AI, Leadership, and Why Great Legal Leaders Let Go: Matthew Campobasso of Zone and Co.

Matthew Campobasso0:00
Lawyers cannot risk being the long pole in the tent. We just can't. Because again, even if we're giving good guidance, if the business thinks we're leaving dollars on the table because legal is not keeping pace, people are going to go around legal.

Cecilia Ziniti0:18
Welcome back to CZ and Friends, the podcast where we talk with legal leaders, operators, and technologists driving business today. Today, my guest is Matthew Campobasso. He's the chief legal officer of Zone and Co., a software company in the financial services space. He's led companies through IPO readiness, complex MA, global compliance design, and board-level risk strategy. He teaches law and fun one. He's also a podcast host, so it'll be fun to turn the tables. And he's writing a book called The Case for Letting Go. Um, if you're not intrigued by that title, I don't, you know, I don't know. I don't know if you haven't had your coffee yet. But Matthew spends a lot of time thinking about control, judgment, certainty, what legal leadership looks like, and then now today AI. Let's get into it.

Matthew Campobasso0:58
Matthew, well, really, really good to be here. Thank you for having me. Uh excited. I'm a fan of the podcast, and I've listened to last few episodes you've released, and I'm excited. Also a little nervous. I feel like you're gonna ask some tough questions, but you know, keeps it interesting, I suppose.

Cecilia Ziniti1:13
No, it's good. It's good. Um, I think uh it's uh being in the chief legal officer seat, you have these moments where it's like, all right, you're gonna do a podcast, you're gonna do this, you're gonna do that, and you just have to step it up. You said something, I guess, uh, you know, this is my show notes say quietly radical, but basically you think the legal profession has a control problem. That is uh an interesting place to start. People are very competent, but they have a problem with control. So what's the unpack that for us and and let's dive in.

Matthew Campobasso1:44
Absolutely. I think that's gonna be a thread that I probably touch on a lot here today, especially if we chat about the book. The simplest way I can explain it is to distinguish between the two, competence and control. I think competence is a skill. It's something that you develop it's from education, it's from experience, it's from making mistakes. I think control is kind of woven into people's identity. And by that I mean, you know, I've spent years personally, white like white knuckling outcomes that I was really never in charge of in the first place. I I convinced myself I was, you know, whether that be a grand jury deliberation back when I was a prosecutor, evidentiary hearings when I was appearing in front of federal judges, or more recently as an in-house lawyer over the last eight years when it comes to board decisions or market shifting or other things that involve, you know, peers of mine on the executive committee, things that I would find feeling like I had to kind of grip tightly to control. But ultimately when I stepped back after the fact, I realized, you know, I did my part up front with respect to inputs and I had no control over the outcome. So that's that's a big part of what I mean by that. You know, I think what it what it is and how it manifests in me, CZ, is I, you know, I am managing my own anxiety and I call it professionalism. And the irony in that, I think, is that the tighter that I grip or the tighter that any lawyer grips, the less effective you become because you're not managing risk anymore, right? You're managing your ego or this concern that you have about, oh no, what's gonna happen. And so that's a big part of what I what I think about when I consider those concepts.

Cecilia Ziniti3:15
I mean, is the anxiety a feature though? So I'm thinking um it was Mental Health Week a few years ago, and this now famous investor, April Underwood, she was an early product at Twitter, and she basically tweeted something to the effect that anxiety and nervousness is a feature, not a bug. So it's basically if you're somebody who has anxiety, it shows up as being ultra prepared, considering possibilities, making sure that things go smoothly, which I think are lawyer traits. And so where do you get to where it's like, is it a feature, is it a bug? And it sounds like you're saying it becomes a bug. When does that happen and how do you deal with that?

Matthew Campobasso3:54
That's exactly what I'm saying. I think it could be a feature if if you have that self-awareness and you can harness it appropriately. I think it becomes a bug when it goes unchecked, or maybe you feel the things that present in your nervous system as anxiety or the need to control, but you have no idea what it is and it has its hands on the steering wheel and you have no, you have no agency. So I think one of the ways I think about it is a way that it can show up in a healthy way is in a company, you know, you can have one of two ways how legal is there, right? They can either be a function or I try to have my legal be built to be a partner. And so if every contract or every product decision, every partnership has to pass through legal the same way, it's it's not scalable. I think that erodes the trust that you're trying to build with the business. And so I feel like lawyers, and this is a CLO, a GC, a deputy GC, anybody who's working in-house, especially, you have to learn how to hold authority without pretending to control the outcome. And so that is where I have found CEOs and partners of mine on our executive leadership teams and just other parts of our business trust you. And with that trust means they come to you. And I think a big part of being capable and effective as a lawyer is just having that steady stream of information. Because if you're not a place they can bring that to, because they're gonna say, oh, Matt's gonna grab the wheel and do what he wants, they sidestep you. And then you're in the dark and the company's gonna be taking on risk. So I don't think wanting control or wanting to have your hands on the wheel in and of itself is a bad thing. The idea to me is it's not about the tightness, it's lightness. You can have your hands there, it can be felt, people can be aware that legal is involved, but I think that it just has to be how tightly hold how tightly am I holding this, and what is the long-term impact of that on the relationships I'm trying to build to help me and my team be effective.

Cecilia Ziniti5:48
Is there a particular example you can point to, maybe the rollout of a new regulation or an MA or something? I had this conversation, a similar conversation with another um CLO recently, and they said something to the effect of like, you got to let the business burn their hand, and then they'll know not to touch the stove. And I kind of was like, well, but like you could have warnings or you could be like, hey, you know what? You know, when you're making this flambe or whatever, you might get burned. Like, what's the can can you give us a real story?

Matthew Campobasso6:18
Yeah, I think that's a great that I I love the the turn of phrase there because I think sometimes, you know, I'm a I'm a dad to three kids, and there are times where, you know, the last thing I want is one of my kids to burn their hand on the stove, but you can only tell them so many times until they have to take that conceptual pain and and realize it. And hopefully the stakes are low and it's, you know, it's more of a subbing your toe than it is a burning your hand off. But the idea is the same. You know, for me, I had a an encounter, I'll say within the last two years of my career where another executive came to me in the context of just a commercial contracting issue we were trying to figure out a solution for. And I gave my perspective, I said, look, this is my starting point. Let's figure out how to find a common ground that helps you accomplish what you need to, helps me say that, hey, we had the conversation and we're going to protect the business the best we can. And the reaction was one that I was not expecting, which was this is why I tell my team not to come to legal. And I caught me off guard, right? As a lawyer, that's the worst thing you can hear.

Cecilia Ziniti7:18
You just need to slip that out. That's great.

Matthew Campobasso7:19
Well, it was like unapologetic. And, you know, I don't know, perhaps that executive was having a tough day, or perhaps they hate lawyers. I don't know, or a little bit of both. But it caught me off guard and I said, Look, I'm sorry to hear that you feel that way. I believe that my team and I have given you and your team all of the tools and the support that you need to be effective. It's never going to be a good thing if you sidestep legal. I'm here to do a job just like you're here to do your job. And the few times, you know, and then there is that instinct between what your prior guest had said, which is, you know, I'm just going to step back and watch you set yourself on fire. But then you look around and you're like, you know what? I'm not here to serve my own ego. I'm here to serve the company. And so I, it's not to say, and again, a a burn can, you know, there's degrees of burns, obviously. And that instinct.

Cecilia Ziniti8:08
Yeah. So did they do the deal? Yeah. I I did it.

Matthew Campobasso8:10
We did it. I kind of forced, I said, look, here's minimum requirements. Every additional one of these things that we layer on top is going to protect the company. But I am one voice in this conversation. And my baseline is we're not breaking the law. We are saying doing what we say we do in an agreement. And we got to an outcome. And I don't work with this person anymore. It's unrelated, but um, it was a tough lesson because, you know, I take a lot of pride in what I do. And I thought to myself, hey, I'm just trying to make this better for all of us. And to be met with that energy, again, you don't know what somebody's dealing with. So I always try to give them the benefit of the doubt. But that one caught me off guard. I've been practicing now for almost 20 years. And to have a conversation like that in my 19th year of practice was, you know, it's it's rare that a day presents me with a new set of circumstances to navigate.

Cecilia Ziniti8:54
But I mean, that's fascinating. So you were a state attorney and I think you did criminal matters. You know, you just compared that experience to, to, to the corporate. You know, I always thought, you know, I used to do patent litigation and or, you know, the what I do now. And a girlfriend of mine is like a like a family lawyer, and you know, she talks about how acrimonious the divorces are, and just like, I'm like, okay, I thought that that the stakes are different in my stuff. But how is that, how was that transition and anything? Do you think the experience or how has that the experience of having practiced in such a varied area shown up and and helped you when you have meetings like that?

Matthew Campobasso9:30
I think it's helped me a lot. I will tell you, there's very little diplomacy when you're in a criminal courtroom running a call with 200 matters. You know, I I spent two years, two and a half years as a prosecutor right out of law school. And it's the highest burden in the law. It's, you know, people's freedom is oftentimes at play. And so a big part of defense bar is there's a lot of theatrics, right? They want to inspire confidence in their clients that I'm, you know, the state's trying to squish you, I'm here to protect you. And uh it's not for me to editorialize on how everybody anybody builds their business, but it was a pressure cooker. Two, two and a half years of that, you know, having judges say, you know, Matt, you did it 95% of the way, but it's the highest burden in the law beyond a reasonable doubt, and so therefore not guilty. And I thought, okay, wait a minute. This guy punched this person in a bar unprovoked, and now he's walking free. That's my failure. And so when the stakes are that high and the burdens are that high, not to say that my job has gotten easier as I've gone on in life, but then I transitioned to a civil litigation firm in Chicago, where I spent 11 years as an associate and a partner. And instead of people going to jail, it was, you know, entire businesses that people had built that were on the line. Because if they lost a lawsuit and they were found to have breached the contract, they have to dissolve a business and 200 people lose their jobs. And so I think the things that made me want to run from the courthouse as a criminal prosecutor screaming served me really well now at this point in my career because I have been told a lot in my career, you know, Matt, you're pretty unflappable. It really takes a lot to, you know, do you ever like lose your cool? And I do. I mean, I absolutely do. I try to limit it and, you know, but you know, I feel like I've seen it all. There's not a lot of lawyers in my experience that have done the criminal side, you know, the law firm side to the degree where it was, you know, 11 years and then have had success as an in-house lawyer, which is what the last seven and a half years of my career have been. So I've kind of seen the law in boardrooms, in courtrooms, and jail cells, and grand juries. You know, the variety has been great. It's allowed me to kind of build out my toolbox, I think, in a way that makes me a lawyer who has some good range. But yeah, I there's new ways that my experiences present as adding value regularly. I'll find myself reflecting. You know, you get two decades into a practice and you start to really look back and think, what a weird ride. You know, it's been a weird ride and I'm grateful, but you know, I'm still learning every day. And I learned things from my job this morning that I didn't know, you know, when I punched out on Friday.

Cecilia Ziniti12:02
So 11 years, saving people's businesses, civil cases. What are you most proud of from that time? Any any cases stick out that, like, you know, if you were creating the highlights, real case.

Matthew Campobasso12:14
Probably the one one case that that springs to mind, and I am really proud of this, is a case that did not yield any billable hours or revenue for the firm. During the time in my law firm days, two of our partners had set up a legal clinic on, I think it was Tuesday mornings for about three years through their church. And I didn't I wasn't a congregant at the church, but they had mentioned it to me. They knew I had some background that I might be able to help people navigate criminal things that they were dealing with. And so I volunteered at this clinic for three years. And one of the people who walked in one day was an employee at a grocery store that's pretty prevalent in the Chicagoland area, and she had been given a pretty raw deal. And she was an immigrant and she just was in a really bad spot. And so I petitioned the firm. They approved me, I think they said initially 200 hours. I think I spent like 600 over a period of two years. It was a big commitment by the firm, though. And I think hopefully it was a reflection of how hard I worked on my billable work, too. You know, they were like, Oh, we're not losing money on this guy, so we're gonna give him the rope here. But we were in federal court and we took it to the eve of trial, literally courthouse steps, and we settled for a sizable six-figure amount that I know to this day impacted her life because 10 years later she still sends me holiday cards with pictures of her boys and and says thank you. And so, yeah, that one is for me the one that, you know, I'll tell my kids about someday.

Cecilia Ziniti13:37
Is um having had those experiences like that, now taking it to the corporate job, got in a really good discussion on the pod last week about kind of like what is the law versus what is right? And I'm assuming at your company, you know, you you you push that culture, but how how do you do that? And you know, when you've got that environment where folks are saying, hey, I, you know, I this is why I don't go to legal kind of thing, you know, bad day, whatever. But is there a kind of like trying to get to a point where the your stakeholders kind of do the right thing without you in the room? How do you teach that? And then how have you thought kind of about the moral compass, especially given, you know, that the case you're most proud of was actually taking a corporation to task, it sounds like Yeah, I think one of the other things you'll hear me probably weave in and out of my comments today is you know, being a dad.

Matthew Campobasso14:31
I I like I mentioned I have three kids, my son's sixteen, my daughters are twelve and seven. There is nothing more important to me than them. You know, I think that that's anybody who has kids probably can understand the sentiment. It sounds cliche, but it's true. I think about the impact, and I'll say, you know, not to be dramatic, but my legacy within my company or the companies I've been with in some ways similar to how I think about what I hope my legacy will be with my kids, which is, you know, especially my 16-year-old. You know, he has a car, he's out in the world 98% of the time without me. You know, my seven-year-old daughter still wants to hold my hand when she crosses the street, which I love, but my son's not looking to hold my hand when he crosses the street. He's he's not looking over his shoulder at my face to say, is this right or is this wrong? And so I think about the job is when I do have the opportunities, whether it's with my kids or with my colleagues, is to be clear in communicating expectations and to equip them with the judgment. I don't want to work with people, lawyers or otherwise, that just do what you tell them. I want to be challenged. I make mistakes constantly, as a dad as well. And the first thing I do when I make a mistake is I apologize, whether that's to my kids or my colleagues. But I feel like if you show up and you, you know, walk the walk and you do the things that you're telling the business you expect from it or your kids, it's a lot easier for them to mimic that out of respect, out of a shared vision for what we're trying to accomplish. And so I I do hear times, I've been with Zone now for almost nine months. I do hear stories after the fact, someone might come to me and say, Hey, you know, on a meeting, this issue came up, you were blocked out on your calendar, so I couldn't grab you. But somebody mentioned that, hey, Matt helped me with this thing before, and this is what he thought would make sense. And so here's where we landed. Are you are you good with that? And I say, I'm so good with that. And I'm I'm so happy because I was able to focus on something else because something that I've spoken about, I did it in a way that was clear and understandable and reasonable. So the business felt like they could take that and apply it. And so I can't be in every room. We're a we're a relatively small company from a headcount perspective. We're about 300 people. My last company was 1300. We would do trainings across the whole business to raise collective awareness, not around the law. I would tell people it's not your job to be a lawyer. I don't need you to study for the bar exam. In fact, I strongly recommend you don't. Um, but I need you to have your antenna up. So if you hear something and you think, you know what, I should go talk to Matt. Number one, you feel comfortable, or my team, somebody on my team, you feel comfortable. And then when you come find us, you feel like you can communicate it to us in a way that's gonna help us get our head around what does this mean for the company? And then collectively we can, you know, either we'll take that baton from you and run with it, or if it's a collaborative thing, you know, we want to be in the ring with you guys working this through to the right outcome.

Cecilia Ziniti17:19
You know, the the kid metaphor is a good one because I I did a lot of trainings. Something I'm super proud of was at Amazon we trained folks on privacy around Alexa and you know, got great perception, what have you. But it is similar, like you said, where when you hear of people making the right decisions or of thinking like you've essentially trained them to think, it's like seeing a baby walk. You're like, oh, this is so wonderful.

Matthew Campobasso17:48
Right? Like I this wasn't here and now it's here. And exactly, exactly. Because it also validates you, right? You're doing something right. And it's you can see the extrinsic value in it. And to me, that's one of the greatest parts of being a dad. And I find my happiest moments at work.

Cecilia Ziniti18:04
So in that story, there is a little bit of like, you know, on the operational side, you said letting go of, you know, being in that meeting, letting go of reviewing that contract, uh, pick the thing. So um, you know, do is that an operational thing or like unpack this letting-go concept from your book and then, you know, let's tie it back to kind of like legal operations and running a department. So maybe do those two things.

Matthew Campobasso18:31
Absolutely. I'll talk about the book for a moment if that's okay. Just the ideas, because I think that'll lay a good foundation for the operational question. Thankfully the book's almost done. To anybody listening who's ever written a book, you have my hats off to you. That it is such a process that I did not understand going into it. So I have such an increased respect for anyone who's written a single book, let alone, you know, like a Stephen King who's just crank out what seems like a book every six months. It's such a process. But for me, this particular book, the case for letting go, the central thesis is lawyers are trained, whether that's in law school and then in the practice of law, that if I'm not the person who catches every risk, who spots every flaw, who controls like every single outcome, then what is my worth? And I think that's an existential question that our profession avoids because we like definition. And so I think law is one of the few professions where the downside of a mistake is can be both public and personal. You know, you've got malpractice, you have sanctions, there's reputational damage, could be the end of someone's business and 200 jobs that they can no longer afford to pay. So for me and for a lot of lawyers I spoke to over the last couple of years, I think our default becomes like never let go of anything ever. And the math feels rational until you think about the effect it has over, you know, a four-decade career. And more importantly, to me, at this point in my career in my life, the toll it takes on you personally. And so what I've realized and what the book posits is letting go isn't lowering the standard. I think people will see the title or hear the idea and say, well, no, what do you mean? Are you just giving up? As I wrote the book, what I grappled with was you have to choose the standards that actually matter. So you're letting go of the illusion of control and you're focusing on outcomes, which I think really is what great lawyers prioritize. You're holding on to things that are like preparation or what are your values? What kind of judgment do you bring to a situation? Every lawyer I've spoken to, as I've written the book and I've I've set aside time, I've asked certain friends and peers and colleagues to read a paragraph, they've gotten that reaction immediately. And I think it makes them uncomfortable because it's kind of the quiet part that I'm trying to say out loud. And the phrase of letting go, I think, is threatening because I feel like for lawyers, having your grip on something has become synonymous with competence. And so the idea here isn't to have the ceiling on your career be your skill. It has to be your willingness to release the identity so you can build those reputational characteristics that want people to that people see and they make them comfortable to come to you. And so again, it's not about giving up, it's not about apathy. It's just about understanding, again, that grip I mentioned earlier. It's not, it's not tighter, it's lighter.

Cecilia Ziniti21:18
It's interesting because I hear that, and obviously, you know, to a hammer, everything's a nail, but I hear that and I think about founder mode. So there's a big debate in Silicon Valley. Paul Graham, who was a very successful investor, founder of Y Combinator, investor in Airbnb and Stripe, and you know, uh has is a gazillionaire. But he talks about how founders, you know, there's data that founder led companies do better than those with professional CEOs generally. And part of at least his theory is that founders do need to not let go of some things. They need to stay involved in the details and do that. And so I hear that. And then I separately see all this stuff about scaling and let go and all these things. And you mentioned not reducing the standard. So for us, I still interview every candidate that applies to G, you know, that we hire for GCAI. And, you know, but I'm wondering when do I let that go? And so like, how do you how do you do it? How do you have that standard and yet let go? I mean, I think in this case we've written our cultural values. So we've done a bunch of things that I think help. But there's definitely that moment of like, okay, we might make a mishire. But I suppose we might make a miss hire when I interview them anyway. So I yeah, I don't know. So how how do you like in the moment, how do you do it?

Matthew Campobasso22:33
It's a work in progress and I think it will be forever. And I think it's not knowing there's not one bright line rule. It's not black and white. I think hiring to your point, I've never hired a member of a legal team in my whole career that I have not personally interviewed. You know, I'm not at a point where I'm running a company and hiring a thousand people. You know, you kind of have to balance the the long-term vision with the short-term pain and there's only so many hours in the day. And so if I think about your example, Cezi, where you're saying, hey, I interview every single person we hire for GCAI, you know, there may come a time where you feel like you've hired the person that has the same lenses and the same set of principles that you have and then you trust to hand that baton off to them. I have two lawyers that I work with at Zone. We actually work together at my prior company and I trust them both implicitly. And you know, they still bring things to me and say, hey, just FYI, you know, let me know if you disagree and and I sometimes will joke and say I think at this point, you know, even if there's like a disagreement on 2% of it, I'm not, it's not a good use of my time. I'm going to step back. I trust you. There's a reason why you're here. And yeah, that's the thing. And it's it's not always letting go so it doesn't get done. Sometimes it's letting go because you're just not the right person to do it. And so it's about balance because for you growing a company and for me helping a company grow, there's no end to what we could do to add value to our companies. But also it's not a sprint for either of us. Whether there's you know an IPO or an exit or some sort of a strategic transaction, you know, days are long and you have weeks and months and years. You have to stay capable of a baseline of production. And I feel like trying to control everything at all times is it's an impossible task. And so to me it's not about not controlling some things or letting go of everything. It's about being deliberate in what you hold on to and to your point at the right time having faith in the people that you've hired or the processes you've built to let go of certain things.

Cecilia Ziniti24:39
I I think I it's literally a debate I was having myself I had a plane ride recently and we're trying to get all the interview schedules and I'm like I might it might be time but but good one. All right so let's bring this back to um to building a legal department. So you said legal is the most interesting seat at the table in tech. I've had people say GCs are the new CTOs now where we have to understand data, we have to understand flows, we're driving on AI.

Matthew Campobasso25:01
What's your point of view on that yeah I think I'm gonna I'll I'll focus on AI CZ I think because AI is rewriting the operating system of how businesses function and within businesses how functions function legal is very fortunate to sit at that intersection of of these four areas. You have risk you have regulation product design and commercial strategy. There's no other seat within the business its own my last company that touches all four of those things. And so I feel like the GC or the CLO or even an aspiring GC or CLO that touches those four quadrants has more strategic leverage right now than probably anyone other than a CEO. And I think the issue is you have that access and you have that ability to influence the business but a lot of legal leaders that are still in those roles are operating from an old playbook. And that is a reactive playbook. It's waiting for the product to ship reviewing a contract flagging a risk sending a memo to me a lot of that is downstream it's reactive to the business. And something that I have spoken about and I write about in the book is thinking about things upstream. And that's about building an architecture. And so to use the example of technology and and AI at Zone my team we sit with our product and engineering people from the design phase. When we are building features that touch AI or compliance or enterprise data or flow of funds, we're not a checkpoint at the end. We are a voice in the room from day one. And what I've realized is on that first meeting to kick off a new product function or a new product altogether, legal may be involved in 5% of that conversation. But every meeting from that point on, that number multiplies and so you don't have to play catch up. And a lot of times in product kickoff meetings, I'll sit silently maybe until the third or fourth meeting and I wonder to myself, do people wonder why I'm here? And then that fourth or fifth meeting comes around and I start asking questions that inform the quality of the product, the speed to market and the trust that the team's placing in the fact that we're protected when we do go to market. So I think a lot of times historically and I'm I'm in my late 40s and so I'm kind of walking I think the sides of two different generations of lawyers and I and I kind of I'll look at older mentors and younger lawyers and I think, okay, what can I cherry pick from each? Because neither is doing it wrong. Everyone's adapting. If you're at the you know on the 18th hole of your career there's a lot less incentive to be cutting edge in learning and understanding where the world is going because you think okay I've got 12 to 18 months. Not that those lawyers don't care but it's they're kind of locked into a set mindset. And so there's not a lot of incentive to step back and say hey how can I be more fluid and be a better partner to the business.

Cecilia Ziniti27:52
I mean it it's it's a I I was still read about law firms there was a law firm that just published something that they went to partner meeting and debated if they were used going to use any kind of AI, not just like GCAI or Harvey or Gemini. They're like and they said no like they will not do it. And you know to me that feels a little bit like 18th whole thinking where you're like all right we're gonna we're gonna protect our PP or you know our per partner profit in the short term. But I I think it's you know it's funny because you know being on a podcast and whatever all the metaphors but I do think one of my business idols is Taylor Swift of like having these eras that like it is a new era of legal and you know you can join it when you want to but the later you join like this is where the world is going. Like it's not fathomable to me that you know I a debate I have is like when is it going to be malpractice to not use AI? And I think that's we're close within five years. I think we're close. I mean and think about you know even your other experiences with a lawyer and so so like what are you so make some bold predictions. You've weathered a bunch of different eras obviously from you know criminal prosecutor through to you know civil late litigator now and then to GC you've used AI how do you does it change being a lawyer and how and then give give us some some bold predictions absolutely first of all before I answer your question I can now finally tell my daughters that they should listen to a podcast I was on because Taylor Swift came up so that's a win.

Matthew Campobasso29:16
This is the first one.

Cecilia Ziniti29:18
I mean I'm gonna tell them hey you're gonna have to she's she's an incredible she has great lawyers also so another thing.

Matthew Campobasso29:23
She has a great system all the way around her. She's built really well. But yeah I think about AI and I am anyone who knows me, when the topic of AI comes up they probably start looking for the exit because I will talk about it. I have opinions and theories I think to your point it will be malpractice at some point for law firms or lawyers who are not using AI. I think five years is probably the drop dead I think it'll probably be closer to a year. And I just had a conversation actually last week on my podcast about AI and about integration and about utilizing it. And I think the idea here isn't that lawyers are going to go away. The idea is that lawyers who know how to issue spot and who have range who I you know I call generalists are going to be the ones who are best situated to be effective with AI. Because I think about my law firm practice, you know, those are subject matter experts. You have the Midwest's leading expert on antitrust law. And I remember if I had a case that touched antitrust, I would schedule time with him, I would sit down, I would debrief him on everything, let him kick back the information and what was pertinent. And now I can do that with AI in about five minutes. And it's not to say that it's the same level of depth or expertise or the analysis, but probably 70 to 80% of the value in that I can extract pretty quickly from utilizing AI. Or if you don't want to take the human out of it, you use AI to help put a fine point on the questions that you have for that person. And it it creates an efficiency or it streamlines the amount of time and the cost to the client. And so I think that lawyers are going to be effective the lawyers who will be most successful in the age of AI or the AI era are going to be the ones who understand materiality or relevance of information and they're gonna understand those are the inputs. They're gonna know how to craft effective prompts and they're gonna be able to get from point A to point B in a way that maybe took a lawyer 10 hours previously and now it can happen in 10 minutes. And I think business is not slowing down. The world is not slowing down companies are shipping products and technology is evolving in a way that we've never seen and I think it's just getting started. Lawyers cannot risk being the long pole in a tent. We just can't because again even if we're giving good guidance if the business thinks we're leaving dollars on the table because legal is not keeping pace, people are going to go around legal different reasons than the conversation I mentioned earlier with a former colleague, but we're out of the room.

Cecilia Ziniti31:56
That idea of like that you can get from point A to point B in 10 minutes instead of 10 hours do you just go more places? The metaphor I use is like okay giving a trained lawyer AI is giving a marathon runner a bicycle where they're like already I'm already like crazy fast and like I'm not gonna wear you know wear your little like helmet and your strappy shoes and that's annoying and by the way it falls down half the time you know so like early models did. So I but then you know once you get a good bike and a good rider people who are marathon riders are going to be really fast and really good and they're gonna go more places you have the muscles, right?

Matthew Campobasso32:31
You have the lung capacity. You have the leg capacity.

Cecilia Ziniti32:34
Exactly that's my thinking. So okay so like and then then you think it's like okay even like the electric bike or whatever, but there's still going to be times where you're in tricky spots and you're you know trying to go up a mountain bike or whatever where you're gonna need that. So what do you think like are there times where like what is when you or your team have like a great day and you're like we were great lawyers today. Like what what what has happened and is that different with AI? And if there's any specific examples, of course I always love that.

Matthew Campobasso33:01
Of course. Yeah I think great days for us are where we are doing more than just reacting to what the business is bringing us. We're actually affirmatively staking out new pathways for the business. And I think AI has gone a long way towards allowing us to do that. You know, I mentioned earlier just a few minutes ago thinking using the analogy of the bicycle for the marathon runner, what used to take me maybe 10 hours over the course of two days, I can get done in 10 minutes. And what that allows me to do is I remember a point in my career as an in-house lawyer where I might be going from point A to point B. And along that way I might see something and say, oh wow, I should really come back and spend some time with that because if things go really poorly, that could be a big problem for our business. But when it takes you 10 hours, sometimes you don't have the time to go back to that thing. And what I find my team being able to do more frequently now than ever, in large part due to AI, is we do go back, you know, we we cover that point A to point B in 10 minutes and then we do double back and find that thing that was left untreated that we just happened to encounter on our journey and then we can pick it up and build a process around it or put guardrails around it. And so the first time you think about it is not when it's on fire. You're actually wrapping it in something that's fireproof.

Cecilia Ziniti34:17
Yeah yeah yeah no that's great. I mean I I was talking with a a friend yesterday who said that their company it was a software company that did sell to the government and sold to some different countries and they hadn't done their export registration for like five years or something and they go to sell the company and it comes up in diligence they're like oh we filed it it's just late we filed them all and they filed them like that day or something and retro retroactively but so it sounds like you're gonna you're gonna have fewer own goals. So what else if I as a CEO, what can I expect out of legal with AI?

Matthew Campobasso34:51
I think speed again that's a be a broken record. I think the first thing is speed and you know I have in the last two years I've put together LOIs which sometimes you know if we went to an outside firm might cost $50,000 and take three weeks. And now you know I can have a conversation with our strategic team on a Friday at 10 a.m and have a relatively fully baked LOI by the end of the day. And so you know that doesn't everything that I do is categorized and I don't want to oversimplify it as reactive or proactive. Reactive doesn't add a lot of value. Right? To me, I'll use the example with my son who's 16, he had a little bit of a fender bender like a week after he got his car and we went to the body shop and they were like oh it's going to be $2,000 and I thought okay I'm gonna write that check what is the value I'm getting for that nothing. Because I'm reacting to something that went wrong. That's not a good use of money. What a good use of money is would have been you know a different again I can't think of it exactly within the metaphor of the car.

Cecilia Ziniti36:01
No, it makes sense. But there's an investment you can make so well it's also like the the this idea of like that, you know, the Fender Bernard example is a good one in college a a girlfriend of mine lost a deposit on something because she didn't plan it right and she was like all upset and I'm like look you know parents they have this thing and now it's funny because I'm a parent where there's like a stupid tax. And like for me it's a fender bender. For you it's this deposit that you lost on some vacation that you're not taking. And I think there is a stupid tax that companies pay. Like it's just like and we we had this we paid a fraudulent invoice we had an outsourced accounting firm pay a phishing invoice that in retrospect was actually quite clear it was phishing um which is which is a bummer. But anyways obviously we're putting systems in place and we're fixing it. But you're right, what do we get out of that $20,000?

Matthew Campobasso36:45
Literally nothing a lesson like right you burned your hand on the stove.

Cecilia Ziniti36:49
Exactly I burned my hand then it's like okay let's set up a procurement process and let's set up you know ramp approvals. I think I had been asked to set up approvals in sort of like our our system and you know maybe it should be NetSuite but it or you know zone and code but anyways I've been asked to set up approvals in our system and kind of been like, oh yeah, fine, do it if you want to but I didn't but then that happens and I'm like well okay actually this is there's no reason that I should have wasted the $20,000 on this fraudulent invoice that we can't get back and you know it would have cost less and been better and we'll prevent the $100,000 thing to to do it. Exactly I think it's actually anything from a regulator perspective you've you've been on the prosecutorial side you know and then we talked about malpractice like at what point I think I heard SEC chair gunsler said something like, hey, you know, it'd be a shame if your filings weren't perfect you know now that we have AI. So are you are we going to see that standard from from everybody?

Matthew Campobasso37:42
I think so. I think you're gonna have the the hairy eyeball of AI all over everything from from regulatory filings to contracts. I can I I know for a fact I can see the companies that we're selling to that come back to us with AI generated red lines to our contracts because it's the same things that you know we've dealt with 10 times and we're trying to evolve ahead of that to remove that friction from our sales cycle but it's there. People are outsourcing that stuff wherever they can to AI most people are I think about AI you asked a question we start talking about my son's fender bender obviously that was very cathartic for me so thank you. But I I think about my CEO and one of the things that AI does allow me to bring to the company on behalf of my team is the idea of, you know, we're a relatively lean team of three lawyers. We are kind of all Swiss Army knife applying range bouncing around the business as we see things or need to react to things. AI has become a force multiplier for us. And I think my team of three lawyers, I would say if you were to sit down and try to quantify how much work we do by headcount, I would say in any given week it's probably between the work of five or six lawyers. And that is because of AI. And I think that's not to say you just outsource every bit of legal work or thinking to that tool because there's risk there obviously but you know you're not going to give an electric bike to a five year old who's only riding with training wheels. I I have confidence that in my team I have you know world class athletes who know what they're doing.

Cecilia Ziniti39:17
They know the terrain and so that is something else that AI has allowed is we can do a lot more and I think the value is that a lot of what we're doing now is future value add versus you know cleanup on aisle three I love that um you've argued before that the legal profession selects against traits that make great leaders and then somehow we're surprised when lawyers struggle kind of at the boardroom table or in executive roles. What trait would you say that that the profession does a bad job of selecting against I think there's a few.

Matthew Campobasso39:53
One I've I've spent a little bit of time today talking about and that's range. Law school and law firm practices specifically they reward deep specialization and excellence in one particular area. That's how you justify saying hey if you want an hour of my time it's going to cost you $2,000. But I think that for lawyers to be effective in roles like mine or my team, you have to have intellectual breath. I think you need to understand finance, product, people, how businesses operate and culture. And so the legal system produces I think brilliant specialists and then they put them they put them in generalist roles and then they wonder why they struggle. So that's one area where you have this siloed very deep knowledge but to your point earlier, when you're a hammer, everything looks like a nail. And I think the reality is you can't just have one great hammer if you're going to be an effective lawyer within a business setting. You have to have diversity of tools. Another characteristic I think that lawyers struggle with is comfort with ambiguity. Lawyers are trained to find the answer you know, what's the question? We got to resolve it, let's close the loop and I think a lot of really effective modern leadership is comfort sitting with open questions, making decisions with incomplete information and really being vulnerable and comfortable saying, I don't know yet and here's how we're gonna figure it out together. I think lawyers view I don't know or let me get back to you as an acknowledgement that they're ineffective. And I don't know a lot of other professions like that. And I think it's something that we struggle with. And I think the last one that I would mention is emotional intelligence. And that's not to say that I don't know lawyers who are emotionally intelligent. I do, I know many of them, but I mean it more in the operational sense. So reading a room, managing up, managing down, giving hard feedback with empathy and building teams that want to follow you, law school does not teach you any of that. Law school teaches you how to read case law, how to memorize wrote facts and how to win arguments. And actually if you think about you know being in a room with a team and trying to get to the right outcome, it requires almost the opposite skill on every one of those.

Cecilia Ziniti41:58
What a list. I mean all of those resonate and I get a lot of questions from people who want to make the transition from CLO or from legal to a non-legal role and they kind of like wonder and I I come back to them with with that answer of like these are the things that you need to be able to to sit with. I like this concept of sitting with uncertainty. So how do you how do you learn that or if if I was to say all right Matthew we're gonna help lawyers learn to sit with uncertainty boom how are you training them? What do you do?

Matthew Campobasso42:27
So I tr I think depending on the situation, I usually have an example or two in my back pocket of a time where someone rushed to solve something and got it horribly wrong, almost burn their hand on the proverbial stove by rushing to do something that they weren't equipped to do. And so it is hard because a lot of what we've spoken about today is about speed and velocity and and the way the world is moving. And so sitting in uncertainty, it evokes that image of slow down and you know I think you have to be able to parse through things and decide okay what, you know, this is my initial feeling or my initial reaction. And I think being a member of a team or a leadership team where you have confidence in the other people and the ability to be vulnerable and not worried about how you're appearing, you know, oh well Matt doesn't know or Matt doesn't have the answer or Matt's unsure. Those are things that I think as lawyers we're trained to feel our negatives. And if people see us that way, it it erodes the confidence that they need to have in their lawyer because of the sorts of things that we get involved with. But generally speaking when I get into a meeting and I want people to be comfortable sitting in uncertainty, the first thing I'll say is this is the issue. I don't know what the answer is. And so if I'm the executive on the call or the manager of the team or the sponsor that's running this initiative and I say I don't know, I think that gives people the comfort or the cover to say, oh well if he doesn't know then it's safe for me to say that I don't know. And I might give an example of an idea that I had that upon reflection I realized was horrible. And so it's just about being Human. And I think what that does is it unlocks other people's desire or willingness to be human. And then what that tends to do is just get everybody's guard down and realize it's not me versus you versus him versus her. It's the four of us or the five of us sitting together and aiming towards getting to the right outcome. So I don't have a an exact recipe for every situation. It really depends on the bodies in the room.

Cecilia Ziniti44:22
Let's go to the lightning round. So what is a book, mentor, or concept that has shaped you?

Matthew Campobasso44:29
So I if it's okay with you, I'd like to give you one of each. I'll make it quick. I know this is the lightning round. Yeah, yeah, go for it. The book is Dan Heath uh is the author. The book is called Upstream. And so you've heard me use that word. You know, it's not, he didn't invent the word, he didn't invent the concept, but he wrote an incredible book a few years ago that I would recommend to anyone to pick up. And it is about that shift in mindset from reactive to proactive. And it has really, you know, I think I'm in my upstream era, to use your Taylor Swift analogy from earlier. It has really helped me step forward and not be an island within a business that people come to when they need something. I'm right there on the front lines with our CEO and our CFO and our board. And the book itself, for anyone who hasn't read it, it opens with a fable that I think I've probably told a thousand times by now. But it's about two fishermen sitting on the bank of a river and a child starts floating down the middle, flailing their arms. The fishermen drop their pole, they swim out, they save the kid, they get back, they look at each other, they say, Whoa, that was crazy. And then it happens again and again and again. And the fifth time, one fisherman jumps in, he swims out, and he looks over to his fellow fisherman to say, you know, what's happening? And he's the other fisherman's not there. And the fisherman in the water looks downstream and he sees the other fisherman running up the riverbank and he says, Where are you going? And he said, I'm gonna go find this person throwing kids in the river. And it's like, how many times do you have to fish somebody out before you realize, hey, you know what? Like we're reacting too late. And so the book opens that way. I read it and I just remember thinking, okay, this is going to forever change how I view my role within a business. And, you know, it obviously can have that effect, whether you're a lawyer or otherwise, but I used to be a litigator and litigation is reaction. It, you know, you drop into the middle of a war, a battlefield, and you're trying to make things the least bad version of what they are. And there's not a lot of that that fills the soul. And so getting closer to the root and being able to influence business ideas up front has been, I think, what's given me new life at this phase of my career. So that is the book I would recommend.

Cecilia Ziniti46:30
Oh man, I love that book. It also, you know, it it's it's just some great business examples. I think the example of like Expedia found that they reduced customer care calls tremendously just by having you put in your email twice because half their calls were people emailing. Hey, I got disconnected or I didn't get the right response. Because you put in the wrong thing. So, yeah, incredible examples. I mean, it's also one of these things where it's like once you have a concept like that, it is like Shakespeare where you see it everywhere. I just love it. Yes. All right, mentor. Let's let's talk about mentor.

Matthew Campobasso47:04
For me, I've had a lot of mentors in my career. I'm incredibly grateful. I could probably spend an hour talking about each of them and what they've taught me. But recently I wrote a post on LinkedIn about probably my first mentor. And when I was a criminal prosecutor, he was the first judge I was ever assigned to. And he was a former public defender who was elected judge. And so, needless to say, he had a very defense-friendly lens when he came into the courtroom. He was very fair, but he understood the gravity of beyond a reasonable doubt. And so I lost just constantly in front of him. And I don't say that because it was about wins and losses, but I just was like, what that allowed me to do is to continually look at mistakes I'd made and to commit to myself. I wouldn't repeat those mistakes. And I'll be honest, I hated it. I hated every second. There were times where I was like, this is not fair. And that was just my ego as a young lawyer. About two years after I appeared in front of him, I left the office and joined law firm practice. I stopped by his chambers to say, you know, I'm leaving. And he hit, he said, Hey, come sit with me. And and we had never really had a human-to-human conversation. You know, there was a couple of times where he was like, you know, Mr. Campobasso, I see you're rolling your eyes, you do that again, I'm going to hold you in contempt. Things that, you know, it with the benefit of hindsight, I'm embarrassed about, but I think they led me to where I am and had helped inform how I show up in in my day-to-day. But we sat in his chambers and he said, I know I pushed you. I know I challenged you. I know I held you to the highest standard. He's like, I probably held you to a standard higher than beyond a reasonable doubt. And he said, and there's a reason. You're a smart guy, and I can see that you care. And I think there's going to be a day, someday, maybe not today, where you're going to look back and say, you know what? Like that old curmudgeonly guy, like he helped me become the best version of the lawyer that I am. And this is 18 years later, I'm telling the story. And so maniacal preparation, leaving no stone unturned and just trying to stop and say, okay, if I don't do this, if I take a shortcut, how does this blow up on me? Because I'm sure there were times I tried to take shortcuts on cases I was trying in front of him. And every single time it blew up. So he was an incredible mentor to me. And I think I'll look back, hopefully, at the end of a legal career, and I'll think, thank God he put me through the ringer every day for a year and a half. I hated it at the time, but I think sometimes those are the best mentors.

Cecilia Ziniti49:21
Yeah. Well, and this idea of like these early experiences with excellence. I mean, back to the hiring point, you know, people get down on big law, but that's the standard. And it's like, you know, good enough is not really good enough. And I agree that, like, I mean, what a gift for him to have given you. And I'm lovely that you that you spoke to afterwards. I'm I'm would have Yeah. I'm sure it was an incredible day to have that conversation.

Matthew Campobasso49:46
It was. It was. And it'll be something I always look back to with a lot of gratitude.

Cecilia Ziniti49:50
Amazing. That this has been so lovely to speak with you. If you wanted to leave listeners with advice for your former self or just anybody early career or CLO, what advice would you give?

Matthew Campobasso50:04
So I think I would tell my younger self, and as you mentioned at the onset of this episode, I I also teach a class at a law school in Chicago. I gave this advice to my students on the last day of class. I said, stop performing someone else's version of success. I spent the first decade of my career collecting credentials that it looked impressive to people, you know, trial wins, promotions, pro bono awards. And I can tell you that with each one, it felt increasingly hollow. Not because what was being recognized was hollow, but I thought, okay, it's title, it's this line on my resume, it's this job. That's what's going to impress people. And when I looked back at it, you know, probably about seven years ago, I thought, who is that for? You know, it wasn't for me. And it felt like the game I was supposed to play. So I told my my students uh in September, actually my students from the September class in December, I said, stop and ask yourself once in a while in your career, did I choose where I am or did I not, did I just not stop the path that I started on when I felt like something else mattered? And I think that's a huge difference between a life that you design and a life that you kind of just default into. And I really wish that I had interrogated that distinction myself when I was 30. Not that I would change anything. I've had a really great career, but I think that, you know, that's the they say, right, youth is wasted on the young. It takes you to get older and you fall down and you make your mistakes, you burn your hand on the stove. The only other thing I would say is, you know, focus on the relationships that make you a better human being, not just those ones that are advantageous for you as a lawyer. Because even if you have good intentions and you lead with kindness and humanity, they can somewhat be transactional. And I think the last thing I would say, knowing where I ended up in my career, is get uncomfortable outside the law sooner. You know, every non-legal experience that I've had, my podcast, the writing, cross-functional work has made me a better CLO. And while the legal profession tells you to specialize, I think your career and success in your career for most lawyers will tell you the opposite.

Cecilia Ziniti52:07
Love it. Wow. My guest today was Matthew Campabasso, the CLO of Zone and Co., former prosecutor, uh book author, dropper of incredible wisdom, data three. Really truly enjoyed the show today. Thanks for joining, Matthew.

Matthew Campobasso52:20
CZ, thank you for having me. It was really a pleasure. It was everything I'd hoped it would be, and then some. So hopefully your listeners get some value out of it.

Cecilia Ziniti52:28
Oh, all right. So follow CZ and Friends wherever you get your podcasts. If you're interested in learning more about AI, uh visit gc.ai where we've got Matthew and others podcast. Hope you have a great day and are able to work upstream to the advice of our guests today. Thanks so much.