Feeling overwhelmed by the endless legal tech solutions? Bombarded by vendors offering the latest shiny tools? In this episode, Legal tech analyst and writer Ari Kaplan, with over 18 years of expertise, shares practical advice on evaluating legal tech solutions for your department. Ari discusses how to work effectively with vendors, streamline legal operations, and assess your department’s needs to ensure successful tech implementation. Plus, hear his thoughts on AI in legal and why embracing this game-changing technology is crucial for staying ahead in the industry.

—

Listen to the podcast here

 

Flirting With AI And Tech In The Legal Department

Introduction And Overview Of The Episode

On this episode of the show, I’m happy to welcome Ari Kaplan who is an analyst that covers the legal industry and is the Principal at Ari Kaplan Advisors. He has been described to me as the Switzerland of legal tech. We are going to peel back the curtain on all things legal tech and try to figure out what solutions in-house corporate legal departments should be pursuing and how to negotiate with these people. Ari has also been in the thought leadership business for almost twenty years. I’m going to pick his brain a little bit about that as well.

‐‐‐

Ari, how are you?

It’s great to see you. Thank you so much for having me.

Thanks for being here. I want to dive in. You do a lot of writing in the legal tech space and do a bunch of reports. One of the reports that you sent me had this quote that stuck with me. I think this is a good place for leading off. The quote from an in-house lawyer is, “It’s not enough to be good at law. You need to understand data and tech.” This is probably truer now than it has ever been. I want to get your take on why you think understanding tech is so important for lawyers.

It’s interesting to me that people have described law firms as previously service businesses that use technology and evolving into technology businesses that offer some services. We will see this evolution of technology. We are seeing it. We will see technology having a greater influence. It’s affecting what services law firms provide and what in-house legal departments receive. We will see it affect pricing. We will see it affect time. We will see it affect talent. The idea of someone not being particularly familiar with technology or sufficiently familiar with technology will eventually be a deficiency.

I started practicing in 1997. I graduated from law school in ‘97 and started practicing in 1997. I was writing a column with a partner I worked with, a wonderfully generous individual who allowed me to co-author with him. We were writing. I was doing international trade. I had lived in Japan, the Czech Republic, and the UK, and I had worked at the State Department when I was in law school. I had all this wonderful experience I was very lucky to get.

We were doing international trade and we were writing about the harmonized tariff schedule and the importation of Chinese wood. A year into this co-author project, I said, “I’ve been reading a lot about this internet. I really think we should write about the internet. I don’t know what that is and I don’t know where it’s going, but we should write about the internet. It’s 1998 and this seems like something.” He was like, “Honestly, I don’t want to write about the internet. With what I do, there’s a strong expertise here. I’m a super well-recognized global expert. We’re going to write about that. If you could bill your time, write with me, and somehow find time to write about technology, go for it.”

It was very interesting to me. There always seems to be an early day in every kind of movement. In those early days of writing about that, there was a lot to uncover. I feel like over the years because I’ve been doing this for quite some time, there have been these moments where we are there at the beginning again. I feel like we are in that period. It’s exciting, and it’s a wonderful opportunity.

The people who simply step up, raise their hands, and express some interest and curiosity can gain a competitive advantage. Individuals who somehow figure out how to do what they’re doing not to overwhelm themselves but to do what they’re doing and add a layer of understanding about the impact of technology will elevate their role and the opportunities that they have.

You’re right that we are at one of those beginnings or after the beginning. True confessions here, I am somebody who has been tech-averse for a long time. I did an episode with Sterling Miller and did a shout-out to WordPerfect, which was a word-processing solution that I used when I started practicing at the firm. As our healthcare industry, in particular, explores artificial intelligence, I’m wading into the tech a little bit more.

How To Work With Legal Tech Vendors

I want to talk a little bit specifically about the in-house legal department because that’s our main audience here. I got back from a conference and I was, like any legal conference, attacked by legal tech vendors. It is very overwhelming. Everybody says they’ve got the new shiny thing that can make your life easier, faster, and better. Since you’ve been writing in this space for almost twenty years and work with a lot of different vendors and a lot of in-house lawyers, what are those tech solutions we should be considering?

I understand your position of being overwhelmed when you go to one of these events and people are trying to reach you because they’re trying to engage you in conversation. There are a couple of things I  want to recommend when this happens. First of all, some of these tech vendors are quite large and quite well-established. I had friends who attended some conferences who were in-house. They talked about the same experience. Their badge has the name of a company. They have a very important title. Everybody wants to talk to them.

Feeling overwhelmed by all the legal tech solutions? Take a breath. Evaluate your needs and find what works best for your legal department. Share on X

I suggested that they do two things. One, because a lot of the in-house leaders I know tend to produce some kinds of content like thought leadership on LinkedIn, tips, or experiences, I suggested that they try to ask those vendors if they have newsletters or publications where they could contribute because it amplifies their voice in significant ways. I also suggested finding out if they have non-customer advisory kinds of boards or opportunities where they get to shape technology in ways that they otherwise wouldn’t be able to do independently. There are really interesting things that you could talk to those individuals about. Those are two.

Instead of recoiling, engage with a purpose.

That’s right. Embrace it. Understand that you’re a celebrity in those circles. Where are we celebrities? Let’s be honest. When I come home, there’s no celebrity happening here, so I’ll take it wherever I get it. In those situations, there may be ways to take advantage of that. They want to talk to you, so you want to talk to them. There’s a mutual respect there and a mutual opportunity. I suggest that people consider that.

I appreciate that. That’s great advice. I’ve never thought of it as being a celebrity. If that’s what being a celebrity is, I do not want it.

You’re a host. The idea of what value you will gain should also be in the terms of selection of software and services. A lot of these events we go to offer both. There are people there offering both. The question is, what are your challenges? What is your objective when you go there? You want to learn, get CLE credits, and connect with your peers, but also, what are the challenges that your team is facing at this moment? They’re usually pretty discreet things, whatever they might be. You’re like, “We have an overwhelming number of contracts. We have a significant litigation that’s taking place.”

The question is, are there actual solutions or real practical things that can move the needle within your organization that can also allow you to have a more thoughtful conversation with the C-Suite executives that you serve and with whom you work and who are also facing similar challenges? I often suggest that when you are engaged in the selection process, you try to engage people in a practical conversation to see if they have dealt with your issue before and if they have an actual solution to your issue or if they have a generic solution that can be applied to your situation. That’s a really important area that people don’t always think as much about as they could. Only you know what your docket looks like and what your transactional process looks like.

Before choosing legal tech, ask: Does it solve your specific problem, or is it just a generic solution? Tailor your tools for success. Share on X

A lot of the people that I know at legal technology companies and legal services companies are highly experienced. They have dealt with many more actual situations than the people they’re serving. They serve those people and an exponential number of others who are doing something similar and have variations on those issues. The objective is to try to find the people who know their product and your situation. It’s not so easy, but it ends up being the best way to start that selection process.

Those interactions and the process of scoping out a solution, I want to get into that more granularly. Let’s take a contract lifecycle management system because that is one of the foundational solutions that most in-house departments that do any transactional work should consider. It’s not, “Get it off the shelf. Upload it.” To really implement a new solution is a giant process. It’s very overwhelming. Maybe this is one girl’s view, but you have such a deluge of actual work coming in that scoping, going through a software implementation, and changing process is major. It feels almost like an Everest that you may not be able to climb.

The contract is a very interesting area. I have been researching CLM contract issues as part of either my general counsel research or my legal operations research for years. One of the components is this. One of my favorite quotes is from Charlie Munger who was famously Warren Buffet’s partner.

I met Charlie Munger. He wasn’t my favorite, I have to say. He wasn’t too crazy about women in leadership roles.

I knew you were going there. I didn’t mean to bring that up. He was in his late 90s or something and they asked him what his secret to good health was. He said, “I don’t know the secret to good health and a long life. It’s probably good genes. I can tell you the secret to happiness. The secret to happiness is low expectations.” I always liked that quote. Even when my kids were little, I would talk to them about that. It’s so important in any of these activities to set expectations and recognize exactly what you said, that this is going to be a much bigger process than you think. If you set expectations properly, you may be pleasantly surprised.

The challenge that I mentioned earlier that comes up in so many of my conversations in these different reports is that no one wants to own contracts. Legal wants a piece of it but not everything. The business unit wants it. Procurement expects a piece of it. Sometimes, they’re IT-related. It’s a big challenge. It’s like a hot potato in the law department. If you’re then selecting a piece of technology that’s going to solve this problem, whose input is most valuable? Where is all of the work going to reside? Who’s paying for it? Who’s going to work on that implementation? It’s an issue.

I feel like you’ve been there.

A lot of my research is anonymous, so it becomes very cathartic for people to tell me all of the issues. I’ll say, “What about this?” They’re like, “Ugh.” I hear the sigh and I’m ready for it. I’m looking forward to the conversation. It’s such a privileged place to sit. I’m the Switzerland of legal. I’m not selling anything. I’m not trying to persuade anybody. I’m trying to learn, and I’m trying to then share what I’ve learned for the betterment of the entire community, whether they’re in law firms, law departments, or the vendor side. It’s a lucky place to sit.

It’s important for the buyers to recognize that the sellers, whether those sellers are services or technology, that it’s going to be a hard process and that they won’t have all the answers. That’s another part of these expectations. It’s like, “Overall, this is what we’re going to try to solve. We’re going to take whatever your universe of contracts is and we’re going to try to organize it a little better. We’re going to try to help you find things. We’re going to try to help you add clauses and identify clauses. We’re going to help you streamline. We’re going to help you assign. We’re going to change the workflow,” but that doesn’t happen with the push of a button.

As a podcaster, you’ll appreciate that. I tried an AI editing tool. I was very excited about it. Someone recommended it to me. I upload the episode and  I think, “Get rid of all the uhms, the you-knows, and whatever else, and try to organize the sound.” I push a button like AI or something and then I get it. I’m like, “That’s not what I meant.” I pushed a different button. I could not figure out what to do. I used up all my credits for this editing service. I thought, “This was not as push button as I thought. Maybe I’ll go back to using the editor that I hired to edit the episodes.” That’s where we are. We’re like, “Do we go back?” It becomes an iterative process.

I want to get into AI in legal, but I first want to talk more about blocking and tackling some of these solutions. CLM or Contract Lifecycle Management is a multi-party project. It’s not something that legal can grab and go with. A matter management system is something that legal could own because that’s our world.

I talked to a lot of in-house counsel. I was speaking with the head of litigation at a very large nationwide company. They told me that when they got into their role, their company was tracking litigation on a Word document. That made me feel a lot better because not all legal departments have a lot of tech. It’s what I said earlier, which is that implementing a new thing feels like another huge project and I don’t have time to do it. I wondered if we could talk a little bit about some of those legal-only solutions and whether in your travels as a Switzerland you have any thoughts about, without identifying any companies, a lit management system.

There are a couple of things about that. You mentioned not all companies are doing it in a sophisticated way. Not all companies have a particularly substantial litigation docket. People who sell technology to law departments make an incorrect assumption that they have a massive amount of this or a massive amount of that, or that they have teams of people who are available.

I do an annual general counsel report. I’ve been interviewing corporate counsel since 2007 or 2008. I’ve been producing this research. I’ve produced something like 60 reports. Most of them address in-house issues. Often, I’m speaking to a single general counsel legal team. They may have a paralegal. They may have a deputy. They may share time with somebody else. Yet, that company could have billions in revenue. It’s a really interesting disconnect. When people are selling into the law department, they think that there’s a massive team where all of this is happening and there’s a docket of cases. There’s sometimes a misunderstanding of who they’re selling to and what their needs are.

The other thing that is important to recognize is that not every law department needs the biggest, most sophisticated application. It’s incumbent on whoever is buying. It’s not always the general counsel, but if the general counsel is the only person in the law department, it’s that person. You mentioned being at a conference and speaking to people. The other thing to do is to look at the universe of what’s available. You’ll recognize that there are market leaders. Their advertising may be in different places or their thought leadership may be in different places, but there are certain market leaders that are very easy to identify, and then there are competitors.

Sometimes, because a company is newer or has fewer customers, although it should have some customers in terms of people that you can speak to, you may benefit depending on the needs of your department in working with a smaller, less known company that you can help iterate to make their product even better. They will, in return, acknowledge you and service the issues that you have in a way that you might not get at a larger, more established company with hundreds of thousands of clients.

Finding The Right Legal Tech Fit For Your Department

It’s a Goldilocks though. I’ve had legal tech solutions where we used a smaller company and then they went out of business or they got bought by somebody else. We didn’t have the services that we had or we didn’t have the client rep that we had. Its functionality went away. On the other side, with the behemoth companies, you have no ability to negotiate. The price is super high. You get what you get and you don’t get upset. It can be really challenging to find that Goldilocks or right fit.

There are a couple of things that happen when you make a decision to move from gum and duct tape to an actual system. What happens is you end up streamlining all of your processes. You end up centralizing your data. You end up cleaning up all of the material that’s in there. You put yourself in a position of being mobile. You can move from one system to another. Most of these systems are Cloud-based, so it allows for migration in a much easier fashion. This may be controversial.

 

I’m excited here. Mic drop. Let’s get ready for it.

It would be comically controversial, but if you’re choosing a new system, whatever it might be, it should be Cloud-based.

I feel uncomfortable with that comment.

I understand. This comes up. I host a series of dinners with corporate counsel all over the country. I even did one in Frankfurt, Germany on Monday, March 9th, 2020. That’s a story for another day. This issue comes up. Lots of people will agree to that, and then someone at a highly regulated financial services, healthcare, or other manufacturer will say, “We can’t be in the Cloud.”

The truth is there will eventually be no choice there. You won’t have updates for those tools. Tools won’t be built for tools that are on-prem. You end up delaying the inevitable. That’s probably not an issue we can resolve here, the two of us. It’s also probably not an issue that legal will resolve. It will have to be resolved at an enterprise level.

It’s going to happen to us. It’s what you said. I did a C-Suite episode with Sarah Richardson. She was a former CIO. She’s at a company that sources or gathers other CIOs to evaluate different tech solutions in healthcare. We talked about needing to have a risk management program around Cloud and having conversations with your CIO about Cloud technology. You’re right. There’s not going to be very many on-prem solutions anymore. We are all outsourcing all of that to the Cloud.

Also, the updates. We’re not going to talk about AI yet. Any of the updates or any of the advancements are going to be pushed into the Cloud tool. As a result, you end up lingering further behind rather than leaping a bit ahead if your infrastructure is designed for something that’s older and isn’t getting updated for the things that are newer. That’s a real issue.

If you are even slightly more sophisticated as an in-house leader, you can participate in that conversation. That’s why that quote says so much about what’s happening. Those who are not even remotely familiar with what’s possible end up lingering behind. They lose an advantage rather than gain anything. There’s an impression. It’s like social media. Everyone’s life is amazing. Everyone is doing this incredible thing and you’re slogging away at work. It’s really important to level set and give people the grace that we’re all figuring this out, even the most sophisticated GCs.

I remember interviewing an incredibly sophisticated GC at a household-name company who was having meetings with Oculus Goggles. It was fascinating. Still, they were dealing with, “Is this the right tool that we should use? Should we implement that? How long is that going to take? Are we working with procurement?” They were following a very similar path. It’s important to acknowledge that. I’m sure that when you’re going to these events with your peers or certainly when I host dinners with a group of general counsel and leading in-house counsel, they are pretty honest with each other. They take a sigh. They release this breath that’s like, “That feels so much better.”

It’s because you know you should be exploring it. It’s what I said. It’s very overwhelming. It doesn’t feel like it’s in the core strike zone of your day-to-day duties and what the company’s looking for you to do. It’s a hard thing, so you have to be really choosy. I’m going to give a shout-out to Mary O’Carroll who was on the show talking about legal operations.

I hired a consultant to do an assessment of our department from a legal ops standpoint. That was super helpful. When you were talking earlier about how you need to match with a vendor that can help you with what your needs are, you need to first know what your needs are. If you’re not living legal operations day-to-day, it’s helpful to have somebody from the outside to look at your department, figure out what you need, and give you advice.

Also, people are really eager to be part of that process. A newer professional, a junior professional, or someone who’s in an ancillary department, depending on the resources that you have available, may want to help with this. People are eager to learn what options there are in terms of different technology platforms, where the company is benefiting from AI, where the enterprise is investing that legal may not be familiar with, and where legal might benefit from that at almost every organization.

I’ll ask two different questions. Is your legal department using AI? Is your legal department using generative AI? That varies. The numbers vary and they’re not universal. I’ll then ask, what about the enterprise? Every company is investing something in developing some kind of framework, some parameters, or some tools where they’re trying to use something generative. If legal wants to, they could maybe take advantage of what the enterprise is investing in. It doesn’t cost them anything. There’s probably an already established framework. They can appreciate that.

Mary’s right. I’m a huge fan of Mary. I respect her work very much. Acknowledging where you have strengths and where you have weaknesses is extremely important. There are lots of regional and national events where peers simply get together and ask these questions. If you’re in an area or a sector that doesn’t have that, create it. Ask ten friends. That’s how CLOC got started. Connie Brenton used to call it a book club. They would sit around a conference table.

There was a group of leaders out West who were doing this and there was another group of leaders out East. The technology companies were doing it out West and the insurance and financial services providers were doing it out East. It was like Biggie and Tupac. They had this East Coast and West Coast thing going on. They were trying to solve problems but they were doing it in this very intimate way where they were asking each other questions and being honest with each other in a safe space. If you are not able to hire somebody or identify that, you can probably do a lot simply with peer support.

I want to echo that. That’s a tip I give everybody, which is to have what I call my coffee clutch. Other healthcare GCs in my state, we get together quarterly and talk about all things including legal technology and solutions we might need. It is therapeutic, and also, you get a lot of practical advice on this system, that system, this vendor, and that vendor. I couldn’t agree more that having people to talk to about all of these major decisions is helpful.

Embracing AI In The Legal Department

We’ve been flirting with AI in this conversation. Let’s go to dinner. Let’s dig into it. It is everywhere. I was at that conference. There was a lot of talk about how it’s going to make my life different and better, maybe help me with staffing, and maybe help me with processes. You talk to a lot of vendors. I looked at your podcast and it seems like you’re knee-deep in AI and legal tech. What’s out there? What do we need to have our eyes on?

I host a Zoom call almost every weekday at noon Eastern. It’s called the Virtual Lunch. Our theme is demystifying AI for legal. You are correct in some ways. In my podcast, I often feature AI discussions. I’m sure you can relate. It’s part of every conversation because you have to ask the AI question. Thankfully, we hadn’t gotten to it the minute we started. It took a while. That’s important because it shouldn’t be the center, but it should be a component of what people are doing.

Someone made a recommendation for me that I thought was very helpful. If your organization allows some kind of generative AI tool, whatever that might be, whether it’s ChatGPT, Copilot, or whatever your organization allows, and you should only use what your organization permits, keep that window open and available. I’ve been doing that in terms of creating podcast narratives or very simple things that I know are non-proprietary and don’t have anything that I’m interested in protecting. It has been super helpful, but I probably wouldn’t have done it if it wasn’t right there available to me. I recommend that people do that.

The other thing that you want to try to keep track of is the activities. The difference in a lot of ways from moving from a law firm to in-house is that you’re no longer typically tracking every six-minute increments of your day. I, as best I can, try to use a tracker even though I don’t bill for my time to try to see how I’m spending my time.

I will increasingly keep a notepad or have it on my iPad or something the podcast episodes or anything where I’m thinking, “This is a waste of 5 minutes or 10 minutes.” It’s usually a tiny bit of time, which is negligible so people don’t realize it. Putting away $50 a month into some market-bearing fund over 30 years, you’ll have a lot of money. Time is a very similar component and element. People should be mindful of where they’re spending time and ask their teams. In a team meeting, ask, “Does anybody have any suggestions?” They could be like, “I’ve been spending a lot of time on X.” You’re thinking, “That’s got to be a place where we can apply technology.”

Before people get too excited about this thing changing the world, and I’m pretty confident that it’s getting better more quickly than we realize, try to identify a task or an area that you think it could help. Even if it’s 5 or 10 minutes a day, it saves you half an hour or an hour a week. Before you know it, it really frees you up. I don’t think you necessarily even need to spend that time, certainly in-house, on more work. Maybe get the work done. I don’t think it’s got to be, “I have to save another time and then I can win the pie-eating contest and get more pie.” I don’t think that’s what we’re trying to do here, even that hour of being thoughtful about doing something else better that you haven’t been able to do.

 

You mentioned, “We have so much work. How do we then implement this? How do we then try to collaborate with our peers on something else?” If you could find yourself with 30 minutes, you could have a nice call with someone. There’s probably something else that can be done that doesn’t necessarily say, “Here’s a way to save time on work so you could do more work.” There’s something more meaningful that can come out of this.

No question. You have AI and you have generative AI. There’s a lot more fear around generative AI. We have a contract lifecycle management system that allows for some automated review of certain things. We’ve explored that with if we have ten of the same contract and it has the same terms and we’re trying to update, why would I pay an outside counsel or use my valuable in-house time making a rote edit? I’ll eyeball it at the end, but I don’t need to hands-on ticky type and get that change made. I’m not fearful but I’m skeptical. You were in the legal professional services business. I’m in that business. It’s hard to put your mind around that machine learning can somehow replace our issue-spotting and problem-solving. The fear of this taking over lawyer jobs is a little outpacing the actual threat.

In a lot of my research, the idea of fear comes up. Certainly, generative AI will replace certain jobs. People pretty much agree that it will not. However, it will come quietly. I did a report where I spoke to law firm leaders. I said, “Are you replacing any roles with generative AI?” They were like, “Absolutely not.” I then said, “Are you replacing any roles with technology?” They’ll often give me examples of a docket clerk. They’ll say, “We put in a docketing software. The clerk didn’t need to spend all their time as they used to because the technology was doing a lot of the work, following up, and identifying dates and deadlines, so we assigned some other tasks. When that person left, we did not backfill that role.” You start to see that fraying. We will start to see this.

Generative AI is not replacing jobs outright—but quietly. Slowly, roles change as technology does the heavy lifting. Share on X

It’s interesting you made that comment that generative AI seems more risky than AI. It’s only because generative AI came along. AI was seen as risky and people were concerned about it, certainly in the nuances of eDiscovery, legal technology, and the use of predictive coding. It took many years. Even if the courts validated it, it was finally like, “Oh.”

I told you at the outset that I’m tech-averse. This is one girl.

It’s interesting to me that lots of us think that. It’s all mysterious. Generative AI is a little bit more comfortable in some ways for people. It happens in real-time as opposed to a black box of magic occurring. You throw in 1 million documents and it comes out with 20,000 documents. You’re like, “That’s amazing. That’s what we need.” As opposed to now, it watches it on the screen, which is quite amazing. If I had to give people some guidance here, I would suggest that they try to understand the organization’s policy and how the organization itself is using it.

They might even be writing the policy. That’s the other thing. Talk about building the airplane while you’re flying it. GCs all over are in the center of that. We don’t even have a, “Let’s pull it off the shelf.” It’s your internet policy from 1997.

That’s right. They’re going to need to collaborate with the CISO, the CIO, and all the other leaders who are having pieces and parts of this. Every year, I do this general counsel board. Every year, I try to identify the general counsel as some sort of special role. For example, in 2020, it was the general counsel as the chief medical officer. In 2021, it was the general counsel as the ambassador of their organization because of the geopolitical risk and all the things that were taking place or the social warrior. There were all these different ways that the general counsel was being asked to do something that went far beyond the legal services and supporting the business.

The general counsel is almost like the GC and CEO of legal. The GC has to know. That was one thing that came out of a lot of my discussions. There’s an expectation that the general counsel pretty much knows everything and the answer to everything or quickly knows how to find the answer to everything. That’s what 2024’s theme has become. There are so many issues. It’s like, “She knows the answer. If she doesn’t know the answer, then maybe it’s not knowable.” General counsel has to know the answer to that question.

The emergence of some of these tools is an answer to that. There’s almost no way to do the work without some supplemental tool that will be able to at least give you more time to think about it or at least give you a starting point. I don’t think that anybody thinks this is a set-it-and-forget-it or completely trust it. It’s not trust but verify. It’s more like mistrust and verify. It gives you at least a starting point because it’s so much harder to begin with a blank page.

Tech won’t replace you—it will give you a starting point. Use it to solve problems, not to eliminate human insight. Share on X

Developing Thought Leadership In The Legal Tech Space

That is true. I want to shift a little bit. You mentioned it earlier when we were talking about vendor interactions, which I took good notes on. You talked about your experience writing from international trade. You were ahead of the curve or at least ahead of that supervisor at that point recognizing that the internet was a real thing that was going to take off. I know you spent several years at a large national law firm. How did you, if you wouldn’t mind sharing, develop your thought leadership into a business?

I always say I get to do lucky work because of the idea that I’ve been on my own for eighteen-plus years and have made a living. It has been a gift. I practiced for nearly nine years with large firms in New York City. It’s because of that partner’s inspiration that I became a writer. I published probably something like 125 articles during the period that I practiced and realized that you can use writing as a vehicle to meet people and develop a reputation. I would use my writing as an opportunity to interview general counsel or in-house counsel or to write about new areas of technology, whether they were domain name disputes in 2001, the CAN-SPAM Act, privacy issues, or anything like that.

I’d been walking these two roads for a very long time. I used to joke with people that I was a lawyer on the side, but that wasn’t possible. I would write in the middle of the night. I made the decision that I was going to leave and become a writer. Everyone thought this was an incredibly stupid idea except for my wife who is wonderful and supported me. I’m always grateful to her for that.

I thought I would freelance. I honestly thought I would write for magazines or something, but once the direct deposit stops and you’re a practicing lawyer at a senior level, you realize it’s not easy to replicate. I was able to start ghostwriting for companies on legal services and legal technology issues, writing white papers and case studies.  In 2007, someone approached me and asked me to start doing market research. That really changed a lot of what I was doing.

I also, in 2006 or 2007, created a CLE course to teach lawyers how to get published and how to leverage that for their business development. That became a very popular course. It allowed me to start speaking. I wrote a book for Thomson Reuters called The Opportunity Maker and was lucky to get to speak at lots of law firms and conferences. I’ve spoken at over 50 law schools. Each thing built on itself. We have this saying in my house of chipping away. There is not some extraordinary one thing that changes everything but a series of steps that you get to hopefully get a little bit better and a little bit bigger each day.

If you were advising somebody, especially with AI and it appears as though you push the button and some thought leadership is going to pop out of the AI machine, what would it be? You taught the course on how to get published. Are any of those lessons enduring still? What advice would you give to somebody who’s trying to develop their thought leadership?

I agree with you on both counts that you can create thought leadership very easily. It’s not lost on me. In fact, I wrote a second book called Reinventing Professional Services. I’m always thinking about this idea of how we reinvent ourselves, how we reinvent our businesses, and how we reinvent our practices. Content creation for me always was a vehicle. It was a conduit to something else. Wrote words on paper, anybody can create. It’s not just generative AI that could have done that. You could outsource articles and white papers for years. There’s no mystery there. There’s no secret. It was much more about whether you can use it as an opportunity to create a lead or use it as an opportunity to meet someone.

In almost all of my work, I try to use it as a chance to get to talk to someone like you or talk to others in a space that I want to learn more about or be part of. People miss that. That hasn’t changed as a result of technology. It might. I’m constantly thinking about what’s changing and where this is going. For me, it has always been a vehicle to get greater insight into something as opposed to simply putting words on paper. Also, I’d like to think that some of the stuff that I still do is a little bit more complicated, although that won’t last. That advantage isn’t going to last. The ability of generative AI to produce work changes every few months and gets significantly better.

It’s backward-looking. You talk a lot about the dinners that you host and the interviews that you do. Generative AI can’t know what’s in my brain. You’re going to learn that through personal interactions.

I agree, but on some issues, it can anticipate what people are thinking. It’s not so uncommon. It’s not uncommon like, “We are human beings.” I feel like there is a commonality there.

That fear is not misplaced. I really enjoyed the conversation. Where can people find out more? You referenced several reports. Where can they find you and your thought leadership?

You can visit AriKaplanAdvisors.com. I would encourage you to listen to my podcast, ReinventingProfessionals.com, especially because it features something like 900 episodes. It’s got to be one of the largest audio archives of legal tech because there’s so much content and so many different individuals talking about setting forth a vision for the future. You can listen and determine whether they brought that vision to fruition.

That’s cool. We’re going to close out with my final question. What is your pump-up song?

I’m a runner. I used the listen to Everybody Wants to Rule the World by Tears for Fears on a cassette tape.

This might be one area of disagreement.

That’s not my pump-up song, but I did see them live for the first time when they played at Madison Square Garden. It was a few years ago. It was amazing. It was really fun to see them. There’s a song called Feel Again by OneRepublic. It’s a great, optimistic song. It has a great theme. I highly recommend it. I’m always thinking of pump-up songs that instead of running onto a stage, it is much more like running into the distance. I would select that song.

I like that better than Tears for Fear. Thanks for being in the show.

Thank you so much.

‐‐‐

Ari Kaplan Baseball Stats.

Ari Kaplan’s Fun Fact And Closing Thoughts

My name is Ari Kaplan. I am a legal industry analyst and the Principal of Ari Kaplan Advisors. My fun fact is that I finished a 10K swim. Somehow, I was surprised by the fact that, unlike a marathon run, you cannot walk, stop, or take a break in any way when you are swimming 6.2 miles.

 

Important Links

• Ari Kaplan Advisors
• ReinventingProfessionals.com
• The Opportunity Maker
• Reinventing Professional Services
• C-Suite Series: How to Partner with the CIO and IT Sarah Richardson This Week Health
• How To Use Legal Operations To Level-Up The Legal Department: Mary O’Carroll Chief Community Officer Ironclad

 

About Ari Kaplan

Ari Kaplan is a writer and analyst who covers developments in legal technology. Ari is the author of Reinventing Professional Services: Building Your Business in the Digital Marketplace (Wiley, 2011) and The Opportunity Maker: Strategies for Inspiring Your Legal Career Through Creative Networking and Business Development (West Academic, 2nd Edition 2016), which is about how law students, lawyers and other professionals can stand out in a stagnant economy.

Kaplan offers strategic and cost-effective suggestions for immediately transforming one’s perspective, profile and practice. He spent nearly nine years with large law firms in New York City and focuses the delicate balance between self-promotion and professionalism.

A legal industry analyst, Kaplan has published over 200 articles, served as an Internet law commentator for CNET Radio and has been interviewed on CNN. He received Apex Awards in 2010, 2008 and 2007 for feature writing, and was named a “Law Star” by LawCrossing. He is the principal researcher for a variety of widely distributed benchmarking reports and has also been the keynote speaker for events in Australia, Canada, the United Kingdom, and throughout the U.S. Kaplan is also the founder of the Lawcountability® business development platform, a finalist for ILTA’s 2015 Innovative Solution Provider of the Year award.

Named a “Law Star” by LawCrossing, Kaplan provides law-related ghostwriting for a number of companies, firms and individuals in the legal industry. He serves on the Board of Editors for ALM’s Marketing the Law Firm and Cybersecurity Law & Strategy, and is a member of the content advisory board for Legaltech.

Ari is the founder of the Ari Kaplan Advisors charitable book collection through Boston University’s Intergenerational Literacy Project in Chelsea, Massachusetts, and the co-founder, with his daughter, of the Wyoming One-Can-A-Week project, which has donated over 1,000 cans to the local food pantry.

He is admitted to the bar in New York, New Jersey and Washington, D.C. He earned his J.D. from George Washington University Law School and his B.A., magna cum laude, from Boston University.