Sandy MacDonnell, Head of Legal Ops at DocuSign, and Krysta Johnson, Senior Legal Ops Evangelist at DocuSign, highlight the importance of metrics, data, and AI in transforming the legal profession from cost center to strategic, growth-oriented role.
Sandy MacDonnell, Head of Legal Ops at DocuSign, and Krysta Johnson, Senior Legal Ops Evangelist at DocuSign, highlight the importance of metrics, data, and AI in transforming the legal profession from cost center to strategic, growth-oriented role. Sandy and Krysta both stress the need for adaptability at a time of rapid tech changes, as well as best practices for implementing new legal technologies.
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SANDY: I think this is true about the rest of the industry as well, is that, you know, it's really seeing legal and putting legal in that more strategic kind of role and being that partner to the business, and being that department of yes and like, how does the legal team help our sales team sell more, not just tell them how they can't do things. So I think that's been a really fun evolution of, of the legal operations function. Um, and I'm just excited because I think it's opening up a lot of career opportunities for folks who've been in these types of roles. It's much more creative, much more kind of fun and, like forward looking, I guess I would say.
SANDY: I think if there's anything I've learned in legal operations, it's like things change all the time, right? You had like one thing you were running towards and the next day the GCs like, Hey, actually I wanna go chase this other thing. Being flexible, being, uh, adaptable, continuously learning, right?
Like in this world today that we're living in with ai, we're seeing, you know, like the legal landscape always changed quickly when I think about technology. But today it's changing so much more rapidly. So if you have some, you know, if you're hiring someone to do legal operations for you, that person better be super excited about change, about, you know, learning the new technologies, what's coming down the line, how are we gonna reshape our department to, to adopt those new technologies. Just so essential.
KRYSTA: We operate currently in most of the corporate world, in these very, somewhat isolated silos. Yes, there's some cross-functional collaboration, but I think the idea of these silos is what really kind of stifles a lot of change that could move a lot faster.
And I think we're going to see more centralized operations functions where there might be a, like dedicated people that support legal operations, but they will sit in a more dedicated operations function under say, the COO versus sitting within the legal team. As you said, Sandy, like there is a lot of democratizing of technology and like ability to educate yourself.
And I think just like we've seen changes in the past 20 years in the legal, like the legal field itself, we, we'll see that change in operations as well where you, you don't have people doing a lot of the more menial work.
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More about Docusign
[00:00:00] Jessica: Hello everyone. Welcome to another episode of In-House, the podcast for in-house legal professionals. I am really excited to record another episode after a several month hiatus because as many of you know, if you follow me on LinkedIn, I did this thing called "Have a Baby" After 12, have a having 12-year-old and 10-year-old.
[00:00:26] I'm like, you know what? What would make my life easier? That's already really complicated. I don't know, having a newborn. So, uh, I did that crazy thing. But she is a wonderful bundle of joy and as expected, her hair is about six inches high at this point. All my babies have pineapple troll hair. You cannot see this folks who are listening, but my guests are smiling.
[00:00:48] My co-host is smiling and they're clapping their hands. As you probably know, my name is Jessica Nguyen, I am your host and Deputy General Counsel of DocuSign Intelligent Agreement Management. Today is a really fun episode because I have known our guest for a while now and one guest I've known for over eight years.
[00:01:10] I know. Why Is she still my friend? I do not know. It's also really exciting because over $3 billion have been invested into legal technology over the past two years. Yes, there is a lot of hype and excitement around legal tech and AI really disrupting the legal profession. So what better topic to talk about today, folks, than to talk about legal operations.
[00:01:40] And joining me as my co-host today is the wonderful Ken Priori. Hi Ken. How are you doing?
[00:01:48] Ken: I am good. Jessica's very nice to have you back.
[00:01:51] Jessica: Oh, good. It's good to be back, and talk to people who do more than babble and, and, and spit on you. So it's really nice.
[00:02:00] Ken: I'll, I'll, I'll try my best to meet that bar.
[00:02:01] Jessica: Okay. Okay. And you know, little thing about, you know, I know I follow you on LinkedIn and folks, if you don't follow Ken, you should follow him. He has so much great content. He posts on LinkedIn about the evolution of legal profession and artificial intelligence.
[00:02:18] Ken: Yeah, no, I'm re you know, I'm really excited for this episode and to, to really do this deep dive on what the future is going to be for, uh, legal operations and legal tech. I think it's a very exciting moment.
[00:02:30] Jessica: Absolutely. And what better guests we have today, Ken, as two really wonderful women who are really experienced when it comes to legal technology, given their roles in legal operations. Our guests are Krysta Johnson, senior legal ops evangelist here at DocuSign and Sandy MacDonnell, head of legal ops here at DocuSign.
[00:02:52] Uh, let to kick it off, Krysta I, I'll, I'll pick on you first since, uh, we've known each other for a very long time. You know, tell us a bit about your background and history in legal operations.
[00:03:03] Krysta: Yeah, absolutely. Thanks for having me. I've spent about 20 years in the legal field, all, all told, and the last 13 of which I've spent in-house. I was lucky enough to, to snag a paralegal gig at a game company, which was a really fun way to get my in-house career started. And from there it was kind of time to move on.
[00:03:22] So I took a shot and applied for a job at a little company called PayScale, not knowing that at the time they were also in the process of hiring Jessica. And so, Jessica, you can correct me if I'm wrong, but I think you were only a week or two in when you interviewed me for the PayScale role.
[00:03:38] Jessica: I, I, I was, I was, but I was excited to have, not, not, it's always exciting when you're a general counsel to say you got headcount. It's always like, it's like speaking dirty to a general counsel. You have, you have given the gift of more budget and headcount. You're, yes.
[00:03:55] Krysta: Absolutely. And so, um, it was really great to, uh, because Jessica was the first legal in-house legal hire, um, to get, to help Jess build out the legal function at a company that had actually been around for 15 years without in-house legal support, um, which was very interesting at times. But, uh, we had a lot of fun along the way.
[00:04:13] And I worked then at AWS for two years where I really got to see a really good balance between operational work and transactional work, which is not an easy thing to do. And you did tell me that you, when I, when I left PayScale, that you would call me back one day and offer me a job, and I, at the time was like, yeah, sure, whatever, like knowing we'd stay friends, but, uh, lo and behold, you did call me.
[00:04:39] And that led to me joining the forces at Lexion where we got to build a really amazing product and an amazing company together. So it's been a, it's been an interesting ride over the last year, but it's been really fun to, to get to do some new things and work with a lot more people that are really excited about agreement tech.
[00:04:58] Jessica: Yeah, the Lexion acquisition for folks listening was just, we just hit our one year anniversary from the acquisition and it's been such an amazing opportunity to work with a lot more talented people in the legal space. But Krysta actually, when you just mentioned about leaving PayScale and that conversation we had, one of my favorite stories when I share, when I go to conferences about management is that conversation where I actually said, yeah, go, you should go. And it wasn't because I didn't want you to stay, of course I wanted you to stay. It was more me asking, why did you wanna leave? Because if you go through the process of interviewing and applying, something made you wanna leave, that was more than about job title and money. And when, when we got to the root, right, the root cause of why you wanted to leave, I was encouraging for you to have those other growth opportunities.
[00:05:45] I.
[00:05:46] Krysta: Yeah.
[00:05:46] Jessica: Then we've come back together.
[00:05:48] Krysta: Yeah. The fact that you kind of gave me that permission to move on rather than I think some bosses could hold resentment or something like that. So I, I appreciate that moment as well.
[00:05:58] Jessica: Well, you know me, I have the resentment level of a goldfish I already forget, like within five minutes after the conversation. Alright, Sandy, so great to have you here. How are you doing?
[00:06:08] Sandy: I am doing great. Thanks for having me on. Such a fun group today.
[00:06:12] Jessica: Such a fun group. It's nice, it's a nice way to ease back into the podcast world post having giving birth to a human and really talking to very little adults. For the past four, it's been about four months or almost four months.
[00:06:25] Sandy: I feel like you never left us.
[00:06:27] Jessica: Oh, really? Oh, that's so sweet. And also sh you're like highlighting to folks how neurotic and obsessive I can be. Well, Sandy, um, enough about that. Tell us about your journey in path to legal operations and what you do here at DocuSign.
[00:06:40] Sandy: Yeah, absolutely. So like a lot of people, I'd say I fell into legal operations. I thought I wanted to go to law school. But some part of my brain thought maybe not. And so I, you know, took the lsat, was ready to apply and instead went and worked for a year. I got a, a role at NetApp in the legal department, where I was an an admin.
[00:07:02] But NetApp has a really, really progressive legal ops department.
[00:07:06] And it really opened my eyes to a unique role that would fulfill that interest in kind of curiosity about the legal field and working within a corporate legal department, but without having to go to law school. So that was my introduction to legal operations. I ended up doing a couple of different roles at NetApp, corporate paralegal at one point, which was not my calling.
[00:07:28] And ended up leaving kind of, you know, similar to what Krysta was saying. I was looking for just that next growth opportunity and ended up going to a smaller company called FireEye, where the department was really only 13 people at the time, the legal department. And I started the legal operations function there and grew it.
[00:07:45] So by the time I left the, the company and the department had tripled in size and we had a really robust kind of early legal operations team there. I ended up taking about a year off and after that had the opportunity to travel and live in a lot of different places all over the world. And during that time, I supported the corporate legal Operations Consortium.
[00:08:06] And I got to meet legal operations folks from all over the world as part of that role, setting up regional groups, attending their, you know, their early conferences and, and really getting embedded in that ecosystem. I did an MBA, you know, the, the law school thing didn't call my name, and so I thought business was gonna be the, the route for me.
[00:08:25] But has actually been super useful in my role here at DocuSign. So today I lead the ops team at DocuSign where, you know, my team has kinda all of the core legal operations functions, but we also have this really unique role where I spend about 50% of my time implementing DocuSign at DocuSign.
[00:08:44] That involves, you know, not only implementing DocuSign for our own internal use cases, but also partnering really closely with the product team, providing feedback to the product team, and that is one of the coolest parts of my job and, and a lot of fun. Gives me the opportunity to work with you and Ken and, and Krysta and, and other folks across the organization and makes this role really unique and, and special.
[00:09:06] Ken: And I've gotta say that product plugin is so exciting, and I might have just seen you in a barrister wig for a hackathon submission.
[00:09:14] Sandy: That is true. Last week was our hackathon and uh, we all decided we should be, uh, barristers. That might be the only time you ever see me, anything remotely close to an attorney.
[00:09:25] Jessica: Oh my gosh. You know, I'm so jealous. Being a part of a hackathon team wearing ridiculous outfits is right up our alley. But there's always next year, and we are rooting for you, Sandy, in our, in our wonderful legal hackathon teams. And also Sandy, you rocked it at CLOC the Corporate Legal Operations Consortium. Did I say that right? I can't say that 10
[00:09:45] Sandy: Nailed it.
[00:09:46] Jessica: Yes. You nailed it on the main stage. So kudos to you for being such a great rep, representative of DocuSign and legal operation leaders.
[00:09:55] So there's a lot of folks in our listeners who don't work with legal operations professionals that often they have a lot of experience at law firms and working closely with other attorneys. We kind of would love to learn from both you and Krysta about really learning about the legal operation role.
[00:10:14] And to kick it off, you know, how have you both seen the role of legal operations evolve over the pa or if anything, evolve over the past few years, or has it not changed?
[00:10:24] Krysta: Yeah, I think a lot of people, especially people that aren't as familiar with the legal ops space, which has been the name legal operations came into place about 10 years ago, maybe a little bit before that. And people like to think that that legal operations is something new.
[00:10:39] And the thing is, is it's really not, I look back on my career and I know Sandy, we've had this conversation that in our many other legal support jobs, we were always kind of doing that legal operations work just because it, it had to get done. It was not always prioritized. It wasn't thought about as being super important and we weren't really focusing on a broader strategy, but we, we had to get some of that operations work done.
[00:11:04] So I think that's an important thing to note is that this is not a new function. This is just the legal op, the legal operations or the legal departments are starting to. Flex that strategic muscle and recognize the importance of legal operations in being able to be that strategic arm. And that's what's changed really in the past five years.
[00:11:23] Jessica: Yeah.
[00:11:24] Sandy: I've been doing, I would say I've been doing, legal operations, uh, you know, on and off as I I said, for, for really over a decade. As, as Krysta alluded to, she's right, there were always functions within, legal departments that were doing operations type work. And then over the last 10 plus years, it's been a much more kind of defined career path, a defined function within an organization.
[00:11:48] What I'm seeing now is kind of even the next evolution of legal operations. And it's not so much about just, you know, implementing workflows or about helping your department save money and manage outside counsel spend. It's, it's becoming a much more strategic function within a, a corporate environment where, you know, we're really closely partnering with the general counsel, with our IT organizations, with hr, with finance, and really thinking about how do we run this legal department like a business, like where, you know, where are we gonna help drive revenue? That the much more of my conversations about like how, or about how is the legal team driving revenue for the company? Not about like, did we save money on those outside counsel bills? It's, it's really like the conversation has really shifted.
[00:12:39] And I think that's really fun. Part of it's maybe unique that, you know, here we are sitting at DocuSign where, where we are our own customer and we can help really define who we're selling to and, you know, the future of our, our products and all of that. But I think this is true about the rest of the industry as well, is that, you know, it's really seeing legal and putting legal in that more strategic kind of role and being that partner to the business, and being that department of yes and like, how does the legal team help our sales team sell more, not just tell them how they can't do things. So I think that's been a really fun evolution of, of the legal operations function. Um, and I'm just excited because I think it's opening up a lot of career opportunities for folks who've been in these types of roles. It's much more creative, much more kind of fun and, like forward looking, I guess I would say.
[00:13:29] Jessica: Yeah.
[00:13:30] Ken: Krysta and Sandy, I have a, I have a, a question I, what. I've seen over the last, uh, maybe five years was this initial push to, for legal operations to help drive metrics and numbers that come out of the operation. Do you think that was the foundation of, well, now that we have numbers, that's where we can go strategic.
[00:13:47] Sandy: Yeah. I think it was building a baseline. A lot of it was like, we don't even know what to measure. What are we even looking at here? And now we have that baseline and that's, you know, having that, that data now allows us to really gather insights and to make decisions and to look at like how do we staff this department? Where are we over-resourced? Where are we under-resourced? Like where are our dollars going? Are we seeing huge increases in like, the volumes of tickets on from the privacy team? Like, okay, maybe we should go do something about that. But it is giving us kind of the, the insights to make the more strategic decisions that we just weren't able to do before.
[00:14:26] 'Cause we didn't have the data and you might not have had, like, we didn't have the data because we didn't have a workflow where we didn't have a billing tool to capture it. So I think that that's exactly right, Ken. That's why we're seeing this evolution.
[00:14:36] Krysta: Yeah, I mean, even looking at my own journey with metrics, I think the first big metrics related project I did was about seven years ago. I had no guidance. I, I looked out there in the ether trying to figure out, okay, like what metrics do we use, what do we measure, how do we show it? And unfortunately, because there wa I did not find a lot of resources out there.
[00:14:56] Unfortunately, I did not find CLOC at this time. I had to kind of just come up with it and use metrics to tell a story and do do my best. But I think that the big journey that I've seen since I did that project seven years ago is that we, we started with just vanity metrics, like how many contracts are we getting done? Things that don't really tie back to bigger goals and they don't tie back to money or even necessarily time. And I think the big, the big shift is that we, we are now measuring much more impactful metric metrics and we have substantially caught up to where the rest of the business is in what they measure and how it really impacts those like foundational company goals and OKRs that are set versus just trying to prove that we have some value.
[00:15:40] Jessica: Krysta, I'm doing some math, and seven years ago was when you were at PayScale, so apologies in advance for making you do all that metrics collection manually that I know that you did. There's a mental math there. Uh oh.
[00:15:52] Krysta: No, no, no. It, I mean, it, it was, it was a very good learning experience, honestly, especially going from there to AWS,
[00:15:59] Jessica: Mm-hmm.
[00:15:59] Krysta: an incredibly metrics driven organization. Um, it, it was a, like a great way to kind of kick off that journey because I knew you and I were trying to tell the same story.
[00:16:08] And it was telling that story to the rest of leadership, which unfortunately. It did not work so well, but it, again, like I, I like to approach these things as much as I can with a growth mindset. As frustrating as it can be, to be told, no, you can't have more headcount. Um, I still learn a lot from that journey.
[00:16:24] So
[00:16:25] Jessica: Yeah.
[00:16:25] Krysta: builds upon itself.
[00:16:27] Jessica: A recurring lesson and theme I'm hearing from both Sandy and Krysta can is that the evolution of the legal operations role and the legal department in itself is One, to be more metrics and data oriented, and then two, being more positioned in. When I hear strategic, I, I also hear growth oriented versus, versus this is how we mitigate risk and this is how we reduce costs.
[00:16:50] Unfortunately, a lot of legal folks or in-house legal folks in particular are associated with costs. So when there's a time to, oh, there's less growth, how do we reduce our costs? And it's always looking at how do we reduce legal spend or legal budget. So associating with growth is always really important. Alright, to tie back though, into making sure folks hire the right legal operations professional and set up their legal ops team for success. Any advice here for in-house attorneys or new general counsels who are looking to hire their first legal ops professionals on what to hire, what to look for, how to scope the job, how to make sure you integrate that person for instead of set them up for success?
[00:17:34] Sandy: What a big question.
[00:17:36] Jessica: Huge
[00:17:36] Sandy: Um, yeah,
[00:17:37] Jessica: About like if you parse it like five questions.
[00:17:40] Sandy: yeah. No, no. It's. Yeah, and it's, it really gets to like, what are the, the, you know, identifying like what your department needs. Some departments are going to need someone who's like, really tech driven. Like that's their mindset. Some departments are gonna need someone who, who is, you know, gonna be more focused on some of the like, chief of staff capabilities and thinking really about the structure of the team and, and, and you know, how you align to goals and that sort of thing. I think one of the key things to hire for in legal operations is someone with a growth mindset. Krysta said that earlier, but under, you know, someone who is adaptable and flexible and can, you know, can roll with the changes.
[00:18:22] 'cause I think if there's anything I've learned in legal operations, it's like things change all the time, right? You had like one thing you were running towards and the next day the GCs like, Hey, actually I wanna go chase this other thing. Being flexible, being, uh, adaptable, continuously learning, right?
[00:18:40] Like in this world today that we're living in with ai, we're seeing, you know, like the legal landscape always changed quickly when I think about technology. But today it's changing so much more rapidly. So if you have some, you know, if you're hiring someone to do legal operations for you, that person better be super excited about change, about, you know, learning the new technologies, what's coming down the line, how are we gonna reshape our department to, to adopt those new technologies. Just so essential.
[00:19:11] Krysta: Yeah, I, I completely agree with what everything Sandy said. I think I, two things I would add to that. One is a piece of advice. I think in this day and age, especially like with where the economy is and everything a lot of the roles that I see that are opening up are really truly hybrid roles.
[00:19:28] They are not legal operations roles and any operations function is not going to be well suited to a hybrid role where you have demands on top of whatever the operations work is. So in my experience, trying to do legal ops work while also trying to work on contracts, which are always gonna take priority 'cause that is what's driving revenue operations always gonna take a backseat.
[00:19:49] If you really want a legal operations hire a pure legal operations hire, do not hire for a hybrid role because you're not gonna see those efficiency gains that you would see from that pure hire. I also think the, the other piece of advice that I would give is, consider looking outside of legal.
[00:20:05] I know it's very easy and helpful to hire somebody with a legal background. I mean, both Sandy and I, we worked our way up from very junior like, legal roles and that that's great. We speak the language, we know how things should work and are, are done and, and work in this industry, but hiring somebody with like that diverse perspective that still has that operational mindset, I think can be really important because it allows you, it, it allows them to challenge you and push you to grow in ways that you wouldn't otherwise.
[00:20:34] It's been hard for me to let go of being super risk averse and sometimes taking those, those leaps. it's difficult when you spent your career learning to ask for permission rather than forgiveness, but really in, in an ops role to be innovative, to drive change, you have to be willing to take those leaps.
[00:20:53] Jessica: Okay.
[00:20:54] Ken: if I can, I wanna resonate, uh, with what Krysta said. You know, I was fortunate to spend uh, time at Atlassian and I think that from an operation standpoint, we brought someone in who was deep in the program management side. And I think it really enlivened some of the operation aspects that we had.
[00:21:10] Now, I wanted to ask a question to kind of Krysta and Sandy to get their feedback. I think it was something that you were thinking about talking to, uh, a new general counsel or a small company and doing that first legal operation hire. What would you say about going through the act for that person?
[00:21:25] To go through the exercise of like, lay out their year goals. What, what are you trying, what is this role trying to accomplish? And how do you think they're going to accomplish it? What would you think that as an exercise for someone, um, trying to bring in the first operation person, um, do you think that would be a, a great, great place to start?
[00:21:43] Sandy: Yeah, that, that's exactly kinda where I was going with, do you need someone who's like gonna come in and just implement 25 new technologies this year? Do you need someone to just come in and even figure out where to start? Like what should the department strategy be? Always understanding, you know, what your priorities are is super important. I'd say even when I started at DocuSign, the priorities for the legal ops team were very different than what our priorities are today. Like, they needed someone to come in at that time and really, you know, kind of finish out building the infrastructure of a legal ops team, right?
[00:22:17] Like we didn't have a, a consistent metrics program. We didn't have a truly like robust intake mechanism. We didn't have some of these kind of like foundational pieces, um, at that time. And so that's what, what, you know, several years ago, um, the previous DocuSign GC needed someone to come in and do.
[00:22:38] I'd say now this role has evolved significantly for me. I spend a lot more time on our, our DocuSign and DocuSign strategy. I spend a lot more time thinking about department structure, how we're organized.
[00:22:50] So I'd say yes, that's a great place to start. If a GC who wants to bring in a, a legal ops person, a, that's, they're already ahead of the game. They know they want a legal ops person. But the second step really would be defining like, what does this person need to accomplish in that first kind of year?
[00:23:06] Like, what would success look like? What are our biggest pain points? What do we need to, to optimize and understanding that will absolutely point you in a direction of like, Hey, do you wanna bring in someone who's maybe even has like a data sciencey kind of background and they just totally get how they're gonna bring together all of that data and make it really useful for the department.
[00:23:25] Or do you need someone who leans more on the legal side? 'cause that still can be a valuable kind of background. Yeah, no, great, great question and and point there, Ken.
[00:23:33] Jessica: I think the answer there was, it depends.
[00:23:36] Sandy: Yes. Always. That's always the answer in legal.
[00:23:39] Ken: and, and once again, uh, a great lawyerly answer.
[00:23:43] Sandy: Yeah.
[00:23:44] Jessica: Sorry, I had to, I had to throw that in there.
[00:23:47] Sandy: Spoken by the lawyers on the, on the call, right.
[00:23:49] Krysta: you know, you know, that is like one of my personal favorite sayings that I, as I smile a little bit every single time I say it depends whether it's personal or professional. So, um, no problem. I agree with Sandy and I think, um, it can be really easy to try to boil the ocean and. SI think one of the, there's, there's two ways I think a GC can really go about figuring out, okay, I know I want a legal ops person, but what do I need them for?
[00:24:14] Go to your network, talk to other companies that are, have a more sophisticated legal ops program, and figure out what they're doing and how they got started. That, that can definitely give you some ideas, but also just spend some time with your team and figure out where are their pain points with within the team,
[00:24:29] as you try to figure out how exactly you want to leverage this person.
[00:24:34] Jessica: Yeah. Good points there. So, Krysta I'm gonna actually challenge you. I think part of the challenge for smaller legal teams is if I'm a gc, I only have given one headcount, but I do know that I need some automation and some tools. That's where the the need for someone who is a generalist and hybrid is needed versus, hey, I'm a legal department of let's say DocuSign, size over 50 people.
[00:24:58] I can have a sandy and direct, she can have a team that focuses on operations. So that's, so I think, Ken, a lot of your questions is, it depends on even probably the vertical of the industry B2C versus B2B, very different focus and priority. I imagine in terms of when a GC is like, I need help with CLM or contract automation and B2B because that's a big pain point, and B2C, I need more help with counseling and compliance, or spend management and litigation management because it's B2C.
[00:25:29] So I see that those really, it depends, right, Sandy?
[00:25:33] Sandy: Yeah, it all, it depends, and you're exactly right that it, it depends whether, you know, it is, let's say you're a GC and you're hiring the second person for the legal department, I'd say that person historically was often like a commercial counsel kind of person was gonna be negotiating contracts. And then there's kind of this shift where we started to see that second person being more of a legal ops type of, of role that in that second hire or second, third, fourth, fifth kind of hire, that person is a little bit more hybrid.
[00:26:02] Even though, as Krysta mentioned, like having a dedicated ops person is always preferred. If it's that early on in, in kind of a, a legal department's, um, development, it may very well be a hybrid person if it's a DocuSign sized company. Like, yeah, no, my whole job is, is legal operations. Um, and there's a lot of facets to that, but I'm not expected to also be negotiating customer contracts on the side.
[00:26:27] Krysta: I've been that second person who had to come in and do a lot of this stuff, and I think that there are ways that you can make it successful. As a gc I think you need to, you need to expecta like expectation set with yourself and externally that you're probably not gonna get as much operational work done as you want.
[00:26:43] Also, I do think, um, having seen this be successful where you do take on more of a hybrid role at, at AWS if leadership is willing to have your back and push back and say, no, these operational things are really a priority over getting x, y, z done. That, that is, that is a model that works. But unfortunately, I feel like, especially for most small companies, the revenue's king.
[00:27:08] Like if you can get one of those done in a hybrid role, you, you are ex exceeding expectations.
[00:27:14] Jessica: We talked a lot about technology earlier and talked about the, and the role of legal ops.
[00:27:19] there's a lot of hype right now about legal technology and AI. Generative AI in particular disrupting how folks in the legal department do their work. Where are you seeing legal tech or ai, uh, really working right now for legal teams.
[00:27:35] Krysta: I mean, I think it's pretty obvious from the conversations that I'm hearing as I go to events this year that con contracts is the space where it is starting to make a difference. And I don't think this is any surprise. I think, you know, with, with the tools being built over the past couple of years and the spaces that legal tech companies are investing in, I don't think that's surprising.
[00:27:55] The problem, I think, with that is that we kind of are a little bit hyper-focused on those, on use cases and, rather than trying to figure out how to, how to just use AI to move the needle. And it's discouraging some experimentation, especially I think with some of our more administrative work that we all have to do, drafting emails, putting together a business case or a business proposal summarizing things.
[00:28:17] I think we, we overlook some of that simpler stuff, that low hanging fruit when we are really pursuing these, these bigger use cases like contracting or e-discovery. I, I wanna make sure that folks aren't overlooking those very small efficiency gains as well as some of those bigger use cases.
[00:28:34] Jessica: Yeah, I love that.
[00:28:36] Sandy: I love that point too, Krysta, because there's been so much focus on, you know, well we have to find these big legal use cases. We're gonna build out all of this, you know, infrastructure. It's gonna take like until next year, but it's gonna be great. A lot of organizations, ours, ours here at DocuSign included, already have access to enterprise wide applications that do all the things that you just mentioned.
[00:29:00] If I think about the number of, of emails anyone in our legal team writes in a day, or the number the number of pieces of content someone has to digest, that could be easily summarized by ai. Some of those like day, day-to-day tasks easily enabled by tools that, that many organizations already have access to.
[00:29:21] I feel very fortunate about that, but whether it's throwing something into Notebook Lm and to digest 50 pages of something that I really needed to read, that's been super helpful to me and I think to a lot of folks across our department.
[00:29:35] But it does get to that just experimentation, just try something, dive in, give it a go. And that's where, you know, I think we do need to provide a bit more guided kind of experiences for some of the folks on our, our legal teams who are maybe not just ready to, to dive in the ops folks, were ready to dive in.
[00:29:53] Some of the other folks. We gotta gotta bring them along on that journey. And defining some of those use cases, even if they are some of the simpler ones. I think we'll go a long way. But also to what Krysta has said, you know, contracting does seem like a, a really natural place to use ai and we've already gained, um, a number of efficiencies in our department, using AI assisted review to help with, you know, running playbooks against our, our contracts.
[00:30:18] So we're certainly seeing value there. I am, you know, I'd say wait and see on some of the other more specific legal, legal tech tools, but Ken knows this landscape well. I don't know if you wanna jump in with anything here.
[00:30:30] Ken: Well, I want, yeah, thank you. I wanna give kind of a hot take. So as for, for folks know, sort of my lens is slightly differently. I, I try, I'm on the product development side, supporting the product and partner legal teams. One thing that, uh, I want to throw out to, uh, to Krysta and Sandy to get their feedback on is I think the technology is moving in uneven ways. In some places it's going very fast and other places it's going in circles. But I do believe what that's leading to in this moment is the idea of legal operations sits over there, is kind of become, the lines are starting to dissolve and what was legal operations is just gonna be what is legal, whether it's sales or contracting.
[00:31:13] And, and there will still be aspects that will be quote unquote for those who aren't on the video. I'm air quoting here, operational, but I think the technology is allowing folks, uh, in all these spaces to, to, to start to extend into new spaces. For folks who are closer to what I would say was traditionally operations, what do you think of that statement?
[00:31:33] Sandy: I think you're exactly right. As I've thought about the way that we operate as a legal team, there shouldn't be well, legal operations does this, everyone else does this, or we have to wait for legal operations to roll out something. It is just gonna be the way that we operate.
[00:31:51] Some people use AI and some people don't use ai. If you think about some of the older technology, it really did require extensive IT resources to come in and implement things for you. And now we don't need that for some of these.
[00:32:04] Jessica: Mm-hmm.
[00:32:05] Sandy: When you're coming out, right? Like, no one had to really show me how to use Gemini or how to use Notebook Lm like, I can log in and figure it out. I don't need it to come in and set that up for me. They don't need to build me a notebook for me to use.
[00:32:19] And so that's where it is. It's like democratizing technology for the legal department because, you know, Ken and your team, you, your whole team can now just go in and use these things. You don't need to wait for, you know, legal operations to host a training for you on how to do this. I'm with you on that one. I think for me it's more just like a matter of getting everyone on that bus and heading in that direction.
[00:32:41] Krysta: We operate currently in most of the corporate world, in these very, somewhat isolated silos. Yes, there's some cross-functional collaboration, but I think the idea of these silos is what really kind of stifles a lot of change that could move a lot faster.
[00:32:57] And I think we're going to see more centralized operations functions where there might be a, like dedicated people that support legal operations, but they will sit in a more dedicated operations function under say, the COO versus sitting within the legal team. As you said, Sandy, like there is a lot of democratizing of technology and like ability to educate yourself.
[00:33:18] And I think just like we've seen changes in the past 20 years in the legal, like the legal field itself, we, we'll see that change in operations as well where you, you don't have people doing a lot of the more menial work.
[00:33:31] So just like I don't Bait stamp documents anymore, like with a physical bait stamp, um, you know, it, they, it's just, it's just technology growing and I think technology is really what is gonna break down those walls between departments and allow, allow everyone to use technology better, but also just work more collaboratively to really push the business forward rather than being like, that's not my problem.
[00:33:55] Ken: Do we need to explain what bait stamping is for folks because,
[00:33:59] Krysta: Did I just date myself?
[00:33:59] Sandy: I was like, am I old enough to know what that is?
[00:34:02] Ken: my first, my first legal role before a law school was to sit in a floor of a building in Los Angeles, which had a document production in those man folders and to sit by a phone to go retrieve numbers.
[00:34:14] Jessica: Oh my gosh.
[00:34:16] Krysta: I had, I had a physical, I had a physical bait stamp back in the day, so I have literally seen the iteration of physical bait stamp to moving to stickers. Which was like a huge thing. I'm not even sure it actually saved you more time, to be honest.
[00:34:30] And that's just like what 20 years of change, like we are gonna see in the next 20 years I think we're gonna see exponential change that just keeps going up. So it's, again, it's about having that growth mindset and embracing that technology, embracing the change and the chaos that newness brings.
[00:34:46] Sandy: I often tell the story of my job at FireEye where I walked in on day one to my cubicle and there was like stacks of paper in it, and I, i, my mind was like, what is this? And it turns out it was all of our executed contracts that had not been like filed into the file cabinet yet. And they were like, oh, Sandy, you're here.
[00:35:06] You can file these documents. And I was like, no, actually I'm just going to implement DocuSign so everyone e-sign documents so that I no longer have to do this anymore. Um, and sure enough, I ended up bringing in DocuSign there. This is, you know, more than a decade ago. So now every time someone says that they're signing on paper, I just look at 'em like they're crazy. 'cause I don't even know where to find a printer.
[00:35:29] Jessica: Love that.
[00:35:30] Sandy: Yeah.
[00:35:30] Jessica: So, uh, a lot of folks here are listening may have had some war stories with trying to source or implement legal technology. Krysta, you're nodding your head. You, we've had some misses. We've had some hits. Any advice to the listeners here about how to approach evaluating legal technology to be successful and, and have successful implementation or successful actual adoption and use of the tool?
[00:36:00] Krysta: I think first and foremost, the question you have to ask yourself is buy or build.
[00:36:03] Jessica: Hmm.
[00:36:04] Krysta: Having, not had budget to buy tools for many, many years. I had to, I had to get creative and scrappy, and I was able to build some things that really drove change and allowed the business to move faster, but still allowed the business to self-serve as many options as possible. Like automating IP clearance searches in a way that allowed me to, to move through them faster and not do a lot of copy and pasting.
[00:36:27] There were point solutions that could do some of these things at the time even, but there was no way I was gonna get budget for it. But I was able to, to build the skills and level up and, and build these things and actually deploy them and have them be successful. So don't don't overlook building something internally.
[00:36:44] It might be the right solve for you. And if you're gonna go the tool route, it's very easy to get hooked by a flashy demo. So I think you really have to understand first if you've decided to buy, you have to understand what you're actually trying to solve for. Don't say, well, we need a CLM because everyone has a CLM.
[00:37:05] You need to know like, well, why do you actually need a CLM? Is that the tool you really need? Are you looking to, um, like do more automation and be able to auto extract ai? Or are you literally just looking for like a document repository?
[00:37:19] Then go through, like, go through an RFP process before you even look at a tool.
[00:37:23] And then once you've narrowed down your list through that RFP, actually get your hands on the tools. Test it with your own, um, your own. Quote, I'll say quote unquote data. You don't have to use your own data, but like, use your own temp, like use your templates just with random blanks filled in, uh, in the contract example, for example, like, don't trust.
[00:37:44] I feel like we're all a little bit skeptical in the legal profession anyways, but, um, you just, you can't trust that a, a vendor, the, the tool is gonna operate exactly like you think it's gonna operate, like, until you get your hands on it. So that sandbox and trial environment is incredibly important to, to making that decision.
[00:38:03] Sandy: Yeah, Krysta really covered it.
[00:38:05] If you don't have that list of requirements of what I need it to do, it is really easy to get distracted by the, the shiny demo or the tool that everyone else has bought, whether or not it actually meets your needs. The other thing that I would, um, consider is, you know, the, the people. It's often underlooked, but are the people that you're partnering with at that, at that tool are they really gonna help you on that journey?
[00:38:32] Whether it's the professional services that, that are gonna help you implement it. Are the people there really committed to. The vision of the product. Like, are they gonna continue building that product into the future? 'cause you're, you know, ultimately when you're buying software, you're buying it as it is today.
[00:38:48] And hopefully it meets your needs, but you're also buying it for the future. So having that team that you're kind of on that journey with into the future, I think can be really important. And some of my most successful implementations have been where I've had the, like, the best relationships with the folks that I'm working with at that partner.
[00:39:06] 'cause they're gonna be there when you call them and you're like, Hey, this isn't working. Or, Hey, I need this, you know, fe feature added. Um, you wanna know that someone's gonna pick up the phone and, and actually help you through that experience.
[00:39:17] When it comes to people, also make sure you've got all the right internal stakeholders aligned and onboard and part of that conversation. So if it's a tool that's gonna impact more than just the legal team, like let's say it touches the sales team or the finance team, hr, whoever it might be. Bring them all into that conversation as well so that they can be part of that evaluation process and part of their, then they're pre-bought in when you do go to roll out something at the end of the day.
[00:39:41] And there is that change management part, which is by far the hardest part of buying a tool. The folks who are gonna actually be using it have been there with you and that they are part of that decision making process bought in. Whether they have the final say or not, at least they've been part of that conversation. That makes for much easier implementation down the road.
[00:40:00] Krysta: Yeah, I completely agree with that. That's exactly why my first CLM in debilitation failed. I mean, I'm not afraid to, to say that I've had a failed one. I think a lot of us have had either failed tech, but especially CLM failed CLM under our belt. I neglected to, to think about that stakeholder component just because.
[00:40:16] I was so early in my legal ops journey that I didn't have the necessary like project management chops to, to really think about it the right way at the time.
[00:40:25] Jessica: Yeah. So I'm gonna double click there. Sandy, what you said is change management is by far the hardest part of any technology, whether it's legal, tech or not. Legal, tech implementation and rollout. And so what I have seen is that, right now in the market. 'cause as, as I follow the market and read the tech news, there are so many legal tech point solutions and yes, some of 'em are really, really great, but they're not all gonna survive because there're gonna be some adoption challenges if they don't already live in or exist within an existing tool. So that's my point of view. Ken do you have any point of views on the, the market?
[00:41:03] Ken: Yeah, I mean, the way that I think about this, I want to kind of thread a couple ideas here together is, um, you know, and a lot in the product development, particularly around emerging technology ai, we talk about where is the human in the loop. And that's really what jumped to my mind when, both Krysta and Sandy were talking about who are the human stakeholders.
[00:41:20] And many things are moving so quick. Many things are point, uh, point, solutions. I, I always think in terms of kitchen gadget, like some things are uni taskers, like that great egg splitter is incredible what it does, but how many times do you really need it? But really thinking about the technology I. That PRD or that requirements, that RFP, like what are you trying to accomplish and then where are the humans going to exist? In the loop of all of that, knowing that you may buy something today in early June, and by the time you implement it in September, it actually may look like a different product.
[00:41:51] But if the humans are perhaps in the right portion in that loop, you can adapt, you can still get value of out of it. And also consider, like, do some use cases will need that, you know, that, egg splitter or that egg, you know, that egg peeler. Um, but in some cases you're actually just gonna need a knife and trying to figure out which is more appropriate for your solution.
[00:42:11] Jessica: Absolutely. Let's shift a little bit to the future of the legal operations profession. Given all of this talk now about technology and AI and AI really disrupting the work that we do. And candidly, for a lot of folks who worked their way out from the ground up from legal operations, you did a lot of the thero tasks that can be done now by ai. What do you see? How do you see the role of legal operations evolving with ai?
[00:42:41] Krysta: I mean, there are already tools out there. I mean, I can think of like lucid charts as one that comes to mind for pro like process management and being able to, rather than me having to go in and drag and drop and fill things out and starting from that blank canvas, I can kind of brain dump and I'm able to spit something out that actually may not be perfect, but it's just saved me a ton of time. Versus like sitting for an hour or two to build out this process chart.
[00:43:10] So, We're already seeing that impact today and I think we're gonna continue seeing that impact where it allow, AI is just going to allow us to scale better generally as, as professionals. And it's not gonna be about de like decreasing the amount of work. It's just gonna cha change the work that we're actually doing and allowing us to open up time for that more strategic work.
[00:43:33] And by that I mean the projects that all get put on the back burner, um, you know, update, how many times do we try to update legal terms? And we would talk about how it needed to happen and it would be like. Six months later, and we still hadn't gotten started, like just imagine if you could open up just a chunk of your day, each day to dedicate to a project like that that really can impact like the, the speed of your negotiations and your customer's perception of you as a business.
[00:44:00] Like that is incredibly impactful work that I wouldn't have gotten done otherwise 'cause I just didn't have the bandwidth. So I think creating and keeping that flywheel effect going is what, is what I've seen in the paralegal profession, in the contracts management profession. I think we're gonna see that same thing, really start transitioning into the, the legal profession as these tools become more mature.
[00:44:19] Jessica: What I'm excited about, uh, in, in the legal ops space with, you know, with the addition of tools like AI is to some extent being able to, to self-serve more. So I talked a little bit about that, but like less reliance on, it to create your workflows or build your lucid charts for you or implement some complex, integrations, those, those sorts of things. Like, I'm excited about the ability for us to, to do a little bit more on our own using tools that leverage ai. So that's one thing that I'm, I'm can't wait for in the legal ops space. The other part is that, you know, I'm really a, a people person.
[00:44:55] Sandy: I enjoy like going out and, and talking to the folks that I work with, understanding what their pain points are and how I can help them. And I, I see myself having more time to do that because I'm not spending as much time on some of those mini type tasks. Like, I'm not needing to go through and like, analyze survey data anymore. I'm just dumping that into Gemini and saying, Hey, identify five themes for me.
[00:45:18] Opportunities for us, places to improve. Like, I, that stuff used to take me hours and if I can do it in a matter of seconds with Gemini, that gives me more time to go out to my internal stakeholders, folks like Ken and say, Hey, what, how can I help you? Like what is it that that ops could be doing to better support you, to make your job easier? And I see myself getting to do more of that, which is what I love, and I don't think AI can yet to do that for him in a way that we have like a really holistic view of our department, of our cross-functional stakeholders.
[00:45:51] And not saying that we won't get there at some point, but today I think we still do need that human in the loop to connect some of the dots to feed ai the prompts. There's still a human element that we need. And I think I will be able to better prompt AI by having more time to, to really understand kind of what's happening across the department, what's happening across DocuSign or at any company. So that's what I'm most excited about, is it just gonna be more time to think and use the tools that I have. That I didn't have before 'cause I was spending time analyzing survey data.
[00:46:26] Jessica: How do you think the role of an entry level legal, legal operations, professional, or even just an attorney, is gonna evolve now with the gen, you know, with with ai now that we don't need a entry level person to do that first draft for us anymore.
[00:46:43] Krysta: So I do
[00:46:43] Sandy: gonna. Hi. I'm in my first year at this company. What should I do?
[00:46:53] Krysta: um,
[00:46:54] Sandy: Sorry, Christy, you were gonna have a real answer.
[00:46:56] Krysta: okay. No, your, your answer, your, your answer was great too. I was just like laughing 'cause um, I still very much prompt that way. A lot of the time, even though I think my, my custom GPT solutions know me pretty well at this point. I had a legal intern, um, at last year at lexion and one of the tasks that I was able to work on handing off was NDA negotiations, those pesky pre-contractual NDAs that we all know, know and love.
[00:47:22] But I mean, that's how a lot of us cut our teeth, right? I mean, the contracting space and, thought really long and hard about like my own journey to, to negotiating contracts and was actually up able to leverage some of our tools to help kind of expedite her training. Because I'd already built, I'd already built the playbooks, I'd already built the foundation and kind of like the, the knowledge and the tool, and she could, she could run, go in and run those playbooks and then she was able to get answers from like inward tool that would explain well, why these things need to be changed.
[00:47:53] So it really did still give her that education piece that I would've offered. And for anything that was missing from that tool, she was still able to, you know, highlight and leave a comment. But instead of having 50 comments to go through or 20 comments, there were like three. So it also used kind of less of my time, in that sense and allowed her to really focus on just, just the questions that, that she still needed answered.
[00:48:17] So there's still a lot of, there's, there's still a lot of knowledge out there to learn, and I think chat GPT can be used as a really powerful learning tool if you choose to use it that way. So I think we just need to continue to find ways to, to help people level up using these tools. And that's just gonna take experimentation.
[00:48:38] Jessica: Mm-hmm.
[00:48:40] Sandy: I mean, I think you could say the same thing about like when there was Google instead of a library or something, there it is just a different skillset. And our, our, you know, our legal interns this summer have been really fun to work with because they are just so, that's just how they work.
[00:48:55] Their inclination is to like first go to an AI tool to help them do most anything. And I, so I'm actually really excited about having more of them in the workforce and the, and the, the amount of kind of stuff we can learn from them, because that's just how they think. That they're wired that way. I don't, they're not digital natives anymore. They're just, they're like AI natives. I don't know what we call them. Um, but I'm, I'm excited personally about having that next generation to work with. And
[00:49:23] It gives folks like Krysta more confidence to pass off work to, um, to an intern because she knows that they're, they're being kind of backed up by ai or that AI is helping them do that first pass red line. And that gives Krysta more confidence actually than, Hey, just giving, a stack, a virtual stack of NDAs over to the intern. I'm not worried about that. I think it's just gonna evolve and it'll be different, a different experience.
[00:49:48] Krysta: I completely agree. I just wanted to, I, I went to a legal innovation conference last week and we were talking a lot about technology when we got involved in the legal space versus now, and you talking about doing legal research or just research in general, made me think of a conversation I had last week where we were talking about going to a law library and actually having to shepherd eyes using actual physical books, which I only luckily had to do for a small window during my paralegal certificate.
[00:50:11] But, we literally had to learn how to do that. And then today, I don't even know what Westlaw and LexiNexis look like today for, for this kind of stuff, but I remember like just even the flag system and being like, oh, thank God. Like I don't have to go do this manually by myself and take hours to the library.
[00:50:26] Yeah, I like, likewise, I'm not, I'm not afraid just because we add technology, things are gonna change. Sure. But that doesn't mean. It's things are gonna go away.
[00:50:36] Jessica: Okay.
[00:50:36] Ken: And I, I think I thread together of some of the themes I've heard, and bring in my perspective is that, uh, the technology is far from perfect, but it does allow to allow a lot of leverage or a lot of capabilities.
[00:50:48] I think there's gonna be just new roles that don't quite exist today that folks will gravitate towards that will be operational roads. That, that despite us saying like, it shouldn't be a hybrid. I think this is gonna be that new hybrid, like that thing that just. Is exists because of where the technology is.
[00:51:04] But I would lead as someone who tries to stay close to sort of some of the best practices. I do think that human in the loop is still so critical because these systems are great, but they're not reasoning and, and do, to pull on that example of, of citations, right? How many times do we see a week of counsel who think they can trust the citations that the cases that the AI is pulling up and that case doesn't even exist.
[00:51:28] So that's where you need the human in the loop to still say, is this technology performing the way that I need it to?
[00:51:34] Jessica: 1000%. I mean, Krysta, Ken, and Sandy, I too had a job that is no longer existing when I exist, exists. When I was an intern, I had my portable Walkman and I used to scan docu, like scanned Discovery doc. I wa I was an intern Krysta for the King County prosecuting office Where you're, yeah. For your, um, what was it, your greats
[00:51:56] Krysta: My great uncle. Yeah.
[00:51:58] Jessica: Your great uncle was the prosecuting attorney.
[00:52:00] And I was an intern there and I was putting stickers on discovery doc litigation documents and then scanning them and wearing my Walkman. So that, that dates me how
[00:52:10] Sandy: Offenses don't even exist anymore.
[00:52:12] Jessica: No, and I had to scan my favorite songs onto a cd. A CD that I probably got from Napster.
[00:52:21] But long story short that there are still legal interns.
[00:52:24] So I love that. Well that is the show and we're gonna end it with a very fun segment. we call it the Redline segment because I have a history as a contract nerd and doing a lot of contract webinars and so fun.
[00:52:41] Are you ready for some fun questions? You gotta go with your gut. You Sandy? You like game? I I'm gonna, I'm gonna pick on you first 'cause you're like, I, your energy is like,
[00:52:51] I'm on it.
[00:52:52] Krysta: I love, I love, this kind of stuff.
[00:52:56] Jessica: All right. look, Krysta, starting with you would you red line out reality tv?
[00:53:02] Krysta: No way. I would keep reality tv.
[00:53:05] Jessica: I know you live off Bravo.
[00:53:07] You Bravo.
[00:53:08] Krysta: as a, a lifelong reader, when I got really involved with contracts and I was doing so many contracts, working crazy long days, the last thing I wanted to do was go read afterwards. And so, especially during the pandemic, I got really into Bravo TV shows, and that has stuck with me and is still one of my main like decompression activities, watching Bravo at the end of the day.
[00:53:30] Jessica: Yeah. I, I love that.Sandy Reality TV for you.
[00:53:34] Sandy: Oh, absolutely. Keep it.
[00:53:36] Jessica: Keep it.
[00:53:37] Sandy: Yeah. Oh, yeah. Yeah. I still have like Bachelorette and Bachelor watching parties to
[00:53:42] Jessica: Woo.
[00:53:42] Sandy: at my house, so, um, yeah, no, I, I'm a, a big reality TV fan.
[00:53:48] Jessica: right. I'm gonna pick on you. Uh, do you have a reality TV show.
[00:53:52] Ken: Can I selectively redline some shows or do we have to get rid of them all?
[00:53:56] Sandy: That's against the playbook.
[00:53:58] Jessica: Okay. How about which, which one would you selectively
[00:54:01] Ken: Oh, I'm not gonna alienate, but there would be some that I would selectively
[00:54:05] Jessica: Uh,
[00:54:05] Ken: I'll just say that.
[00:54:06] Jessica: Okay, fine. You got out of it. All right. The last question, and actually I, uh, don't really have like a this or that for you, Krysta is I wanna, you're the experts here. Which legal technology tool were you forced to use that you would just wish you could just redline out or any tool? It doesn't have to be legal tech.
[00:54:25] Krysta: Does it have to be a specific tool? Something else that's gonna maybe date me. Um, actually no, no, no. I, I know what mine is. Uh, mine would be using, using mine would be using iManage outside of its intended purpose as a document management system and using it as a contract.
[00:54:41] Jessica: Ooh.
[00:54:42] Krysta: I still, to this day, have nightmares about iManage and like accidentally checking out a document or not being able to find a contract that I know exists when I'm really stressed out, even though I don't use iManage today.
[00:54:54] So. I think that experience with iManage and the fact that I know we were not using it properly, um, it still like gives me like heart palpitations, so that one's mine.
[00:55:04] Jessica: I see. So using a tool that was not intended purpose, that's actually a good one. It doesn't, you know, it's not picking on iManage, it just, just picking on a, the company that chose to like put a square peg in a round hole type of situation. Sandy, any, any, any nightmares you have, like Krysta on a tool you were kind of forced to use for a square peg round of.
[00:55:25] Sandy: No, that, that was such a good one. Um, and I think I'll just piggyback on that. You know, anytime you're, you go to your, um, IT team and you're asking for a new tool and they tell you you can't have it because something that you already have in your tech stack does exactly what you're looking for. The one that comes to mind in a more recent example was.
[00:55:45] Getting critiqued for having a e-billing tool here at DocuSign, because certainly Oracle could do everything that we already do with e-billing. Just again, along the same lines of like doing things with tools that you're not meant to be doing or that, you know, when it comes back to you and tells you, oh no, there's no reason to buy a new tool because this enterprise tool does everything you could possibly want.
[00:56:09] Um, I've had a lot of those situations.
[00:56:11] Jessica: Oh yeah.
[00:56:12] Sandy: does not go well. There's a reason that there is legal tech and I, you know, can't say they're all perfect, but, um, there's a reason that there are purpose built kind of technologies. And to throw it way back to my NetApp days, you know, we, we called it like the toaster of data storage because it was like, you can toast things with an oven, you can toast things on the stove, but like a toaster is like purpose built for this exact
[00:56:33] Jessica: Oh, that's a great analogy,
[00:56:35] Sandy: Yeah, it's a really good analogy. And so, you know, a lot of really good legal techs are purpose-built and they are really good at what they do, and there's a reason that we need to purchase them. And that Oracle doesn't fulfill all of our legal e-billing needs.
[00:56:49] Krysta: Yep.
[00:56:49] Jessica: Well, thank you so much for joining Ken and I today. Uh, for folks who are listening, where can they find your connect with you? You wanna kick it off? Oh, LinkedIn. Oh yes. Both of you're so active on LinkedIn. Maybe CLOC event or legal ops.com event.
[00:57:03] Krysta: And I think Sandy and I will both be at running legal, like a business this fall in Las Vegas. I will be at Summit by the Sea in mid-September, hosted by legal operators as well as Legal Geek and, the CLOC of MIA Summit in London in October. So, please, if you see me around, I always love, uh, meeting people and would love to chat.
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[00:57:26] Jessica: Ken, it was so awesome to have Sandy and Krysta join us on this interesting discussion about the evolution of not just legal operations, but just the legal profession generally and, and how AI is gonna impact it. One of my takeaways was AI is here to stay and really baby steps when starting to learn to use ai. It doesn't have to be a full-fledged enterprise-wide workflow change and incorporating AI technology in that. It could be just your everyday task of summarizing information, summarizing a meeting note taking. I was actually thinking about your example, Ken, when you mentioned what can a general counsel or do to onboard and set goals for a legal operations professional?
[00:58:13] Why don't they just use generative AI to do that? To create that onboarding plan and to set priority for this type of company that I worked on of this size Help me draft an onboarding plan, uh, for my new legal operations professional hire.
[00:58:27] Ken: I think there's a lot of this conversation around hype or not and, and around the emerging technologies around AI and I think the reality is, is probably both, right? There is a lot of hype, but there's a lot of capabilities and some of the themes that came up how historically legal operations ha is moving from metrics to being even more strategic.
[00:58:47] And I think what we are, what we are realizing with this technology, that those boundaries between what was legal operations and what just was legal are, are diminishing. And this will allow legal operations roles to become even more strategic because they're gonna be closer to the business.
[00:59:03] They can really help them understand what are their goals that they want to do to help move from that cost center to being more aligned with, with how they drive value. And, and even within the, the more traditional spaces as these new technologies come online, there also seem to be this understanding of what are you trying to accomplish with them?
[00:59:23] Are you going to get that toaster? Are you okay with an oven that toasts? Right? And, and, and I do think that's important because there is a lot of great technology out there, but if you don't know what your strategy is around that technology you might wind up with a toaster you never use.
[00:59:38] Jessica: Yeah, my only worry is I'm gonna end up with 20 toasters, try to double down on Sandy's awesome analogy. And that I only really just need one or two, and I'm overwhelmed by the toaster option in the market. So we will see where the, where the space takes us and the future takes us, but it's, it's pretty exciting where it's going.
[01:00:00] Well, thank you, Ken, for being my co-host today. And,
[01:00:02] Ken: Thank you Jessica.
[01:00:03] Jessica: Amazing. Thanks, Ken. Bye.
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