Tune in for highlights from the State Bar of Texas’ Annual Meeting! During the conference, Laurence Colletti talked with presenter Dyane O’Leary about her session on how a modern mindset helps lawyers stay current with best practices and evolving legal technology. Dyane shares tips for maximizing efficiency through tech-powered practice management and gives insights on where to start if you’re looking to expand your knowledge of modern legal trends.
Dyane O’Leary is an Associate Professor of Legal Writing and the Director of Legal Innovation & Technology Concentration at Suffolk University Law School.
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Intro: Welcome to the State Bar of Texas Podcast, your monthly source for conversations and curated content to improve your law practice. With your host, Rocky Dhir.
Laurence Colletti: Hello. Welcome to another episode of the State Bar of Texas Podcast recording live from the bar’s annual meeting here in Austin, Texas. And as you have no doubt heard, I am not Rocky Dhir. I am just stepping in here briefly. He’s going to be coming by with a special guest coming up here pretty soon, but in the meantime, they’re allowing me the privilege of standing in here to do the State Bar of Texas Podcast. So thank you so much for letting me do that. It’s been a lot of fun here so far. And I got another wonderful guest joining us. I got Dyane O’Leary, and she is fresh off of one of her presentations called Keeping Pace creating a More Modern Mindset. So I’m really interested. We did a little pregame conversation here and I think it’s going to be a really interesting interview if you’re into automating innovating your law practice. So, Dyane, welcome to the show. Thank you so much for joining us.
Dyane O’Leary: Thanks for having me.
Laurence Colletti: So now you teach at Suffolk Law School, but tell us a little bit more about what you do, obviously from Boston, but tell us about your position and the kind of work you do there.
Dyane O’Leary: Sure. So after practicing at Big Law for about six years, I realized I liked the law, but I didn’t want to practice it anymore, so I get to do the next best thing and just talk about it all day. So I teach the first year legal practice skills course, which is kind of that required skills course that all law students take. But over the last decade, I’ve been more interested in legal innovation and technology. So on two fronts, I integrate that into our first year curriculum, but also direct our legal innovation and tech concentration, which is kind of an academic major and a bundle of classes like coding in the law, design, thinking, automation, project management, all sorts of new skills we’re trying to pass on to our law students. So that’s my role up at Suffolk.
Laurence Colletti: Well, please tell Andy and Gabe hello for us. It’s been a while since we’ve talked to them. It’s one of our favorite visits to go out to Suffolk Law School. Kind of the Boston Commons area, right? over there?
Dyane O’Leary: Right on the Boston Common. Yeah.
Laurence Colletti: And it was so funny. I remember I was taking a little break there and this is just so fascinating. I walked across the street and there’s this graveyard. I had no idea, so I just walked in because everybody else is walking and I did not realize how many historical figures are buried there.
Dyane O’Leary: Yes. Often you can look out your window from the building and see all sorts of field trips going through there. So that’s our admissions pitch. Right? Come to law school right on the freedom trail.
Laurence Colletti: Yeah. And Paul Revere is buried there. And so I’ve never been able to get a satisfactory answer to this. Why do people leave money on his grave?
Dyane O’Leary: My father was a history teacher, and he’ll be horrified that I don’t know the answer to that. But now, after we finish speaking, I’ll have to look it up as well.
Laurence Colletti: I’m telling you, it’s going to be hard. I looked it up even on Wikipedia. I didn’t even get some colorful sort of idea about it. I couldn’t find anything.
Dyane O’Leary: Then we’re going to ask my dad, the high school history and social studies teacher.
Laurence Colletti: Okay.
Dyane O’Leary: He’ll know the answer.
Laurence Colletti: Fair enough. Well, anyway, thank you so much for joining us. And so I want to get into our topic here. So this modern mindset, just as a starting point, obviously, technology, the innovation loop by which new technologies and game changing technologies are coming out, that pace increases. So let’s start at the very beginning. How do you define moderate mindset in terms of running a law firm and keeping abreast of those changes, what exactly does that mean?
Dyane O’Leary: Yeah, I think first, let me back up. Why do I define or not how do I define it, but why even define it? So everything you just said, innovation, technology, kind of the rat race of new products and software and updates and tools, frankly, all of that is behind the scenes if you don’t care about it, right? We talk about it as if it’s a given that lawyers pay attention and care about those things, but it’s really not. So to me, all of that is kind of gravy in the background. The first step to even get there is to motivate, to think about it, and to frankly appreciate that it might be part of a good law practice. So I like to kind of start there because I think we kind of take that for granted, that lawyers will be interested and they do care about technology, and I don’t know that that’s always the case.
So it’s more kind of the modern mindset to be willing and aware. This presentation was part of the adaptable lawyer track, right? And they love that word of kind of it’s not survival of the fittest, it’s survival of the most adaptable. But I think that’s why, at least for this presentation, I didn’t want to get into gadgets and shiny technology and ChatGPT and all those kind of scary things, because frankly, that’s polarizing for people. They feel uncomfortable about it, they feel new about it, but a mindset for change and kind of be willing to motivate and how to find little pockets where you can do that, I think is something more manageable for folks. So that was the angle for the presentation.
Laurence Colletti: Well, let’s throw some examples of that. You mentioned ChatGPT, and that’s been a really fascinating thing to observe. And so, I take an office space over and we work in San Diego, California, and I have some friends that I don’t work with. It’s kind of like a co-working, share office space thing. But I hear about some of the projects they’re working on. It just blows me away the pace at which people are creating new products and services on that platform. And this has nothing to do with the law. And so give us some examples of that. You were talking about the mindset, but it blows me away how fast that moves.
And the practice of law is built on precedent and things that are not necessarily supposed to change quickly, or at least if they do. Everyone needs to kind of be in lockstep before you change legislation. It becomes law and we all have to understand the rules. That’s kind of what makes laws more enforceable. And so, the modern mindset keeping up with technology. Let’s talk about some of the examples of how that’s playing out.
Dyane O’Leary: Right. And to put this in context, right, lawyers have been doing this for decades. And not to sound silly, right, it was the typewriter from file cabinets or it was hard drives or it was paper research in law school to starting to use those scary online research systems, which frankly, a lot of the chatter then sounds like the chatter now about generative AI, right? So these are kind of the arc of technology in any industry, not necessarily law. So I think sometimes us lawyers like to think we’re so special and it’s so unique to the legal industry, but it’s really not. It’s just kind of the latest in a cycle for decades. So some concrete examples. So one example I like to think about is sometimes how lawyers are just building their documents. So documents are a lawyer’s tool, right? It’s not that fancy, but that’s what lawyers do all day. And something we talked about this morning with the group was kind of more automated templates and macros and different ways to make that more standard.
So, for example, a lawyer who opens a Word document, or nowadays my students and more junior lawyers, Google documents, which is a whole another issue, but starts to type things manually, like United States District Court for the district, anything like that. That’s not being standardized now from kind of a macro or a template is frankly silly. And that’s not new flashy ChatGPT, that’s basics of Microsoft Word, right? Kind of building Lego blocks, if you will, that are personalized to you. Same thing with email. So if I send clients emails every week that say, hey, I thought you’d like this article, it’s interesting. I shouldn’t be typing that out. I should be saving that as a simple email template and Outlook and I should be using that every time. So those are super simple, but they’re just examples of tools that we already have that frankly a lot of lawyers might just not be using well. So that’s one example, at least in kind of that starting document space, which is accessible to a lot of lawyers and kind of a pain point for a lot of them as well.
Laurence Colletti: So what I’m hearing there is save some time, right? So that’s a question. Maybe the mindset aspect of it comes down to a series of questions you should be asking yourself about the work that you do. So how do I save time doing this? What tasks do I do over and over again? How can I make something more accurate? How am I going to create a process where I make less mistakes and things don’t slip through the cracks?
Dyane O’Leary: Exactly.
Laurence Colletti: What are some other questions to help you kind of get into that modern mindset to get the most out of a very busy day?
Dyane O’Leary: Yeah, so another example that we talked about this morning is kind of the office management approach that’s still in silos. And so what I mean by that kind of a less modern mindset, if you will, has kind of the business of law still operating on individual people’s computers, right? So maybe we share a little bit, but think of how much knowledge is trapped in an inbox, right? Timelines, people, dates, assignments. That’s like siloed in an email inbox. So again, kind of one concrete transition would be a law firm that’s willing to use different cloud based dashboards and portals and better task management system, right? Again, productivity software is available in all industries. One tool I talked about this morning was called dashboard legal, a really neat tool that I like and I’ve showed my students. But again, the contrast there, that’s concrete for folks is document management. That’s folders and email is not document and task management these days, right? It’s cloud based platforms that allow people to really collaborate is, I think, where most law firms, if they haven’t moved already, are moving to. So that’s another example.
Laurence Colletti: Building on that, where do you think the biggest bottlenecks are? So you’re talking about an inbox, but where are the bottlenecks? Where are the pain points right now in that practice of law? You’re in a firm, let’s say, let’s just call it a smaller firm. So let’s say 10 to 20 people and you’ve got clients coming in, they have problems, they don’t know which attorney to talk to, all of that. So where are the pain points today? How do you address that?
Dyane O’Leary: Yeah, so I hate to do this, but I’ll fight the hypothetical a little bit. That’s what us law professors say. Because I’m going to be the first to admit I’m not a solo or small lawyer, right? So one of my challenges is to not talk about this stuff and pretend I’m in with the solos and I know their pain points. So I like to be pretty upfront about that because I think, frankly, it’s silly to pretend I know the ins and outs of small and solo practice. What I do know, though, is I talk to a lot of vendors that do hear that, right? They go around and those are their clients. Folks like fast case or dashboard legal or Clio, right? These products. And the number one thing that they tell me is those silos is the kind of lack of transparency. So if you’re an associate, you’re kind of sitting back and waiting to be told what to do, which is frustrating for you. That’s also frustrating for your supervisor, because they want you to be proactive. But if you don’t have kind of some sort of central dashboard that you’re sharing that information, both of you are kind of inevitably stuck in those pockets.
So that’s at least in terms of the law, practice management, something I hear a lot of, of course, also kind of billing and those type of more business of law things. But I think just the way lawyers aren’t sharing information in a helpful, collaborative, and efficient way.
Laurence Colletti: All right, so we’ve got into this just a little bit, but I’d like to be a little more concrete about it. So just in terms of a modern mindset, in terms of basically reengineering how you practice law, how you’re doing your workload. So you’ve got a modern mindset way of doing things, and you’ve got the old way of doing things. Can we do some comparing, contrast, maybe some case studies or just maybe it’s an applicable process from what you’ve observed or what you’ve heard from vendors. So, like over here is an example of old way, and here’s an example of new way.
Dyane O’Leary: Sure. So let’s move to a different bucket. Legal research, right? That’s an area that has evolved, of course, for decades online. So old way, a client asked me whether to move a case, say, from, I don’t know, Texas to Oklahoma. Old way is I chat with people in my office. I maybe think about my files and my experience and my hunch, and I say, well, I’ve heard this. My gut instinct is this, right? And I advise them because that’s what they’re paying me to do. That’s old. New is taking advantage of kind of the phrase of now data driven lawyering. Right? So I use this example this morning. Tonight is the NBA Draft. I don’t know if you’re a basketball fan.
Laurence Colletti: No.
Dyane O’Leary: Okay. Tonight, NBA Draft. Those teams are not drafting players based on hunches or gut instinct, right? They’re using actual data and mounds of information.
Laurence Colletti: I’d like to think so.
Dyane O’Leary: Right. That they can pull patterns, at least we hope the Celtics are. But that’s kind of, again, kind of that old approach is my gut instinct, my feeling. And that new approach is combining, not ignoring that gut instinct. Right? You’re a trusted advisor. It’s not ignoring it. It’s not the robots are coming to replace you. It’s the idea of all these tools. Fast case. Westlaw, Alexis, Docket Alarm have so much information out at our fingertips. So the new modern mindset is, I can say, oh, Judge O’Leary in Oklahoma seems to grant motions to dismiss 80% of the time. So client, guess what? If we transfer there, we might have this percentage more success, right? And it’s not magic. It’s not guesswork. It’s just more information. So in the research context, I think that’s one kind of concrete example.
Laurence Colletti: Excellent. So there’s some firms out there probably listening right now. They’ve got a pretty good practice model going, but they would like to get more out of it. But they’re really busy, right? So it takes time to make those investments. And you got clients, you got bills to pay. So I guess with that in mind, and since as your role as an educator and educating people out there all over the country, where do people get started? Where does a firm get started? Do you have some resources that you like to turn to, to keep up with that information? Where do you go when you want to learn more about improving the profession?
Dyane O’Leary: Yeah, such a hard but important question. One thing is to get started and create space for it. So I have some colleagues and folks I talk to at firms that say I’m the only one interested in this. Other folks are just too busy. And my pushback is, are you sure? Have you asked folks that you’re working with? Your staff, et cetera? So a lawyer I know in Boston started lit lunches, one lunch a week, 30 to 60 minutes, an opportunity for folks to just come and say, hey, this process stinks. Can we work on it? Or hey, this new billing feature came across my desk. Is it something we should explore? So that’s kind of one concrete thing when we think about how do you even start to do this. You have to make time and space, because who are we kidding if it’s not in our calendars these days and it’s not available and it’s not a priority, it’s not going to happen. Right?
Like you said before, kind of the pace is crazy. I don’t have a real lawyer job, right? I’m an educator, and yet I still can’t keep up with this. So how do we think others do? And I think we just rely on the curation of other great people that do this. So, for example, Bob Ambrogi, who I’m sure you’ve heard the Law Insights blog has a great kind of legal tech funnel of just staying in the know of things going on. So that’s one, I don’t know if you’ve met him or worked with him.
Laurence Colletti: Wait, who’s Bob? No, I’m just kidding. He’s been a host for many years.
Dyane O’Leary: Yes. Not a name that most don’t know in the legal tech space. Josh Kubicki at University of Richmond most recently has started a great newsletter called Brainiacs, all about generative AI.
Laurence Colletti: Yeah, I’m not sure I’ve met him, but I know him on Twitter.
Dyane O’Leary: Yeah, I think his consulting business used to be called Duck Studio. I might be messing that up. I spoke with him a few months ago, but kind of in the academic business space. So that’s just one example. If you are overwhelmed on the generative AI front, he’s just been doing a really great job of boiling down kind of your need to nose. So I think that’s another example. And then I think overall, it’s overwhelming. If you’re thinking about legal tech in general, we say that phrase as if that’s something you can stay abreast of, and it’s not. So I would just encourage lawyers to think of what their frustration is. Like, I hate my billing procedures, or, wow, that associate that always does things this way, that’s so frustrating to me. Or this is an expense we need to get down. How can we do that better?
And the more you narrow kind of your friction point, I think it’s easier then to feel like you’re keeping up with what you need to in that particular pocket.
Laurence Colletti: So necessity being the mother of invention.
Dyane O’Leary: Yes. Or as I read the other day, niches lead to riches. I guess that’s true in your practice, supposedly, but in the innovation space, right? Innovation is not some macro huge concept, necessarily. Sometimes I think the best changes, frankly, don’t even involve technology. They might just be a little bit of a different way of doing something in your practice.
Laurence Colletti: Well, Dyane, thank you so much for joining us today. If our listeners out there, they want to follow up, I have questions. How can they find you?
Dyane O’Leary: Sure. So I’m on Twitter at D O’Leary or Suffolk University Law School in Boston. I recently wrote a book through West Academic Publishing that came out last year that’s in different law school classes called ‘Legal Innovation & Tech a Practical Skills Guide for the Modern Lawyer’, where I tried to mix kind of some high level tips with some more concrete how to. So if folks are interested in that, I encourage them to dive in.
Laurence Colletti: Excellent. Well, thank you for joining us today.
Dyane O’Leary: All right, thanks for having me.
Laurence Colletti: And thank you, listeners, for tuning in. If you like today’s episode, please rate us in your favorite podcasting app or on Apple podcast, Google podcast, Spotify, all those major podcasting apps. I’m Laurence Colletti. Until next time, thank you for listening.