Jessica, Ken, and Jenny Hamilton (CLO of Exterro) share personal experiences, practical insights, and expert opinions on AI’s transformative potential and its challenges in legal.
Ken, Jessica, and Jenny Hamilton, CLO of Exterro, discuss AI’s potential in the legal profession. They dive into their favorite tools and how to apply them, as well as the importance of human oversight to ensure accuracy and compliance. Jenny also shares strategies for driving adoption within her team and making sure new tech meets the needs of her team.
Tune in to hear personal experiences, practical insights, and expert opinions on AI’s transformative potential and its challenges in legal.
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02:20 - About Ken
03:49 - About Jenny and Exterro
05:05 - What’s exciting, what’s scary about AI?
09:28 - Helpful tools
17:58 - Driving adoption
23:23 - How to be a new adopter
26:18 - Advice for entry level associates
37:39 - How AI disrupts the law firm model
46:25 - Keep or redline
49:46 - Final takeaways
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Find Ken Priore on LinkedIn
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[00:00:06] Jessica: Hello everybody. Welcome to another episode of In-House, the podcast for in-house legal professionals. I'm not gonna lie, last night was a rough night of sleep because my baby woke up, not once, not twice, but three times. But there are more than just a baby keeping me, keeping me up at night.
[00:00:30] I also am thinking a lot about what's gonna happen to the legal profession with the rise of AI. and as I play with so many different new AI and legal tech tools, it's one, making me more efficient and allowing me to spend a lot more time with my kids, which is a huge plus. But then I also think, wait a minute, it can do a lot of work that I used to do when I was a junior legal professional, and what's gonna happen to the legal profession?
[00:01:01] I. Well, to join me in this interesting conversation today, you may recognize his delightful NPR ready voice, uh, my co-host, dun dun, dun, is Ken Priore, A GC at DocuSign. Hi Ken.
[00:01:18] Ken: Hey Jessica, how are you?
[00:01:21] Jessica: I am highly caffeinated because if you just heard, I got up three times last night. I am reliving the newborn baby life. It's, am I crazy for doing this after a 10 year age gap?
[00:01:34] Ken: Yeah, we'll, we'll hold off on that. Well, uh, it's good. It's great to, to see. Well, things are, um, things are literally hot, hot, hot here down in Palm Springs. I was
[00:01:43] Jessica: Ooh, you're in palm.
[00:01:45] Ken: I think it's appropriate that we, that we have, uh, such a sort of hot, hot topic of conversation around sort of legal tech and, uh, the impact on the practice.
[00:01:54] Timely, um, program from my perspective.
[00:01:57] Jessica: Yeah, I know it's top of mind for so many, both experienced and inexperienced legal professionals and nervous law students as well. And we'll dive into that deeper later. Ken, for folks who are just tuning in for the first time of in-house, don't you quickly give a spiel of, you know, what you do here at DocuSign in your role.
[00:02:17] Ken: Yeah, no thanks. Thanks. Uh, Ken Priore, I lead the product and partner legal function here at DocuSign, and we are, uh, responsible for new product launches and integrations. And then our partner motion, and, you know, there's a, there's almost not an aspect of the work that we do that doesn't touch on, uh, I'd like to say emerging technologies.
[00:02:37] 'cause, uh, 'cause otherwise we'd be saying ai, every other word. Um, But really it is sort of this forward looking to say, um, what are the technologies that make sense today? What are the technologies that that are emerging that we, we want to work with as they start to drive impact to our customers?
[00:02:53] Jessica: Yes. Well, we have a guest today, Ken. Everybody listening, please meet our guest for the day. Jenny Hamilton, chief Legal Officer of Exterro. Hi, Jenny.
[00:03:07] Jenny: Hi, Jessica. Hi Ken.
[00:03:09] Ken: Good to see you.
[00:03:10] Jessica: It is so good to see you, Jenny. I think the last time I saw you was at a conference last fall and I was very pregnant.
[00:03:17] Jenny: Yes, we did talk about it. 'cause I have lots to give unsolicited advice to people who are pregnant.
[00:03:26] Jessica: Oh, good. Well, yes, right. You are a wonderful mother and I don't know how you do it all, and I'm learning from role models like you, but we, before we dive into just, we can probably talk for about 10 hours about motherhood and being a CLO at the same time, especially at a legal tech company. But speaking of legal tech companies, tell the audience a little bit about Exterro.
[00:03:49] Jenny: So Exterro offers software solutions to help manage data risk, and that could be eDiscovery, it could be cyber, it could be data forensics and data privacy, information governance, and I, learned about Exterro in 2010 when I was at a large public company looking for our first legal tech solution. So it's been a privilege to get to know the company from both perspectives, from the outside as a trusted vendor and then in-house as someone who's now responsible for a broad spectrum of data risk.
[00:04:29] Jessica: Yeah. Yeah. Interestingly, and I, couldn't think of a better guest to bring on today because on AI and just legal, tech and innovation.
[00:04:38] It just was noticed for me that you were very passionate about this topic, so I couldn't have thought of a more suitable guest for us today on, on the show. Well, let's just dive into it. So folks, I admitted that I really think about a lot, what is AI gonna take my job? Or what the heck are my kids gonna do in the future if AI can create such great output, great first drafts, et cetera. What are the things that worry you about AI or you just excited you're, you're bullish?
[00:05:09] Ken: I, you know, it, it's, it's a really good question. Um, I'll, I'll give you the hot take. I'm not worried about it taking my job, I'm worried, I would say, I do believe that it's going to fundamentally change almost every job. In the legal function, and it will cause some jobs to draw. Change more dramatically than others.
[00:05:29] And there will be work product or workflows that the technology will take over. But, but I do believe that the technology is imperfect at best, especially today. And there's always gonna be the opportunity for legal professionals to make sure that they have the human in the loop and are controlling that.
[00:05:45] I, I do think, uh, for folks who really want to stay in the same exact spot where they are. That's gonna be, it's gonna be really difficult because, um, because it, the technology is getting very good at acting like a lawyer. It's not a lawyer, but it's certainly gonna act like one.
[00:06:07] Jessica: Oh, interesting. How about you, Jenny? Does AI keep you up at night or does it excite you?
[00:06:12] Jenny: It definitely excites me. I think that AI is gonna remove a lot of fat. In any profession, in the legal profession historically, if you look at like law firm traditions of having associates who are way overqualified to do things like, you know, make photocopies. Now this is really gonna date me from my time in the law firm once over 20 years ago.
[00:06:36] But making photocopies, paralegals doing things, you know, filing with the clerks. Where everybody's over Qualified to ensure like the highest level of quality and a higher billing rate. And I think that this, the, the fact that AI can distill, summarize, format, communicate in a certain voice that will be more easily heard by the recipient, by the client, depending on their personality, their point of view, what they're looking for.
[00:07:08] I think that it's going to really flatten the hierarchy. I, I am more, more worried about the associates, the first and second year associates. The first time got turned loose on an AI product and I asked a few questions and it started generating output. It occurred to me that this is making practicing law fun again. Because I don't wanna do any of those things. I don't wanna format, I don't wanna, you know, summarize, I don't, you know, wanna spend time on the, you know, the form over the substance. And the second thing I thought was, oh my God, what's gonna happen to the first year, second year associates? Because if I feel this way, there's a lot of senior experienced lawyers, and I'll say also in the.
[00:08:00] You know, at law firms who that was never really like their thing, they didn't like become a senior partner in part to mentor younger associates and train them. That was more of like something they just had to do in order to enable a team to support the client. So, you know, if, if you. Can just get what you think you need to get out of AI and you don't need a first year to do the research and draft memos, then.
[00:08:30] Then what's gonna happen to that group coming outta law school? That's been my concern.
[00:08:35] Jessica: 1000%. I, I think to connect the dots for what both you just said, I too am bullish about ai. I too, Jenny, do not like to do that work anymore. The grunt work, the summarization, the first drafts, but we are very senior in our careers. But can I also do agree with you as well that we are in a profession where a hundred percent accuracy and being right matters.
[00:09:01] And so human in the loop will may be sustained for quite a while, and I'm not sure if will we will ever be out of the loop and AI can do our jobs a hundred percent, uh, because we don't wanna commit malpractice or give the wrong advice just in case AI hallucinates. But in terms of tools, it sounds like both of you are AI tinkers and have, have extensive experience with legal technology.
[00:09:28] What are some of the tools that you're using right now that have been really helping you be more efficient and do your job better?
[00:09:37] Ken: Yeah, I, uh, for those who aren't on video, I sort of smirked a little bit when Jessica said a, uh, tinkerer. I, I, I've probably at this point, uh, have a full workshop.
[00:09:47] Jessica: That's all right. Ken. I thought it was just your face. I
[00:09:49] Ken: yeah. Yeah, yeah, yeah. But like any, like anything else. So I'd say my, my current, my current favor, and this is, uh, from a lot of folks, is Notebook, LLM.
[00:09:57] What I like about it is it creates a known universe so that you can upload documents and have conversation just with those documents. So it removes, uh, the hallucination aspect, uh, or the, the try not to ize the, the sort of, the guessing that the, that the technology's trying to do. Claude tends to be my favorite from, uh, I just want to get to a writing style and I want something to communicate with senior leadership because, uh, again, I feel it, it, it gets to the points and gets to the fact. Um, and then a lot of, from my social media writing, I do a lot of research, uh, using chat GPT to sometimes go out and say like, what are the latest articles at Forbes or the more mainstream media? And then try to tie that together to a persona that, uh, that I've built around sort of legal technology, emerging technology. And I think Chat GpT can be really good at, uh, adding persona to source materials. So those are sort of the three tinkers that I, that I've been doing lately.
[00:10:53] Jenny: I would add to what Ken said, that, you know, using a chat GPT like product for legal work has been surprisingly delightful. And how it can you draft up a bulletin for executives on. You know, let's say all of these changes that have been happening and some of the laws, um, the Corporate Transparency Act, for example, that rollercoaster, if anybody wrote that and trying to keep them apprised but not annoyed, I.
[00:11:23] Um, we started playing around with a tool I heard a lot about called GCAI last spring and pilot tested it and we actually were the Guinea pig of our own AI policies and I. Our governance structure and putting that through the process, uh, and vetting it with all the other groups. And then we bought licenses in the fall, so we've been using it for a while.
[00:11:50] And for a small law department just to help scale, it's been really phenomenal and, and a lot of different applications.
[00:11:58] Jessica: GC AI and many others are a great example of a generative AI tool that has. Legal focused. Has there, and other than GCI, is there, has there been any other legal tech tools? It doesn't have to be AI powered that have really given your legal department value, Jenny, like in contracting, so I think AI assistance, but contracting or litigation or et cetera, compliance e-billing.
[00:12:27] Jenny: Yeah, contracting for sure. For sure, because we are a smaller company, but our customers are very large, very sophisticated. We have customers for a long time and we've also acquired a series of companies in a short period. And so it just trying to keep up with managing all of the contracts and then the reporting, the redlining.
[00:12:53] All the things that you need in order to, to manage a large volume. It's absolutely critical. I've, I've been looking at contract tools since, let's see, probably about, uh, 2019 as part of a, my. My large company experience, they put me in charge of a technology initiative the last year I was there to try to identify how you can scale as a law department and improve all the things, you know, collaboration, efficiency, both with internal clients.
[00:13:30] And also within the law department, and so I went on this journey because I had done this before with eDiscovery and litigation and other like typical legal ops tools and eDiscovery was very transformative and the. Cost savings you could show, and the business acumen you could show by utilizing those tools, which by the way, were some of the earliest AI tools that the legal industry has encountered.
[00:13:57] Like it's a precursor to the generative AI tools that I just knew that that. The thing, when I did the research of all the different possibilities and all the different types of work in a law function to meet that criteria of what the company wanted to get out of the initiative, it was contracting.
[00:14:14] Contracting was the next wave that had the potential for as much transformation, um, in the, in a business sense as eDiscovery had for litigation. And so I started looking, I said 2019, even though that wasn't really had anything to do with my, my previous role at Deere at these tools, and I've watched 'em very closely because I am just genuinely interested and curious about the evolution inside each different type of legal tech, what they're doing and where it's headed. It hasn't disappointed. You know, now you look at using generative AI embedding in these tools to redline agreements to do the first and second pass. I mean that's, that's huge to automate playbooks in a way that we've envisioned and wanted, but it hasn't actually come to life yet.
[00:15:05] There's been a lag as there isn't any group to watch the tech catch up, you know, to what's really going to help. You know, in my case now, with a much smaller organization, law department than I had before, again, like scale for hypergrowth.
[00:15:21] Jessica: Yeah. Uh, I am really glad you brought up e-discovery, you know, because I think that is one of the tools that has been very transformative to the legal profession. Ken, do you, and you, you smirked or nodded your head in violent agreement with Jenny, all the things she's just said. Ken, how have you seen tools like eDiscovery really transform the legal profession and do you see parallels with AI today?
[00:15:46] Ken: I, I do and, and I think where the smirking is, I, when I was a younger lawyer, I remember, uh, being in a document discovery and you know, it was cutting edge at that point to have access to those source emails in a digital system. So you could just review those emails rather than having to go into Bates stamped documents.
[00:16:05] For those folks who don't know what Bates stamps are as chat GPT, it'll tell you. Um, and I think the theme that that comes to mind is much as eDiscovery still exists. And as much as the tools have created much greater efficiency by going from hard copy to digitization to being able to search, um, I think that is the parallel that we're going to see in, in various aspects of the legal practice and contracting is probably the next one sort of breached by that or, or, or have that application.
[00:16:34] But, but it's not a perfect fit. I think even in e discovery, there still was a lawyer. Now looking digitally at the email rather than looking at the piece of paper and then even in the, the tools that would summarize what they thought was that we think these are the relevant emails. Using that as an example, need discovery.
[00:16:49] The lawyers, a lawyer or a legal professional still had to sort of look at this and sometimes spider out and go, yeah, but you missed these over here. I think that's the parallel, parallel for contracting, uh, AI assisted contracting review, um, is going to be like, where is, I'll go back to the human in the loop.
[00:17:05] It's like, where do I make sure my legal professional could be associated? It could be a, a mid-tier attorney. Where are they coming in to say, look at what the tool has done and say like, okay, close or great, right? Those could be, or no, not even close, and, and, and nudge it in the right direction.
[00:17:23] Jessica: Nice. Nice. So Jenny, I really loved your story about your law department's adoption of a legal, a assistant tool that is legal focused. One of the challenges that I hear from various general counsels and folks in the legal community is, uh, lack of adoption. Like a lot of folks, uh, buy these great tools or they're told by their CEO, you need to find a way to drive more efficiency in your legal team.
[00:17:51] Explore AI tools, great, but then no one, you buy something and no one uses it. What have been some of the strategies or tactics that you've employed that have been successful in driving that adoption, uh, within your legal team?
[00:18:08] Jenny: I'm gonna take you way back for many years. Because this is not a unique topic for ai. I think there's a potential for legal teams to adopt AI faster than other types of legal technology. Out of curiosity or, you know, that was the gift of chat GPT where people just like tested it out and you start to see the possibilities once you get your hands on it.
[00:18:33] But it, it is definitely a more fun, sexy version of legal tech as we know it. And I think this has been a curiosity of mine that goes back to 20. Well, 2006 when I was hired to figure out the eDiscovery thing. And you know, if you're in that world, you know that we are dogmatic about people, process and technology.
[00:18:57] And you look at your process. Is it the process issue? Is it a lack of tech? Is it a people issue? And all these things keep coming back to that triangle. And so when we looked at our gaps and realized. That, yeah, there was a technology issue that, you know, trying to preserve records and issue legal whole notices at scale and track them is just really impossible to do it well.
[00:19:21] And defensively in a spreadsheet or with less sophisticated technology, it's tech that, you know, you create yourself. It's not purpose built. I started to see this play out in a large setting, in a larger organization where you are always going to have you look at the research, you're gonna have this group of bleeding edge adopters and early adopters, so the innovators and the early adopters.
[00:19:47] And you're gonna have this group in the middle who's like, just. Trying to see like which direction this is gonna go. They're not necessarily jumping on the bandwagon. They're a reticent. There's a lot of inertia. That's normal human bias, right? That's our first thing is like I am doing something that works for me now, even though maybe it's not as efficient.
[00:20:08] I have a lot of fear about moving to something that might get me some efficiency, but break my. Break my process and then you've got the people who are just never gonna come along and are rather retired than deal with it. And what I found to be successful is to, one, take the people who really got it and wanted to be part of the transformation and really kind of segment them away from the rest of the population so that we could have, you know, think tanks and participate in thought leadership out in the industry and get outside the organization's bubble and inertia, natural inertia. And they also realize that the, the people that you need to market to, to spend your time with, it's that early group. The innovators and the early adopters because you're, the more you try to convince people, the more resistant they become generally.
[00:21:08] And then also you oversell the tech. So you got those people who get in there who weren't really. Wanting to make that change anyway. And all of a sudden, you know, they're the flying, they're constantly bombarding the team. Usually not like the largest team in the world with all of these, like, you know, bunny trails is what I call 'em.
[00:21:29] And yeah, they're important. You gotta address them, but it really, you know, could. Kind of, you know, capsize all the good work that you can be doing and the time and energy you need to spend on that. So, um, we did things, we tried to make it fun. We tried to make it engaging. We tried to elevate the people who were adopting the tech and trying things.
[00:21:50] Even though it wasn't perfect, we gave out awards. Every year we had eDiscovery awards. Um, when, uh, ERO actually created eDiscovery Day, we started doing meme meme contests. I did it recently. We did it at ai. Um, you know, lawyer joke contest, my company to get people more familiar with the guardrails around using AI and, and give them something fun to do.
[00:22:17] Make fun of lawyers, people like to do that. So those are some of the things that have worked well.
[00:22:21] Ken: You know, it, it's where my mind went to was also, um, and Jenny, I'd be curious to get your feedback on this, was this idea here of making sure you're not just applying tech for tech's sake. I think sometimes there are these moments where you look at a lot of emerging TE technologies, um, and you say, well, that, that seems like that's a G whiz, or that seems like that's gonna be really great. And then maybe that teams sometimes get disconnected from what is the problem that we're trying to solve or the scale we're trying to create. And sometimes that can get lost in that implementation stage because you start to be really focused on the the G whiz factor, and then you kind of, disconnect from the, but what are we trying to land with this? Because I think for me that's really important inside an organization is you're asking for folks precious resources and time. Time being probably the most precious. For, I always try to say like, like, make sure there's something on the other side of this and, and make sure there's a path to it.
[00:23:15] Like it might not be the, the results might not be immediate with the first implementation, but it'd be really great to have those results as a fast follow, right? Because sometimes a new technology does create a little bit, can create a little bit of pressure and a little bit of slowness, but it's gotta have an uptick fairly quickly. Does that make sense?
[00:23:33] Jenny: Absolutely. I was, I was lucky enough early stage to get a business analyst when we were just starting out and I was just doing this, it was really tinkering. In my part-time. I had a, a caseload and I had a responsibility as an in-house litigator. That, uh, was my day job, but they gave me this business analyst and they said, you know, you can use like 20% of his time.
[00:23:58] And he came from an IT audit background. I. That was absolutely one of the best, you know, partnerships that I've had with these IT auditors, because he really could see across the org what groups got it right with selecting the right technology, having the right expectations, so the process. To vet, get them in and even get it up and running.
[00:24:24] And one of the things he did early on is he forced a group of people who did not commonly buy technology, and I'm sure when the last time they had bought technology was to sit down and really be clear about what the requirements were versus the wishlist, the things that the wiz bang. Features. And so, and the way he, the way he forced that question about the requirements to make sure that the tech did what we actually needed it to do when we get distracted by the fund stuff is he took us through this process that I think a lot of IT departments are, are familiar with and not a lot of legal departments called the user stories.
[00:25:06] And it was so painful. I mean, he had to order lunch and lock us in a conference room for two hours where he, like dogmatically took us through like step by step, what do you need to do first? What do you need to do second? And this is like not the most exciting thing in the world is like issuing a legal hold compared to, you know, all the other things we've talked about.
[00:25:28] And, and when we got through it, it was. Worth the investment of time. There was a lot of clarity around that. No one ever forgot it. And they often participate in other RFPs because they really understand the power of that structure and separating the fund factor from what, what's going to get the job done.
[00:25:48] That helped with everything. Selection, implementation, you know, adoption, the whole
[00:25:55] .
[00:25:55] Jenny: part 2
[00:25:56] Jessica: Really great point, Jenny. Actually, let's, let's switch gears a little bit. Uh, I would love for us to address the very big elephant in the legal industry room, which is AI is gonna really change the workforce and really have a huge impact on entry level and junior legal professionals.
[00:26:17] Any thoughts there, Jenny, advice you would give to a law student or entry level junior associate on what skills they should, uh, acquire during the era of ai? I'll call it the AI era.
[00:26:31] Jenny: This is really. Clear to me in using AI tools for legal work, how important it is that they take their analytical skills that they're developing in law school and they broaden it way out. So it's gonna be analytical skills plus relationship skills. And what I mean by the an analytical skills plus is that.
[00:26:55] You know, we come outta school and we go into our first job trained to analyze court opinions, contracts. And, and apply that, and that's still going to be required. Still gonna need to know how to do that. You're gonna need to know how to research. You're gonna need to know how to apply that to AI so that you are driving the ai 'cause not every law firm partner is gonna jump on the AI bandwagon.
[00:27:20] So you could be very instrumental there and figuring out how to use it to, to be that go-to associate. Or go to in-house lawyer for your, for your partner or your client, but even more so in the sense of analyzing the context around the matter. So not just the law, but the business needs and the business strategy.
[00:27:50] I think that if you're just coming out of school right now, I don't know what the law schools are doing. To train you or to open you up to these things. I know that they're having more classes where they're getting students in touch with people in these roles. Like, I'm going to do one in San Francisco on the GC journey for a small company gc.
[00:28:13] And I've been doing more of that work this year, but, but in terms of what the law schools ever do to prep you for the real life experience, that that could create a real gap. Um, of understanding where people aren't getting a good jumpstart on their, on their first job.
[00:28:32] Jessica: Ken, do you have any thoughts? Your LinkedIn profile about the impact of AI in the profession and what it can do and what it can't do.
[00:28:43] Ken: Yeah. I really like Jenny's point of, you know, it starts from the Loft school experience is, is crafting the analytical mind and that's not going to go away, right? There's still going to be this foundational training. I don't know how everyone else experienced in law school, but it was a really, um, impactful time where I, I, I learned how to think differently. I learned how to break problems down into discrete patterns and, and, and discrete parts, and then reconstruct them in a way that answered a question or a, or, or, created more questions. And so that basis from law school is gonna be augmented by this technology.
[00:29:17] But, but I doubt those fundamental elements will change in the near term. The skills of relationships or, or how I sometimes thinking about it is connecting the dots. Um, especially for folks who are in-house, is, is a skill that the tools purport to be able to connect disparage data sources and bring all this information together, but that. Analytical reasoning element that sits on top and can really identify what's important.
[00:29:45] Once not the, the tools today are still predictive math models and, and those predictions are often, off when it comes to their strategic elements. So I still think for in-house counsel they're gonna have this opportunity, especially folk, even folks who are early in their roles, um, to be those connectors for, to really point out what really matters and the tools themselves. Are just gonna become these enablers to take in more information, sift more information.
[00:30:11] Jessica: Ken, I really love the word that you just used, connector. Uh, actually when you said that a memory went back when my Microsoft years popped up that. The client, my, my Microsoft Outlook email clients weren't valuing me because I had legal knowledge, but I helped them connect the dots throughout the organization.
[00:30:31] But rather than just think about that advice in a silo, what I would do at Microsoft is think about, Hey, let me connect with our Google partnership team because they're a partner as well.
[00:30:43] Let me talk to our sales organization. Google's also a customer and make sure that our approach gets their buy-in as well. 'cause we don't wanna do or take an approach that would burn that customer and partner relationship in this giant organization where we can get so lost and siloed. And AI is not that connector.
[00:31:02] Is that, is that's what I kind of felt Ken. And that memory was triggered when I thought the value I bring as an attorney, uh, beyond what AI can do. Jenny, you're nodding like, yeah, we have that. We have that power of that full contextual, holistic perspective that a machine may not have.
[00:31:21] Jenny: Yeah, and just that, that really meaty source of information. And to do that, I'm sure that you brought your relationship skills to bear, to like reach out and connect and, you know, you're taking people's time. And to do that, you know, that's, that's part of the skill that I wish I had understood, and not the skill, but the investment of time.
[00:31:46] I wish I had understood when I started in-house is that you're probably gonna be there for some period of time. You're gonna be there long enough for issues to cycle and recycle and people will cycle and recycle. But it, but there's such an important store of knowledge and ability, um, to get things done.
[00:32:07] And having those relationships, it's gonna be more important than what the AI tells you about. You know
[00:32:16] Jessica: Yeah. Yeah, that's,
[00:32:18] Jenny: the legal issue?
[00:32:19] Jessica: It's the relationships, right?And I think that, uh, is irreplaceable. I read an article this year that there is a record breaking amount of law school applications, which,
[00:32:29] yes. You, you read that too, Jenny. That is really interesting. What do you think is driving that and are you worried in the age of AI that there's gonna be too much law school, recent law school grads versus supply of, of, of jobs for recent law school grads? I worry about that to be very candid.
[00:32:51] Jenny: I think what I read, and this makes sense to me in times of uncertainty, we're experiencing now at this scale that people tend to apply to law school. They feel like that gives them some control and power to do something impactful. They sense there's a, a lot of injustice then that's their, that's their source.
[00:33:12] And so it makes sense to me. And I think when I was going to law school where it was the Alex McBeal days, just to give you. And there's always a show that also precipitates a rise in law school applications. Right? Was it LA Law? The generation before me, Alec McBeal suits. I think that is still pretty popular.
[00:33:34] And so maybe it's a convergence of factors, but I do think that the uncertainty, people are thinking that the law is a profession that gives you a lot of, um, options and it, but to your point, Jessica. In some ways that might not be true right now because traditional legal work is a lot of wordsmithing and a lot of that can be done much more efficiently.
[00:33:55] With ai, you don't need as many bodies doing the kind of entry level type of work. So it's back to your point about the Ken's point about strategic thinking, developing the strategic thinking skills, that bigger context. Um, and, and so I don't know, I. I don't know if the jobs will be there or not, and the way that people are thinking that they'll be there.
[00:34:20] Ken: First of all, Jenny, you, you, you made me smile because my husband thinks, uh, that Harvey Specter from suits is what my job. Is like, and I always have to kind of tell him that it's not. I wish it was that exciting. I, I, I agree completely that, I don't know what the roles traditionally have been.
[00:34:38] What, uh, what new grads can expect outta law school are going to going to be the same. I'm optimistic because I think there has the potential for lots of hybrid new roles that that simply don't exist today or that the technology will require. And even in-house, we are playing with the understanding of what future roles will look like.
[00:35:00] And you've already seen in the legal tech space roles such as legal engineer, prompt engineering, legal tech specialists coming up both within the legal tech, but even within traditional law firms where they're looking to say, we need to bring in a new type of role now. Is it gonna be the scores and numbers that it's been in the past?
[00:35:18] And will those be available to the same degree for new, uh, entrance, uh, out of law school? Dunno yet.
[00:35:25] Jenny: I agree though I, I am gonna chain this out for a second because the role has changed. There are some hybrid business legal roles that probably didn't exist when I started law school. I think that's gonna increase the chief of staff position. Did anybody but David Cowen predict that that was gonna be a big thing. To the gc, the chief of staff, which I now think is one of the most critical new functions you can have in, in-house department. And we have to also look at like Europe and other, other regions of the world and how they use lawyers, law school, there is much more of an entry level degree than it is here.
[00:36:03] People go get law school, like they get a poli sci degree and they don't all practice. But that doesn't mean it's not valuable. And I guess as an age, just to chain again off of what you're saying, Ken, it's so complex and regulated. Marketing is not regulated. Like everything is so regulated right now on a global scale.
[00:36:24] Jessica: Whether it be sales marketing, any other function, your law degree can be a differentiator where when it's not a differentiator in the legal profession 'cause everyone has a law degree as a lawyer. So it's very interesting. last but not least is I want us to talk about is the rise of all of these legal tech companies.
[00:36:44] I think I read somewhere, Ken, I don't, I don't know if you have the number in your head, but I think it was billions of dollars have been invested by VCs into various AI legal tech companies, which just as a signal as VCs are composed of analysts, that they have a thesis.
[00:37:02] That the this, this, our industry will be materially disrupted in the medium or long term by ai. They have this thesis why they're putting billions of dollars into it. So what are your thoughts, Jenny, as to, with this rise of legal tech companies, how do you finally see the industry being disrupted? And actually what I'm thinking about more is not in-house departments where we're already incentivized to adopt new, uh, new tools.
[00:37:25] But yes, we have challenges with adoption and implementation. Law firms, they're so slow to actually adopt new technology. They can do it. And you've seen it with eDiscovery in your career, but it takes time. How do you see AI disrupting the law firm model?
[00:37:44] Jenny: Well, first I'm gonna say is it a material disruption or is it a material fit?
[00:37:50] Jessica: Huh.
[00:37:51] Jenny: It's a material fit with a legal profession. You know, it's words, it's prose. I'm gonna draw on Lias Needies fabulous presentations about, you know, the lawyers love prose and, and we use it.
[00:38:05] That's our first love and that's. A lot of what AI can, can offer us. And so I think because it's such a material fit and I also, I'm gonna, I'm going to get to your issue about the law firms, but I'm gonna get there by way of in-house. 'cause I 'cause my big thing and I've been in a lot of thought leadership.
[00:38:26] Organizations and sometimes they, they seem to struggle about whether to cater to in-house or whether to cater to law firms. And, and I, I've had some pretty frank conversations with some of those leaders when I see them leaning too hard one way or the other. And, and I remind them, you know, you gotta get back some balance because it is an ecosystem, right?
[00:38:46] But the reality is that law firms, a lot of the really successful ones are really good at working and championing the right in-house lawyer. They can get a significant source of money from the right in-house legal champion. And so I see that's where law firms are traditionally slow to change, but that's as long as their model is not being upset and they have to spend too much time chasing around revenue and it's too disparate and they can't cross sell and upsell within corporations, then.
[00:39:21] Then they will change, believe me, very quickly. Um, and, and I think that AI is gonna play a role in how they can cross-sell and upsell, but it's still gonna be pivoting around that relationship with the right champion at the client, um, being their go-to and feeding them work that they can then disperse in the law firm.
[00:39:43] I think that, um. There's conversations in law firms right now, are they organized in a way that they can make sure that the right law firm experts are in the right conversations with those clients so that like Employment council isn't writing an AI policy that really should be written by the data risk, um, team at the firm, but incorporating the employment lawyer's expertise.
[00:40:12] So I, I think, I think this is a, the right conversation. How are they organized and to, to, to support the client in the most integrated, holistic way. Um, and can they, can they work quickly to provide that value and work together collaboratively? Or are they gonna be fighting about who's the originate originating attorney?
[00:40:36] I had a situation one time, I was just talking about this weekend. I wanted this one particular lawyer to be segund from the law firm, but the originating attorney was kind of blocking my ability to get her to cover my leave. Now, we had the ability to feed significant amounts of work from numerous groups in the Global Law Services John Deere, and I just could not believe that he didn't understand that.
[00:41:07] That this like blocking me from getting what I needed was going to have a big downstream effect on the firm overall and then, and then on him, even though he was looking at it from a very small perspective. So I mean, this can happen with or without ai, but maybe AI will exacerbate this or accelerate it.
[00:41:27] Ken: And I think maybe, maybe one point Jenny. I think, I think, uh, I think that all makes a lot of sense, in the legal tech space we're seeing sort of this interesting con convergence where, you know, look at Harvey, which is one of the leading tech providers in Lexi and Nexus, and they're coming closer to a traditional legal tech company that's very embedded in the law firm experience. You also have law firms who have innovation teams who are really looking at this technology. And I think what really resonated with me, Jenny, and what you said was the traditional model, the sort of, the leverage that happens in the sort of tiered partner concept context, um, is going to change because smart in-house counsel are going to say, why did an associate spend X hours and X time reviewing this when we know you should have access or do have access to this technology that can take that away? And, and I think that perhaps more than anything else. Is causing a disruption, um, in how, especially firms at scale that work with in-house council, um, are going to have to rethink their billing model.
[00:42:31] But the other side of that is it could be this tremendous opportunity for smaller boutique council to be able to leverage. Their particular narrow scope, but also be able to create output that normally you needed the, the leveraged associates to be able to get there at a cost competitive, which then feeds into lower prices from the larger firms.
[00:42:51] So I think it's fascinating and I do think that the legal tech that's being powered by this emerging technology, um, is, could just be that sort of, that marble that rolls down and really starts a cascade of change.
[00:43:04] Jessica: Yes, Ken and Jenny spot on. What I'm seeing slowly happen and gradually, and I think it's gonna cascade very soon over the next, my prediction over the next two years, is, clients demanding that, hey, I'm not paying a fresh OUTTA law school junior associate 500 plus per hour to basically train them. They're gonna be really inefficient and really manual, all their work.
[00:43:27] So I expect you to use AI to do this. And then, hey, partner, junior, partner with experience, double check the AI output that isn't gonna really disrupt the the model, which also means though, what are the junior associates gonna do? That's how, that's how I learned. And, and for, and you and Ken learned to be a lawyer.
[00:43:44] Law firms are gonna have to learn pretty quickly if they're gonna do that work, or they just become specialist, uh, that they can demand the a thousand dollars per hour what they are demanding now, I cannot believe that is what they, they charge now per hour it is. Or are they going to then create a role of if junior associates are gonna become these tech ex legal, tech experts and give the first draft and a quick skim of the first draft to check the output. Who's gonna train the junior associate to have that judgment and experience? How do we accelerate that? 'cause you know, frankly it took many years for me personally to get there.
[00:44:24] do you think law firms are gonna become tech companies or tech companies become law firms?
[00:44:29] Ken: I think it's going to be this general blending that we're seeing because of the technology where legal work is going to be existing more at the edge than it has in the past. And I think because of that, law firms, just as they've had, they've had technologists in them for decades, right?
[00:44:43] Like the folks who are running their servers and sort of the, the way that they were traditionally leveraging technology. So in some ways. This feels like the next evolution. I think the difference is, is that they, um, they're looking at this emerging technology and say, well, rather than relying on the Harvey's and the, and the Thomson Reuters actually, can we do end rounds or, and runs around this and can we actually create a proprietary in-house knowledge bank of our own creation, that actually gives us that value proposition that we know that no other firm can go to a legal tech company and, and create. And so it gives them something tr truly unique that perhaps then will support the higher prices that they want to charge.
[00:45:28] Jenny: I am gonna say, I am doubtful that they can achieve this. There can be some law firms, but they're gonna have to be total badass and bold to, to overcome the inertia of the partnership model.
[00:45:41] And just, again, getting them to invest, getting 'em on the same page, getting them out of the risk mindset is, it's very difficult for these really large firms. I'm curious to see which ones have the ability to, to overcome that inertia.
[00:45:56] Jessica: Well, my, my bet is this race of AI adoption and evolving billing billing models is on these legal tech companies that are also law firms, because they're gonna be able to create a financial model that is competitive, whereas these big law firms are still run by very senior partners who make a lot of money with the status quo.
[00:46:19] So how do you incentivize the folks who are making a lot of money with the status quo model to change? They have no incentive to.
[00:46:25] Alright. For the final part of the show, we like to have a little fun here on In-House and the past episodes. We've done this segment called Redlines because I do love contracts and nerd out about contracts. But because our conversation had this really fun discussion point about how TV shows have inspired folks to join and apply to law schools, we're gonna call the next segment.
[00:46:50] Hire or fire. All right, Jenny, I'm gonna kick it off with you and I want you to go with your gut hiring or firing, draw your people manager instinct and let me know if you would hire fire this fictional legal character. All right? Because we mentioned his name on the show, would you hire or fire Harvey Specter?
[00:47:14] Jenny: I, I, I would hire him because he pushes boundaries.
[00:47:20] Jessica: Yes. Yes.
[00:47:22] Jenny: But I'd have to have very clear boundaries around, around the, the values that, that he's gonna have to support in pushing other boundaries. But I think we talked about the inertia of, you know, the success that we've had in the legal community and it's gonna take, it is gonna take boundary pushers to overcome that.
[00:47:45] Jessica: Okay, so someone like Harvey could maybe be your ally to help influence senior partners to adopt new billing models or, or whatnot. I think Harvey is very though self-interested, so he might even be like, but what's in it from me though? From my take from him? Ken, what do you, what would you hire or fire Harvey?
[00:48:05] Ken: Oh, that's such a tough one. I'm gonna have to go with my first instinct was fire, because you know what? He's too, he's too good looking and no one would get anything done in the office. But, but also as someone I, listen, I just spent, uh, I spent, spent a couple weeks, weeks with the, uh, IAPP, the Interna International Association of Privacy Professionals help helping draft the AI and legal ethics section. And, uh, Harvey's not someone where I'd say, who puts legal ethics on the front burner.
[00:48:34] So,
[00:48:35] Jessica: No, no, he is definitely a, yeah. Ethics is below priority in terms of results. All right, well, Jenny, it was so fun to have this conversation with you. Thank you for joining. Ken and I, um, for folks who are listening, who would love to connect with you, where are some great places to find you or events to meet? See you at.
[00:48:57] Jenny: We have our, actually we have our big customer event coming up in September and Denver, and some great topics including ai. And also I'm gonna be teaching a class in San Francisco coming up in the, uh, third week of August for a small company gc like what's the day in the life? So if you're around San Francisco area at the end of the third week, I would, uh, love to connect.
[00:49:30] Jessica: right, folks. You heard it. Follow or connect with Jenny on LinkedIn and see if you can get an invite to the Exterro customer event or that GC training session. Well, thanks Jenny for, for joining us. Great to have you.
[00:49:43] Jenny: Thanks.
[00:49:45] Ken: Bye, Jenny.
[00:49:46] music transition
[00:49:46] Jessica: Oh, Ken, that was so fun to talk about the future of the legal profession with, with Jenny of I also thought it was very interesting that her instinct was to hire Harvey Specter, and yours was to not hire Harvey. Maybe she didn't wanna just admit that he was so attractive that she, but she had another reason to hire him.
[00:50:07] But the reality was he would also inspire her to come to the office and do her best work.
[00:50:11] Ken: yeah. Yeah, that's a good take.
[00:50:14] Jessica: Well, what are some of the takeaways, you know, or a takeaway you learned today, Ken, from this discussion?
[00:50:20] Ken: You know, for, for, for me, it was, uh, I, I, I think sort of change and disruption and uncertainty were sort of some themes, uh, that came up during the discussion. And, you know, my, my biggest maybe, uh. Idea here is to sort of lean into what is happening because the, the technology is continuing to evolve, is going to impact, uh, whether you're in-house or in a law firm, whether you're in the middle, beginning or, or, you know, in a, in a, uh, towards the end of your career.
[00:50:52] This technology is here and, and I think much like, uh, often when new technology comes onto the scene, um, the, it, the adoption won't be quite as fast as folks think, but then also will come in surprising ways. And I think the best advice for, for anyone, uh, particularly in house, who is to really. Is to really look at this technology and say, alright, where can I find the value today that's meaningful for my work?
[00:51:15] And where can I get curious around, uh, what's coming in the future? And, and hopefully a little bit of that uncertainty will be, uh, be understood.
[00:51:24] Jessica: Yeah. My takeaway from this discussion was the evolution of the practice will be that AI will force both law firm attorneys and in-house attorneys to be more focused on results and impact versus activity. So much of whether it be the billing model, again, you're incentivized to work as inefficiently as possible.
[00:51:48] Activity. Activity. Uh, in-house, a lot of our metrics that we report on is how much documents or contracts we reviewed, how fast we or slow we reviewed them. That's activity I really love. I mean, what excites me? 'cause I'm, I wasn't the gal that loved sitting around reading case law and, and analyzing the holding of the case law is to allow us to focus on the impact and results.
[00:52:12] So I'm excited for the future. I am bullish on AI and I think all three of us were as well. All right folks, thank you for joining us. And Ken, always a pleasure to have you on the show. Thank you for being my fabulous co-host.
[00:52:26] Ken: Thank you Jessica. Really great conversation. Uh, great to chat with you.