Fresh Voices on Legal Tech with Erika Pagano

Episode Notes

Transcript

Announcer:

Web 2.0. Innovation, trend, collaboration. Got the world turning as fast as it can? Hear how technology can help, legally speaking, with two of the top legal technology experts, authors, and lawyers, Dennis Kennedy and Tom Mighell. Welcome to the Kennedy Mighell Report here on the Legal Tok Network.

Dennis Kennedy:

And welcome to episode 413 of the Kennedy Mighell Report. I’m Dennis Kennedy in Ann Arbor.

Tom Mighell:

And I’m Tom Mill in Dallas.

Dennis Kennedy:

In our last episode, we talk with Toma Officer about legal design and AI. In this episode, we have another very special guest in our Fresh Voices on Legal Tech series. In fresh voices, we want to showcase different and compelling perspectives on legal tech and much more. Tom, what’s all on our agenda for this episode?

Tom Mighell:

Well, Dennis, in this edition of the Kennedy Mall Report, we are thrilled to continue our Fresh Voices on Legal Tech Interview Series with Erika Pagano, head of legal innovation and design at Simons & Simmons and based in Madrid, Spain. We want our Fresh Voices series to not only introduce you to terrific leaders in the legal tech space, but also provide you with their perspective on what you need to be paying attention to right now. And as usual, finish up with our parting shots, that one tip, website, or observation that you can start to use a second that this podcast is over. But first up, we are so pleased to welcome Erica Pagano to our Fresh Voices series. Erika, welcome to the Kennedy Mall Report.

Erika Pagano:

Thank y’all so much. It’s a real pleasure to be here.

Tom Mighell:

Before we get started, we want to know a little bit more about you. Tell your audience about you, what’s happening at Simmons & Simmons in your role there. Where would you want to get started?

Erika Pagano:

So it’s a funny title, Head of Legal Innovation and Design. And if you ask 10 people what it means, you’re going to get 10 different answers. So what I like to say is that I’m a lawyer who gets to do a lot of really cool stuff. And what does cool stuff mean? I suspect we’ll get into that later, but I count myself very lucky to be able to operate in a space that’s constantly growing, constantly challenging. And frankly, I get to have a lot of fun.

Dennis Kennedy:

Cool. Erich, first of all, it’s great for us to have you as a guest on the podcast. I’ve been enjoying what you post on LinkedIn. I always like to start by addressing what I think is one of the most interesting problems for people who work in legal tech and innovation. It is just not easy to talk with lawyers about tech, even when they need to use it. So sometimes I get frustrated with how difficult it still is to explain technology, both the old technologies and new ones and the benefits to those in the legal profession. I really like the way you’re able to communicate about these topics. Would you talk about your approach to communicating with lawyers and others in the legal profession about technology and innovation and what you found that works well for you?

Erika Pagano:

Thanks, Dennis. On this one, I’d like to think that I have a little bit of a natural born advantage. What I mean by that is my dad was in broadcasting and a serial entrepreneur. My mom was a lawyer. So I grew up at the sort of natural intersection between legal stuff and communication. And I like to think of it as being a fan of a few things. First, I’m a huge believer in Eli Five. Explain it to me like I’m five. Some may like the KISS rule, keep it simple, you know what? And I don’t think that this means dumbing things down. In fact, I think it’s quite the opposite. It’s a real skill to be able to communicate and take something complex and say it or explain it in a simple way, or the art of articulating something that could be complex in a relatable way.

I use a lot of analogies. So I’m constantly making analogies, whether it’s at work or when I’m teaching about closets, like putting on clothes, cleaning out your closet, organizing your closet, dating, car shopping, you can tell what’s on my mind lately, and planning holidays. Because I think too often in legal, we ignore that real world, I guess those real world experiences, right? Our real world context. We’re like, oh, we’re lawyers. We have to do it this way. This is our world. This is what matters. But actually we should be bringing in that real world stuff more because it’s informative and it’s helpful for context, for logic and decision making, especially when we’re looking at things like processes and technology, let alone our relationships with people.

Tom Mighell:

So when you’re talking to lawyers about technology, when you’re explaining things or when the people that you’re working with on a daily basis, we talk a lot on this podcast about technology competence and what lawyers know now, which we have traditionally been a little bit jaded about and what a lawyer should be knowing. So we always like to ask our guests, what are you seeing out there? What are you seeing in terms of technology competence for lawyers? And then maybe the more important future looking question is, what does a technologically competent lawyer need to know these days? And what’s interesting about that is that, to me, the interesting part of the question is I’m not just asking about using Word or document automation or things like that, but I want to talk more about legal innovation and design thinking, which is probably newer to lawyers than some of those other types of technologies.

Erika Pagano:

So how much time do you have? I think that those are some pretty chunky questions and I suspect we’ll get around to answering several of those throughout the course of our conversation. There’s this school of thought that says that you start with people, so looking at their needs, their goals, their priorities, and then you should look at process, right? Their ways of working, the way things are going, the way they could go, and then go to technology. But I think, and I suspect we’ll touch on AI later, that in legal tech, specifically the last six months, we’ve seen that process go completely in reverse, right? Look at the tech, then move to the process and then move to the people. I’m not a huge fan of that, and I’ll tell you why. So I use this analogy, I told you I like analogies about cake, right?

Birthday cake, right? I feel like lately there’s this sense of you wake up in the morning, you’re about to go to the gym and whoever you live with says, “Hey, take some birthday cake.” And you’re like, “I don’t want any birthday cake. I’m going to go to the gym. I’m going to do this really intense workout.” But the cake is beautiful. The cake is artisanal. It’s amazing. It’s one best cake in the universe. Take the cake and they’re shoving it down your throat and you’re like, “Hey, buddy, I don’t want cake right now. I’m going to go to the gym. It’s not the right food. It’s not the right time. It’s probably not the right nutrient profile right now. I might have some later when the time is right, when I’m hungry for it. And cake is great. It has its place, but maybe not right before I go to the gym.” That’s a little bit about how I feel where we are right now in terms of thinking about technology.

And this is really where that design thinking can come in. We’ve got to start with that human-centric thinking. If you don’t do that, it’s a waste of time. It’s a waste of money. It’s an effort to shoehorn probably something very expensive. You’re not going to get your ROI, you’re not going to get your adoption. And so I think that there’s a whole lot to unpack there. The cake might look really nice, but you’ve got to decide if it’s the right place, if it’s the right time, if it’s the right dessert for you in that moment.

Tom Mighell:

There are a lot of good looking cakes out there that people want to try and I get the issue.

Dennis Kennedy:

So I teach students at the University of Michigan Law School and I’m four classes in, and I’m really intrigued by their perspectives and what they need to know versus the amount of change that’s happening in the legal profession. And my students are going into firms like Simmons & Simmons, and I’m trying to get them to think in sort of systems approach, complex systems approach. And they’re concerned about a lot of different things because I think they have a really interesting perspective on the world and they’ve seen things, systems that are kind of dysfunctional or breaking down or definitely being challenged. So let me ask you this. From your vantage point and the things that you’re trying to accomplish in your role, what are the areas of the legal profession that you feel need the most attention these days? And then how do we actually get people to pay that attention?

Erika Pagano:

That is a key question that I spend a lot of time thinking about as an academic, as a lawyer, as someone who leads a team, who’s working with clients at all different levels and lots of different countries, but most importantly, who’s also seeing juniors in the profession and those that are about to come into the profession. My sense is that where we need to be focusing our time, I don’t know, you could divide it in a couple of different ways. Let me backtrack a little. A few months ago, I was in the Middle East and I was chatting with a friend of a friend who used to be a very senior leader at one of the biggest firms in the world, and he was asking me, “Where do you think we’re getting it right in the profession and where do you think we’re getting it wrong?” And I said, “Look, I think one thing that we’re forgetting about with all of this tech advancement is succession planning and relationship management because at the end of the day, Law is a service industry, right?

We’re no different than say a clothing store or dare I say it, a bar or a restaurant.” So for example, when my students are asking me, “I don’t know what kind of law I want to go into, what kind of job should I get? ” I have always said, and I still say, “Go work at a restaurant or go work at a bar because you are not only going to make bank on commission if you’re good, you’re also going to learn skills that are totally transferable and will be so helpful to you in your legal career.” So when I was in law school, I actually worked at this really cool boutique popup shop in Miami for a long time. And I learned so much, so much of what’s helped me become a great lawyer came from working at that shop. So I think we’ve got to think about the succession of our service industry.

So what does that mean? It means that sure, maybe you’re a whiz at using AI to make your job speedier. And there’s a new study I want to tell you about later that I just read that I think is really interesting about this. If you don’t know how to handle a client relationship or read the room or have the humility to be able to say, “Okay, you know what? I think this particular contact at the client is going to get along better with my junior than me. Maybe I should let them lead the relationship instead of me. ” I think we’re going to have problems there because at this point, technology can certainly do a lot. I don’t mean just AI. Tech in general can do a lot, but what it can’t do is, for example, I’ve got a wonderful client who doesn’t like emails past 11:00 PM.

Why? Because she doesn’t think her lawyers should be working past 11:00 PM. Now, of course, there’s delay send and stuff like that. I can tell my team, sure, I might be able to program a rule, but at the end of the day, it’s that kind of knowledge, knowing that somebody’s preference is this, they’ve just gotten a new dog named this. All of this kind of stuff that helps make our relationships great, we’re still not there. And I think for any of us who have tried writing something using some sort of AI writing tool, it’s pretty easy to suss out when someone you know has written it versus when it’s not coming from their voice. So I think we need to be very careful in terms of how all that, I don’t want to say soft skill stuff because it’s actually the harder stuff to develop, how all of that stuff is being treated in law schools and also in terms of juniors and in looking who we’re promoting in the chain.

Do they have those skills not only to be flexibly adaptable, but also to be able to understand that key relationship component?

Tom Mighell:

I worked at a bookstore for three years during college and it totally formed how I looked at serving people and talking to people. And I’ve moved from law firm now into consulting where it’s not any different from a law firm. It’s very still much client customer relations and it’s so important. And it’s a skill that has to be learned because there are so many people who are experts at their job and just have no idea how to talk to a client or deal with them. I agree. It appears that I’m the one here who’s asking the people process technology questions. So I’m going to shift to that in a certain way and talk about collaboration. We love to talk about collaboration on the podcast. We love to talk about technologies, but we’ve always argued that collaboration is really not an option for lawyers. You have to work with all the people that you’re working with, whether it’s colleagues or across the aisle or judges or businesses.

So we’re always interested in understanding how our guests like to collaborate. So what makes for good collaboration for you? And that could be people, process, or technology or a combination of all of it.

Erika Pagano:

So my middle initial is C. Okay. The letter C, it stands for obviously the initial for family name, but you might as well swap it out for collaboration because I think that’s probably one of the things that I love the most and that I love helping other people discover. Just like your leadership style, your collaboration style, your personality, it’s going to have its own hallmark, right? We don’t all collaborate in the same way. We don’t all need to collaborate in the same way and not even in the same way for different things, whatever. It can be a very individual thing, but I do think that it is absolutely one of the most important skills. When I’m teaching, most of the class is a collaborative class. And when I’m working, I’m very proud to say my team. So we’re four across four different countries. Three of us are lawyers by background.

One is not. He’s an ex- fire juggler, chef and philosopher and educator, but would probably be one of the most phenomenal lawyers you’ve ever met that has no interest in being one. And that’s why one of the many reasons why he’s great on the team, we collaborate all day, every day. Part of that is recognizing each other’s strengths and contributions, how we want to help each other. We spend a lot of time creating that psychological safety. I think, again, working across four different countries, coming from different cultural backgrounds, it’s super important. But I’d say the factors that I think are most important here are being able to lead up and down, right? Being able to bring something to the table and say, “Are you okay? Seems like you’ve been working a lot today. Is it time to sign off for 15 minutes?” I always say to my team, “Okay, I’ve got really strong opinions about things, but I’m very open to having my mind changed.

Here’s how I feel about this particular issue, but feel free to change my mind.” So I think that these are some of the essential things for collaboration. At a law firm, we know this that in the industry in general, I don’t want to say just at a law firm, collaboration is something that’s in most situations kicked out of us before we enter the profession when it should be just the opposite. You have so many people and organizations bringing this to life in the market, but I think by nature, we also need to remember that law is a business and a lot of the financial structures and incentives don’t often permit collaboration. I know you’ve had lots of guests on your podcast talk about this. So it’s also about finding champions within your own organization and frankly, clients who will go to bat for you, who will fight for your collaboration.

I mean, I think that fight for the reward for your collaboration, I should say. I can think of a particular partner recently who said, “Oh, I want to give you the credit for this. ” I said, “But why? You brought this opportunity to the table.” And they said, “No, no, you built the relationship with the client so well that they came back to you, not to me for this particular piece of work, so you deserve it. ” Now when somebody is role modeling that the right way, and it could be somebody below you, it could be somebody above you, it could be someone in a completely different practice group, I think it gives you the permission and the incentive to do the same thing.

Tom Mighell:

No, that’s so true. This is not exactly on the topic of collaboration, but you brought up that you’re open to your mind being changed. And I just wanted to give another shout out. I gave this out a while back. Adam Grant’s book, Think Again, I think is such a great book on being open to thinking about new things and to thinking about things in a different way and about the way that some of our biases prevent us from doing that and why that’s not necessarily a good thing. Anyway, we’ve got a lot more questions for Erika Pagano, but we need to first take a break for a quick word from our sponsors.

Dennis Kennedy:

And we are back with Erika Pagano at Simmons & Simmons. We founded a Fresh Voices series that we love to hear about our guests career paths, and especially Tom who wants to always follow in some guests career path and our audience does as well. You have a great career story. Would you talk about your own career path and what kinds of things you’ve done to get you into your current role and focus?

Erika Pagano:

Sure. So I’ve said this before a few years ago, I found a list I had written when I was maybe 10, and it had 10 things I’m going to do when I’m going to grow up, right? 10 things I want to be. And of those 10, the only thing that I’m not currently doing is driving the Lamborghini. And I say this, number one, because in Spain, my American driver’s license is not valid. So I’m actually in the process of starting from scratch, including the theory test and learning how to drive again. But secondly, I think I had written that list the week I learned how to spell Lamborghini and it was a really fancy car, right? But everything else that was on that list, I never said I wanted to be a lawyer. I actually wanted to be like a fighter jet pilot or an astronaut.

I guess being a pioneer in legal innovation has some of the same adrenaline and danger and adventure. But I wanted to speak with people. I wanted to teach. I wanted to be creative, stuff like that. I travel a lot, work with clients all over the world, people all over the world. So I’m doing all of that stuff. But back then, legal innovation was not a thing, right? And I don’t think I had a very linear path. I finished high school pretty early at 16. I went to Georgetown. I finished early there as well, lived in China and worked for a while. And then it was time to come back to law school according to mom and dad. So came back to the US, went to law school in Miami, thought I’d go back to China, never went back to China to work, did go back to visit, and found my way then to London and then to Madrid.

And it’s not a path I ever expected. It was definitely a path I think I got lucky with and created opportunities for myself along the way and had some great advice and support from people as well. For people who want to get into the legal tech world, and like you both, I hear from students all the time or traditional lawyers who want to make the jump, there is no set path, which makes it easier and harder at the same time. But I think that there are a couple of things folks can do, which is listen, right? Listen to what they’re hearing, read, listen to podcasts like this, reach out to folks. One of my favorite tips actually that I started doing last year is maybe once a month or maybe more. I will reach out and connect with somebody on LinkedIn who is completely outside the legal industry, but someone I really admire.

For example, it could be the founder of a shoe brand where I really like their story and their brand and their ecological practices, whatever. It could be a content creator on Instagram or TikTok that I think is really inspirational and cool. So folks like that who will just broaden your perspective a little bit and maybe even broaden your network because you don’t know where those things can go and it just takes you outside of your comfort box. So that’s a little bit of a tip there. I don’t think we can … Sometimes this legal echo chamber and bubble can be a lot. So I think the more you can broaden it in that sense, and we’re all on LinkedIn all day anyways, so it’s quite easy to do. And I think be open to opportunities. Law firms in the legal industry for a long time is very sort of lockstep.

You go in, the next step is prescribed, then the next step, next step. It’s not like that anymore. So I think folks, especially young graduates, feel a lot of pressure. They go out there like, “I got to work for big legal tech. I have to do this. ” But then they go to apply and it’s like you need three to five years of experience. Ignore that, right? Ignore it. Go apply anyways, make your case because chances are if you’re entrepreneurial, you’re going to want to be at a place that’s entrepreneurial. So I don’t think that there’s like a set path or a set key. I think you got to figure out what’s good about yourself, make your own formula and just try and make it work. That’s what I did. I think I got lucky too. All

Tom Mighell:

Right, let’s talk about AI. And I’m excited to ask this question because we haven’t talked with somebody in the innovation space in a while. And so I’m interested, given the rate at which AI is changing, I feel like the answers change all the time too, but how do you see AI and generative AI in particular affecting legal innovation and design thinking? I would imagine that it both has amazing potential and terrifying reality. I don’t know if it’s somewhere in between, but what are you seeing right now? Does agentic AI have a role to plan all of that? What’s on your mind about AI and what you’re doing?

Erika Pagano:

So first, I am not an AI skeptic or an AI hater, right? I think it’s fantastic. I use it a lot. I actually use it probably more outside of work than I do at work. And here’s why. Outside of work, I get a chance to play around with it a little bit more. I get to use it for creative projects if I’m helping my partner or if I want to do something fun for a friend. And then there’s a little bit less risk and I can then apply those learnings into my work day-to-day stuff. So much of what we do at work is human-centric, and we certainly do use AI, the right tools for the right purpose and the right situation. We can have a whole separate conversation around the fact that personally, this isn’t about Simmons or exclusive to Simmons, and I’m not speaking about any clients in particular.

Do I think there needs to be stronger governance in general? Yes. Do I think there needs to be stronger training? Yes. Do I think that we need to think a little bit smarter about how we’re using it and when we’re using it and how we’re enforcing all of that stuff? Yes. But here’s what I wanted to share with you. So I read about this study last night by Anthropic. Okay. It just came out. And the question of the study in general was, does AI make us faster or better? Have you read this yet?

Tom Mighell:

I saw a headline, but I haven’t read it.

Erika Pagano:

Okay. So I’m going to give you a couple of rundown facts about it and let’s see what we think about how this applies to the legal industry and also legal education, frankly, because those who are coming down the pipeline, they’re the ones that are getting them started young. My students have access to Harvey, which is insane. So okay, Anthropic did this experiment and they found that experienced developers actually were slowed down by AI even when they thought AI was speeding them up. So if we think about that in the legal profession, experienced lawyers, maybe they’re using AI and they think it’s speeding them up, but is it also actually slowing them down too? I question whether or not everyone is actually going back and checking what things are producing. Everyone’s going to say, “Oh yes, I abide by the whateverBar Association’s codes and I do all the ethical stuff, but are they really checking?” What’s that saying?

Character is who you are when nobody’s watching, right? I wonder if that holds true here, but anyhow, there’s more in the study. MIT did a related study. This is what I find very interesting. They found that brain activity actually drops when we’re using generative AI to co-write with us. So in essence, your brain is actually more active when you are writing alone. Lawyers were trained writers. This is our craft. So if our brain activity is dropping when we’re co-writing something, is that a bad sign that we’re not using our full capacity or maybe it’s a sign that that capacity gets used elsewhere? I don’t know. But the interesting second part of this MIT study was that they found that there was less recall of the material when someone was using AI to write something or to co-write something and better recall when someone was writing things themselves.

I mean, to me, I read this and I was like, “Yeah, this seems pretty obvious, but I don’t know if we’re actually thinking about this as a profession, especially when it comes to training our juniors.” I suspect within the next year or so, I’ve heard some grumblings about this, but I suspect in the next year or so, we’re going to be seeing some really interesting statistics about the impact of AI on younger lawyers, whether they’re just coming in, whether they’re interns, whether they’re trainees, wherever you are. I worry that they are not getting the same sort of training in terms of their logic and reasoning and writing and things like that, that it’s making things maybe easier and faster, but is it making it better? The last part of this whole anthropic paper that I wrote down that I wanted to share with you was junior developers, they had them use AI to learn a new skill, and then they tested their mastery of the skill.

And they found that when they tested the mastery, those who had used AI scored 1717% lower on their mastery, so they weren’t mastering the skill as much. So if we combine that, the less mastery, less recall, you’re getting slowed down. You start to wonder, okay, do we need to look more into this? It’s not, is this bad? Stop, pull the plug. It’s do we need to look more into this, how we’re using it, how we’re checking our stuff, how we’re governing it, how we’re monitoring it. Just a few thoughts there.

Dennis Kennedy:

That’s great because I haven’t done it on this article yet, but I have a new AI, I call them protocol prompts, but it’s basically my critical reader. And I’ll take an article and run it through this prompt and have it look for the logic gaps, look for other things, red team it, score it in those ways. And it’s really good to, because I’ll say like, here are these headlines and these conclusions and what does it really mean? And I would just like to have an overview that points out to say, and in one case, the study they’re relying on had 30 people who participated, who were self-selected. I’m going like, “It is what it is. ” I can guess the worth in that. And I think that you said something real interesting that I agree with is that we’re having these findings and the important thing is not to say like, “Oh, this tells us the old way is the only way.” It’s like, what is in there that we need to learn?

So one of the things I tell my students, this sort of stat that I’m going to use throughout the year is that we sort of know, or we believe we know now that human eyewitnesses have an accuracy in the 50 to 60% range. And if we say AI facial recognition is in, let’s say 80 to 90% range, what does that mean? How do we as a legal system reconcile those things? And we can go a bunch of different ways. We can say humans, we trust humans, right? But we’re making some kind of trade off. So which is a long way of asking you is there are things that are working with AI these days or seem to be working. There are things that aren’t. I’m really interested in from your perspectives, what do you find that’s really interesting to you in AI? And it could be in your legal work, could be elsewhere.

And where’s the action? Where are the outcomes and what gets you excited about AI these days?

Erika Pagano:

So going back to that intersection of business and law, right? We all know that a bad pricing practice is finger in the air pricing, right? Back of the napkin, haven’t really thought about it, touch your tongue, feel the air, it’s going to cost about this, right? And we tell ourselves not to do it and we’re trained not to do it, right? It still happens. I think there’s an interesting movement. I’ve got three points here, right? This is the first one. An interesting movement here going on with clients who are now asking in RFPs, “Show us the savings that you will generate by using AI.” Now, I think that there are cases where that can be done, but to me, there’s still a lot of finger in the air pricing style behavior going on there. I’m not sure we’re at the point where we can tell people that accurately from The beginning.

In some cases, absolutely. But in some cases, no. And a related point there is companies who are looking at not just law firms, but companies who are looking at how do we judge people based on their AI metrics? Because I can go in and ask Copilot 50 different recipes on how to make fancy popcorn. And that means I’ll ask Copilot 50 different conversations with questions. Does any of that have to do with work? No, but oh my God, my user stats are going to be really good. So I think there’s a question there about quantity versus quality and how we’re looking at people’s, let’s say, AI performance. The second thing that I’m still watching from a distance, I’ve seen some great ones. I think especially the developments that have been happening with people rushing to get their Mac Minis this weekend and try all the cool Claude stuff to make their own agents.

I think that’s one to keep an eye on. I know that there’s been a bit of an agentic boom. Personally, I haven’t built myself an agent yet, but believe it or not, I still have a paper diary. Yes, I rely very much on my digital calendar, but I like that art of making and thinking through my day and booking my own flights and things like that. It gives me a lot of joy. So I’m not sure I’m the biggest candidate for a personal agent, but I’m excited to see how that takes off in the profession. The third thing is where I’ve seen things go really well and also not. And this is a bit at the intersection of work and play. So I play around with lots of different AI tools and periodically I will ask it or ask them to do human-centric type stuff.

So for example, I have a workshop of X number of participants, Y profession, Z level of seniority. We’ve got so much time. Give me an exercise or design an exercise that helps me do A, B and C with this group. Whether it’s team building, collaboration, problem finding, you name it.

Anybody who has any experience, serious experience, facilitating this kind of stuff with people and with lawyers and thinking about lawyers psychology, we’ll look at the output of these for now. I’m not saying it’s going to change and just go, “Oh my God, this would never actually work as an exercise and here’s why.” This just wouldn’t work. I couldn’t facilitate this in a room. There’s something fundamentally wrong. Now, it looks really good. It reads really well. It’s like, “Oh my God, it gives me all the instructions, everything I have to say.” And then if you were to actually test it out on a group of real live participants, you’d be like, “Oh my God, no, this exercise is so flawed and it’s not going to get me anywhere. In fact, it’s going to harm the safety of the room or the container of the experience or whatever you want to call it.

” But on the other hand, you can do some really neat stuff. Small things that make a huge difference. For example, on our team, when we have out of office emails, we use AI to write little riddles so that people can, if they want, read the riddle and guess where we are. And that’s fun. Or for example, if it’s a colleague’s birthday, we can use it to do some creative stuff. Now, it’s not all, I don’t want to say small value things because actually these small ticket items when added together actually have a huge cultural value. We have used it for some pretty big stuff too that I can’t necessarily talk about here. That’s quite fun. But I think for the human centric, feelings, thinkings, finding pain points, how do we actually work as people with souls? It’s not quite there yet.

Dennis Kennedy:

I was laughing a little bit because as you were saying that about the design thinking and other exercises, I was thinking about a series of texts I got just this morning from a lawyer, a colleague complaining about the spaghetti and marshmallow exercise that all lawyers hate.

Erika Pagano:

I mean, I actually don’t hate that one, surprisingly. I think it’s kind of fun. I like doing things with my hands, right? I like creating and building and things like that. I think why lawyers hate it, honestly, and I say this as one, is because they fail to see it as, dare I say it, a way to have fun and be creative and it’s okay to fail for this one. It’s like, “I must be right. I must be the best. I must win.” And that’s great. That has its place, right? But I think for the majority of folks who do it, they’re in it to win it. They’re not in it for the learning experience that it is. Right.

Tom Mighell:

All right. We’ve got more questions for Erika Pagano, but we need to take another quick break for a word from our sponsors.

Dennis Kennedy:

And now let’s get back to the Kennedy Mighell Report. I’m Dennis Kennedy.

Tom Mighell:

And I’m Tom Mill and we are joined by our special guest, Erika Pagano at Simmons & Simmons. We’ve got time for just a few more questions. Dennis.

Dennis Kennedy:

So Mark Lawrence, who is a recent guest, has asked, “Do you find that it’s getting harder to make good legal technology decisions?” We think the short answer is definitely yes, but how do you try to answer the question for yourself and how do you advise others to answer the question of how do I make good legal technology decisions where it seems like it’s getting harder and harder? And I’ll point to the Legal Tech Hub’s great chart of what I call the self-identified legal AI applications. It now is up to basically a thousand and you need a magnifying glass to read. So as you look at technology, bringing technology into your firm and into your own group, how do you try to make decisions in a world where there’s just so many choices?

Erika Pagano:

That’s a great and timely question for a number of reasons. So is it getting harder? Yes. Right? How do you build that culture? How do you make those decisions? Let’s go small to big here. So on my team, we’re four, very similar, but very different people in terms of skillsets, backgrounds, experiences. We have the same beliefs and values. We are all generally good people. Anyhow, what I’m trying to say here is that we don’t all need to be experts in the same tools. So for example, one of the amazing folks on my team is working on a really cool project for a client today using a piece of technology that I have no idea how to use. And I really don’t want to learn how to do it or how to use it. And that’s okay because that can be his specialty and his domain.

Where I can add value is them going in and saying, “Okay, cool, but tell me how this works.” And playing like the client. Well, why is it like this? And poking the holes and answering the questions and being the good foil there, right? That’s where I can add value, not by spending time learning how to actually build the thing, right? Maybe eventually I will, but we can be complimentary there. So I think that’s the first thing. Not everybody has to be the expert at the same stuff, right? The second is that I think, like I’ve said earlier, we need to be flexible in how we approach things going back to that, “This is how I feel, but I am open to having my mind change.” And it happens so many times. And frankly, when you approach things with that kind of mindset, it can feel kind of good when you get your mind change.

You can surprise yourself. So it might be, “I don’t think we really need that. ” And then you look at it, you try this tool and you’re like, “Oh, this is actually life changing.” I can think of a few tools that have been that way for me. But I think if we zoom out a little bit more about how do we build this innovation culture or mindset, right? I will not be the first person or the last person to say this, but innovation isn’t just one office or one group of people or one room, right? It really is a mindset that needs to be instilled and encouraged in folks. So one thing I will always ask folks is when we are promoting people to partner and we are asking, are you innovative? Are we actually asking them to show us how they have been innovative?

It’s not enough to say, “Oh, I worked with the legal tech team to produce something.” Okay, that’s great. That’s one example, but that legal tech and AI itself is not innovation alone. Innovation can also happen with how you work with people, how you approach relationships and things like that. So I think we need to look at systematically how we’re rewarding innovation, how it’s being looked at in terms of say annual reviews and things like that, but also how are we bringing people along the journey with us? All of this goes back to one key ingredient, which is people, right? People, process, technology, not technology, process people. We’ve got to start with the people. That might be as simple as asking your people, what does innovation mean to you? Do you feel innovative? Tell me about a time where you feel you’ve been innovative. When do you wish you could have been innovative, but you couldn’t?

Maybe it’s because the client said no. Maybe it’s because the partner at the time said, no, we don’t have time or money for that, or what a silly idea. So I think we need to understand and get a baseline of where we’re at first before we start building that culture. I think it’s also not just about understanding people’s wants and needs in the present, but also thinking about the future. If we decide to take on board a piece of new legal tech or some kind of fancy whatever, what kind of impacts will this have in terms of process, right? Legacy and succession planning and also learning for the firm in the future. And also how will it impact things like relationships and decision making and growth? Because we also see from a law firm perspective, lots of clients will say, “Okay, we’re cool if you use AI.

You got to tell us first and we have to approve it before you do it and/or if it’s not the same tool that we have, then you can’t use it, ” kind of thing. And I think we’re going to see a little bit more friction around that as we go forward. So hopefully that’s helpful there. Making decisions, it’s getting tougher, not impossible. It’s getting tougher, but that’s naturally a consequence of how things are at the moment. And then also building innovation, it’s got to start with people and it’s got to be across the organization at all levels.

Tom Mighell:

All right. We’ve got time for just one more question and it is our self-serving question of the podcast, which is we always rely on our guests to help point us to other guests. So who are the voices fresh or not? Who are the voices that you think our audience would most benefit from listening to?

Erika Pagano:

Who would I love to see featured? I believe that we should be featuring more juniors in everything that we do as lawyers. So putting more juniors front and center in client relationships, putting more juniors out there for leadership roles within the organization. And I don’t mean necessarily putting them on the boards, but in terms of leading things like employee resource groups and different initiatives and things like that, Law may be hierarchical in nature, but it doesn’t mean that juniors can’t lead up and they certainly need opportunities to shine and cut their teeth. So I would nominate a few people. So my amazing team, we’ve got Callen Brown in the UK who’s doing incredible groundbreaking work on accessibility. You’ve got Glen Byrne, who is a tax lawyer originally, turned legal designer, who’s working on some really cool content around understanding the parallels between graphic design and cinematography and how that applies to law.

He also just published a really great paper in the legal design Journal around an evaluative framework for measuring the impact of legal design if you want something more sciencey and less visual. And then Denise Callan from my team who is at the forefront of legal design and innovation in Germany just has a really fresh approach there. Beyond my team, which is a selfish but an honest move because I think my team is amazing. You have folks like Catalina Pedromo who’s very active in the legal AI space. Folks like Marcia Ryan Weldon, who’s a huge champion and mentor of mine, former Fortune 500 WGC just turned all around amazing advocate for a number of different causes. James Peters, formerly of Legal Zoom and now with, I think it’s Law Hive. And last but not least, Anna Donovan at University College London, who is Vice Dean of Innovation for a while and started the Center for, I want to say it’s Law and Ethics.

But she’s written a couple of books. She’s on her new book and just has some really amazing thoughts around this intersection of behavior and lawyers and compliance culture. Those would be my recommendations.

Tom Mighell:

That is amazing because I don’t think any of those names, I think they’re all new to us. So that’s fantastic. I love getting all new names. So yay, thank you very much for that. We want to thank Ericha Pagano, head of legal innovation and design at Simmons & Simmons for being our guest on the podcast. Ericha, tell us where people can learn more about you or get in touch with you if they want to.

Erika Pagano:

As they say, you can find me on the internet. The best way to find me is on LinkedIn. Of course, I’ve got my fancy law firm bio as well, but if you want to get in touch, please do.

Dennis Kennedy:

Yeah. Thank you so much, Erika. You were a fantastic guest as I suspected you would be when I first started reading some of your stuff on LinkedIn. Great information, great advice for our listeners. And as usual, so many topics to discuss and so little time. And I’m looking forward to getting the chance to follow up on a few things as well. But now it’s time for our parting shots, that one tip website or observation you can use this second this podcast ends. Ericha, take it away. I

Erika Pagano:

Thought about this quite a bit this morning and I thought what’s been on my mind lately. I have a lot of great new books, great new podcasts, great new restaurants to try, but I’m actually not going to give you a tech tool. This is low tech, no tech. And in fact, it’s quite personal. And I think it’s something we need right now in the world and especially in our profession, and that’s to take a moment to be kind to yourself today. It could be as simple as saying something nice to yourself like a positive affirmation or a moment of gratitude in the mirror before you get to bed. It might sound silly, but I do this kind of stuff all the time and it actually helps. Take a moment maybe to enjoy your coffee device free in the morning. If you ride the bus to work like I do, maybe take a look around and don’t be glued to your phone.

I read a piece of advice last night that said sometimes you don’t need to tell yourself one thing that you did well that day. You can just say, “Here’s one thing I did okay today,” and that’s just fine. But to wrap it up, take a moment to be kind to yourself and thank you both for being so kind.

Tom Mighell:

Wow. Okay. Mine is a tech tip and I know that we are sick and tired of seeing technology tools that we know come out and say now with AI, but this is a tool that Dennis and I have used for a while and that we both recommend. We recommended it in our collaboration tools book and it’s raindrop.io, which is a collaborative bookmark manager. And they’ve recently added a new AI tool, Stella, is what they call that, Into Raindrop. And I’m looking forward to it because it offers two different features that I think are really interesting. One, it will help you organize your bookmarks. It will help you put them into folders or an organizational structure that makes sense to you. If you’re what we call in my business, the information governance business, a piler instead of a filer, the AI will help you with that.

But then also my other problem with Raindrop is I start putting things … I am a filer, but I start putting things into … I create multiple files that I didn’t realize I had copies of. And Stella will let you ask, “Hey, where’s that one article that I saved or where’s that one tool that I saved?” And it will go and find it for you. So it’s your smart search tool within Raindrop. If y’all are using Raindrop, you can give Stella a try.

Dennis Kennedy:

So I’m going to, of course, go hybrid on this. And I’ve been thinking about this a lot as I’ve been doing slides for my class. And the tip is when you’re creating slides or presentations, really go out of your way to make the effort to go beyond default images in AI generated visuals. AI image generators do a poor job with diversity and originality, possibly even as bad as a lot of humans. You tend to get gables, scales of justice in men in suits every time you use the word Law and a prompt to get an image. So make the extra effort for your audience to find images that are non-cliched and actually represent the diversity of the legal profession. And I’ve actually gone a step further and I create a little cliche test or prompt for myself and test what I get and see if there’s something that it will tell me I shouldn’t use or won’t be understood by the students who see it.

And a rule of thumb would be if your image could appear in any generic legal presentation from the last 20 or 30 years, it’s probably time to find something better. Your audience deserves more thoughtful visual communication.

Tom Mighell:

You’re here. And so that wraps it up for this edition of the Kennedy Mall Report.

Dennis Kennedy:

Thank you to the Legal Talk Network team for producing the show. You can find show notes and transcripts on the Legal Talk Network website.

Tom Mighell:

If you like what you hear, please subscribe to our show in iTunes, the Legal Taunt Network site or in your favorite podcast app and leave us a review.

Dennis Kennedy:

You can also connect with us on LinkedIn with your questions or to share your thoughts about this episode.

Tom Mighell:

And so until the next podcast, I’m Tom Mighell.

Dennis Kennedy:

And I’m Dennis Kennedy, and you’ve been listening to the Kennedy Mighell Report, a podcast on legal technology with an internet focus since 2006.

Announcer:

Thanks for listening to the Kennedy Mighell Report. Check out Dennis and Tom’s book, The Lawyer’s Guide to Collaboration Tools and Technologies, Smart Ways to Work Together from ABA Books or Amazon. And join us every other week for another edition of the Kennedy Mighell Report only on the Legal Talk Network.

Continue Reading