The Hidden Power of Technology for Midsize Firms, with Ari Kaplan

Zack Glaser (00:12):
Hi, I’m Zack.

Jennifer Whigham (00:13):
And I’m Jennifer Whigham. And this is episode 529 of the Lawyerist Podcast, brought to you by the Legal Talk Network. Today Stephanie talks with Ari Kaplan about leadership qualities and the evolution of decision-making in his firm.

Zack Glaser (00:27):
Oh man.

Jennifer Whigham (00:28):
Yeah. Happy Halloween.

Zack Glaser (00:29):
Yeah, yeah, yeah. Happy Halloween.

Jennifer Whigham (00:31):
Thank you. I mean, it’s not Halloween right now, but because things are recorded earlier, we’re pretending So we’re cosplaying Halloween,

Zack Glaser (00:38):
Which

Jennifer Whigham (00:38):
Is what Halloween is.

Zack Glaser (00:40):
Yeah, I mean, yeah, I guess it’s,

Jennifer Whigham (00:44):
You know what I wish we had thought about is somebody, and now I can’t remember who, maybe it was just me compared us to Jerry and Cookie from Best In Show. So Catherine O’Hara and Eugene Levy’s characters in the movie Best In Show, and I wish we had dressed up as them because it is accurate.

Zack Glaser (01:00):
My God, that would’ve been pretty good.

Jennifer Whigham (01:02):
Yeah.

Zack Glaser (01:03):
Well, okay, what are you dressing up as? What are your Halloween plans?

Jennifer Whigham (01:07):
I don’t have any, but every single year since I was 20 years old, so 67 years ago, I dress up as Courtney Love.

Zack Glaser (01:16):
Oh, that’s good.

Jennifer Whigham (01:17):
That is my go-to is Courtney Love A little smear, a little mess up the hair.

Zack Glaser (01:22):
So like whole days or Correct?

Jennifer Whigham (01:25):
Oh yeah. Courtney Love nineties, whole days. I love whole the band. What about you? Who are you?

Zack Glaser (01:32):
Well, so this is a costume. This whole persona is a costume. I know who you are for real. I’m a high speed stock trader in real life

Jennifer Whigham (01:42):
Stock Trader.

Zack Glaser (01:43):
So yeah, this is my costume. No, we do some We a Christmas, not Christmas. We’re talking about Halloween, right? We do Halloween party for my cross country team. And so I usually go with some sort of coach.

Jennifer Whigham (02:01):
Ted Lasso. That’s right. Your Ted Lasso costume was spot on. I wish everybody could see this, but Zack as Ted Lasso. Perfect.

Zack Glaser (02:10):
It’s pretty simple. I like simple when it comes to, I like costumes that you can wear somewhere else. You can go out throughout your day dressed as that. If you go karate kid on it and you dress as a shower, you’re not going shopping in that dress.

Jennifer Whigham (02:28):
As a shower.

Zack Glaser (02:29):
Did you not see Karate Kid?

Jennifer Whigham (02:31):
You know what? I am of the demographic that I should have. I’ve never seen it. So that sounded random to me. I’m sorry.

Zack Glaser (02:38):
Okay. Well, I mean he dressed as a shower.

Jennifer Whigham (02:40):
Okay, I believe you.

Zack Glaser (02:40):
But then William Zab, the other character dressed as a skeleton that you can go do things like that.

Jennifer Whigham (02:52):
I guess unless people think you’re dead.

Zack Glaser (02:54):
I mean those people would be pretty

Jennifer Whigham (02:59):
What?

Zack Glaser (03:00):
Oh no, I want to say dumb, but then I’m like, I don’t know people.

Jennifer Whigham (03:03):
They would just be, I think they would, I don’t know where we’re going with that one, but anyways, but on Halloween, do you give out candy? Because we shut all of our doors.

Zack Glaser (03:11):
We give off so much candy.

Jennifer Whigham (03:14):
You’re better than me.

Zack Glaser (03:15):
Well, my wife and I, we don’t have kids.

Jennifer Whigham (03:17):
I don’t either have and that’s why I shut the blinds.

Zack Glaser (03:22):
So I guess there’s two ways you could go with this. I go the other direction where we, I mean Kira will, my wife will pour the bowl into kids bags, just handfuls of candy.

Jennifer Whigham (03:39):
I love that.

Zack Glaser (03:42):
It is fun. It is neat. I like seeing all the little kids come through and just be excited about their, what are you?

Jennifer Whigham (03:51):
I like that you’re convincing me. I just don’t want to open hear my, someone knock on my door. It makes me want to hide.

Zack Glaser (03:56):
You have to keep your door open.

Jennifer Whigham (03:57):
Fall off shelter. You live in Minnesota. I can’t keep my door open. You know what my heating bill would be?

Zack Glaser (04:03):
Well, you could just go outside, right?

Jennifer Whigham (04:05):
Don’t want to go outside. This is too much of a barrier for me already.

Zack Glaser (04:10):
Dresses like an Arctic Explorer.

Jennifer Whigham (04:12):
I could.

Zack Glaser (04:13):
That’s your costume.

Jennifer Whigham (04:14):
Or I could just hide. I do every year. But I like the spirit of you. You have a better spirit than I do for Halloween. And with that said, I think we should listen to Stephanie’s conversation with Ari.

Zack Glaser (04:26):
That would probably be much more productive.

Ari Kaplan (04:29):
Hi, I am Ari Kaplan. I am an analyst that covers legal and it’s a privilege to be here today.

Stephanie Everett (04:34):
Hey Ari, I’m excited to talk with you. You have a kind of cool job because I mean, in my words, not yours, you would explain it better. You get to dig in and figure out what’s happening with law firms, what they should be thinking about doing. What else? How would you describe that?

Ari Kaplan (04:51):
I don’t even think I have a job. I don’t think I’ve had a job in over 18 years. It’s kind of an incredible gift in that I practiced law for nearly nine years. I left in the summer of 2006 to become a writer, which I have to say pretty much everyone thought was kind of a dumb idea except for my wife with whom I just celebrated our 24th wedding anniversary. And she said that if you think this is the right way to go there, and it’s been a wonderful journey over the last 18 years. And you’re right, I do what I do, I think is very cool. And I get to speak to leaders in the field, but they’re really not limited to law firms. I mean, I just finished speaking to a whole range of general counsel in 10 countries. I was lucky as to speak to chief operating officers and chief information officers in general, some executive directors at law firms across the country. I’ve just recently been in the midst of speaking to law firm partners in many countries around the world in connection with trends and litigation. So the work that I do is just, it’s wonderful, really a gift. But you’re right, I get to have these conversations and to learn where people are shifting and adapting and changing direction and then try to summarize it to share those trends in the aggregate with the broader community. So I always say I get to do lucky work, and I think that’s very true

Stephanie Everett (06:22):
For sure. I mean, you probably have a pretty good pulse and sense of what’s going on in legal in this big thing, this big industry that we’re doing on all these different levels. And so I’m excited to hear a little bit more about what’s happening, what we should be thinking about, and this new report that you have coming out that I think attempts to summarize some of those changes.

Ari Kaplan (06:47):
Yeah, I mean I guess I always think that I have a pull, I understand the pulse of what’s happening and I have no idea. And so I remain curious us all. I mean, I think that that’s probably a pretty fair assessment that we all think we know where we’re going except we don’t know it all. And because the ground continues to shift and the expectations continue to change. And so this report is really about that. It’s called the Changemakers Report, how mid-size law firms are achieving growth through adaptation. The point was really to try to capture a sense of what are firms. And the focus was really, although I spoke with people at firms between 13 and 230 lawyers and 22 to almost 400 professionals total, it was really about what are mid-size law firms, a number of small law firms, but in general mid-size law firms thinking about and how are they adapting to this shifting climate?

(07:50):
And if I can just get to the chase here, there’s a lot of opportunity. And as someone that wrote a book called The Opportunity Maker, that really speaks to me and I think it’s really important for people to recognize that in this market, good market, bad market, changing market, there’s opportunity. And I feel like as much as there has ever been, there is tremendous opportunity, particularly for small and mid-size firms, which are the firms that I studied, because technology is giving them an incredible opportunity to scale in ways they otherwise wouldn’t have been able to, whether it’s providing a level of administrative analysis or professional support that they couldn’t necessarily do, whether it’s advancing the nature of the automation that they’re using and enhanced client service. All of these different elements that lead to success are now increasingly possible by leveraging technology more effectively. And so it’s giving people a chance to not only compete at levels they otherwise wouldn’t have been able to, but it gives them in fact a competitive advantage in some of those markets because it really enhances the quality of their work. Yeah,

Stephanie Everett (09:14):
I love that. I always say working with the smaller firms is working with little speedboats versus the big barges. They see the technology and the opportunities coming and they can jump on ’em where sometimes I go in. Recently I’ve started working with some larger firms and it always surprises me, I haven’t been in that world for so long where they’re like, well, would you like to be on the committee that we’re going to study that for this one? Firm’s like, will you be on our AI committee and help us study AI for the next six months? And I was sitting there thinking, okay, anything that committee does will probably be out of already irrelevant in six months. It’s changing that fast. So I’m just curious what you’re seeing in that regard.

Ari Kaplan (09:55):
You’re certainly seeing more rapid decision making. Small and mid-size firms have historically been able to make decisions more quickly because as you note, there isn’t as much consensus required. However, larger organizations are also accelerating that process. They too recognize that in order to remain competitive either in their peer group or because there are smaller nimble firms that are now competing on certain types of work, they’re making those decisions. Those committees are a very common way for firms to acknowledge that they are addressing the emergence of generative AI and all of these other advancements. But I think that those committees are increasingly empowered and are relied upon to make quick decisions. I was very lucky to be the mc of a large innovation conference in Europe called lpo. And there was a presentation, this is in Amsterdam, and there were a number of presentations by remarkable leaders at mostly continental European law firms.

(11:04):
And there was a individual there at a law firm who talked about failure and they were all generally large organizations, but large organizations acting like their nimble, smaller counterparts. And he talked about this idea of failing fast and how that’s a very common refrain. You need to fail but fail fast. But in a large organization, it’s not so much about failure and failing fast because the risk is so high. He talked about how it’s about failing better, how failing quickly isn’t as effective as failing better. And how iteratively learning and making some mistakes and never making those mistakes again essentially equates you to a machine. And that was a very interesting point. A machine will make a mistake but not make that mistake twice. Humans make the same mistakes all the time. And that is our competitive disadvantage to what’s coming. And this was such an interesting presentation because it talked about institutionalizing the idea of failing better and that is a concept that a lot of firms seem to be adopting.

(12:15):
So again, a really wonderful moment. I mean, I’m lucky to have a 21-year-old and a 19-year-old, and I always say to them that they will eventually do jobs that probably don’t exist yet. And with any luck, we too though I’m a later generation than them or earlier generation than them still. I think that as well, I think that we all could be doing something that doesn’t yet even exist. And that’s kind of exciting. But it puts a little bit of a responsibility on each of us to recognize that if we’re not constantly sharpening our skills or learning something new or ourselves being willing to fail, succeed, fail, succeed, fail better, then we may not necessarily be able to keep pace. And so that was the theme of this report. How are firms doing that? How are they approaching change? And I was really fortunate to speak with a lot of leaders in this space.

Stephanie Everett (13:17):
What are some of the big takeaways that you have from doing this work and preparing this report?

Ari Kaplan (13:26):
One of the things that we really tried to understand was how are law firms driving change? What does that look like? How do you overcome change fatigue? How do you make change seamless? How do you build consensus? And lots of firms talked about this idea of being super prepared, highly commutative and incredibly resilient. And if you follow that model, you’ll be able to bring people in and have them join you on this journey of change. And that is a core component. It was a sort of a recurring theme for a lot of these issues. And we also talked about what does leadership look like today? I’m a big fan, obviously of your leader, Debbie Foster. I’ve known her for many, many years and just watched her exceptional leadership in the community and your organization Bear Fruit in so many different ways, not only for your clients but for your team.

(14:32):
And so one of the things that we looked at was what are the qualities of leaders in terms of their curiosity, their ability to listen, their empathy. And of course the pandemic really changed this. It really accentuated and emphasized the need for leaders to build increasing levels of humanity into their approach and into their interactions. And sometimes people just want to be heard. They just want you to listen. They don’t even need you to say anything other than an I understand or a nod and just an active listening person on the other side. And I think that people are starting to realize that in some ways, less is more. Being familiar with what’s happening in the industry and observing is going to be really powerful. I always tell a story that when I was a kid, my dad used to always ask me to hold the flashlight and it sort of just became this common thing.

(15:37):
He’d be doing some plumbing or some electrical work or whatever, painting, and he’d always ask me to hold a flashlight, didn’t necessarily have to do the thing. I didn’t know what I was doing. But if he was doing some wiring or some plumbing and working with some pipes under the sink in the washing machine, whatever it was, I’d have to hold this flash night. He’d always make sure I was focused on whatever he was doing. Sometimes the light was on and sometimes it was daylight. And at some point I didn’t really understand it, and it was kind of annoying. If you’ve ever hold a flashlight for a really long time, it’s kind of irritating. And then I remember he would ask me, he’d be doing something in the yard outside, he’d be like, get the flashlight. And I’d be like, at some point I became older.

(16:19):
I was really a teenager and sort of annoying and I was like, you know what? I don’t want to do this anymore. And I stopped holding the flashlight. And it wasn’t until I became an adult, I realized my dad never needed the light. He just wanted me to learn what he was doing. And it’s such a powerful, especially he’s not here anymore, but it’s such a powerful thing for me because I am pretty handy guy and I attribute it completely to my dad. And I think that the thing about that is that leaders are often now encouraging their teams to kind of spotlight that for them and to spotlight that for themselves and to be more mindful of what their organizations and what the individual component parts of their organizations are. People are concerned, right? There’s a concern that technology, for example, is taking part pieces and parts of what people are doing.

(17:15):
And I’m constantly thinking of that. I’ve been working on my own for 18 years, and over the course of 18 years, there’s been automation or outsourcing or other ways that people can do some of the things that I feel like I’ve done. And so I’m regularly thinking, how do I adapt? How do I make this better? Where can I add value? How can I provide a level of client service that is so delightful and so helpful and so value added that it will really make this relationship just super powerful and sustainable? And I think that a of organizations are trying to do that and leaders are trying to get their teams, the leaders of the different teams, managers of the different groups, even the individuals who are being led to look at what’s happening in that client interaction or look at what’s happening in that employee interaction just to elevate the entire organization and to build such a great culture that it has the fortitude to adapt to whatever is yet to come.

Stephanie Everett (18:18):
Yeah, love that flashlight analogy or story. You talk about change fatigue, and I was curious if we could dig into that a little bit because I see it and feel it, and I think our leaders feel it. They know they’re trying to push and they’re trying to be better, and they want to drive their organizations forward. And yet teams sometimes do feel that fatigue and are like, oh, now what are you changing? I mean, I know my team feels that. So what do you have for us on that? How should we approach that differently as leaders? Well,

Ari Kaplan (18:54):
Your organization in fact is a key driver of change. You’re going into organizations and you’re helping them change their strategy or helping them adjust their technology or helping them optimize what they’ve already done. And so I would want to learn from you guys, but what I’m hearing and what leaders have talked to me about is this idea of really focusing on the change that matters the most and trying as best as they can to have lots of other things that are shifting just occur in the background. And the point about seamless automation or a seamless shift and an ability to accommodate the way people work rather than force them into a new workflow is just going to be much less disruptive, much more convenient, and especially in an environment where the workplace is different, where people are not necessarily with each other every day, where they’re not in the same location where they can’t quite communicate in that personable eye contact driven manner, it really needs to be simpler.

(20:11):
So a lot of leaders talked about breaking things down. So instead of this massive launch that rips apart the existing infrastructure and shifts it completely try to gradually get people without irritating them. You don’t want to have sort of a thousand cuts here. You just want people to recognize that this is changing. But oh, I guess the buttons here buttons. There’s funny how small changes really bother people moving something from left to right on a screen. Changing the color palette, it’s tough for some people to accommodate, and that’s something that needs to happen, but it needs to happen in a way that’s gradual enough that people can become accustomed to it and then adjust themselves, but at a pace that’s comfortable for them. So the other thing about change fatigue is that it needs to be acknowledged. We’re constantly being bombarded with different changes. We use so many tools now and so many different devices.

(21:18):
It’s funny. So when my children will call me from college, for example, they’ll FaceTime me. They’re the only people who FaceTime me, which I love, but they’re the only people who FaceTime me. And when they do, every device in my office goes off. So I have an iPhone, I have an iPad, I have a MacBook Air, I have an iMac. The whole office just goes crazy. And so I really don’t want to keep the sound on anything, but I forget sometimes I’m watching something here. Sometimes I’m waiting for a call. So I put my phone on and it’s just really comical. And if the ringtone change, I’ve tried to keep my phone on, but try to maybe set specific ring tones for different people who are calling me, usually just my wife, son and my daughter. And sometimes it’ll go off and I’ll be like, Hmm, who is that calling me? And then I get so confused, I’m like, ah, shut the volume. Forget it. I don’t want to deal with that change. So silly example, but I feel like it’s relatable. And if it was associated with my workflow, it would be too disruptive. I would lose too much productivity. And I think that that tends to happen in the workplace. So we need to acknowledge it and we need to address it and find ways to accommodate.

Stephanie Everett (22:30):
How are firms approaching change in terms of readiness and research? We always say on our side of the industry that lawyers can be really slow to make decisions and we understand why. We understand why these people, I mean we’re precedent based profession. And so I’m curious what you found out in terms of the amount of knowledge people feel comfortable having before they’re ready to make a decision that could move their business forward

Ari Kaplan (23:00):
Forward. Certainly the people that I spoke to when I asked questions about making changes in a specific area, specific technology for tasks that they happen to need to address on a regular basis, they’re obviously persuaded by their peers. They’re certainly persuaded by what they see in the market and they are willing to take a chance with something in terms of piloting it if there’s some kind of immediate benefit, if it requires lots of upfront effort to implement and grow adoption, it’s slow. And that is a big issue. So it’s really important that the technology have some kind of immediate effect, even if it is not the composite effect, even if it doesn’t necessarily transform, if it does show a small level of improvement or make something just slightly easier, I think people will be more willing to do it. For example, I do a lot of research as you mentioned, and I have several reports that are coming out that our works in progress.

(24:20):
And for example, I interviewed all these people at firms and I wanted to just get a median for all the different data I had to try to show the median number of lawyers at this firm, the median number of cases that the litigation team is handling is X. And so I put it into Excel and then I put forgot, oh, forget. How do I get the median? I put it in ascending, descending, sorted. It just didn’t work. So I pulled up chat GPT, which I have set by the way to not share. So that’s an interesting security component that my friend Ross Guberman, a brief catch taught me, but assuming you set it to not share it, won’t share it, won’t use it as training data. Not that these numbers matter. They’re just random numbers. And so I said, Hey, can you just put this into, I almost said it.

(25:07):
Can you just put this into find me the median? And it perfectly found the median. And then it said, which I thought was fantastic. It’s like, would you like me to put this in order so that you can actually verify what the median is? And I was like, yes, amazing. And it did in two seconds. So I wasted my time on Excel that I opened up numbers. I am a Mac user. Then I went onto to YouTube. I was like, wait, there must be an easy way to do this. I’ve forgotten this. And in a second it worked. And then I thought, oh, I’m going to keep doing this. This seems amazing. And so I just feel like that’s a very easy way to make this work. Now I’m trying to also figure out how I can, I got to automate some of the appliances in my house, make the coffee at a certain time, not just that, but when my wife wants coffee, I wanted this thing to turn on without me having to go and turn it on. So I’m working on these things.

Stephanie Everett (25:58):
I can hook you up later. I have this crazy coffee machine that I can use an app on my phone so I can be upstairs getting ready and I turn the coffee machine on and do all these things.

Ari Kaplan (26:09):
Beautiful. Look at the value that I’m getting here. Thank you so much.

Stephanie Everett (26:12):
But also for anyone wondering, I’ve been using chat GPT lately to say, create write an Excel formula that will accomplish this with this data, and it just writes the formula and then I can copy and paste it right in. And I was like, wow, my spreadsheets are working so much better now. So I love that. But those ideas of quick wins, how are we using the technology to get these quick wins that just make life a little bit easier every day?

Ari Kaplan (26:37):
And also, we should acknowledge that that was once a real skill that was coveted. Being an expert in Excel, it’s still a coveted skill, but if anyone can simply ask an application that is free, I use a paid version, but if it’s free, you could ask it. That skill isn’t as valuable anymore, or at least the base level of that skill isn’t valuable. So you need to either upskill and continue to upskill or recognize that there’s got to be some sort of supplement to that particular skill to maintain the value that it has offered you up until now. And that really serves to elevate our entire community. I really just feel deeply like that. If what I’m doing is not providing the same level of value, then it’s really incumbent upon me to find ways to equal that value and exceed it on a consistent basis.

(27:40):
And so I think that there’s again, lots of opportunity for people to reevaluate. I wrote a book called The Opportunity Maker, and I wrote another book called Reinventing Professional Services. And so I’m constantly thinking about what kind of mindset is necessary to stay the type of person who thrives to stay, the type of leader that drives an organization that thrives, and how do you do that in a practical and not theoretical way? There’s lots of people out there that are very sophisticated and can discuss theory. I feel like I’m in the trenches trying to understand a practical, what button do you push? What words do you use? What timing is most valuable and how much grit is necessary to achieve your goals? That’s really where my mindset is.

Stephanie Everett (28:36):
I listened to a podcast recently and the guy said, he was talking about using AI in education, and he was like, if you use a tool in education, it’s considered cheating If you use the same tool in business, it’s innovation. And that’s kind of been rolling around in my head for the past couple of weeks because I’m like, Hmm, okay, interesting.

Ari Kaplan (28:57):
When my children were little, I suggested if they were writing a book report, for example, which is always very hard. I think it’s sort of the writer in me, it’s very hard to start certain kinds of things. So sometimes I would say, okay, shut the screen and just start typing. Leave word on, but make the screen black and just start typing and see what happens, what comes to your mind. And then I would say, you know what? Instead, take out your phone or whatever they had at the time, an iPod touch or my phone, and this was when this was possible. I said, I want you to dictate and the phone will immediately transcribe what you’re saying. And that didn’t give any answers. It didn’t write anything, but it did automate and accelerate the process. I mean, you could walk around the block and write an entire book review if you were familiar with the book, and yet not comfortable with typing exactly how to start and where to end. And there’s clearly a happy medium somewhere there. But I think it’s a challenge certainly at those levels in terms of education because you want people to become critical thinkers and each generation develops a different style of doing that.

Stephanie Everett (30:11):
Yeah. Well, if people want to learn more about the report, read it, see all the, I mean this thing, I can confess that I’ve seen a preview of it and there’s a lot of information in there. You go into a lot of areas with folks. We will make sure to put the link. I think the best thing to do right now is just to say, we’ll put the link to this report if anybody wants to access the changemakers report in the show notes. Anything else in terms if they want to learn more about the work you’re doing and how to get in contact with you, Ari, where would you point people?

Ari Kaplan (30:47):
Sure. So my website is ari kaplan advisors.com. I’m my email is ari@arikaplanadvisors.com. I share a lot of my research, almost all of it on LinkedIn, so I’m happy to link in with folks who are interested. I host a daily Zoom call every weekday for the most part, every weekday at noon eastern. I started this during the pandemic on March 16th, 2020. I thought, you know what? We’re going to be working remotely. I thought for two weeks. I literally put in the LinkedIn post, two weeks. It looks like we’re going to be around for two weeks. I’m going to host this Zoom call every weekday at noon, and I’m going to call it the virtual lunch. And so I continue to host that four plus years later. In fact, I’m on episode 1085 or something, and we have really interesting discussions. We typically have special guests every Friday, but I’m generally, on most weekdays, we do kind of deep dive discussions about different issues, which I post about on Tuesdays, but sometimes other days. And so people can join that as well. I also have a podcast, it’s called reinventing professionals.com. It features somewhere around like 900 episodes, and I’m routinely featuring leaders in the legal sector and beyond, both in the United States and all over the world. And it’s just incredible work. I feel very lucky to do it, and I appreciate you speaking with me today.

Stephanie Everett (32:20):
We’re excited to learn more about all the amazing work you’re doing. So thank you. Thanks for being with me and make sure we’ll put all the links that Ari just mentioned in the show notes, so make sure you check those out.