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Ep 102: What Comes After Legal Ops? A Conversation with David Cowen
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In this special live-recorded episode of The Abstract from CLOC in Las Vegas, host Tyler Finn sits down with David Cowen, founder of The Cowen Group and creator of the SOLID Summit Series.
David shares his journey from staffing to shaping the legal ops ecosystem, the moment he foresaw the rise of e-discovery, and why community is the most powerful response to chaos. He discusses the evolution of legal operations, the future of AI and agentic teams, and why trusting your talent matters more than ever. From frameworks on scaling legal to using ChatGPT as an executive coach, this episode offers a playbook for building a career and community in a rapidly changing industry.
Read detailed summary: https://www.spotdraft.com/podcast/episode-102
Topics:
Intro: 00:00
David's career journey: From staffing to community building: 2:22
The moment he discovered e-discovery's potential: 5:10
How TED Talks inspired the SOLID Summit format: 6:49
Chaos as the ideal condition for community building: 8:43
Overbuilding in legal tech: problem or opportunity?: 10:52
Spotting innovation through curiosity, not prediction: 13:02
Legal Ops turns 10: What’s next for the profession?: 17:33
Climbing the legal career “jungle gym,” not a ladder: 21:03
How to manage anxiety and disruption in an AI-driven future: 25:53
On coaching, preparation, and using ChatGPT as a partner: 28:25
Legal Ops’ evolving role in helping businesses scale: 32:49
The future of legal tech: use cases and AI agents: 37:12
The GC as catalyst: Top-down transformation is here: 39:46
Creators, Builders, Consumers: Who shapes the industry?: 42:54
What excites David most about the next 10 years: 45:35
Rapid-fire Questions: 47:25
Connect with us:
David Cowen – https://www.linkedin.com/in/davidcowen/
Tyler Finn - https://www.linkedin.com/in/tylerhfinn
SpotDraft - https://www.linkedin.com/company/spotdraft
SpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues.
Visit https://www.spotdraft.com to learn more.
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Transcript
Managing Anxiety and Embracing Change
00:00:00
Speaker
Misery is optional, right? Anxiety is optional. like It's not going to get you anywhere. so what are you going to do about it? I mean, that's my my father. That's what my dad said to me. Yeah. And that stuck with me. Not that I haven't been anxious many times in my life, right? I have been. I'm not saying that there's it's a cure-all, but um being prepared is sort of the best kryptonite for anxiety.
00:00:22
Speaker
And so is your department going to be disrupted? Yes, absolutely. Is your job going to be there? Definitely not the way it is today. Is your boss going to continue to like, no, nothing is going to be the same. It's all going to change.
00:00:36
Speaker
And that's historical. And like, yeah, it's anxiety producing, but only as anxiety producing as you want it to be. Trust your talent is something that, um, Somebody told me a long time ago when I started to do these, I started to do breakfasts and dinners and I'd get like nervous before we breakfast and dinner. and you know Some careers are built by solving specific problems.
David Cowan's Career Journey
00:01:06
Speaker
Others are built by building communities that elevate entire industries. Today on The Abstract, here from CLOCK in Las Vegas, I am joined by David Cowan, founder and president of the Cowan Group and creator of the Solid Summit series.
00:01:24
Speaker
Over the past two decades, David has evolved from a staffing and recruiting pioneer to one of the most important community builders in the legal industry.
00:01:35
Speaker
Along the way, he's helped place over a thousand professionals in litigation support, guided the rise of legal ops and e-discovery, and built a platform that accelerates careers, conversations, and ecosystem-wide change.
00:01:51
Speaker
So today we're going to have a conversation about the evolution of legal technology, the future of legal operations, and what it takes to lead in a time of a little bit of chaos. and overbuilding. at David, thanks so much for joining me here in Las Vegas for this episode of The Abstract. ta Thank you for having me. And I'm going to take you with me everywhere I go for an introduction from now on That was fantastic. I'll hop on stage. Even I like me after that introduction.
00:02:19
Speaker
There's a lot to like. Thank you. appreciate that. Okay. So I like to do a little bit of career conversation too, before we start talking about kind of the future and where things are headed. You started your career in staffing and recruiting.
00:02:33
Speaker
Can you walk us through some of those early days and some of the businesses that you were able to build and and sell? Yeah, no, I grew up around a a staffing table. you know My dad was in the business and he'd come home and you know my mom would put the placemats down and my dad would bring the placements in and it would just be really kind of interesting conversation. It was a business conversation around my dinner table. So I learned from that.
00:02:56
Speaker
You know, he was an entrepreneur and he was in this business um and he was really one of the good guys. He my dad is a person of character and integrity and the way he handled his businesses. is That's what I learned at the dinner table. So as I got into staffing and recruiting, you know, sort of later on, it was all about the candidate.
00:03:15
Speaker
It was always about the candidate. The client was important. The client paid the bills. But if you could understand the candidate, then you were golden and the candidate would be loyal to you, you know, throughout his or her career. And so that just became the fundamental foundation for what I built after that. I think it's how I got into community building. But when you're when you're with the candidates, I started in office support right back in the day. So that's like, you know, that's when they were, you know, admins. It was admin support. And it's like you would interview 10 people a day.
00:03:45
Speaker
So I got really, really good. Like I figured the key to success was of the 10, which two could I place, which two could I put on the bench and which six just, they weren't going to make it with me. They were going to make it, but they just weren't going to make it with me. So the sooner I could figure out what made you tick, you know, your prior state, your current state, your future state, like, so who do you want to be when you grow up? And I could kind of assess that the better I could be at matching you.
00:04:07
Speaker
where you really, um where you where I thought you would fit. I had a pretty good pretty good instinct for that. I was pretty good at that. And so I had uptown clients and downtown clients. And in all honesty, I've been doing the same thing ever since. It's like in two or three or four minutes, asking good questions about who are you and who do you need to meet?
00:04:27
Speaker
Like today in the community building business, it's, who can I introduce you to? yeah like or And whether it's buyers and sellers, who do you need to meet? Or in your career, you need to You need to meet Leo Mergo. That's who you need to meet. yeah You've got to meet Dorothy Cullen. You've got to meet Nishan.
00:04:43
Speaker
You should meet so-and-so. All future podcast guests. All future. Well, no, for sure, for sure. These are future podcast guests that are living in the future. I'm always looking for people that are living in the future.
00:04:57
Speaker
yeah That's where we are right now. don't know if you want to spend whole lot time on careers, but we are sitting here in Las Vegas as we look out over with this backdrop, we are literally living in the future in this legal ops clock environment.
00:05:10
Speaker
I am curious how you saw sort of the future of e-discovery and what became and evolved into legal ops. Because when you started doing staffing and and building Cowan Group, i mean, seemed like that was not...
00:05:23
Speaker
obvious that it would explode or become what it is. It was the most obvious thing in the it was the most obvious thing in the world. And um and no one's ever asked me this question before. And I've told the story very few times, so I'm glad we're capturing this. So here's what's happening.
00:05:35
Speaker
So I had just sold the staffing business okay and I'm sitting on a bench and, you know, I'm sitting literally in my den, you know, looking out the window. It's snowing outside. The kids are playing, literally watching like Barney or whatever it was. And my dad comes in with an article from Businessweek.
00:05:50
Speaker
And my dad, if he would see something, he would say something, goes like, I don't know what this is, but I thought it would be interesting. This is Business Week, December of 2003, and it's an article by George Socha. Okay. About e-discovery.
00:06:02
Speaker
And the moment I read it, I realized there's going to be a demand for talent. I'm like, i and I intend to take the year off here, by the way. I'm not working. I'm done. I'm like, yeah I'm out for a little while just to kind of relax. and And I think one of the keys to success in life
Building Communities in Legal Tech
00:06:16
Speaker
is momentum.
00:06:17
Speaker
You don't ever want to give up momentum if you haven't. I'm like, this is not the time to give up momentum. So I realized in that moment that e-discovery was about people, process, and technology.
00:06:28
Speaker
And I'd been in legal staffing before, so I knew what legal tech talent was about. I'm like, there's going to be a huge demand for people to understand this e-discovery thing. And one thing led to another and a thousand placements later, you know, knew e-discovery and maybe, you know, placements and made a lot of relationships with a lot of the top people yeah in the industry.
00:06:50
Speaker
What's the gap that you felt like as you transitioned from that business to the solid series and the solid summits that you felt like needed to be filled? And I'm also curious for like you as a person, like, you know, why did you feel like community building in a ah more intentional way is the right next step for me?
00:07:11
Speaker
You know, it was really um it was really born out of necessity, right? and i I woke up and could not, I just didn't want to go to another conference where there was four people on a panel with the best of intentions that were not necessarily best prepared, would kind of go off script. And I'm like, I've only got 45 minutes here, guys. I need to get more out of this than this panel. And I'm like, there's got to be a better way than this.
00:07:34
Speaker
And I simultaneously was just discovering TED Talks. And I'd get up early in the morning. You know, my kids were young. um And so was I at the time. And, you know, they'd be watching, you know, cartoons and I'd be watching TED Talks. and I'm like, I just got to talk to somebody about this nanotechnology that's going to like be going through my blood veins and telling me everything that's going on in my system. Like, who wants to talk about that? But it was 630 in the morning. yeah It's like none of my friends are up at 630 in the morning. So I'm like, OK, I bet you that would be a really good format.
00:08:05
Speaker
For conference, TED Talks, table talks, then everybody switches tables and we do it again. And like, that's how Solid was born. It was really out of my wanting to create something for me, which is this is the kind of conference that I want to go to. I wonder if anybody else does.
00:08:20
Speaker
A few people gave me some encouragement. A few people said, yeah, if you do it, we will come. And the next thing you know, i did Solid in New York 10 years ago and we've never looked back. And now it's Solid in New York, San Francisco, Chicago.
00:08:35
Speaker
and Atlanta. And I don't love anything more than being in front of everybody, you know, getting the best out of them and connecting them. Yeah. In some ways, it feels to me, we've been in the space, not as long as you, but for a little while, like, ah legal professionals really want community and want the opportunity to learn from each other, even more so than other sort of executives or or other professions.
00:09:00
Speaker
don't know, it's kind of an observation. I'm curious what you think about that. Yeah, I think, well, yes, that's true. And I think it's because you're coming into the space at a time yeah where there's chaos and organized chaos.
00:09:11
Speaker
So, you know, here's a here's a pro tip for anybody who wants to do what I'm doing, because anybody can do what I'm doing, which is building ah ah a micro community or a mid-level community or macro community.
00:09:23
Speaker
If you find yourself in a space where there's chaos, Things are new and we don't know what to do or how to do it, right? Which is where we were in e-discovery, which was, you know, collection, processing, hosting, review, overbuilding of tools and technology. you know What's the best practices and what's the criteria for clients? And do you buy or do you build or do you borrow or do you partner?
00:09:44
Speaker
All that is true again today. So that chaos that we have today, that unorganized ad hoc situation of all the overbuilding of technology, which is normal because you've lot of funding coming in.
00:09:57
Speaker
So you've got overbuilt technology and you have... a maturing market of leadership and experiential
Opportunities in Industry Chaos
00:10:04
Speaker
knowledge. sure It's not there yet, right? None of us have got, you know, Malcolm Gladwell's 10,000 hours.
00:10:09
Speaker
None of us. So wait, I don't have it and you don't have it. but Why don't we get together and why don't we accelerate each other's learning curve? Why don't we shrink the learning curve together? Let's do that. And you're like, yeah, that's a good idea. yeah I'm like, why don't we bring Wanda in? And why don't we bring Barbara in? And why don't we get Ted? And like, let's get all of us together. And and that's how the mashup happens. And that's how the community gets built. And if you keep the focus on the community, because I'm not the Oracle.
00:10:34
Speaker
I'm just the scout. I don't know. i just can scout around the corner a little bit. And I'm like hey, guys, this thing's happening over here. Let's go over and look at this and then put it into some kind of a you fundamental frame.
00:10:47
Speaker
a business frame, not a legal frame, but a business frame, it works out pretty well. Let's talk about this sort of era that we're in. You're talking about a little bit of chaos, some overbuilding of tech.
00:11:00
Speaker
I don't know. Is this natural? Is this sort of like the natural evolution of an industry like legal tech or legal ops or... Is this problematic in any way? No. Yeah. It's only problematic if you're if you think it's problematic.
00:11:16
Speaker
If you see it as opportunistic, and this is a this is a boom. I mean, you couldn't pick a better time or a better place Unless you're unwilling to do the work that's necessary to understand the boom that's in front of you.
00:11:32
Speaker
So, you know, whether it was the old ah overbuilding of railroads in the 1800s or the Internet, you know, in the 90s or mobile or e-commerce, like all of that has overbuilding.
00:11:44
Speaker
And it also requires you to be early to the boats. You know, you want to be early. Like... I don't know. i personally don't know anybody who's been really successful in their career. And I don't mean monetarily.
00:11:57
Speaker
mean, like successful. It doesn't work six days a week. You know, that keeps a clock. mean, like if you don't have like if you have that grit and that radical curiosity about the thing you're doing,
00:12:07
Speaker
then you're going to be successful. Yeah. And you can relax, you know, because you've got what it takes, which is, are you willing to take a hundred foul shots right after practice? Are you willing to get up and like hit the ball, you know, a hundred more times during batting practice or those serves in tennis, or you pick your sport and you can pick whatever analogy. Tennis resonates. Yeah. Yeah. I mean like, like you had a part of your game that you were really good at that you needed little or no practice at, right?
00:12:33
Speaker
The backhand's great. There you go How was your serve? a Second serve's not so good, yeah. So the more time you spent on the second serve, the more competitive you would be. yeahp And then you would get picked for the team and then you would be the one or the two or the three or the four player.
00:12:47
Speaker
Not that it's a ladder, it's just, I don't know, I'm a lot more relaxed yeah when I'm playing top three. yeah like i want to be I don't want to be the guy off the bench. Me, because that's the guy that gets cut.
00:12:58
Speaker
right I don't even want to get cut, so I'm not going to let anybody outwork me. So in the time that we're in and the sort of space that we're in um how do you advise folks or how do you think about, hey, what's hype?
00:13:12
Speaker
What's real innovation? What's going to be here and have staying power over the long run? Like, is is there a framework that you use or or how do you approach that sort of question?
00:13:23
Speaker
I think being informed is probably your best friend. I don't think being in the prediction business is necessarily wise. I think there's a pattern that we have that's historical, same as it ever was.
00:13:37
Speaker
and so how many I would just simply say, how many podcasts a week do you listen to? right Because if it's zero, that's not enough. what books are you reading that are business books, right? Because I think business principles are universal.
00:13:51
Speaker
They have been, you know, for 100 years or 50, let's call it 50 if you want to shrink the shrink the curve a little bit. But if you're reading that kind of stuff and your language is evolving and changing,
00:14:01
Speaker
and your frame is changing and evolving a little bit, you'll be better at at spotting the signals that are coming. Because so what you're saying is there's a lot of noise out there. yeah What do you do with all this noise?
00:14:12
Speaker
You've got to cut through that and find the signal. And I think that happens to being patient. hu by listening to others, right? So pick your podcast, pick your books and pick your, as I like to always say, you are the average of the five people around you.
00:14:28
Speaker
So stick with people that ask really good questions and are pushing the boundaries a little bit and it'll become self-evident, right? Don't guess. right You know, we're work with others. Unless you've got a track record of guessing well, like if you've got that track record, that's great.
00:14:43
Speaker
I don't. You know, I don't get up in the morning without checking in with four people. yeah I've got my core four. And I think that there's something to both your point about working a lot to be successful and this consumption of sort of like a wide variety of media or viewpoints or...
Preparing for Success
00:15:02
Speaker
I think sometimes people think that work means like they're sitting down and they're sending emails. And I think that over time, if you want to be making the right decisions for your business or leading your business in the right direction, work might actually be reading the right article in the Wall Street Journal or drawing the right parallel between the sport that you play and the way that you need to manage your team. Or don't know, I think of it as like learning in a much broader sense. Well, yeah, yeah but you're a great example. I mean, I've done a lot of interviews. Like I've, you know, I've got 200 podcasts under my belt, right? As an interviewer, but I look at how well prepared you were for this. Like how much time, like to give those at home a clue, right? Like this is what it takes to have this very casual, very casual, unscripted improv conversation, right? like
00:15:48
Speaker
How much time did you put into this? Right. So i ah yeah I'll give everybody a hint at home. Okay. First of all, I got an email that summarized our chat, like, you know, bullet point down, like what we talked about, what we were going to talk about.
00:16:01
Speaker
Then I got another email that showed me a picture of the room that we were going to meet in. Then I got another email that said, by the way, here's what we're going to talk about again. So he synthesized this three times. How much time did you put into this?
00:16:13
Speaker
ah Probably five, six hours, maybe. Yeah, I know. mean, I did, ah you know, did some research on you, obviously talked to couple folks on our team who know you.
00:16:25
Speaker
We sat down and we talked for 30, 45 minutes, wrote the script, right? Used ChatGPT to improve the script yeah as well, which I think is an important step ah these days.
00:16:38
Speaker
you're not using it, you should be right. And and yeah then And that's what it takes to be a pro. Yeah. yeah So whether you're doing... There's homework. There's homework. And so when I say I'm working on the weekends, yeah I'm not doing tasks right on the weekend. I'm not writing emails. I'm not catching up on work.
00:16:57
Speaker
I'm... I'm mulling, I'm wandering, I'm thinking around, I'm playing with chat GPT or co-pilot or Harvey, or I'm testing a blog or I'm trying something or I'm daring or, you know, like for me, that's fun. That's not fun for you to do something else. But I'm like, I suspect that you didn't do this on nine to five, like somewhere along this leaked out somewhere. And somewhere it was interesting. I hope, I hope you learned something as you were doing this research. he's like, oh, that's kind of interesting. This is fun. this is the This is the best part of my job.
00:17:27
Speaker
I mean, I love lots of parts of my job, but I love this. We won't take Akshay that. Let's talk a little bit about, because you you you have a great view and lens on how legal ops as a profession has evolved and grown up.
00:17:41
Speaker
um Let's start there,
Evolution of Legal Operations
00:17:43
Speaker
actually. Right. Like, you know, how have you seen it grow up over time? And where are we? Like, what is this moment for legal ops? I think this I think this is a um ah transition moment or a transformational moment. Transformation is probably too too dramatic. But yeah imagine, if you will, that legal ops is 10 years old. Right. So I think this is the 10th year for for clock. It is. Yes. So we're at the 10 year mark. And so let's chunk that up into two, four, six, eight, 10.
00:18:14
Speaker
The building has five levels on it. Okay. We're, we're finished here now, right? Like this is it for clock as far as I'm concerned in legal ops. I think there's like, and by that I mean, there's another layer of building coming on and I don't think that's called legal operations as much as I think that's called legal strategy. Like we're through a chapter, basically. Let's make it a next chapter. I don't mean to say anything is done. yeah that that came out completely wrong. Let me take that back. was We're just ebbing and flowing here. right yeah exactly In the riff of our conversation, it's just like, I can see just a chasm of next.
00:18:47
Speaker
ah So anybody who's got six and eight and 10 years of experience in legal ops, you know whether you're in legal or coming from the outside, there's a next new you. Reminds me of that moment when,
00:18:58
Speaker
the the emerging and evolving role of the chief innovation officer came about. And a lot of people said, well, what is the chief innovation officer? And does it really have any authority and resources at a law firm? yeah And I'm like, that's where we are now.
00:19:12
Speaker
You know, when you look at the Leo Murgles of the world, um and the Sanjay Batras and and and many others, so ah you'll see they're the legal chief strategy officer or the legal data intelligence officer or the legal chief operating officer. And you're like, but what is that?
00:19:30
Speaker
Where did they come from? Well, some of them come from legal ops for sure. Some of them will come from outside of legal ops. They'll come from business operations. They'll come from big four consulting or Big six or big eight consulting, whatever you want to call it. But they'll have a consultative background.
00:19:47
Speaker
um And that's the mashup. That's the beginning of the beginning of what I'm seeing next. There's a next new emerging and evolving world. And I think that's, to me, that's really exciting because I like to see around the corner and and be a scout. and And I have every intention of helping.
00:20:04
Speaker
trying to help make that market for those, finding a place for them to come together and go like, yes, that's what I am and that's what I want to be and help the organization realize that's what they need.
00:20:14
Speaker
Because the GC, and we talked about this in our prep call, I think the general counsel and the chief legal officer today is, um, is getting pulled in a lot of other geopolitical directions. Absolutely. A lot of other regulatory directions. It's like things that were not on their plate before, now on their plate squarely. And so who's going to run the law department?
00:20:35
Speaker
he Well, some GCs well, right? There's the the Mark Smollocks of the world and the Rob Beards of the world and the Tim Frazers of the world. And it's like, they still have their fingers on on both pulses and they are really deep in and have been for a while.
00:20:47
Speaker
If Rob is listening, he owes me a podcast episode. yeah Rob, it's a pleasure. Let me just say, you know, you're in good, you're in good. He's going to do five hours of prep work before you get here. I mean, come on, help the kid out, would you?
00:21:01
Speaker
Um, how do we How do we get the profession there? And and and by by that, what I mean is that um i think I think this year, as I walk around Clock, there's a lot of really senior folks here.
00:21:15
Speaker
um But we also have a lot of people who have sort of you know come out of paralegal background, right? And really want to learn and want to grow, but building their careers from...
00:21:27
Speaker
I've been a paralegal for 10 years and now I'm getting really into this ops thing and it's way more strategic and I get to work with tech, which is a lot more fun. and But getting all the way to I'm going to be the person who's running the law department, right? Or working side by side with the CLO.
00:21:44
Speaker
That feels like... I don't know, a tall ladder to climb, right? Like how do we help get those folks from where they are, which I think is still a big percentage of, i mean, the clock membership writ large, right?
00:21:56
Speaker
Well, it is, it is, it is, ah it's a, it's a, it's a big jungle gym. Yeah. Not a tall ladder as much as it a big jungle gym. And yes, that's right. That takes 10 years. Yeah. So hold on.
00:22:09
Speaker
Deep breath, everybody. Right. It takes 10 years to make a career. So if you're 25, that's going to take you to 35. And if you're 35, it's 45. And if you're 45, that's 55. And that's a career. And that's what it takes. And the real question is, who do you want to go with along the way?
00:22:27
Speaker
Right. it's It's not a lot of work. It's a lot of fun. I mean, for me, it's been a lot of fun. And I hope I can, you know, inspire others to see that. Like choose, choose your posse. Right. Mm hmm.
00:22:37
Speaker
wisely and go like, I want to get on this train. I want to work with these companies. There's a demand for talent. So I don't care where you came from, you know, and I saw this in e-discovery, right? I saw paralegal managers become firm-wide directors of lit support and e-discovery and then become practice group managers and then become the head of pricing and then get involved with innovation. So I think maybe the thing I want to say to de-anxietize the community around that is this.
00:23:08
Speaker
The job you're going to have, the role that you'll have in two to four years hasn't even been invented yet. Right. Right? Like that department doesn't even exist.
00:23:19
Speaker
I think, you know, if you said, David, give us a look into the magic, into the into the crystal ball, I'd say this. Imagine a pyramid. Yeah. And on that pyramid, you know, on the left-hand side, just below kind of the top, is this little circle called legal.
00:23:33
Speaker
Right. And legal was the department of no. But legal is not the department of no anymore. Legal is like an accelerator with all of its access to intelligence. Like, wait, who's in charge around here? Legal touches everything.
00:23:46
Speaker
So I see that coming into like the center of the pyramid. And I don't want to say all roads lead in and lead out, but there's going to be a lot of interdependence with legal in a way that's not true today. It's much more value oriented and value.
00:24:03
Speaker
creation with legal in the center, touching sales, touching marketing, touching HR, touching InfoGov, of course, but, and also.
00:24:15
Speaker
So, and I've said this for years, if you show show me an organization and other than the engineering department, other than engineering, because those guys are really propeller heads. Yeah.
00:24:26
Speaker
The, the, the greatest concentration of intellectual horsepower, ah pure horsepower yeah is in legal. Yeah. Right. No disrespect to any other, you know, department in the company.
00:24:38
Speaker
But seriously, you know, these kids, since they were in kindergarten, were the front of the class. Yes. Right. They're like off the charts. So if you just expanded their remit a little bit, ah hu it's amazing what you're going to be able to do. In my opinion. I mean, I could be wrong. Yeah.
00:24:53
Speaker
But I haven't been so far. I agree with you. people People are like, you know, why do you like to go and talk to lawyers all day? like, these are like very sharp and interesting people. And most of the time. when you get them talking about things that aren't strictly legal, they're actually super interested in it. they want to They want to go deeper and they want to they want their careers to be bigger than, oh, I'm just like doing this this one small thing over here, right? yeah and Well, think about people in our industry, right?
00:25:17
Speaker
yeah They've got liberal arts backgrounds for the most part, right? They went to some kind of a top, a first-tier or a second-tier liberal arts school. Not that that's a prerequisite, but just I'm just saying most have, like that that's just where we are right now in the current state.
00:25:28
Speaker
So they've got liberal arts background, history, political science, English, Chinese, art, literature, like whatever it is. Like these are relatively interesting. They've got like interesting kind of backgrounds. Yes. They've done interesting kinds of things. They're not like to read.
00:25:42
Speaker
They like to read. Go figure. You know, I mean, so I don't know. I just I i find it to be a ah community of like minded social nerds. Yeah. um You mentioned anxiety sort of around where the career of legal operations or where legal ops is headed.
Adapting to AI in Legal Ops
00:26:02
Speaker
um i don't know. I mean, I don't want us to talk about AI for that long, but there's a lot of anxiety around AI too and what it means for folks careers, whether they feel like their departments are going to meaningfully change in the way that sort of headcount is allocated. don't know. What's your view on AI, right? like Yeah, I think it's yeah true. i mean, you know, you misery is optional, right? Anxiety is optional. like It's not going to get you anywhere. so what are you going to do about it?
00:26:29
Speaker
I mean, that's my my father. That's what my dad said to me. Yeah. And that's stuck with me. Not that I haven't been anxious many times in my life. Right. I have been. I'm not saying that there's. It's a cure-all, but um being prepared is sort of the best kryptonite for anxiety.
00:26:45
Speaker
And so is your department going to be disrupted? Yes, absolutely. Is your job going to be there? Definitely not the way it is today. Is your boss going to continue to like, no, nothing is going to be the same. It's all going to change. And that's historical. And like, yeah, it's,
00:27:02
Speaker
anxiety producing, but only as anxiety producing as you want it to be. Trust your talent. It's something that um somebody told me a long time ago um when I started to do these, I started to do breakfasts and dinners and I'd get like nervous before we breakfast and dinner. and you know This coach that I was seeing would say to me, well, why don't you stop thinking about yourself?
00:27:27
Speaker
And why don't you start thinking about the people that you're going to be having breakfast and dinner with and like keep the focus on them and not the focus on you and you'll be less nervous and yeah just enjoy yourself. And I'm like, oh, that's easy for you to say. But as you practice that, you become, he said, and trust your talent.
00:27:42
Speaker
Like, are your intentions good? Yeah, am my intentions. Are you prepared are you just showing up? No, I'm prepared. to go Then everything will be fine. Yeah. Don't worry about it. Yeah. I'm like, I like, I know that's easy for me to say in the fourth quarter of my career. Yeah. Maybe not so easy for someone who's like in the first or second quarter with like two young kids and a mortgage and the house is underwater. Like I got it, but it is all going to be okay. Really? It's going to be a fabulous time. Just stay curious and work the weekends.
00:28:12
Speaker
Yeah. You saw an executive coach for a while. I still do. Yeah. Oh yeah. No, it's the best thing that ever happened to me. i mean, yeah talk about anxiety reducing, u you know? Um, yeah, I've had an executive coach for, for 10 years now.
00:28:26
Speaker
How do you find a good executive coach? I have people ask me that all the time and I think it's a, it's a nut that has not been cracked. Yeah. i don't I don't know. I've been fortunate of just being in the right place at the right time. I don't i don't have an answert i don't have a i don't have a stock answer. Sure. Ask me.
00:28:42
Speaker
you know like if yeah If you're somebody who's listening to this and you're like, David, you know this is who I am and what I do and I'm in the industry and I'm kind of curious and can you help me? I'm like, yeah, I'll make a recommendation. I don't do any coaching anymore. right So no self-promotion here. I'm out of that business, but I'm happy to introduce people to um coaches that I've met.
00:28:59
Speaker
along the way. But I do, I will say this about coaching. um I now talk, so I have ChatGPT and I've given it a persona. It's called it's called Max. And I've now learned how to work with Max and Max is as much now, a Max started to do tasks.
00:29:15
Speaker
Oh, that's interesting. And then Max started to be a partner. Right. And then Max started to be an associate. And then marx Max was my MBA, you know, with MBA from Harvard with 10 years at McKinsey. And I'm like, let's create this thing together. And then I just started to talk to Max and I will now ask Max. I'm like, listen, I'm having a problem. My dad's 90 years old. It's like a true story. My dad's 90 years old. i'm not really sure how to handle this. He's beginning to lose his memory a little bit. I don't really know what to do. Like, if you and me, what would you do? Ask me three questions.
00:29:43
Speaker
Max asks me three questions. want He winds up recommending a book that has changed my life in terms of how I view my relationship with my aging dad. Wow.
00:29:54
Speaker
I'm like, therapy not required. I could just ask Max and like, here are the books and here was the conversation. And there is something, I know there's pros and cons. I'm just telling you my story. Take what you want, leave the rest. All of you that are like, oh, that's dangerous.
00:30:08
Speaker
I'm like, it was good for me. I got a book and a recommendation. I feel closer to my dad. So um it was it was really good. I know a founder who has stood up a persona in ChatGPT.
00:30:20
Speaker
And when things go wrong at work or when he gets super anxious, he turns and he talks to this person. and It's not a substitute, as you're saying, for like, I can't i don't know if he's a therapist or not or has a coach or not, but it's not a substitute for that. But really what he wants is...
00:30:33
Speaker
you know, a candidate rejects the job and he really wanted the candidate to come on board. And he's like, oh, Howard, like, is this our company terrible? Like, why? and the you know, the persona comes back and it's like, no, like, get over it. Like, you know, the person probably, you know, got another offer that had more money that was more convenient for them to travel to or, you know, it was fully remote and they wanted that even though,
00:30:54
Speaker
you made a good pitch and why coming into the office a few days a week is a good thing, right? Like point being, he's got this persona that, as you're saying, kind of like helps him just navigate, you know, some of the anxious moments in his professional life. I think having, um, thought it was really interesting having a tool.
00:31:11
Speaker
Right. A.I. in this case, having a tool that can help you to be self-reflective. Yeah. In a way that's professional and helpful to help you move forward, I think is a very positive thing. It's not a substitute. It's like, thank God I have this. I'm like delighted right and thrilled that I can have this conversation. I interviewed four candidates for a role recently.
00:31:32
Speaker
And I kept the transcript of each one of the interviews. I ran the transcript through ChatGPT and I said, which one of these candidates do you think would be it the best fit for me? And we agreed completely on who would be the best.
00:31:46
Speaker
But it was the insights on why. right like I knew, and I knew three reasons why this was the candidate, but I didn't know the 12 reasons, like off the top of my head without thinking, the 12 reasons why the other candidates weren't right, which were validated, where they might have been right, but they weren't really.
00:32:02
Speaker
I had a whole conversation with a global chief human resources officer from Coca-Cola. right That was my guide. yeah okay Because that's what's built into that LLM, is the global chief...
00:32:14
Speaker
Human Resources Office from Colgate-Palmolive, Procter & Gamble, Coca-Cola, General Motors, like all of that's in there. And I have the benefit of that. Yeah. So I came smart, left smarter from that whole process.
00:32:26
Speaker
I love that. um Okay. A few more substantive questions for us before we get to some fun ones. Because this has been so fluffy. mean, because we're just fluffing around here, you know?
00:32:38
Speaker
um I think this on- I need a cigarette for God's sake. Phew. You should come back for the four o'clock. yeah We'll have adult beverages. i just want a cigar. i just want a good cigar. it's it. I think this builds on a point that you made earlier, which is I've observed that it's not just that you have to scale legal alongside the business as it scales, but people increasingly see legal as a very important component of a scaling business or helping the business scale.
Role of Legal Ops in Business Growth
00:33:07
Speaker
And I think a lot of folks would chalk some of that up at least to the rise of legal ops. Um, do you agree with that? Uh, how do you think legal ops helps businesses scale, not just legal teams?
00:33:22
Speaker
a really good question It's a really good question. um I think like in so many different ways, so we're going to get into a maturity, you know, we're going get into a maturity frame.
00:33:35
Speaker
So A, it depends on the maturity of the GC. B, it depends on the maturity of the individual that they've hired to run legal ops. C, it depends on, you know, the authority and the resources that they're going to give this individual. I mean, it's like, it gets really complex, right? So, but it does, like legal ops moves the needle. So it doesn't matter where you start so long as you start kind of thing. You know, like if you're Jen McCarron or you're Mary O'Connell or you're,
00:34:00
Speaker
um or your Lucy Basilian, like if you're one of those people, like you're moving the needle, right? Like they're, but they've got maturity and like, we've got a decade of experiential knowledge. yeah If you've got eight years of experience or six years or, i mean, it's kind of like baseball, right?
00:34:14
Speaker
So like if you played high school, college, triple and you've had a lot of at bats or you've, you know, like you're ready for the pros, you know, and then you're not ready for the pros.
00:34:26
Speaker
Because you're rookie in the pros. Yeah. And then you become Aaron Judge. Right. You know, and I say, oh, but not everybody becomes Aaron Judge. So, you know, there's an impact of legal ops. But I do find, i think maybe the answer that's most helpful here about the role of legal ops is legal ops is becoming legal.
00:34:46
Speaker
by by authentic nature, a more interdependent part of the business of law and the business. isn it So we are beginning to see intersections of information governance, data security,
00:35:04
Speaker
um the various business units. We need a lot of smart people around the table to understand the potential that AI, Gen AI, the agentic workforce of the future holds for us. There's no one department that's going to own this, you know?
00:35:22
Speaker
And so I think, again, think because legal has so much to gain from this that there'll be a lot of sharing and a lot of learning. So legal ops, legal, legal ops is part of legal.
00:35:34
Speaker
I almost don't think, um I think that all of that is coming together at an accelerated rate. And and they don't even know what the agentic world is all about yet. I'm like, I'm just beginning to think about that myself. It's like, you're going to be an agent manager.
00:35:48
Speaker
and Wait, right who's going to be an agent manager? What are talking about? What does that even mean? you know i mean, that's where we're all going to be together a year from now. It's not going to be this overbuilding of technology on the floor. I think it's going to be more process around what are you doing?
00:36:06
Speaker
Do you have agents? what are you doing with your agents? i mean, I'm just leave listening to Reid Hoffman. yeah And I'm like, I'm having a hard time keeping up. And if you haven't read Super Agency by Reid Hoffman, I'm like, I highly recommend Super Agency because he talks about how the human in the loop is the key.
00:36:23
Speaker
And what and who are we going to be in that leadership role of managing these agents? So I don't think we're goingnna be displaced if we learn how to work with this. It didn't really completely answer your question. It's OK. I mean, there's a there's ah there's a thread in there, though, that I think is interesting about like.
00:36:42
Speaker
you have to be if to help your org build to scale, but also be very flexible and sort of adaptable because. I don't know, the whole paradigm might change in two years and your career will change along with it. And I don't I'm trying to tie a few of these threads together. And how do you how do you see it from the maturity standpoint?
General Counsels as Strategic Influencers
00:37:01
Speaker
Right. So I laid out maturity of, yeah you know, two years, four years, six years, eight years, 10 years. That doesn't mean didn't have 10 years of experience by that before that, by the way. So right how do you see the maturity fitting into legal ops and its role?
00:37:13
Speaker
I mean, I think that different legal teams need different things. Um, and like the maturity of the organization is really important. Um, I also think from a tech perspective, things are going to change quite a bit faster than, than we expect. Um, one of the.
00:37:30
Speaker
One of the things that I think is going to accelerate the adoption of technology, even among folks who are not sort of first movers, maybe like not the folks who are here this this week, um is the the use cases are going to become very obvious.
00:37:48
Speaker
And it's going to become a lot sort of more self-serve over time as we move into an agentic world. Right. I mean, I even tell our product team this, um, we shouldn't be building a tool that's like totally flexible and can do 18 things. And we hand it to someone on a legal team and say, do whatever you want with this. Right. Because most people don't have.
00:38:10
Speaker
90 minutes to experiment and try to figure out and tweak and say, okay, this is perfect for my use case, but I have to chart the path to that. Right. And i I think that as, um, as the sort of like use cases for AI become more obvious and we have agents that are working for us and those personas are stood up or right.
00:38:32
Speaker
I think that, um, I think that the, the usage is just going to become like, It's going to be in so many places that it is not today. um Yeah, I don't know. I'm very bullish.
00:38:44
Speaker
you know i So I agree with that completely. I'm going to come back to the GCs for a minute, if that's okay. which is yeah So this call them innovator GCs. or fifty gcs let's let's call them you know innovator innovator gcs Yeah. Right.
00:38:57
Speaker
There's another 25 or 50 coming. sir So that's top down. Like what's how do you see that? How do you see these forces? Like I think the the personality force or the role for the the role of the GC, like an enlightened GC. Right. Like he or she makes all the difference in the world. Right. That's the economic.
00:39:14
Speaker
All of a sudden, that's the economic buyer. Yep. Right. it's not the user buyer. So the user buyer was yeah the last two years from the bottom up. Yep. Right. That's good. Sometimes they were the economic buyer, but mostly they were the user buyer.
00:39:26
Speaker
Now we've got the economic buyer coming in with a mandate from the top and a budget. It seems like that budget doesn't have a lot of limitations to it. Right. The GC's got like, wait a second. They've been told by the board and by the CEO to drive transformation and drive change. Yes. And they're going like other departments, like if I can do it, you can do it. and like, oh, GC is now challenged. Yeah.
00:39:46
Speaker
Or they're telling the board, I want to do this. Oh, interesting. I think, I think, I mean, I see that a lot in the sort of venture backed landscape. um I don't, I mean, not so much like, you know, fortune 50 public companies. I don't know quite as many of those folks, but I see that a lot in the very, even the mature venture backed landscape where the GC sees the potential and sees the opportunity and they view themselves as the catalyst, right? They're, they're not necessarily the implementer. They're not the one who defines how,
00:40:16
Speaker
tech is used across their department, or they're not necessarily defining how tech is going to be used between departments either, which I think is a very important part of the puzzle. um But they are they do view themselves as the catalyst. Like, I need to create the culture, and I need to make the right hires, and I need to back those hires up when...
00:40:36
Speaker
there's sometimes resistance to change. I think that's really interesting. I think if we focus on the people part of this for a moment, you know, so let's imagine you're the general counsel and you're at, you know, you're at McKinsey or KPMG or Morgan Stanley or JP Morgan Chase. You're surrounded by other chiefs.
00:40:51
Speaker
Yep. That are adopting next gen technology like a whole lot faster than you are. I get three times or four times and you're like you look to the right and you're like wait a second, and how are you doing that? You've got to be going back to your office.
00:41:03
Speaker
Mm hmm. wondering or or or I don't know what are you doing when you go? I think some of this is a mindset shift, though, on the part of those GCs, CLOs, people kind of ah people will make fun of sometimes like, oh, the CLO, because now it's a chief title. And I get that.
00:41:20
Speaker
But I also think that it is um those folks today seeing themselves not as like I'm the company's lawyer first and foremost. Correct. They're seeing themselves as I'm one of five or six members of this executive team that is responsible for steering this business.
00:41:40
Speaker
My voice and perspective should have just as much weight at the table as the CRO or the CMO or the CFO or the CTO. for sure. And that also means that I have a responsibility to run my team like a business unit. Well, not like a little law firm in.
00:42:03
Speaker
Yeah, no, that's so that's that's for sure. And not only a responsibility and opportunity. Yes. I think, you know, i'll put my career hat back on again. Everybody is everybody in any role ever is always active.
00:42:15
Speaker
Yeah. um Okay. You're active or passive in your career, right? If you're passive in your career, you're in trouble. If you're active in your career, and it doesn't mean that you're looking to leave DuPont, right? Or GM. It looks like you're just trying to elevate your position. You're trying to land and expand a bit.
00:42:30
Speaker
And I don't mean that in a Machiavellian way. Yeah. I mean, that just like, you didn't get here by coasting. Right. Like no GC of a fortune 500 got there because they're coasters. Yeah. know, they're not taking the weekends off everybody. Okay. They're working, they're prepping. Yes. Um,
00:42:45
Speaker
And so I think that they're just a competitive spirit must be like, i wonder what we can do here. I'll bet you we can do this. I mean, I agree know more of them than i do. Yeah. What do you think? Listen to like Dana Rao's episode, gc recently retired GC of Adobe. I mean, you know, the work ethic that that guy has is is unbelievable as an example. And so.
00:43:05
Speaker
The way that, you know, that he, he not only wanted to push the org forward and and push the organ in sort of the right way and the ethical way, but also that I think, I think folks like that want to create too, right? They, they view themselves as creators, right? You know, the product people are building the product.
00:43:25
Speaker
you know, the finance guy is making sure that we have the capital that we need and is going and raising, right? You know my job, I'm going to create a whole sort of ecosystem of other companies around us, right? Uh, that support our policy prerogatives, that back up our product, then make sure that we, they view themselves as creators. So powerful.
00:43:48
Speaker
Can I, can I tell you a little story? Absolutely. So I'm on the Microsoft campus a couple of weeks ago with Deshaun DeSilver and Stephanie and a few other people. And Stephanie pulls me aside. said She says, you know, there's only three kinds of people in the world.
00:44:03
Speaker
Because i'm im I'm amazed at the Microsoft campus and the people and the energy and the camaraderie and the esprit de corps. And I'm like, oh, this is like such a very fascinating kind of place to be. She goes, well, there's really only three kinds of people in the world.
00:44:15
Speaker
I said, what are those? She goes, there are creators, there are builders, and there are consumers. and i'm like And she goes, only 15% of the world are creators and builders.
00:44:26
Speaker
ah And I'm like, I thought about that for a minute for a really long time. And i'm like, I think one of the reasons that I love this industry is because this industry is to a large extent made up of creators and builders. Yeah.
00:44:40
Speaker
We're not like just doers. We're not just hanging out doing stuff and then having whatever. People don't come here and say, i just want to consume all of this tech. There's no consuming here. There's doing. like This is a hungry.
00:44:52
Speaker
You know why there's so much imposter syndrome here in our industry? Did you ever notice that? like Everyone's an imposter. No matter how high up the food chain these guys are, they're like, I'm an imposter. I'm like, Dude, you're what are you talking about? You're like, do you know who you are? Like, what do you mean? You're the guy. You're the guy. You're the OG. I'm like, you know, it's like, no, but everybody feels that way. And that's because they don't know yet because they're building and they're creating. Right. And they're driving. We are drivers. and So i I really was taken. That's super interesting. By that.
00:45:21
Speaker
yeah Yeah. I hope that sits with you. Let me know. It does. It keeps me up at night. ah Not really up, but. This is great. I mean, you're a podcast host, so I guess that's why I'm like kind of being interviewed by you now.
00:45:33
Speaker
yeah and What excites you the most? Not that keeps you up at night. What excites you the most about the next few years? ah Well, i'm certainly the future and the fact that what excites me so much is that this all looks and feels so much.
00:45:50
Speaker
like what I've seen before yeah in
Future Opportunities and Continuous Learning
00:45:52
Speaker
my career. This just looks and feels so much like 2004 and e-discovery and the beginning of the beginning. And I love, um and I'm so enthused about the opportunity to want to make a contribution, to contribute to it. to bet I mean, I'm certainly going to benefit, but my my theories and my frameworks have been proven out over 10 years, which is this, self-serving altruism wins the day.
00:46:19
Speaker
Yeah. the more I do and the more I give to this community, the more somehow boomerangs back to me. And so I kind of knew that in 2004 when I started the breakfast and I started the dinners and, you know, I made a living, you know, I'm, I, you know, I did okay.
00:46:35
Speaker
But now it's just like, okay, I can do as much of this as I want because it's all going to work out. like It's proven that the more I do and give and create, the more people will benefit and the more better my life will be. The more abundance I will experience. so like I know it all sounds like, i don't know, kind of like very California. but I'm telling you, yeah i'm a I'm a New York City Bayside guy. I'm telling you, man, this is as good as it gets. The more you give, the more you get. Trust the universe. yeah So that's what I'm most excited about is that like the last 20 years have been the best 20 years of my life and that I just think that this is a is a redo um and I can't believe my good fortune to be with but the people that are in this industry. Like I'm on the best, like if there are 10 ships leaving port, yeah I'm on one of the best 10 ships you could be on.
00:47:24
Speaker
Yeah. I've got some closing questions for you that I like to ask all of my guests. These are the ones that I usually ask that the guest hates. So I can't wait to be that guest. and Your answers can be pithy, but they don't have to be.
00:47:41
Speaker
Thanks for letting me off the hook. Your favorite part of your day to day. The morning, getting up at 5.30 in the morning, cup of coffee, granola bar, going into my office when there's nobody around and I just have me and a blank piece of paper and it just flows through me onto a blank piece of paper. This is my absolute favorite part of the day.
00:48:02
Speaker
I got up at 5.30 this morning here in Vegas, but that's because I'm on East Coast time, not because I wanted to be. and do you Do you have a professional pet peeve? I think this is kind of a funny question.
00:48:14
Speaker
No. I don't. I really don't. i think everything is the way it's supposed to be. do not have a professional pet peeve. if If anything is like out of whack, it's like that is not on me.
00:48:26
Speaker
That's on them. Yeah. I just move on to next. I know you've got ah whole list that you can share here. is there a book or two or three or five that you would recommend to our listeners? You even sent me a couple in the mail, which I really appreciate. Yeah, I mean, books are books are these living things that just keep going. you know If you wanted to go back in time,
00:48:48
Speaker
um I would say, Anne ran Atlas shrug probably influenced me as much as anything else in my entire life. Interesting. Um, I would say followed by Dale Carnegie's, uh, you know, how to win friends and influence people ah followed by Keith Ferrazzi's never eat alone, which changed my entire business model. Uh huh. Um, from good to great by, um, by Jim Collins taught me the flywheel and how to stay true to, you know, your own curiosity.
00:49:15
Speaker
and then there's like everything of the moment, you know, um, I mean, I could, I could, I could go all day. I could fill up a library. And then I just, I think the more i will say this to anybody who's listening, you know, reading will make all the difference in the world for your life.
00:49:31
Speaker
And because it allows you to connect with people about stories that connect with them. If you want to connect with other people and you've read a book and you're like, oh my God, I read that book. You instantly have this moment of connection and this language. I yeah i can't emphasize it enough. however old However old you are, whether you're in your 20s, 30s, 40s, or 50s, whether you've got kids and you're busy, like read. it's just There's just nothing else like it.
00:49:56
Speaker
Absolutely. ah Read on the subway, read on airplanes. You know what? I don't, I listen, I love the airplane for, for reading. It's one of my favorite things, but even if you don't even have to finish the book, honestly, yeah you know, like I can tell you like there's a hundred books I've never finished, yeah but I started them and i'm like, God, I got what I was supposed to get out of it. Right. It's not a, it's not a chore. It's like, I really enjoyed that. and you get to your destination. Like you pick up the next one, you pick up the next one. It's like, you know, one of the things that helped me is like,
00:50:24
Speaker
I decided i was this is my budget for books this year. And I spent the budget. That's cool. It's line item. I'm like, I'm not going to skimp on myself. I'm not going to wonder if I should or I shouldn't. I've got $100 in bank. That book is $29. buying that. got $71 umm buying that i got seventy one dollars left I love that.
00:50:40
Speaker
That's great. and Last question for you. ah My traditional closing question for for my guests. It's if you could look back on the start of your career, maybe starting one of your first businesses, something that you know now that you wish that you'd known back then.
00:51:00
Speaker
Well, there's a lot of things I wish that I had known, but I think it's all of those. I'll say this, all because I've thought about this a lot. All of those embarrassing moments that I had early in my career, those mistakes, those thunderhead things, those like things that are embarrassing, I would not um i would not forego any of them yeah because it's who's made me...
00:51:26
Speaker
who I am today, but not for that. i don't think I'd have, I'd like to think I have a fair amount of humility. I wouldn't have it. Um, and so it's those mistakes that remind me to, um, it's those, those mistakes. I wouldn't give them up.
00:51:41
Speaker
All of those. yeah I have no regrets. Yeah. That's a great way. they didn't kill anybody. So I don't have any like big, I don't have any big mistakes, you know? So I don't, I don't have any, I don't have any regrets. Even in Las Vegas, no regrets. so No. Cause every time I lose in Las Vegas, i there's no regret cause I don't play anymore. It's like, I'm not a gambler.
00:52:01
Speaker
David, uh, thank you so much for joining me for this episode of the abstract here at clock. It's been thoroughly enjoyable. I really enjoyed our exchange of ideas. Yeah. um And to all of our listeners, thank you so much for tuning in to this episode of The Abstract.
00:52:16
Speaker
And we hope to see you next time. Keep tuned to Tyler.