How to Successfully Make New Boundaries in Law: Marco Imperiale's Formula and Philosophy - S9E41

0:00It's a mission to reach our goals, whether with AI or without AI, with tech or without tech. If you think about what legal design can do in terms of plain language, what legal design can do in terms of infographics, what legal design can do in terms of creating customer personas without going for the real personas and changing your project, that's the real challenge. The more we reflect about language, the more we reflect about communication, the more we reflect about engagement with the clients, we can become better lawyers. There are several layers, at least in my experience of legal design.

0:32And once you reach the top level and you enter into impact analysis of what you are doing, the scenario changes because you are providing criteria in order to see the success and see what's working and what's not working on what you're doing. On today's Legally Speaking podcast, I'm delighted to be joined by Marco Imperiale. Marco is the founder and managing director of Better Ipsum. He graduated with a master's from Harvard Law School in 2016. and Marco was also an entertainment and copyright lawyer before becoming head of innovation of a leading Italian law firm. Marco also sits as the president of a well-being committee.

1:07So a very big warm welcome to the show, Marco. Hi everyone, it's great to be here. Ah, it's great to have you on the show. Love your energy and we're talking lots off air, so really excited for today's episode. But before we get into that, we do have a customary ice breaker question here on the Legally Speaking podcast, which is on the scale of one to 10, with 10 being very real, what would you rate the hit TV series suits in terms of its reality of the law on the scale of one to 10, if you've seen it? As any lawyer would say, it depends. I mean, if you think about structured law firms, I think it's seven to eight.

1:45If you think about small law firms, it's probably three to four. If you think about UK and US, it's closer to, seven or eight big law firms, but it's not the same in other countries. So it really depends. But I'm a big law kind of guy, I work with them, and so it's slightly more towards seven, eight. There we go, and a good cross-sectional answer. And with that, we can move swiftly on to talk all about you. So to begin with, Marco, would you mind telling our listeners a bit about your background and career journey? Oh, wow. How many hours do we have? not enough you know lawyers when they start talking it's just on and on and on luckily I'm not a lawyer anymore so I was a lawyer once but I have a company and I provide services to law firms, legal departments institutions and the company is called Better Ipsum and we work in legal design legal operations, legal innovation legal well being, everything that is kind of new fresh and dynamic in the legal field, we are probably in that or someone is asking, you know, something about it.

2:50So that's pretty much it. I am also the president of the Wellbeing and Mental Health Committee of Unión Internacional de Desavocados. I have written recently a book on legal design for global law in business. And here it is. Yeah, and I love that. Let's sort of go back to the earlier days for you, because we'll definitely get into all of that good stuff as well. What drew you to a career in law originally and what inspired you to sort of pursue a career as a lawyer? I wish you could say, you know, I was inspired by great lawyers like Andy or, you know, the rule of law, whatever. But truth is, the law school was the easiest choice for me after high school.

3:33You know, it was Italy. So lots of exams that were, you know, oral exams. And I always you know, love speaking with people and engaging and interacting. And plus, you had to learn lots of rules by heart, and I've always had a good memory. And plus, it was, you know, full of people. And so, you know, it was not kind of, you know, 2030. It was kind of, you know, 1 ,100 students in the law school or in the University of Bologna. And that's why I started. It was kind of, you know, let's start law school and then figure it out. And so I did a thesis in philosophy in the United States, the University of North Carolina at Chapel Hill.

4:15I was a musician at the time. And my first job was becoming a corporate entertainment lawyer to help my peers because they were asking me support about contracts and policies, is how to negotiate with agents and so on and so forth. I love that. And I want to dig a bit deeper onto those days as an entertainment and copyright lawyer, as you mentioned, because you work for stadium artists, booking agencies, labels, media companies. What were some of your memorable cases from back then? Well, I mean, the most memorable case is something I can't tell because it was a stadium artist dealing with an insurance company because of a tour that did not happen.

5:01So it was very tough negotiations, very sensitive data about, you know, what was happening with artists and the health of the artists. So I cannot get too much into details, but there was a, you know, very kind of, you know, big moment because I was a young lawyer. I was just finished my trainee years at the law firm. and you have this kind of million dollar case with stadium artists about a tour that did not happen and then you're on the case. It's exciting. But I could speak for hours about tours, negotiations with labels. I've seen artists delaying the release of an album for 12 months because of a couple of lines in the contract.

5:48And this is not something you expect as an outsider in the artistic world. But when you get to the point that it's a business, the music business and the entertainment business are businesses, and your idols are in the business, you think about what's happening in a different way. It's not about art anymore, and it's about making as much money as possible. How can I monetize on funds? you know exactly and you know business is business in in some respects as well and if people have put a lot of time in their to their creativity or into whatever their their work of art if you like then you know of course there is going to be a lot of negotiations and things behind the scenes and hence leaning on legal teams to create the right deals okay now i want to talk about sort of moving away from the traditional career path because what was the moment you realized traditional legal practice was no longer for you and you wanted to build something different?

6:44That's a very interesting question. So it was not a black and white moment. It was kind of a gradual path. So imagine I leave a boutique law firm, one of the biggest ones in my country. I launched myself as a solo lawyer, you know, in order to stay with the artist and deal with the artist. And then I realized that the world is going fast. The world is going very tech, very data oriented. And so I decided to take a sabbatical and, you know, the sabbatical in my case it was not a normal sabbatical because it was three years no three months in scotland you know doing pupillage for one of the smartest barristers well advocates uh in in scotland and supporting you know lords in their daily practice then my first camino de santiago which by the way i've done 11 times and then my master at harvard law so i decided to use my sabbatical in order to strengthen my skills.

7:37And so after the sabbatical, I just realized, but it took me one year to realize that what was happening in the legal field was very similar to what happened in the music field in 1999 when Napster came. So Napster arrives, and people are not interested in paying for music anymore. They are interested in playlists, and playlists have a specific value. they are interested in connecting with the artists and that's why you pay for you know synchronization merchandising concerts and so on and so forth but they're intending to pay for music anymore so that value dramatically changed and i mean we're speaking about 1999 and 2003 it's itunes 2080 spotify so i could speak for hours about that i also wrote articles on the topic But the idea is that if you are hiring a lawyer for knowledge, you know, that's not something that the market is willing to pay for anymore.

8:39I mean, I realized that in 2015 or 16, and it took several years for AI to rise, you know, especially after November 2022, you know, with GPT and, you know, now general purpose systems are used all over the world and billions of people are using them. But in 2016, it was kind of a leap of faith. You know, tech is going to come and we have to reflect, you have to reflect about what is the value that you provide clients. Is it the trust? Is it the brand? Is it the secret sauce? And can you define in a practical way what is the secret sauce? So this is it. I became the first head of innovation in my country.

9:24Then I took a second sabbatical, but at the same time I was working for the firm. So it was a very hot sabbatical because I was still working. And then I launched the Better Ipsum. And the way I launched it is just, you know, if I have to start a company, I want to do it in my own way. So it's a fully remote company. It's a benefit corporation. It's very much into legal well-being, which I think is one of the, will be one of the main drivers in the legal profession. We try to have a very smart and, how can I put it, bottom-up approach. So I'm the youngest, you know, I'm the CEO of the company, but at the same time, you know, I'm the oldest one and I'm 40 years old.

10:06So we try to have a very dynamic and interactive approach. You know, we work with contractors because we are also similar to a software house. Maybe we will do tools, maybe not. We have a very strong focus on your diverse talents and services. And that's pretty much it. Yeah, and I love everything that you stand for with your organization and your mission, because your mission is to support all stakeholders through this complex yet exciting transformation, helping them navigate the future with clarity and purpose. Really like that. So what is the meaning behind your mission? Give us a bit more.

10:42I mean, I wish I could have a clear definition through this. I'm changing it every seven days. But the idea is making law and the legal world more human. And then you just have to reflect about what makes you human and how can we frame services that are more human. And that's, you know, that's not an easy answer to provide. I have a personal blog where I speak about blockchain, zen, and sense of life. And this morning I wrote a blog post about the fact that maybe AI is coming to dehumanize us. Because most of the times I speak with my clients about optimization, efficiency, automation. and the more we go towards that direction, the more we consider ourselves as zero and one, as data centers, as data points, and we are thinking about entering in a battle with machines where the machines can already win.

11:43They process data better than us. They manage numbers better than us. They can collect information better than us, but they don't have that kind of instinct. that a client comes to the lawyer and the lawyer thinks, this client hasn't told me all the truth. Same for a doctor. There are all these elements that are leading you to a specific kind of outcome, but your instinct is telling you, no. And so it's not a tech-driven company. It's not a tech-driven mission. is a mission to reach our goals, whether with AI or without AI, with tech or without tech. And I think that the legal world, whether we speak about general councils, law firm partners, institutions, is facing so many challenges.

12:38It's a very exciting moment and it's a very scary moment. And we tend to underestimate the fact that we are overwhelmed about data, about information, about numbers. and our brain is not able to cope with all of this and to focus on all of this. So we're kind of in the wave and it's pretty tough for us to have long-term goals and long-term purposes. And at the same time, everything that's happening around the world in terms of AI, in terms of geopolitics is influencing our work as lawyers. So probably, to cut it short, otherwise I speak for hours, but it's creating flexible products, flexible services, and flexible approach towards what we're doing.

13:30So creating a flexible company, that's probably the best definition that I would provide to you. Why? Because prompting 6 to 12 months from now will be probably dead, or dead as we know it, and context engineering, pretty much the same, vibe coping, pretty much the same. But the idea of flexibility, the idea of shifting from being a service company to a learning company, that is not changing. And that's very exciting and it's very difficult. And the Zen word, which I love, when the snowstorm comes, the big tree is cut down in two, but the bamboo that is flexible still stands because it's flexible.

14:16So how can we be still better if soon five years from now, 10 years from now? I don't know which kind of products we will sell. I don't know which kind of relationship we will have with the clients, you know, co-creation, service providing tools. I don't know. And I'm also skeptical about everyone that says three to five years that we will be like that, you know, because I think that acknowledging of being aware of your limitations especially considering everything that is happening around the world it's a matter of being wise it's not a matter of you know being dumb i i love that and thank you for being so refreshingly open and honest and human as which is i know something you you really sort of you know are passionate about and i agree with you you know there are certain unknowns but adaptability is a word i kind of get from that you know being adaptable to the environments you know the only constant is absolutely going to be change and continuing to be as client-centric as possible and look what you've built with better ipsum is fantastic and again just in terms of being human and open with our listeners because everyone will see your impressive experience your amazing background but it's not easy to get there right and it's not easy to kind of build these things so what challenges have you faced and how have you been able to overcome them when building out your business oh so many i could speak for hours about challenges i think that the first and most important one, which is also related to my character and my attitude because somehow, some way, you know, if you're creating a company, you know, that reflects, you know, your mission and your purpose is that if you see things in a unique way and you're kind of convinced that, you know, that's a blessing that the universe gave you and your mission in the world is just you know being strong and stubborn in that in that perspective and hope that somehow some way someone will notice it i think that the biggest challenge is being a magnet and not a chaser so if you have a company like betterism it's pretty easy to say okay let's look at all the companies that have you know these hundred millions of dollars of revenues they have you innovation ads, sustainability ads, that are into A, B, and C, and cold call them.

16:30Or work with several other players, several agencies, in order to reach them as clients. And I thought about that. It would be way more convenient, especially in the short to midterm. But the kind of relationship that you have with them and that you develop with them is not the same as the relationship that you have with clients that come to you. Because what you're asking to clients is thinking and acting in a different way. You really want to co-create with them. And if you want to co-create with them, you got to have on your board clients that are willing to take that quantum leap. So that's very hard.

17:10And so because you have to be strong and still and be ready to face all the problems that your company may have, whether in terms of cash flow, revenues, investors, whatever, and say, if you really believe in that, clients will come and we will work them and creating something that others may consider as an inspiration. and that's very easy to say but when you're waking up and you have bills to pay and taxes, whatever that you may face as a company that's the hard part so everybody loves to be a magnet but I would say nobody but most of the people that I know most of the professionals that I know are not willing to pay the price of being magnets and if you want to be a chaser, good for you but especially if you want to do something that it's really groundbreaking it may be counterproductive and and that's a big challenge it's a big challenge but it's also a reality check and i think it's refreshingly again hard-hitting answer because that's what we want on the show we want you know people's reflections who have been there done that sharing their lessons their sort of opportunities i always talk about the acronym lose you know you never actually lose in life it's just life offering some experience and I strongly believe that because from every opportunity in every every circumstance you can always learn from something can move forward and talking and learning and now I want to move to your Harvard and legal design days because you lectured that Harvard Graduate School of Design what did you most enjoy about teaching on the course when it comes to legal design there oh I mean it was just a small j-term course at the Graduate School of Design because they say oh yeah you took the Harvard now I mean I graduated to Harvard.

18:53I went as a visiting scholar then. During my visiting scholar year, I had the opportunity of, you know, doing a JD term. And at the end of the day, you just enjoy working in legal design with students. That's what you enjoy the most. And say, how about redesigning this contract? How about, you know, reflecting on what legal design is for you? And because of the fact that it was not the law school, but the graduate school of design, it was also kind of, hmm, so we have designers here and the GSD is way more into structural design and architecture than it's into, you know, information design or graphic design.

19:30So it was a really good challenge in terms of structures of the document and customer, client, user experience. But at the end of the day, it's just telling them what legal design is because most of the people living in the design field don't know about legal design. And creating something together, or fully following a specific methodology by reminding them in the same thinking, even the methodology can refine itself. So it's very challenging. And I love, I'm lecturing at Polymoda. I'm still lecturing copyright with Bergman Center and Harvard school courses that are doing pro bono is called Copyright Excel of the Word.

20:15And I've done hundreds of classes. I love staying with students because I'm the one learning the most, especially now. And when I speak with clients, especially partners, they're scared when I tell them that that's tabula rasa. After 2022, after GPT, we are learning. I am, you know, Marco, I am the one learning how to use, you know, Claude. I'm the one, you know, learning how different versions of GPT apply. I am the one testing the products. I am the one working with Gemini. I am the one learning. And there's a 20-year-old guy in some campuses that are learning better, faster, smarter than me.

21:01And so I may have culture about that. I may have culture about processes. I may have culture about people. I may have culture about collaboration among departments. I may have culture about law firms. But when we speak about learning that specific tool, they may know better than me. And so it's my challenge to engage them in a smart way and involving them so that there's not so much difference between me and them. and that's something that law firms find a little bit threatening because you know especially if you're an equity partner earning millions of dollars or millions of pounds if you're in the UK here having someone that can provide a very similar product for a fraction of the price it's threatening.

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22:32If you're ready to leave frustration behind, visit clio.com forward slash UK to learn more and see why Clio continues to be the go-to choice for solicitors across the UK. Now back to the show. I also talk a lot about the importance of 360 mentors, having someone above you, someone at the same level, but someone beneath you and like you referenced there, these next generation people coming through who have got lots of skills, lots of talent, and sort of bringing out and nurturing that. It's wonderful. You talked about legal design. Again, just for folks within our audience and our community who may be less familiar, what's your definition of legal design?

23:07Well, there's a chapter in the book that is called A Definition or Many Definitions. So if you ask 10 legal design practitioners all over the world, they will probably provide you 10 different definitions. I do believe it's a discipline for the creation of user-centric products and services. That's pretty much it. It's a matter of bringing in the legal world the mentality that Amazon, Uber, Airbnb, Netflix developed all over the years. So creating something starting from the consumer, the user, the client, and going backwards. And then you have lawyers that are, oh, yes, but we do legal design.

23:49we really listen to our clients and then just no because co-creating is different than listening to them and even if you think you listen to them you really don't listen to them how many of you have done structured feedback forms how many of you have done co-creation sessions how many of you have reflected about how the clients perceive what you provide how many of you have also you know reflected about how the the clients sees receives analyze the information that you provide them and once you get into that loop you realize that you are really way behind and you are thinking you are providing a tailor-made client-centric service and you are very very far from that maybe you are a verbal thinker and your client is a visual person two-thirds of the population are visual thinkers but most of lawyers and journalists are verbal thinkers like politicians.

24:47Maybe your client is neurodivergent, and or maybe you're speaking about this calculus as a form of neurodivergency. And so maybe your clients cannot process numbers, and you are providing a long list of numbers. Maybe your client is ADHD, and you're asking them to be focused in an eight hour session or reading 60 or 70 times in Roman 12 pages. I mean, I could go forward, but the idea is that legal design is not something that is for legal designers. Legal design is something that is for lawyers because the more we reflect about language, the more we reflect about communication, the more we reflect about engagement with the clients, we can become better lawyers.

25:32And, okay, I can speak for hours, but the idea is that there are several layers, at least in my experience of legal design. And once you reach the top level and you enter into impact analysis of what you are doing. Then you enter in the KPI and ROI of contracting, KPI and ROI of legal design. And the scenario changes because you are providing criteria in order to see the success and see what's working and what's not working or what you're doing. It's a different way of looking at the legal world and it's a different way of looking at your services. Yeah, and we like that. And that's what we encourage here on the show is to kind of expand people's minds and create new ways, new opportunities.

26:12Because, you know, if nothing changes, nothing changes. And the world is changing. And you need to be adaptable. And like you said, flexibility back to your mission point earlier. And you gave some really practical, tactical insights there. So thank you ever so much for that. And now I want to talk more about your book. Because you published it recently. And practicing legal design. So what was the inspiration behind your book? Well, the inspiration behind my book is probably, you know, just a publisher that comes to me and says, yeah, blah, blah, blah, publishing a book. And in my life, you know, my life is a series of why not?

26:45You know, I have many episodes and experiences of, you know, it's very hard for me to say no. It's way funnier to say why not. And, you know, how about, you know, delivering this workshop for our clients? Why not? You know, how about doing an article on, you know, this topic? Why not? How about making a book that is more about the practice and legal design than more about the theory of legal design and say, why not? But, you know, if we are doing it, you know, I shouldn't say it's going to do my way because it's always a matter of, you know, collaborating and conversating with editor. But the idea is we got to provide something that is really practical.

27:25And so there are some chapters about the challenges that we face, you know, chapters about, you know, why things are not working the way they should. and why everybody's speaking well about legal design but why there are no projects in practice. So I really get into the things that we don't say in the field. And I don't think that there's a book in the market with a specific methodology, and this book has. And I don't think that at the moment in the market there's a book with chapters about legal design and artificial intelligence. And also because AI came, especially generative AI, not AI because AI is there since 1960.

28:08But, you know, generative AI disrupted the market. And ignoring that, if you're writing a book, it's, you know, totally counterproductive. And so the idea is, it's a four-part book. The first one is about, you know, the ontology of legal design. We decided to put it there because especially partners, general counsel is slightly less, but especially partners don't know about legal design. Or they think they know, but they don't really know. and the second chapter is about disciplines that are or you know areas of law that are kind of related to legal design but are not legal design gamification dark patterns sustainability AI the third part of the book is the bridge between theory and practice and so you know how to structure a session, it's better live, it's better offline, you know, what does it mean in practice, what are the challenges, what are the advantages, what are the tricks, you know, for great sessions.

29:14And the fourth one is the methodology that we use at Better Epson where we work documents and contracts, which is a, you know, three-layer framework that we developed, and it's called the Leonardo Framework. and after each part of the book there's an interview with a key player of the legal design industry and even if they're not legal designers one of them is Michael Doherty is the first professor of legal design Sally Gouyer, CEO of Work Commerce and Contracting Matthew Berderick that is the typography for lawyers mastermind but is also one of the smartest copyright lawyers I know and last but not least Ashley Ruggles and Macklin Staley who are not only great lawyers, but are also influencers with the law says what I think that they have, you know, 1 million plus people on TikTok following them or something like that.

30:03Yeah, it's incredible and so high valuable and content rich and thoroughly, thoroughly enjoyed it. And I know lots of people who will hopefully check it out after this podcast will too and get serious value from it. I want to go to the third part specifically, because you touched on it there and go a bit deeper because your book has been described as a comprehensive guide to implementing legal design in law firms and legal departments and it's engagingly written featuring real world examples and challenges so how did you balance that sort of theory with the practical realities lawyers face every day because that's going to be the heartbeat of this and we're trying to increase adoption i mean the short answer will be being transparent but don't don't name clients and episodes so the idea is everything that you see here is real but we decided not to you know mention you know the clients or the corporate providers that were involved in order you know for them not you know going to approvals and you know what happens so and it's kind of you know the the manual instruction of the ikea so you you go and then and then you play so when i say if you want a successful legal design project, the first issue is the budget.

31:18Because everybody loves legal design and there's the budget. And then it's not a priority. And so how can you put it as a priority? Or go for the evangelist, which are your key players in the organization. It can be a trainee, it can be a general counsel, it can be the CEO, the CFO, or it can be just an in-house counsel. But the idea is that without the evangelist, the process will not move forward. Everything that I say is coming out of experience. Because I've seen in my life projects suck for months. And I know that if you don't have someone inside, that project is not moving forward. And you can send mails.

31:55And especially now, most of the legal departments and the law firms are just AI, AI, AI, AI, AI, and nothing else really matters. Then you should reflect about the fact that, first of all, how can you match legal design and AI? And secondly, how can you make this a priority in a legal department? There's other priorities at the moment. And you can tell whatever you want, but if they don't perceive it as a priority, it's not a priority. I'm sorry about that. You know, the business is business. And if you sell empathizing with the client as an asset, you should empathize with them, and probably they're right.

32:39And what I see now in the, especially in the software community more than in legal design community, is that you have software and project managers and engineers and other scientists that are just telling lawyers you're wrong. And lawyers that are just, yeah, you're telling us about the end, about the billable hours since 1980s. You're telling us about the AI since years. And you know what? Nothing is changing. and I think that a better active listening on both the ends could really help law firms to be a little bit more forward-thinking and developers and data scientists and engineers to be better listened because they struggle with the fact that this project cannot move forward because of A, B and C and D and the idea is where the other party shoes and maybe your project will benefit love that yeah i always say and even when it comes to negotiations or anything it's not necessarily about you it's about them you know and the benefit to them and i love that lens in terms of the way you look at things some ai ai ai as you say um how do you see then specifically ai and tech interlinking with legal design that that's a $1 million question.