How AI Is Disrupting 35 Years of Traditional Law | With Howard Ankin

Discover how the practice of law has transformed over the last 35 years. In this compelling conversation, we explore the major shifts in legal marketing, the impact of artificial intelligence on traditional billing models, and why building genuine, long-term relationships matters more than ever in the personal injury sector. Whether you are an aspiring attorney or simply curious about the business side of law, this episode offers a rare look inside a multi-generational firm.

Timestamps

01:11 – Meet Howard Ankin

01:49 – The Baseball Collection

03:05 – Managing a 90-Person Firm

04:57 – 35 Years of Industry Changes

13:21 – Empathy and Automation

18:19 – Traditional vs. Digital Marketing

22:16 – The 47 Touchpoints Rule

27:07 – Client Lifetime Value

35:38 – The Ethics of Referrals

Howard: So for us, we're saying is like, you know, we need to touch people 47 times before they even know who they are. The gentleman that's the director of marketing in my office, you know, he lives this. So he's like, "Well, everybody knows us." I'm like, "They don't know us." Like we got to get to the point where everybody gets to 47 times. Once we get to 47 times, that just puts us in the category that we have to get to 47 times just to get to the category of, hey, we could be one of the eight different bars or brands of soap that somebody could buy. It takes us that much to get to that point. So when we say what's the thing that works, is it the radio? Is it the billboard ad? Is it the television? Is it that program on TV that somebody wanted to watch? Is it the ad that got put online? Is it the pay-per-click ad? What is it? Is it their buddy Johnny at work that said Howard did a good job for me?

Awais: Today I'm joined by Howard Ankin, a third-generation lawyer and a managing partner at Ankin Law in Chicago. So we'll talk about building and running such a large law firm and about legal marketing relationships, technology, and how the business of law has changed over the years because not only is he a third-generation lawyer, but he has pretty different ideas about how marketing and building relationships are. So thank you so much Howard for coming in today.

Howard: Thanks for having me.

Awais: Before I start, I basically noticed that you have such a great background with so many baseballs. So could you share why you are a big fan of baseball and why there are so many baseballs there?

Howard: So I market my law practice and my legal services. And I advertise with sports athletes in the Chicagoland area, whether it's baseball, football, basketball, hockey, and so on and so forth. So I typically have whoever the person that's pairing with me as the pitch person for my practice give me some type of signed item. So I'm going into my 35th year coming up here in a couple of weeks of being a lawyer and practicing law. So I got more than a few mementos now of people that have appeared with me during the course of my practice.

Awais: Awesome. Awesome. So you have got a big collection now. That's very nice. Building this law firm from the ground up to 90 plus people, and you've claimed that you love to be a lawyer. How are you managing all this?

Howard: I got to tell you it's very difficult. Last week especially, I had a lot of interventions where people told me I need to not be so hands-on. You know, when you do a good job, your reputation grows and you get to a point where you can't be everything to everybody anymore. And I'm having—I got to be honest—I'm having trouble coming to terms with that. So I feel like the lawyer needs to be hands-on and do things hands-on in their practice. So I'm figuring out how to do that better, whether that's with technology or trusting in other people to handle certain things as my practice moves forward.

Awais: I believe that, and you might disagree with this, the way things are changing these days, it's so quick that it's very difficult for people to adapt. You have been running this law firm when obviously the computer age and internet age were just starting up. So what are the biggest differences that you see that have happened over the years? And also because you were working with your father, have you seen some major shifts that have completely impacted law firms in a good way or a bad way?

Howard: The practice of law today is wildly different than how it was when I first started practicing law 35 years ago. And that's technology. That's age-generational, about people having different ideas about what work and work-life balance are. Different ideas about what it means to be a lawyer. Movements in the law to make law more like a business and less like a profession than it was. So if you want, I can break all these down for you, but just generally, technology-wise, it used to be everything was a yellow pad and a pen, and today everything is AI. What used to take a young lawyer an entire summer to do as a law clerk—such as going through medical records, making timelines, doing routine type motions or complaints, and routine research—that's done in 10 minutes today by a computer. So how we train people, how people get into the practice, and what people are going to be doing in the law practice are completely different. Second, there was always an idea that lawyers did the lawyering and that in order to make sure there were no ethical conflicts, money and business never had anything to do with law. But now states like the state of Arizona are actively wanting business and money to be a part of law firms, which is radically changing the landscape of the framework of lawyers and law firms and how law is practiced. Ultimately, people want things to be like a major chain store in law, whereas it was definitely much more local in the past. And then the third thing is COVID and just different generations. The combination of those two things changed law dramatically. A lawyer working 50 to 60 hours a week, a lawyer working late at night, a lawyer working on a Saturday—that was routine when I got out of law school. Today, a new lawyer coming out of school—overgeneralization is never correct, but in general, a lawyer coming out of law school today is working 40 to 45 hours a week, and that would be considered a hard work week. They're not doing 70 to 80 hours a week unless maybe they're in a major corporate firm.

Awais: I completely agree with this because the landscape is changing, but it's quite different for a PI firm and one that bills by an hour, because I think those guys are in really big trouble. For a PI firm, it might be different, but for people who bill by an hour, AI has disrupted that model, and obviously, it's very difficult to justify that we have been charging you for certain hours when AI can do that in a few minutes. So for that kind of industry, which was running for a very long time, don't you think that is also bad news, and how will they survive this new model where they need to shift towards maybe subscription-based or another way of lawyering?

Howard: It's going to be very interesting in the future for two reasons: one, how do people get trained to practice law? Breaking out the file on a Sunday afternoon on your dining room table and going at it for five, six, seven hours, doing the original drafting, and taking the time with it—that's how a lot of lawyers learned their craft. Today you don't get a chance with that, and so the computer is telling you what you need to know. What's happening is lawyers like myself who always practiced law find that AI and the computer help make us better because it reinforces skills we already had. I'm a little concerned about the lawyer who never learned those skills to begin with and is using AI like the cliff notes of reading a book. If you read the book and understand what it says and you're used to reading technical books, reading the cliff notes reinforces what you do. I think it helps when you're reading the cliff notes to understand how to read the book or what the book says. I don't know what the future of the world is going to be, but we'll see how that turns out. The second thing is a problem we have in our society in general of the haves and the have-nots. People in law firms that are already above the demarcation point where technology is very expensive have more control over the whole business product. I think it's going to be very difficult for new lawyers to start up law practices because the cost of technology is very expensive. Maybe someone might argue the other way that technology will bring more parity to new lawyers or new law firms, which is also a question for the future. Ultimately, doctors and lawyers in past generations might have been among the best and brightest going into those fields. I still think we have great people going into medicine and law, but it used to be people went there because the economics forced them to. Now, if there are going to be different billing models and the economics aren't there for a lawyer, overall we may not get the best and brightest in our society. They might look towards technology or something else because law is a stressful, time-consuming field. If the economics aren't there, are people going to put up with the drama of law, or will they veer toward something else?

Awais: That's an amazing point of view because I completely agree with what you've said. A lot of people are reading cliff notes and reading the book—just like students in colleges passing tests from AI without real knowledge or real learning. That's one big issue. But if I talk about the client side for a PI firm that you've been running, how is it affecting people? You're dealing with people in distress, people who are injured or have been done wrong. When they call a firm and instead of a human sympathizing with them, an AI picks up the call and starts asking questions like "Where have you heard about us?", do you think that's the correct way to use AI, or should we employ more humans when dealing with people in trouble?

Howard: Fifty percent of what a lawyer does, I feel, is giving confidence, advising their client, and being there for them; 50% is the knowledge the lawyer brings. You have to have the lawyer knowledge, be able to counsel people properly, and want to do it. For me or my generation, talking to people on the phone or having conversations is what I prefer to do. It's very difficult for me to imagine someone employing an entire legal conversation or advising session over text. It's just not what I do, and I don't think I can convey the sentiment of what I need to express well by texting or email. But when talking to people of a generation behind me, texting or emailing is a form of communication they are used to using. I don't know that it's the best utilization of communication in law. Anyway, this is all going to have to filter itself out at some point. Where we're at in law and technology right now is halfway up the mountain, halfway down the mountain. In my office, I have people of at least three or four different generational structures, and the people we represent come from three or four different generational structures. How people want to be communicated with, how they understand, how they feel, what strong advocacy is—all those things need to be taken into consideration both internally and externally. But getting back to your point, with technology, there's no way to use an AI bot currently to effectively help people or give them advice. Can it be that for certain clientele, whereas 35 years ago people might have waited until Monday morning to make a telephone call because they knew the law firm wasn't open over the weekend, today people calling over the weekend or at 11:00 at night expect someone to get back to them? That's more of a social norm today. Now people feel that if they call at 11:00 PM, someone might be available to provide legal services. Whether that's an AI bot, someone overseas, someone willing to work a midnight shift, or someone in a different time zone, that's all the back office of a law firm currently. Taking down people's names, numbers, and what they're calling about, and having someone sound more like a person asking questions than an answering machine—that's the point we are at today technology-wise.

Awais: That's a challenge a lot of firms face. Back in the day, people preferred print media, television ads, or billboards. These days, people are more inclined toward Google Ads, SEO, or ranking on Google Maps. Do you think those traditional methods where firms used to spend a lot on brand awareness rather than direct selling are still viable today?

Howard: In my office, we advertise on TV, radio, billboards, pay-per-click online, social media, go out and give speeches, write papers, give lectures—whatever it takes media- and marketing-wise to let people know we're the right lawyer for them. In our highly competitive society, what is better? Is social media better, or traditional radio and television? I'm not sure anyone has that answer. What's really happening is that when we talk about people of different generations, traditional methods of marketing reach a 50-to-55-plus older crowd, perhaps reaching the 50-to-60 range through Facebook. If you're trying to reach a younger generation, you aren't reaching them unless you're on social media; I don't think you're ever reaching them through traditional broadcast television. You need to understand who your target market is and who you're trying to reach. In personal injury, it could be anybody, which is why legal advertising is proliferating everywhere for multiple reasons, one being the heavy effort required to target specific generations.

Awais: My last guest was also a PI lawyer, and when I asked her how she tracks which channel works best, she said it's hard to know precisely. When you're running so many channels and spending a lot of money, what is the key metric you look at before deciding to increase or decrease budget on a channel, or cut it off completely? Do you have a data-backed answer for this in your firm?

Howard: How we work it in my offices is we use the zero moment of truth. Someone might be buying soap; they could choose Dial, Irish Spring, Ivory, etc. You see great commercials, and something ties you to believe one is silky or has a manly scent. There are seven main varieties of soap, and ultimately, it's soap. People try to make law look that way too, with lots of people advertising and trying to be me, but law is not soap. When you go to your local pharmacy, they might have a special display case—five bars for three dollars—or one soap brand might have two feet of space at the point of purchase versus nine inches for everyone else. Price points might vary by 25 cents. When buying a bar of soap, some people are brand loyal while others decide on the spot. Similarly, on Black Friday or Cyber Monday, people are in the market for a big screen TV among 10 different brands that all do the job. When you look up on Cyber Monday and see a big screen at a specific price, that's your zero moment of truth; you could have bought any of the brands. For us, we need to touch people 47 times before they even know who they are. The director of marketing in my office lives this and says, "Well, everybody knows us." I say, "They don't know us." We have to get to the point where everybody gets to 47 times, which just puts us in the category where we could be one of the eight different brands of soap someone might buy. It takes us that much just to get to that point. So when people ask what works—radio, billboard, television, a TV program, an online ad, pay-per-click, or buddy Johnny at work saying Howard did a good job—that final thing is what we mark as the referral. We know we'd never reach that zero moment of truth without everything else preceding it. That's the inciting thing that made them call.

Awais: I completely agree because for a conversion, there are so many touch points a person goes through, and an impulsive decision might be influenced by ads seen a month ago or seeing a billboard. For a family law firm, we saw a dashboard where they tried to track every single penny through all channels. But once you have visibility into every channel, what do you actually do with it? How does it help a law firm grow, manage operations, or handle HR?

Howard: Buying one bar of soap versus five bars of soap affects profitability; a soap company might need you to buy a multi-pack, or a TV sale might be break-even until you buy the attached sound system where the company becomes profitable. Getting legal business is like any other business. If we were fishing off a pier with a worm, we could catch a lot of small little fish, which is exciting. But if you're really going to fry something up for dinner, you have to get out on a boat and spend five hours trolling to find that trophy fish that makes a difference. In personal injury, cases that make a difference for your reputation, change the law, and keep the lights on and the economics of the firm going are the ones where we have to get out on the water. Part of the data that has to be looked at is not just whether it's a case, but whether these are the types of clients you want to represent in the future. We have a broad cross-section of society. Are these the clients the law firm wants to identify with and help? In Chicago, we have multiple cultures and ethnicities, and different neighborhoods speak different languages. There might be clients there to represent, but I go where people want me, where I can communicate well, and where I can be their best advocate. Where you get cases, who the client is, and what type of case they need you for are all additional factors.

Awais: That's a great point that for a PI firm you need to cast a wide enough net to keep the lights on, but you prefer the lifetime value of clients and the relationships you build rather than just signed cases. Am I right about that?

Howard: Yes. Advertising can get you a first client, but if that client doesn't feel well serviced or if you haven't done a good job for them, they may not refer you to a friend or family member. Demographics, age, and background matter. Some people may never refer a case because that's not how they think or identify. Other people thrive on life, are social animals, and are part of networks of people who help each other. If I have a zest for life and represent people with a zest for life, they feel me, and I might get someone referring someone in their time of need. For me, there's nothing more upsetting than finding out someone had a problem I could have helped with and everyone sat on their hands, and I wonder why they didn't think of me as the guy who could help. I put myself out there on shows like yours to say I'm here to help. An injury case is something people might go through a lifetime needing only once and never needing again, thanking God for that. It's an oddity because I'm a one-trick pony for 99% of my clients; they only need me once, never need me again, and may never know anyone else who needs me. That's why it takes a lot to tell people I'm an option when the time comes.

Awais: That's amazing, and I appreciate you sharing that. I'd love to continue this conversation because I want to ask about referrals, how to gauge relationships based on cases sent versus what you're doing for them, and the time or money spent building relationships when some spend thousands on certain attorneys who send nothing, while others send great cases with little effort. We'd love to cover that in another episode. Is there anything else you want to share with our audience before we wrap up?

Howard: That's a very big problem for lawyers because ethically a lawyer can't give something of value to a non-lawyer to influence them to provide cases. If someone refers business to a lawyer, how is that lawyer able to say thank you besides just saying thank you? At the end of the day, if that person knows someone who needs a good lawyer, does everything in society have to be about money, or is it about knowing they did the right thing by sending someone to the right lawyer, doctor, accountant, or pizza place? Do they need a free pizza just because they know that pizza place is the best in town? That's a problem, and that's probably an entire other episode of your show. Anyway, I'll just tell everybody I'm at area code 312-600, which is 312-6 million, and I'm at ankinlaw.com. I'm Howard Ankin. If you need assistance in any way, I'm here to help.

Awais: Thank you so much, Howard, for sharing this. We are going to put all your links and contacts in the description, and write a full podcast episode on our website. For people who want to know Howard, they can call him up, and with three generations of experience, nobody is better at answering your questions. Thank you, Howard, for joining in. It was a lovely conversation, and I hope to see you soon on another episode.
Howard: Thanks for having me.

About the Guest

Howard Ankin is a third-generation lawyer and the managing partner at Ankin Law in Chicago. With nearly 35 years of experience practicing law, he brings a wealth of knowledge on personal injury representation, business growth, and adapting to a rapidly evolving technological landscape.

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