV bot using this book, you know, and it’s great, but also, it’s like, you know, like, 99% point, 9% of these will never see the light of day after like six months.

Sarah Glassmeyer:  I love that about it, this world, but it’s also just like funny to see like, oh, we’re having this big explosion, and then like 99% are not going to survive and be used after year come to anything out of it. But it doesn’t mean it’s a wasted effort. But it’s funny to see all this experimentation, and everyone suddenly excited about things again. But also like with the apps like nine of all like phone apps ever made.

Sarah Glassmeyer: Like 95% of those didn’t need to be an app, you know.

Bill Bice: They need to be apps and never got used.

Bill Bice: And I think AI will be much more useful when we don’t discuss it as AI anymore. You know LMS will be much more useful when nobody’s using that acronym, and it’s just built in like everybody uses AI today.

Sarah Glassmeyer: Yeah.

Bill Bice: But you don’t talk about it that way. I mean, if you used Google Maps, you used AI. If you’re running Outlook, you’re using AI. You just don’t think of it that way. And so it’s a deeper embedding that’s really going to make it valuable.

Sarah Glassmeyer: Right, yeah. Absolutely. Yeah. And I think it’s so funny how, again, not being a computer science person, but no, would be like on the edges of technology and stuff like for so long it was like nothing ever going to pass the Turing test. Like something about chat, TTP. I guess the true test is we’re a lot more gullible than we thought we were. But just like how people were like, ohh, it’s talking to me. It knows all these answers is writing this stuff, and it’s like, no, it’s not. It uses predictive probability like. Guess what? The next word will be, but how do people who absolutely should know better dislike mystified by it? I don’t know if it’s the chat function that’s doing it or the fact that it goes so fast, relatively speaking, that you know you’re, you know if you’re doing like you’re texting at, like, suggest the word or you’re using an outlook. But here it’s like 5 paragraphs and 30 seconds or even less than that. Maybe that’s what makes it so magical to people, but it’s funny how he just really captured the imagination. But I think it’s also, you know, the fact that with, like with your Web 2.0, not so much. But, like with mobile technology, you really had to have some tech chops to build an app. There did become some app builders after a year or two, but this was made as anyone would just like to make an account on Open AI’s website and start playing around. Ohh, what exactly does it like? I love that. Like, I mean, don’t put like, I don’t love it when people are putting in client data in there, or, you know, filing stuff with the court that they get out of that. But I love the fact that people are the interface is comfortable enough that you don’t have to. Be attached to that experiment, and you know, again, it’s like Web 2.0 how that really kind of lowered barriers to entry.
This is Web 2.0 for data analysis, which is how I’ve been thinking of it.

Bill Bice: Well, in that point you just made about the chat user experience, I think it is really important, and I think that’s an underappreciated element of generative AI that that user experience is going to be very valuable and lots of other contexts just because it is a big jump forward in NLP of actually being able to understand what it is you’re saying. Therefore, having the computer be able to help you, even if it’s not generative AI after that point, is creating the response.

Sarah Glassmeyer: Right.

Bill Bice: It’s the part of understanding you that could end up being just as big as advance.

Sarah Glassmeyer: Yeah. And I also think it’s less scary to ask a computer a question. I mean, that was one of those. You know, I went to law school 1st, and then I became a librarian. And one of the better things to come out of becoming a librarian is that I lost any sort of ego about asking questions because everyone asked me questions for, you know, I I get asked questions or when it was a proxy library, I got asked questions all day. It’s not a big deal, but I remember prior to that, and again, this shows how old I am. I would drive around instead of stopping at a gas station to ask for directions, but I would never do that. I was too stubborn, and I would try to force it, and I think that’s you. Come again when nice fun benefits of this tech to type of technology is that it really like it’s just you privately asking questions and privately getting quiet. You don’t have to worry about embarrassment, especially, you know, in a law firm environment, you know, like junior attorneys, associates who are scared to look dumb, look down in front of your computer. No one’s going to know. But you don’t have, like, your partner will never know that you had no idea what this meant, and it is like the idea that it’s a way for people to self-educate in a more comfortable.
UM less intimidating environment, I think, is really kind of interesting as to how that will affect new lawyer training. New lawyer. You know, professional development, that’s fun.

Bill Bice: Yeah, that’s it. That’s an interesting insight.

Sarah Glassmeyer: Yeah. And, just like again, members of the public, and I think like those of us who work around attorneys every day and or may be attorneys, forget how scary it is to be an attorney. To the outside world, people like people think attorney, and they don’t think someone sitting in, you know, wearing sweatpants and a tie-dye shirt in the middle of the spare bedroom, Indiana, they think like someone who wears a suit and, you know, and gruff and cost $500.00 an hour to talk to. Umm, but yeah, I mean, it just really humanizes the ability to get at legal knowledge and legal information for people, and it’s less, you know, again also a lot cheaper than going into an attorney’s office or going even, like, that was one of the things with being a librarian, like how intimidating people would be to come into a law library if they were a member of the public. And we make it that way.
And like we’ve got all the books, all the West reporters that looked the same, that it’s like a very intense environment for an outsider and that this makes a new front door for a library or a legal services organization that people can get the information and knowledge they need without having to be anywhere physically but also emotionally be anywhere that might be kind of hard for them to be.

Bill Bice: So what? What do you think of Brian Inkster’s pushback on generative AI? He’s, you know, he’s a wonderful curmudgeon when it comes to some of this new technology. Document automation has been available in legal for 30 years, and it’s implemented at some level. But not anywhere to the extent that it could be used, right? There could be huge advances that come from document automation, and that has not happened.

Sarah Glassmeyer: Oh, for sure.

Bill Bice: So why? Why is this new shiny thing going to be going to be any different?

Sarah Glassmeyer: No, I mean, he’s not wrong. Like, that’s the thing that, and that’s why I always kind of feel like I get excited, and it’s like, oh, right. Yeah. Yeah, the fact, especially because, like with document automation, you must have your templates and everything kind of you. Again, you me some, plus you have everything all chopped up and ready to go. And then also you must have your attorneys use it. And I mean, that’s the thing like, you know, Grady Lambert, a law firm librarian out of Texas, known him for years. He’s a good guy, but he always says, like all problems are communication problems, and I kind of you very much, so yes. But also, like almost all legal tech, problems are human problems. So, like, it’s not you again. Like what? Everyone talks about that lawyer who used chat GTP to write a brief, and it turns out everything was wrong. They lied to the court. It wasn’t checked TP’s fault. It was never meant to do that. It was his fault that he did it, and the fact that document automation software is not used is not the software’s fault, and it’s not necessarily a problem.

Bill Bice: Great.

Sarah Glassmeyer: That’s not used, although it could be used, and it would be great if it were. It’s because, for whatever reason, the attorneys and other professionals who have access to the software either weren’t trained on it, they don’t see the benefit to using it, or they don’t enjoy using it. You know there is something there that the people are not taking advantage of and it’s not necessarily that they’re wrong, but it’s just it’s not happening. We need to look at the people part of the equation, not necessarily a software part of the equation, and that, you know, that’s the thing. Like there’s a great possibility, and that’s what kind of makes me sad about chat, TV, and LM and all these tools because there is so much work that must go into getting it to work right and getting it too, you know, be trained on your data, and your data must be ready to go. And you know it, it might end up being a huge, wasted opportunity, you know, because you know, especially in the on the access to justice front where you know so much knowledge that a member of the public might need is just not any way accessible that could even be traded. I mean, it’s scary. This is one of the things I’ve worked on in my life. Is that getting access to primary law? Like if you think in America especially that, it’d be super easy to know what law governs you. And it’s like, even like you, when I started all this madness 15 years ago, it was hard to get things like case law and legislation from the national level, let alone at a state level. And that’s improved so much, but it’s still hard to even find your local city ordinances or your local zoning laws or, you know, Karl Malone has done great work getting. You know, like bit building codes, and those sorts of things will just be called incorporated by reference. You see, it’s a private industry that will create a code like this to fire you. We got fire retardants or fire extinguishers that must be made, and then they could private industry build and sell it for money. But then, as the government says, we’re just incorporating all this by reference. But you still must access it. You must pay several $100,000 sometimes. Umm, so yeah, he’s working to make that now like no, if it’s incorporated by reference, it’s public law and needs to be accessible. But yeah, I mean, there’s still a huge amount of data locked away, not even then, to the point that it could be understood by technology and software and parsed and then recalculated and spat out through an interface using an LLM. So yeah, there’s so much prep work that must get done that it’s entirely possible it will be like, you know, how document automation tools just aren’t used as often as they could be. 

Bill Bice: Great. All that prep work just reminds me so much of the document and the challenges of getting document automation fully deployed.

Sarah Glassmeyer: You know, that’s the thing. We let you know one of the things, having started off more in the small world and then moved to big law, like realizing, like you know, how many templates that confirm would have been overwhelming to think of. Oh, yeah, I mean, it’s just so much work. Yeah. And another thing is again you because it’s not exciting, you know, doing the drudgery of organizing, you know, people want the immediate payoff.

Bill Bice: Good.

Sarah Glassmeyer: Like, here’s a brief or. Here’s the contract. You know, like, no, you got to break it down and tag it. Oh, you would get all the different.

Bill Bice: So that there’s another not exciting area that that, that all this really applies to, that I’m passionate about, which is, which is all the back-office functionality. It just keeps firms running.

Sarah Glassmeyer:  Yeah, yeah. I mean, and again, like, I have this idea that I hope someone steals and does, but like, one of the things I would love to see you get.
So you have like many things that I’m really, I only have like so many passions, and I feel like I have many things that really excite me. And I started talking about it.
One is access to justice, especially, you know, people who can’t afford attorneys for basic, you know, issues or don’t need an attorney for that issue. But also, just like new lawyers’ and old lawyers’ professional development. And you want to think, I think it would be so much fun, you know, ways like. So, you upload a document to your net documents or your image account. This is, oh, hey, this is this type of document, and these frequently require redaction. Do you know how to read that? No. OK.
So we’re going to tag into your skill burst account or our, you know, another sort of like CPE Professional development service that we pay money for that no one ever looks at. Here’s a 5-minute video and how to redact this document. I think that this ties your different external systems together, but how can it make your lawyer new lawyer happy? And, just like the tools that because you want to think that I was thought was funny or not funny, but like awful or awful, are you new attorneys? They’re trying to get you to figure out what they’re doing and as a partner will find there, you know, their associate and, like, give all his work to their associate, that associate, whereas the associate B is like starving for work. But like associate a plays golf with him, you know? So, it’s like, oh, you know, a way to make, I guess it’s kind of got overarching. You know you’ll subject matter is how technology can be used to make the world more equitable and to somehow fix some of the mistakes we’ve made in the past. And if there’s a way to take these tools which are good at analyzing data and find me that, like, is there a way to make sure that younger associates are getting appropriate workloads and our work getting, you know, ways of seeing, like what skills they have? What skills they need, you know, is there something in there that can be done, but it’s all like it also, just like making sure they know how, like trained on basic skills that we don’t teach in a law school, like how to do a timesheet, how to do, you know, make sure you’re doing, like, some of these basic technical skills. Like, do you know how to send a meeting invite in Outlook? You know, because I’ve worked with new grads, and many of them don’t know how to do that.

Bill Bice: Right.

Sarah Glassmeyer: It’s real basic, like how to be an adult, you know, adulting, what AI, you know.

Bill Bice: It’s got some important things in school, but in the end, if you’re at a law firm, you still got to enter your time, and bills must go out, and money must come in, and the basic machine must keep working.

Sarah Glassmeyer: Who? Yeah, yeah. Right, right. Yeah. And it’s, you know, very you it’s been a while since I’ve taught in law schools, but that kind of basic stuff is just you got to figure it out on your own, or hopefully someone will show you the ropes. But yeah, it’s, but if it doesn’t get done, you don’t get paid. And that’s important. Yeah, it’s this.

Bill Bice: So, another area that that that is related to this is, and SALI’s a great example of that, which I know you have a lot of appreciation for. For so let, let’s chat about that for a moment cause I think that’s I think that’s huge to have a standard taxonomy in this market.

Sarah Glassmeyer: No, I mean, that’s the yeah. So, I can’t believe how successful it’s been. I’m pleasantly surprised. I mean, I first heard about it. It was before I came to rein in court, even where I was, you know, kind of, I’ve always, you again, really liked taxonomies, really like organizing things, really like open content, and open, you know, things that make it easier to collaborate outside of your organization. And you know, I always say we fly farther, faster together, you know, try to what are these tools out there that can do that? And the fact that SALI has a standardized tax out of E for students to be everything connected to the world of law, it’s going to be so, so helpful. And you know, I grew up in a town of 900 people in Appalachian, Ohio. And so, I get so like one of the things I like pinch myself about is how I get to work with people from all over the world. And that’s the fun thing about legal tech, which is that it is international. You can’t even leave your state for a lot of law stuff. And here in the United States. But you know, legal tech is international, but you, again, like every jurisdiction, do things a little differently. We call things different things, and the idea of having a taxonomy that would just kind of smooth the edges and make it the universal translator between organizations, countries, and various types of technological things is exciting. Umm. And it would. It will make you, that’s the thing. You know, we were talking before the show that I came to this world as, you know, started off as an academic law librarian, and this is 2006, 2007. And at that point in time, there really was LEXIS and Westlaw and the power balance was kind of skewed. And you know, that was the AI was like, start off my career kind of like not scared of vendors, but also just like feeling like they were this, you know, giant that just stomped all over the smaller libraries, and we didn’t have a good relationship. And part of it was because, like they, you know, Westlaw and LEXIS, when I was buying spree in the late 90s and early 2000s and consolidated pretty much every legal publisher in the United States. And so, I’ve always been, you know, hesitant about consolidations. One of the benefits of a consolidation such as what Litera has been doing the past few years is that, in theory, all these different tools work together. You know, like all the Litera suite works together in theory and the same thing with blessing. You know, like all their little product, things work together. The fact that a standardized taxonomy will allow you to maintain, you know, if you don’t want to buy the Swiss army knife and legal tech, you want to have your separate spoon, knife, and fork.

You can do that; they can still interact, and all your systems can still talk together. If we have a standardized taxonomy between them, umm, one of his tortured metaphors I’ve been using for literally 10 years at this point is Disney World. So, if for people who want to ILTACON this year, you made it over to the Magic Kingdom. You know there are different worlds in Disney World. There’s like Lana tomorrow; there’s frontier land. There’s the fairy tale world, and they’re all separate. But what you might not know is that underneath Disney World or Magic Kingdom, there’s a series of tunnels, and that’s why you never see Mickey taking a smoke break or too much like anything unpleasant to the Magic Kingdom, because they send it all to the tunnels and in law, you know, we have big law, we have small law, we have the courts and stuff, but we have our tunnels underneath and that’s how knowledge and data and all these different pieces of information and data that have to talk to each other. And that’s what legal tech is in some way. But you need a standardized way for all these things to talk to each other, or they wouldn’t. So yeah, I’m thrilled to death with SALI’s progress. Kudos to everyone who’s been beating that drum, and you know, again, Damien, who’s been on this road show for 2 years. And it’s really; I think you’re the one I saw that they had, I manage and Thompson and that documents signed on and then a bunch of big law firms. I think what Terry signed on to, I don’t want to include them as well. Yeah, I was like, OK, this is this bill going to work because, you know, once you get these, you know, it’s kind of like an academia, like, once Harvard and Yale say they’re going to do something. Everyone does it. Oh, once you have Thomson and signed on.

Bill Bice: Right, yeah.

Sarah Glassmeyer: OK, I may just do it. Alright, well, we’ll do it too. We’ll make sure we can talk to that set.

Bill Bice: Well, we’ve got to get rid of all those little individual tunnels and have some shared tunnels to make that work, right?

Sarah Glassmeyer: Yeah, exactly.
Bill Bice: That’s the key in.

Sarah Glassmeyer: Just, I mean, I mean, I think, like, you know, if I had any advice for a new legal tech company, is to make sure you can work with that kind of data and make sure you’re not going to be a little island in a greater universe and a law firm or a greater universe of a legal organization because you will eventually be voted off the island or you just long longer be there.

Bill Bice: Which will be good? So last subject for you. So, you’re working at a legal tech hub now and have had this experience with legal tech vendors for a long time. So, just what? What are you? What are your thoughts about what’s happening in legal tech?

Sarah Glassmeyer: You know, the one thing I think is so funny, you know, especially when I came from small law accesses justice world at the ABA and legal aid, I’ve got a job at random court. And I was like, this is going to be amazing. Like you honestly like most of my firsthand. Knowledge of big law: I knew about it, but like person observation, it was like when they were big law. For what host the legal hacker’s event, and I’d be like, oh wow, they have Pellegrino, and they’re backroom for people. This is fancy, and so I assume that legal tech for big law would be fancy and just realizing how small so many legal tech vendors are. Actually. I mean, there’s a lot of theirs like the ones like, again, like the images and the letters that have hundreds of head counts. But many of them are just like I always say; it’s like the world’s worst sitcom. It’s to lawyers in the developer, because again, you know, people who have liked this idea. Like the chattering classes on LinkedIn and Twitter, you see, they’re always like, these legal tech people overpromised and. And they’re just selling a dream, like so many legal tech vendors I’ve talked to are just like former practicing attorneys. Or sometimes there’s still practicing, and they’re like, yeah, I had this problem repeatedly.

And I get it. Like so many of us, like the tech guy and these things, they’re like a brother-in-law and were just like my brother-in-law. Like we should do a company about this. And they did, you know, and it’s, you know, it’s just like a pain point that they personally had and realizing that other attorneys have this pain point. We should fix that. Umm, so that’s the thing. And, just like again realizing with big law, it’s not like it’s still like so much stuff like hinges on an overworked associate not messing up an Excel spreadsheet that they’ve been tracking this billion-dollar transaction. And it’s just like, holy cow, you know, just like real, there’s a very famous, you know, uh XPX CD. What is it? It’s like a webcomic about nerdy stuff, and there’s this one where it’s like this pile of boxes, stuff, and everything. You know, it’s kind of, like, very precariously stacked, and like the one thing on a holding it up, and like the title is like the Internet. And like the thing pointed out, the one little box. So, we end up being like this guy named Steve and Nebraska that’s been running this thing this time clock thing unpaid for 20 years. And like, that’s kind of like so many like legal deals, and like the one thing holding it together, this 28-year-old has got like 10 hours of sleep in the past week. It’s an Excel spreadsheet, and that’s the thing just like and again like this. How? Like, I don’t say unimpressive legal tech is, and I guess also, maybe that’s why people are excited about chatting TP. But like the things that I mean, I don’t like it. It’s not that it’s unimpressive, but it’s like a practice manager or transaction management software. It’s like, ohh, we’re just seeing more of these pieces of paper and who’s has signed them yet, OK. And look, and it’s like.
But when you show practices attorney, they’re like, oh my gosh, that’s great.
You know, and I think that was when I worked at Red in court, I relied a lot on Chris. You didn’t, Sam. Who were both practicing attorneys than big law of context? And I was, you know, I would like to write up my stuff and run it by them or, you know, sometimes. And I’m like, if you saw a demo, too. Like what? Were you excited about that? Many times, like simple things like, ohh, we could easily compare side by side, and I was like, not you’re the natural language processing, not the tool used to like you. You analyze the contract, and so we can’t, like, see side by side. Yeah, that’s easy. It’s like, oh, I know. I mean, that’s the thing. So what does legal tech just kind of face? I mean, like again. Yeah, it’s not like sending people to the moon. It’s just like making sure papers get signed, and that’s important, and it’s good, but it’s also just like, oh, OK, no. So it’s just funny sometimes. There’s just like the biggest ovation is like we’re able to find out all the paper that can get signed in a contract.

Bill Bice: What else is there?

Sarah Glassmeyer: You know, it’s like, oh, we found all the signing papers and that’s really, hard to do. And like, how many, you know, like realize, like, not that long ago like that was being done by an associate. And piles of paper and a big board room. And just like walking around those, you stack, stack, stack, stack, stack, making stacks of papers like ohh yes, I can see why this is an improvement Now, OK?

Bill Bice: It also means there’s lots of opportunity, right?

Sarah Glassmeyer: Absolutely. Yeah. Yeah, I mean. And so yeah, I mean, that’s the thing. I think that why everyone is all sudden, like with a new wave of AI, is that things provide an opportunity to get creative like nothing was creative before, not legal tech. You know, it’s more, I don’t want to say like nothing was cause it’s probably something big I’m forgetting about. But like a lab is just you, eDiscovery, it’s like, we’re just using AI to find you related content that we are looking for or transaction management. Ohh, we’re just making sure everything that needs to get signed gets signed. Umm, and like nothing’s been forgotten about, you know, but this is suddenly like ohh we could, you know, and not even just like the text generation but just like also the image generation then like. Like and the idea that you could create a transcript, I mean, I think it’s also like ever since, you know, just your kind of like that episode of The Simpsons where everyone’s worried, they, you know, they had the Grady clothes and then it rains, and everything becomes rainbow suddenly. I think that’s kind of what we’re dealing with right now. We’re like, Ohh wow, there are some new possibilities out there. We never even considered it possible, you know.

Bill Bice: Well, there’s always a pretty significant gap between consumer technology and enterprise technology. So, what we see in Big Law Right is that enterprise technology is applied in this very specific context.

Sarah Glassmeyer: Oh, for sure, yeah.

Bill Bice: And I care so much about the plumbing behind that because it doesn’t matter how shiny the surface you put it on top. If you don’t figure out the glue between those pieces, then the rainbow will never show through because you must have the.

Sarah Glassmeyer: No. Yeah, yeah.

Bill Bice: Yeah, you must have the data for it to work, ’cause circling back to where we started.

Sarah Glassmeyer: No. Yeah. And that’s the thing. You’ll get, like anyone listening to this. It’s not too late. You can. There’s always, you know, you can always hit your data in order like this. Never. Yeah. Today, tomorrow is the first day of the rest of your life. Start. Start figuring out how to do that, you know.

Bill Bice: Yeah, I think it’s one of the best ways legal techs can play a role in creating a defensible competitive advantage for a law firm, especially for any law firm of any size. But particularly, we talk about big law that does a good job of having a competitive advantage relative to their peers that is worth investing in.

Sarah Glassmeyer: Yeah, I think it’s interesting. Hello, I see how law firms are creating products now, and they always have. Still, it feels like now there are a lot more external products being created by law firms or you the idea that you’re going to split it off or just have it part of their like when they’re working with their corporate clients as like a, you know that just like seconding your attorneys, but also seconding your software. So, it’s interesting to see because creating software differs from running a law firm.

Bill Bice: Yeah, absolutely.

Sarah Glassmeyer: I guess so. It is mildly way too like creating a software product and running a legal tech company is different from running a law firm.

Bill Bice: But OK, good.

Sarah Glassmeyer: So, see how that works out, but.

Bill Bice: I’ve been impressed with what some of the innovation groups in law firms are doing, and a lot of that translates into technology and applications that connect the firm to their clients, making them very sticky with those comments.

Sarah Glassmeyer: Yeah. Oh yeah, yeah, for sure. Yeah.

Bill Bice: Well, Sarah, this has been a this has been a ton of fun. I enjoyed talking to you.

Sarah Glassmeyer: Ohh. On, well, thank you for having me.

Bill Bice: Thank you so much.

Sarah Glassmeyer: I’m always happy to talk to people. Yeah, enjoyed it, too.

Bill Bice: Great session. Thank you.

Sarah Glassmeyer: Thank you.


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