Alex Su: Welcome to Under Review, a show produced by Stanford Law and PLI. I’m your host, Alex Su, and in each month we explore the biggest forces shaping the legal profession with insights from leaders who are driving change from law firms, legal departments, government, and beyond. 

In today’s episode, we look at the quiet unraveling of OCI. And what’s driving it? Then we examine how judges, administrators, and even algorithms are reshaping civil courts. Finally, we spotlight a change maker who’s driving innovation from big tech to big law. Let’s get started.

On campus interviews, or OCI, have long been the gateway to big law jobs for students at top law schools, but the system is breaking down. Hiring timelines are accelerating, processes are moving off campus, and the profession is rethinking what recruiting even means. To impact this shift, Adam Sterling sat down with Susan Robinson, Associate Dean for Career Services at Stanford Law School. She’s had a front row seat to the transformation and detentions reshaping legal hiring.

Adam Sterling: Susan Robinson, welcome to Under Review. 

Susan Robinson: Thank you. 

Adam Sterling: Let’s start with the basics. What’s the mood right now in legal recruiting? Are students feeling optimistic, anxious, or somewhere in between? And beyond Stanford, what are you hearing from peers at other law schools, including outside the top 14? Is the mood and market similar, or are there different challenges at play?

Susan Robinson: I’d say the defining word right now is uncertainty. We didn’t see any significant changes in the hiring of firms for summer or postgraduate jobs. But there feels like there’s a bit of a hesitancy in the market. 

Adam Sterling: Yeah. So students are interviewing for their second summer before they’ve even started their first summer now.

Susan Robinson: Right.

Adam Sterling: Wow. 

Susan Robinson: Yeah, that’s huge. And it’s anxiety provoking for the students. Very stressful to be attempting to do a full-on what is, in essence, a postgraduate job search, in the midst of studying for classes as a first-year. 

Adam Sterling: Yeah. It just sounds like a perfect storm of anxiety. Both shocks to the market and the changes in timing. We’ve also heard reports of firms scaling back their summer programs, delaying start dates, withdrawing from OCI. Can you speak to some of those trends? 

Susan Robinson: I think some of that has been exaggerated by the press. What we’re seeing, as I mentioned, we haven’t seen a significant shift in the hiring numbers for the summer, at least at the Am Law 100 firms. There’s been some scaling back. I think most of the firms maintained a similar summer program size to prior years. We saw some amount of shift in DC. And there to, for a variety of reasons, that was a much tighter market this year than in past years. But overall, we haven’t seen a significant shift away from the summer numbers. Whether that will happen next year is another question. 

Adam Sterling: Great to hear that. I hope for a moment we can think about broader dynamics in the legal profession. To what extent are you hearing from alumni, both those who are job seeking and those who are in hiring roles, what’s changed in how they’re approaching the market? 

Susan Robinson: One change that we’re seeing is this emphasis on specialization on knowing what kind of practice you want to have within the law at an earlier point in one’s career. I think it used to be the case, the expectation was that as an associate, you had 3, 4, 5 years to be a generalist of sorts. 

Adam Sterling: So much, in my experience working at firms so much of the decision making is often driven by FOMO and, fear of missing out, and I oftentimes there’s a sense that if someone’s still looking in their third year, it’s because something was wrong and just how do we educate the firms that they need to be more open-minded. 

Susan Robinson: I’ve been doing this for a long time. So before the ’08, ’09 recession, about a third of law students interviewed in their third year. There was a significant third-year market. It just disappeared when the recession hit, and we’re starting to see it come back a bit. 

Adam Sterling: Great. Yeah. 

Susan Robinson: There are a number of firms that have started to come to us and say we’re doing a limited amount of third-year hiring. I think when they start to see the attrition rates, there’s gonna be a greater desire for that third-year candidate, but also, I think students may end up driving that market a bit. 

So if we have highly qualified students who have received postgraduate offers from their summer firm coming onto the market and saying, Oh, I realize now I need to be in another city, or I realize now I want to do this kind of corporate work rather than that kind of corporate work. I think firms are going to want to hire that talent. And they’ll maybe start to leave room to have that flexibility. 

Adam Sterling: Yeah, I remember, I think, May of my 1L year, I probably still thought I could be solicitor general, and by the end, I was a corporate attorney in Silicon Valley.

So I think it just seems reasonable that after two years of law school, you may have evolved in thinking about what you wanna do, so it’s a great point. 

So I think we’ve talked a bit about what worries you about the pipeline. What gives you hope? And maybe it’s that students will get smart and organize.

Susan Robinson: I think that would be fabulous if they did. This may sound a little hokey, but what gives me hope are the students themselves. 

I think they are incredibly flexible. They’re clever. They’re hardworking. They can adapt. It may shift the timing for them. It may shift what their career path looks like, but I think ultimately they can shape whatever kind of career they wanna have. So, the craziness of this hiring timeline, it makes for an incredibly stressful situation for them in their first year. But I don’t think it will prevent them from shaping the kind of career they wanna have. I think it may shift it; it may mean that more of them are looking in their third year. It may mean that more are looking to shift coming out of clerkships. More are coming back to us as young alums and looking to make that transition then. So I think it shifts the timeline for them, but I don’t think it will significantly impact what kind of opportunities they have. 

Adam Sterling: I agree, but I feel like so much of the attention on back to work policies is on the junior attorneys and sure, I think they probably have the most to gain but just from what I’ve seen, I would encourage senior attorneys to spend time on campus to have face times with students, go back to your alma mater and speak, make yourself available when you’re in the office—broadcast that, because I think for a lot of young attorneys, like they feel, I do come in the office and I can’t find anyone. I don’t know where anyone is, and that’s a challenge. And so I think yes, the younger attorneys have the most to gain, but I think the responsibility is on our senior peers to make themselves visible and available. 

Susan Robinson: Oh, I agree. You can’t have the benefits of these junior attorneys being in the office unless the people they’re learning from are also in the office. So they need to be there. But it’s not just what are the benefits that you’re giving to those junior attorneys—what are the benefits you’re gaining yourself from being in office? You are developing attorneys at, I think, a faster pace, giving them deeper knowledge, and so they’re more useful to you 

Adam Sterling: Yeah, totally. 

Susan Robinson: in the work you’re doing. 

Adam Sterling: And they’ll work harder for you if they know you. Right?

Susan Robinson: Right. And there’s so much research that has been done, particularly since the pandemic, about how working with people in person, interacting in person, makes a huge difference in terms of the relationships you’ve built. And what you can accomplish. So if we’re talking about client management or project management, all of that requires more in-person interactions to be as effective as you can be. 

Adam Sterling: A hundred percent. 

Susan Robinson: So I think it’s important. 

Adam Sterling: It is, and Susan, thank you so much for your time today and joining us on Under Review.

Susan Robinson: Wonderful. Thanks for having me here. 

Alex Su: Next, we turn to a less visible, but equally transformative change in the legal system. Stanford Law Professor David Freeman Engstrom is part of a major research initiative examining how courts themselves are evolving from neutral venues to active managers of litigation.

In this conversation, he and Adam Sterling explore the rise of managerial courts, the role of AI in decision-making, and what it all means for lawyers, clients, and justice.

Adam Sterling: Professor Engstrom, welcome to Under Review. 

What initially drew you and your co-authors to this project? Was there a particular core innovation or a moment that made you think: This is a story we need to tell.

David Freeman Engstrom: Yeah, I wish there was a lightning bolt moment, but there wasn’t; there was something more like a slow burn realization.

So over the last two or three years, I’ve been working a lot on high-volume dockets, especially in state courts. And these dockets are made up of case types, like eviction, debt collection, mortgage foreclosure, and certain types of family law, like child support. And amazingly enough, they’re like a majority of the cases in the American legal system right now, like something like two-thirds of cases. And they’re also really worrying things about these dockets. If you really look under the hood of these cases, you realize pretty quickly that they invariably pit an institutional plaintiff. So, a bank, a credit card company, maybe a corporate landlord, maybe the government, always with a lawyer against an individual defendant without a lawyer. And so these are really worrying, these completely depart from the all the assumptions we have about how the adversarial system works within American law. And so I’ve been working on this for two or three years. I’m leading a couple of different projects right now. I’m leading a big project at The American Law Institute, it’s gonna be a five or six-year project to try to provide guidance to courts on what to do about these dockets.

I also have at the Rhode Center, my team has a big collaboration with the LA Superior Court, largest trial court in the country, and so I’ve been working on this issue from a bunch of different angles, and all the while I was noticing and starting to realize that, wait a second, courts have built vast bureaucracies inside their walls in order to move this avalanche of cases. And again, it’s millions of cases, it’s like two-thirds in some jurisdictions of what these courts move. They’ve built these huge bureaucracies to move cases around and to move personnel around and to deploy non-judges in the adjudication of these cases. And I just came to realize, wow, this is a really important tectonic move. It’s been hiding in plain sight, and someone needs to talk about it ’cause it has big implications for how these cases are adjudicated. It also could have huge implications for things like constitutional due process.

Adam Sterling: And David, you frame this rise of managerial courts as a quiet revolution, you said, hiding in plain sight. For lawyers who may not follow court administration closely, what’s changing in response to what you just described?

David Freeman Engstrom: So I think it’s an enormous change away from what you can think of as like the classical model of how courts work. The classical model, which maybe never existed, like a lot of classical models, but there was still an element of truth to it, was a kind of learned hand notion of what courts do and what judges do.

So learned at hand, of course, the Great Second Circuit Judge who believes strongly in crafting opinions by his own hand, interestingly enough, and that was this idea that, you know, courts are supposed to be judge-centered and judges are supposed to be passive, neutral adjudicators or whatever comes in front of them. And again, they’re supposed to write extensive opinions in which they give reasons for their decisions.

Take an eviction case. In a lot of courts now, an eviction case comes in the door, and it probably gets some degree of triage, probably from a court clerk or from a civil case manager, that might include trying to decide how complex the case is gonna be in order to route it to a different procedural case management track. It might include a clerk, not a judge, determining whether service or process was valid or not. And then, when the case gets to trial, that is to say, when there is a court date, what is often the case in so many housing courts is that a commissioner, so not a judge, but a commissioner, sits at the bench, and the parties come in. It’s generally a cattle call of parties in these courts, you’re told to show up in the morning, and you might be there for four hours waiting for your case to be called. But the commissioner’s job is literally to call the case, to talk to the parties, to tell them to go out into the hallway and attempt to settle. And then bless the settlement at the back end if they manage to settle. If they can’t settle and there needs to be fact-finding, that’s something that’s supposed to be reserved for judges. And so then a judge is actually called in for a trial, which I’ll put in scare quotes because it’s generally a one-minute proceeding at which whatever minimum amount of fact-finding that needs to be done, gets done. And then the case can be decided from there. But I think what’s remarkable is the degree to which judicial attention is allocated. When you talk to state court administrators, they talk about judicial attention allocation. How do we allocate judge attention, which is the scarcest resource in these courts, in their minds only where the judges’ particular expertise is needed. And everything else then is allocated to some other type of actor. And again, just a really significant departure from that learned hand model.

Adam Sterling: So you suggest in your paper that lawyers will now need to understand not just the law, but the pathway a case takes through court. Are you seeing or envisioning a role where we teach, court operations, and law schools? How can we do that? 

David Freeman Engstrom: When I think about that, I think my answer is yes and no. 

Lawyers need to know about this. So what’s interesting is in some courts, there is a pathway system approach. So each case is being routed to a particular procedural or case management track based on case features, the perceived complexity of the case, the amount and controversy—representation status of the two sides.

But what’s interesting is in some courts, at least, that routing is non-public, which is also to say it’s not contestable, which is to say the litigants aren’t supposed to know that the case has been routed to a particular track. There, I don’t see a great role for lawyers, but in plenty of other courts, the pathways and the tracks are actually known to the litigants.

And there, I think lawyers need to know that this is happening; that in serving your client, you would want to maneuver your case into the right pathway. And then in addition, I think in a lot of courts there’s a safety valve, a way to move a case out of a particular pathway or track and onto a different one. And so there too, I think there may be litigation. 

Adam Sterling: What’s the most surprising way you’ve seen AI or automation already reshaping judicial decision-making? 

David Freeman Engstrom: Yeah, so lemme start with the unsurprising. And it’s the thing that’s just talked about so much right now, which is there’s an enormous amount of litigant facing AI innovation happening right now.

Some of that’s out in the world. Legal tech companies like LegalZoom, or Rocket Lawyer, or name a smaller startup that’s doing this. And I think that’s an obvious use of generative AI and a place where generative AI can add lots of value, and also create lots of peril really quickly. 

What I think is most interesting in these courts is the more internal court-facing uses of AI. And so, use of AI to make those triaging decisions, I think that’s a really important use. Maybe the most surprising, important, interesting use case is one that I’m working on quite a bit with the LA Superior Court right now, which is called a default prove up AI assistance. So what’s a default prove up? Over the last few year, a lot of courts have started to do what are called default prove-ups. And that means that when a plaintiff comes in and requests a default judgment in an eviction case or debt collection matter.

The court has a problem on its hands because it has an institutional plaintiff asking for something with a lawyer and a no-show defendant. The defendant has failed to show up, which means there’s been no adversarial contestation in the case at all. What do you do? Some courts have actually done something that I think is pretty revolutionary. They have started to take a much more active and affirmative role in these cases, and they actually have a clerk look at the case filings and the case materials to ensure that the default judgment is legally and procedurally warranted. Alright? At the LA Superior Court, I kid you not, there’s a single person who does this to the tune of 10 thousands of cases per year. 

And the question is, could we make that person’s job a little more efficient and a little more accurate? And so the obvious thing to do is to try to automate the process, at least in part, and to create an AI assistant that can flag problems and filings and even, I guess, direct the clerk’s attention to the place in the materials or the filings where that problem exists.

And I think that’s such an interesting use of AI because I think it’s clearly a way to improve the functioning of these dockets. It’s clearly a way to allow courts, in good ways, to do more with less. And I think it also intersects with this really important thing that I think is happening out in the world where given the realities of these high volume dockets, and given that this is actually a, these cases are a majority of what state courts, and therefore, all American courts move that courts need to take this more affirmative and active role because the adversarial process is so thoroughly broken down. 

Adam Sterling: So in the paper, you and your co-authors explore a tension between efficiency and sort of fairness for individual outcomes. Is there a sweet spot here you think courts should aim for? Any promising models that you looked at?

David Freeman Engstrom: Great question. In some ways, this is the essence of the paper. So really terrific to have identified that and asked me about it. I’m afraid I’ll provide a really underwhelming answer. I may just end up restating the question in a sense. It’s been this long debate about what the optimal amount of distance is that judges should have from their cases. On the one hand, you want judges engaged. You want judges, in a classic judicial role you want them to be engaged with the case. You want them to have some kind of holistic sense of what the case is about. So some degree of engagement is necessary, and yet there are also these longstanding norms of impartiality and neutrality.

And there was a thought back in the 1980s and 1990s, famous paper called Managerial Judges. By the way, Managerial Courts is a riff on that paper, but in Managerial Judges, Judith Resnick, who’s a professor at Yale Law School, said she was worried that judges were becoming too engaged in litigation at the pretrial stage, and that presented problems for judicial independence and therefore for due process, so we weren’t getting that distance amount right within the system. So I think in those distance terms again, and it just, when you look at these high volume dockets, like the classical model of judging simply can’t be right because there are too many of these cases and courts can’t move enough of them to provide the reasonably efficient justice that the civil procedural rules, for instance, promise. And so that can’t be. On the other hand, you worry a bunch about moving too hard in the direction of efficiency, like bulk processing has its costs as well. And so when you put the question in terms of a sweet spot, I think it’s exactly right.

Is there a promising model? I don’t know that there’s a promising single model. One thing that I think is interesting in the paper and one of the virtues of the paper is that by mapping this vast landscape and trying to do it in a really comprehensive way, like trying to get a really synoptic view of how courts are building these bureaucracies and all the different mechanisms and techniques they’re building into their bureaucracies, we can start to think about how they fit together. And we can start to think about, okay in this particular context, say eviction cases or debt collection cases, there are these three problems that are clearly preventing fair and accurate adjudication of the cases, and then what kind of managerial patch might we use? Maybe that’s default prove-ups. Maybe that’s a better allocation of cases to procedural and case management tracks or pathways. But I think what I like about the paper is you can start to see these as different inputs to a bureaucratic system. 

And mind you, I don’t think this bureaucratic system is going away anytime soon. It would be crazy to write a paper, call in for the abolition of the  bureaucracies that have been built over the past four or five decades. I think these bureaucracies are here to stay. The question is how to bring them into line with some of our most cherished due process values. 

Adam Sterling: I think the bureaucracies are the systems. It’s such an important part of the law, right? We, to use a metaphor in law school, we train people to be chefs, and then when they go and practice, right? Like being a chef and having a successful restaurant, it’s about so much more than just the good food that you deliver. Same thing with being a judge or a lawyer going to court, and we spend so little time thinking about the sort of operations of the practice and I think your paper proves how important and impactful those operations are. I just love diving into this.

David, what do you hope court leaders, lawyers, policy makers do with this work? Are there reforms that you think are both realistic and urgently needed, or is it just as you said, something we need to continue to study? 

David Freeman Engstrom: My hope is that this paper can help courts to do something that I think they absolutely need to do within these high-volume dockets.

And something I think I’ve already noted, which is I think courts need to take a more active and affirmative role within these dockets, especially with respect to self-represented litigants. Those folks without a lawyer. And so I think in some ways the paper, when it talks about good examples of managerialism, I think is helping courts to see what that more active and affirmative role could look like.

At the same time, I hope that they can also see that there are some problems with some of the practices that have started to evolve and have started to coalesce within courts. And those are really worrying. They’re worrying because they’re gonna shape merit’s determinations in ways that we might not like.

They’re also worrying because the courts have no source of power other than their own legitimacy, right? It’s the classic Alexander Hamilton notion that the courts lack the sword in the purse. All they have is the perception that they dispense justice in fair and even-handed ways.

And so, I worry a lot then that courts in building these bureaucracies won’t be attuned to that. And they will lose their legitimacy as a result, if they’re just seen to be as another bureaucracy, turning the crank to generate these outputs. 

So if I can say one more thing about that, back in the 1990s, political scientists talked a lot about democracy at the DMV. It’s a concept that I absolutely love. So the idea was that most Americans, their most frequent touchpoint with their government was the DMV. And it wasn’t going well because, as we know, DMVs are a mess. And so there was all this talk about, okay, if what you want is trust in government or if what you want is to legitimate a governmental system, which has all kinds of implications for people’s willingness to obey government or to pay their taxes, what have you, you have to improve the DMV.

Fast forward 30 years, I actually think courts have become a lot of Americans’ most frequent touchpoint with their government. 

And in these high-volume dockets, it may not be going so well. In some instances, I think we can improve the operational courts through these managerial techniques, but as I just noted, in other instances, I think these managerial techniques are actually a problem and maybe even a violation of due process. And so again, I worry about democracy within the civil justice system. I think it’s an important concept, and I think listeners, viewers, may have noticed that our courts are taking it on the chin right now in a lot of ways.

A lot of people see them as important bulwarks of rule of law, and yet there’s less and less trust in courts for a variety of reasons. I think this paper is just one way that courts can think about trying to improve their operations in ways that I think have really direct and fundamental implications for the legitimacy of the courts in the eyes of the citizenry. 

Adam Sterling: So, last question, David. If you had to make a prediction, any thoughts on how different the civil justice system might look 10 years from now? 

David Freeman Engstrom: Yes. Alright, prediction number one is that the civil justice system will look very different because I think there will be a far more diverse supply of legal help.

So right now, this is something else I’m working on at the Rhode Center, and in a lot of my scholarship and a lot of my work out in the world, there’s a movement around the country, especially within State Supreme Courts, to relax the usual rules that say only lawyers can practice law. That, of course, is unauthorized practice of law or UPL rules. And also that only lawyers can own law firms. That would be rule 5.4 of the model rules of professional conduct and the reason to relax those rules would be to try to create space for alternative providers of legal services.

Adam Sterling: Well, David, this is such an incredibly important story study, and I think we wanna keep tracking it, so we hope you’d come back and tell us how this story evolves. 

David Freeman Engstrom: Great. Thanks. I’d love that.

Alex Su: Mary O’Carroll has helped reshape the legal industry, and more than once, she built the legal operations team at Google. And then helped found and scale CLOC, the Corporate Legal Operations Consortium. Then, she drove innovation in legal tech at Ironclad, and today, she’s the Chief Operating Officer at Goodwin, a top global law firm. Mary and I sat down to talk about what operational excellence looks like in big law and how our journey across tech, operations, and law is shaping the next wave of legal change.

Mary, welcome to the show. 

Mary Shen O’Carroll: Thanks so much for having me. It was just a good excuse to come catch up with you. 

Alex Su: That’s right. What have you been up to lately? Tell us about your new, well not super new job, but you’ve been there in the seat for nine months. Tell us about your job.

Mary Shen O’Carroll: Yeah, I’ve joined Goodwin, a global law firm, as their Chief Operating Officer, and that entails running what we call the global operations team, or the GO Team. If you think about that, that’s just basically all the functions of the chiefs. So like IT, talent, marketing, client development, practice management, finance—all the functions. And really, the role is, I think, a little different than just basically running the firm. I see myself as a transformation agent, so trying to help build the firm of the future is what I—if I had to describe the job in a short phrase. 

Alex Su: That’s super cool. And I know we’re friends now, but I’ve been watching your career play out over so many years.

You’ve done a lot of really interesting things throughout your journey. You’ve been the Head of Legal Ops at Google. You’ve taken a C-level role at a legal technology startup. And so yeah, walk me through the trajectory. How did you end up as COO of Goodwin? 

Mary Shen O’Carroll: Yeah, a lot of the stuff when you look backwards, it makes a lot of sense, and it’s oh, of course, all paths would lead me here, an AI company focused on contracts. And then, just less than a year ago, joined Goodwin. So full circle back to a law firm. 

And I’ll say that the reason—like I keep saying, and there was no part of me that ever thought that I would go back to a law firm just because they are so stuck in time and so difficult to move. And the partnership model, if you’re a transformation agent or someone who wants to do that kinda work is, it’s not the place that attracts people who wanna work on innovation. But I really felt like there was enough happening in the industry that’s putting a lot of pressure on law firms to really rethink how they do things. And, here was a firm that was willing to take a lot of risks and to try things differently, and so I figured, let’s try this now, and if we can’t do it, it can’t be done. So, challenge accepted. 

Alex Su: I love that. I love that. I love especially that you never imagined that you’d end up back in a law firm environment, and ever since you joined Google, you’ve been part of all of these organizations, whether it’s Ironclad, co-founding CLOC, and Google. These are rapidly growing organizations, move quickly. There’s this ethos from Silicon Valley where, you know, I think you’ve said it in other podcasts before, where you’re best fit at places where you can move very quickly and launch initiatives and see what works. And how have you found people at the firm to receive that message? Is that—how they responded? 

Mary Shen O’Carroll: Yeah, I think very well. And that was very much a part of my diligence process as I considered joining a firm. You and I, we’ve been in this world long enough to know how difficult it is to transform and it, we’ve talked about how law firms are really particularly difficult. And so I’ve worked at a firm, I’m going in eyes wide open, and I spoke to countless sort of partners in the leadership team going in and I think there are a few things that are required for success in transformation for an organization like this. 

One is a clear vision, which I got loud and clear. The second is the ability to execute, which I think is hopefully why they hired me. And the third is a partnership that is bought in and that has the mindset to move in this direction and to be excited about it. And from the time that I was being recruited, as well as the time that I’ve been in seat now, that has been resoundingly clear to me that there is absolutely an appetite to change. And that to me makes the job fun. 

And, it’s certainly not all rosy and easy, and we all know change management is very hard. And even when the answer is obvious, you’re still moving people’s cheese, you’re like doing things that make people uncomfortable. But I think that’s part of the journey and trying to gain trust and getting people to be comfortable with this new culture that we just talked about, and that taking risks and to try something that may not be the way they’ve always done it. Just give us a chance. Let us try to prove this.

Alex Su: I think being a transformation agent is just gotta be a hard thing in any organization. And so it sounds like you’ve gotten a lot of experience doing that in a variety of different companies before you were at Goodwin. What are some key pieces of advice you would give to other folks who are trying to be change makers and change agents in their organizations as well?

Mary Shen O’Carroll: Yeah, you really need to understand the culture of your organization, and change happens in different ways. And there are cultures where top-down works really well, and there’s cultures where that does not work. 

And the environments that I’ve worked at Google, in particular, was not that way. And it was this, like if you build something or if you want someone to come your way, you’ve gotta prove it to them. And I think that’s the ethos we had at Ironclad, which was the software’s gotta be good enough to persuade people on its own. Like you can’t try and go out and convince people, here’s the ROI, and here are all the benefits, please come and try this. They’ve gotta walk up to something and have this aha moment of this is so much better. Why would I go about doing things the old way? Now, that’s the ideal situation when you’re a change agent is like this new way is just so much better that there’s almost no argument for going backwards. But that’s not always the case. 

And there are some things that, you know, what we call the value of despair, right? It gets a little bit worse before it gets better. And there needs to be an investment of time and energy. And that is where you have to just build relationships, build trust, build disciples in some way where you can be successful with one group and prove your value, and hopefully, have other people champion for you, on your behalf or your team’s behalf of, Hey, they’ve done this great thing for me. You should be really talking to this team, and that is how it’s organically grown in the past. Again, it really depends on the culture and the people you’re working with. There are folks that are gonna be more resistant and folks that are gonna be more eager, and there’s prioritization of your initiatives and thinking about where you can have the biggest impact. But sometimes it makes more sense to start with the willing and get them bought in, and hopefully, try to bring others around.

There’s other techniques of taking the people who are the most vocal, the opposite of an advocate, you know, the people who don’t wanna get on board and turning them into advocates, and then they just have a lot of credibility ’cause everybody knows that they would be the naysayers, and if they’re bought in then there must be something good here. 

Alex Su: Yeah. I find that so relatable because I recently joined a company as an executive, as you know, I’ve been driving a lot of initiatives, and there’s been a similar pattern.

You find the people who are most receptive to the initiatives and change, and who may wanna see change, and over time, you start to convince the others. What tactical advice do you have about dealing with the folks who are a little bit slower to embrace those initiatives? Because I think that’s something that I struggle with. I have this desire to win over everyone, but sometimes people are just really resistant to the change. 

Mary Shen O’Carroll: It’s so true. And, I don’t think you have to win everyone over. It depends what your organization is like, but I remember there being just a ton of resistance in certain pockets of organizations that I’ve been a part of. And no matter what you do, they’re not gonna be happy with it, or they don’t even want to engage. 

And I spent a large part of my time, like butting my head against, while trying different techniques and trying to win them over. And at some point, it’s okay. And even coming into a firm now, I have already told the team, there is always gonna be a 5%, a 10% that we’re just not gonna make happy and that are not gonna come over to this side and try the new things, and we’re gonna have to be okay with that. And I think that is okay. And so again, starting with the people that are willing, and that’s where you can have the impact, where have struggled, similar to your experiences, when those pockets of resistance are the areas where you just know you could have the biggest impact.

Like if you just, 

Alex Su: I know. 

Mary Shen O’Carroll: did this. 

Alex Su: Yeah, that’s right. 

Mary Shen O’Carroll: So that’s hard. And I think it just takes time to figure out what the trade-off is. This level of effort versus impact, and sometimes the level of effort isn’t worth it. 

Alex Su: Yeah, no, I can totally relate, and I gotta imagine that it would be hard for anyone. But you bring a certain level of credibility to your organization, and I’d love for you to talk a little bit about that, because not only have you worked at a large firm previously, you’ve also been inside of an organization that would be a client. And so you probably bring a whole bunch of things to the table where that gives you credibility in asking people or suggesting to people and recommending certain initiatives and change, right?

Mary Shen O’Carroll: For sure. I think that helped me a lot coming on board when people were like, who is this person, and what’s their background? But that only takes you so far. 

So I knew that I had like a window of time, my first a hundred days, 90 days, however, you wanna look at it, to get out there and learn and listen. But in the background, I was constantly thinking, all right, we gotta start moving because your reputation or credibility will take you only, you know, so far, then people start going, okay, but can he or she actually deliver anything? And so, working really fast and furiously to try to show some results and win people over by actually actually having an impact versus promising that we’ll have an impact.

Alex Su: Yeah. I think that’s such a key piece of advice, and I think a lot of the change is probably necessary, and I’d love to talk a little bit about the bigger picture now. You know from where you said you’ve seen sat in many different places within the legal ecosystem.

What do you think are some of the big challenges or big trends that are happening in the industry right now? You’ve obviously seen a lot happening within a large law firm, you’ve seen the AI and technology space—I know you’re very involved in multiple companies—you’ve been at Google, you’ve been involved in co-founding CLOC. So what are the big shifts and changes and trends that are coming? 

Mary Shen O’Carroll: Oh, there’s not much happening right now. It’s really quiet in our industry. No, the pace of change is tremendous. It’s the sense of urgency that I have is already high. And every day I feel like we’ve gotta get moving, we’ve gotta get moving.

And, if you have your finger on the pulse at all in the AI and technology space, the changes that take place in like a two-week sprint from some of these companies and developers, it’s like the amount that they can accomplish and change their product offering is pretty impressive. And so, I think that puts a lot of pressure on the rest of the industry, ’cause we know this is coming, we know that AI is gonna have an impact on our industry, but that’s not the only thing. We’ve seen over the last 20 years an explosion in legal operations, which I think was probably the first big catalyst of change. People whose job was primarily to figure out how to do things in a much more efficient way

Started driving investment into technology, demand for technology, demand for alternative service providers, demand from law firms to try to deliver value in a different way. So those conversations and that pressure has been coming, but my God, it has skyrocketed, I think, in the last couple years.

And again, that’s why this job, why now? There is no more exciting place to be than in the heart of it, in the eye of the storm, so to speak, of where all the disruption is happening. I think firms, law firms, are probably going to be the organizations or the type of organizations that are gonna undergo the most massive disruption and change in their business and their model over the next five to ten years. And we’re seeing it; it’s forcing a lot of conversations. I think for me, AI today that’s the most exciting part of it, is the conversations that it is forcing because everyone has to sit up and pay attention and you can’t be those folks who are like, there’s nothing to see here, there’s nothing happening, I’m sure this is just a fad that will blow over, which we heard a lot of when legal ops was on the rise. But I don’t think you can deny what’s happening in our space now. 

Alex Su: There’s so much change happening even within the startups that are leveraging AI. You and I have talked about this before, but it seems like there are new startups coming out every day with new capabilities. 

Mary Shen O’Carroll: Completely.

Alex Su: This rise of generative AI has really changed a lot. How do you, as a—what advice do you have for an attorney who, maybe a partner who’s very busy with their book of business or an associate who’s incredibly busy with the workload that they have, what would you recommend that they do to stay on top of some of these changes and trends? 

Mary Shen O’Carroll: Yeah, so I was speaking to people whose primary job is to stay on top of these trends, and they literally have to dedicate several hours a day to watching, listening, and reading to keep up with it. But for people like you and I, it’s really hard, if not impossible. I take as many meetings, I try to read the inbound emails and vendors that are coming. 

Just yesterday I heard about two new AI companies that I thought were interesting, and it’s hard to know at this stage if they actually work or the demo’s interesting or if that was a mockup. But like in two months, they probably can do what they say they can do. 

But I would encourage everyone to be open-minded and to try these things and to be okay with a little bit of risk-taking ’cause I think we have a tendency in our field to talk about all the reasons why this is terrible, why this won’t work.

But there’s a lot of reasons why it will. And the only way to start adopting is to get your hands dirty. 

Alex Su: Yeah. These are themes that we’ve been thinking about, you and I, for a long time. And one thing that’s occurred to me in the past is that, for many lawyers, especially from firms, the substance of the work is such that you can’t get anything wrong, which is so different than the business world, where it’s more trial and error and experimentation, and see what works. And it seems to me from the outside point of view, and I’d be curious to get your thoughts on this, that one big looming challenge for large firms and any provider of legal services is how can you tell what types of work absolutely you have to get right the first time, and what types of work are better lent to experimentation and innovation. And I feel like your job right now as a transformation agent is really central to that. How do you make that judgment call of what should stay traditional versus what should be subject to some experimentation?

Mary Shen O’Carroll: So I’m a believer that there’s not gonna be like a policy that you can put in place to say, this is work that has to be done by humans and this is the type of work. We’ve just gotta try things and take a little bit of risk and to be smart about it. I think we’ve hired smart people and we need to trust that they’re gonna do their jobs and we can all use a little bit of AI, but to just blindly use it and to assume everything went to plan, I don’t think any of us would do that with our careers. It’s still work product, right? 

I have long said that in-house corporate legal teams can take a little bit more risk, right? It’s not like they’re gonna get their license pulled or anything like that, or reputational damage, the way that a law firm would. 

You and I both know, like we’ve always said, the legal tech that’s targeting in-house teams, I’ve always thought they had a leg up because the tolerance and willingness to try to do things in an efficient way is just more attractive.

We, as law firms, have to be a lot more careful. But we’ll get there. There was a lot of stuff that we used to check and double-check, and now, would you ever check that an Excel spreadsheet was doing your math right? Or would you ever question that spell check did its work?

Alex Su: That’s a good point. 

Mary Shen O’Carroll: And what human is perfect? None of us are, and a lot of the side-by-side comparisons have shown that we’re worse than some of the technology. So I don’t have an answer. I just think we should be wide-eyed and realistic that it will—it is continuing to get better, by leaps and bounds at a ridiculous pace right now. So it will get there. It will get there.

Alex Su: Yeah. No, I believe it too. We’re still in the early innings, and it’s really exciting to see the pace of change, which kind of brings me to my next thought, which is, for a lot of folks out there, I certainly knew and remember this when I was practicing law as a junior lawyer, there’s a lot of people who are in the field who say, Hey, this is not the best way to do it. I’d like to try to see if we could do it a better way. It used to be how we would put together briefs and the kind of highly manual tasks of discovery and things like that. But there’s so many opportunities like that, I think in the legal industry. 

And so how does a lawyer who sees something that could probably be improved process-wise, how do they get started on driving that change and finding a new way to get the work done?

Mary Shen O’Carroll: Those are the best lawyers, and back 10 years ago, those were all the people who became founders, those are people who got frustrated and said, I’m not gonna do this this way, and I have an idea. If you have that culture that allows you to have that psychological safety to take a risk and to try it a different way, do it, prove it. Show everyone else, go code something, build something on the side, and show everyone else how to do it. If you’re onto something, we will adopt it. Call me, I’ll hire you.

Alex Su: Any advice for folks who wanna to drive that change within their organizations?

Mary Shen O’Carroll: I think it’s lead by example. For all the leaders who are trying to make that happen in their space, you can’t just talk the talk, you gotta walk the walk. 

And show yourself trying those new things, encouraging it, and celebrating it. So I keep going back to culture ’cause I can’t tell you how much that mindset is important in this, and the ability to allow people and the willingness to encourage—taking the initiative to do that stuff and giving people the permission. There’s so many rules, so many policies that we put in place, and in a lot of organizations, fear of getting something wrong. And I think something that you and I have both learned from working in Silicon Valley is fail fast, learn, adapt. Learn to be flexible and agile. 

Those are the qualities that everyone needs to have in the future. And when we talk about the lawyers of the future and how do we need to attract, retain, and train people, those are the intangible qualities that are gonna make people successful. It’s not always about remembering the letter of the law anymore. 

Alex Su: There’s so much I would love to unpack even more, but I know we’re running outta time. Maybe one last question for you, Mary. What general advice would you have for people who would love to emulate your path and get to where you are today?

Mary Shen O’Carroll: Oh gosh. Someone asked me the other day why it seems so easy to get on a podcast or to talk about my journey or to jump in and take a risk, and I think I genuinely don’t care about the brand and what people think of me and my reputation. I’ll just talk, like things will just come out.

And I think just being really honest with the direction you wanna take and to go get it and to just say it, and to not be shy about it. So, I think it is a lot about taking risks and being okay with it. 

Alex Su: I love that. And we’ll leave it there because I think that’s a great message for our audience.

Mary, thank you so much for joining us today. We really appreciate your time. 

Mary Shen O’Carroll: Always great to see you, Alex. Thank you. 

Alex Su: That’s it for this month’s episode of Under Review. We’d love to hear from you, whether it’s feedback on this episode or ideas for future topics and guests. Connect with us through PLI, Stanford Law School, or on social media.

Your input helps shape this series. Thanks for tuning in, and we’ll see you next time.