The Case for More Specialized Lawyering

Sigalle Barness | September 14, 2022

On this week’s episode of Lawline's Lawyers Who Lead podcast, Sigalle interviews Harlan York, managing partner of Harlan York and Associates. Harlan shares his journey to becoming an immigration attorney and why a focus on specialization has helped him build a successful team and practice that plays to everyone’s strengths. Listen to the full interview or read highlights of the interview below! Transcribed answers were edited for readability.


On Gratitude

Maintaining Stability and Focus Through His Daily Routine


I'm really structured. I'm just grateful that I'm on my routine. So I'm grateful for without getting too metaphysical, you know, all this stuff that some people take for granted until you reach a certain point of life. I mean, I'm 52 now. So I'm grateful that certain things that are happening every day are just happening.

So I get up early and I try to stay off the emails and not get on them as quickly as some lawyers who live on their phone. Although my principal role, some days as the boss here, I suppose, is just reading, writing emails, if I'm not talking to or meeting with people. So I'll get up in the sixes and the goal is to get the phone outta my hands and get on the treadmill or the elliptical and get that done now, meaning at that moment in time. 

I've got one kid away at college. I've got another kid going away to college in six months. So the routine is very different than when they were younger and I coached their teams and all that. Get that 30, 40 minute workout in, do 10 minutes of meditation, obviously shower, brush the teeth, put on the clothes and go to work. Uh, drive to the office and then I get in here in the tens. I used to get here earlier, but for me it works better to get in a little later. Start talking to clients, seeing consultations around 10:30, do that till about 4:30, 5:00 with very limited breaks. And then afterwards, depending on how the rest of the day works, I'll be here till 6:30, 7:00 some days later, some days earlier, as I've gotten older, I've cut back on the amount of hours I'm actually in the building or in the office.

And to keep the mental health strong, especially given the last two years of COVID, I feel like structure is key by keeping your day, and even segments of your day, and your week, and your month, and your year structured and organized. It really helps you maintain stability and focus.


On His Journey to Immigration Law

Finding Work “That Would Always Be a New, Exciting Adventure”


It's usually two or three things that I always tell people about. Number one, I was a Spanish student in particular. That was an area of strength for me. When I was away on a scholarship at a boarding school in New England from a very young age, I was like 13 when I went away, they had a very advanced foreign language department where you could take everything. Chinese, Russian, Latin, you name it. And I just found a real strong interest in learning the Spanish language from a young age. And I went on a summer abroad as an exchange student with 50 other kids when I was like 15. Spent time living with a family in Spain, studying in Spain. By the time I came back from Spain in 1985, I had basically become fluent in Spanish. Went on to major in undergrad as a Spanish language major. Certainly I kept my fluency. 

Then I got to law school as the second component. And I just started taking all these classes as we do when we're law students. And I kept making a mental checklist and I kept almost like mentally taking a red marker and crossing off the list every time I took a class in law school and saying to myself, this is not something I could see myself doing for the next 30, 40 plus years. Meaning things that colleagues of mine are great at that they enjoy, whether it was trusts and estates law or contracts or negotiable instruments or torts or whatever. Anyway, point being, that I got to immigration at some point in my second or third year, and it was a great adjunct faculty member. And I approached him after class one evening and I started telling him I speak a foreign language. Plus this stuff seems really interesting to me unlike a lot of my classes in law school and long story short, he invited me down to his office to kind of chat more.

And the more he told me about what immigration attorneys do, and this is about 30 years ago, it dovetailed. So between the ability to speak a foreign language, along with the interest, by the time I got out, and then the question became, did I stay in the south where I was getting my degree in New Orleans or move back up north where I grew up in the New York, New Jersey area.

I ended up gravitating back up north and there you have it. I mean, between the lack of interest in many other areas of law and the interest in immigration law, coupled with the doors that opened to you being fluent in a foreign language, obviously, this sort of became a natural result, I suppose of just being able to handle what I deemed to be interesting work that would never be boring. That would never be monotonous. That would always be a new, exciting adventure. What have you, and 26 years later, I'm still confident to say that while there's plenty of stressors along the way, it's inevitable in any area, I'm pleased that I made the choices I made. Some of it's serendipity, some of it's destiny, but yeah, that's the short version of it.


On What Drove Him Toward His Practice

Helping People and Bringing Families Back Together


Yeah. I mean, some of it sounds a little corny, but we have five attorneys in our firm and all of us have our own personalities, obviously and our own backgrounds. But one thing we all share is a very strong interest in helping people, which again, sounds a little corny and a little cliche, but there is some huge merit to that. You're making a difference, but you can do work for businesses, which is a portion of my practice doing corporate immigration.

But the vast majority of my cases, our law firm, is representing people. And I could give you the most dramatic ones, like winning a political asylum case for a little boy who had been shot multiple times, who got caught in a crossfire of a gang war in Central America. Or representing a woman who escaped Kosovo, during a horrible time and was gang raped by soldiers. I mean, these are the most dramatic and graphic cases I could think of, but when you win asylum for those people, which is only a portion of our practice, obviously. How could you not feel a tremendous sense of accomplishment in making a difference in someone's life, giving them means by which they can protect themselves in the United States of America? 

But to the less dramatic, but just as important, you're working with people all the time in terms of uniting and / or reuniting families, bringing people here who haven't gotten here yet, who are stuck overseas. Sometimes the detention aspect of what we do, where we're getting people out of custody and back to their families. There's so much different work that we do within or underneath the umbrella of immigration law. 

And circling back to one of the sort of parts of your question, I never forget this. About a dozen years ago, I met with an old friend from some school I attended or camp or what have you and she'd worked for like every investment bank on wall street. And she had hopped around and I'm sure she kept getting promoted and getting offered all these nice deals. So she kept jumping from that bank to this bank and she's very successful. And she looks at me at one point and she goes, wow, you've only ever had one job. And I'm like, yeah. I went to this building in downtown Newark in 1996. And there was this older attorney who I briefly worked with as an associate. And then he and I eventually became partners and he's long gone. He left the field, left my firm many years ago, but I've always been here. I've been in one location. I've never moved. I've been in downtown Newark for 26 years. The firm has grown. Quite a bit. And here we are just helping people. 


On Emotional and Psychological Health

Work on One Case at a Time and Keep Your Eye on the Outcome


To be quite candid, I spent 15 years trying cases and appearing on behalf of my clients in the immigration courts and the immigration service and ICE offices in New York, New Jersey, Pennsylvania, Connecticut, and once in a blue moon would go elsewhere, Virginia, Florida, et cetera. Over the last 12 years, more or less, I'm here all the time. I run the practice. So I'm not going anywhere anymore. It's not that I burned out. I just determined at some point in order to grow my practice, I needed to be here all the time. 

And I've got an amazing team. My partner, who started out as a law student intern with me 18 years ago, has been with me close to two decades. I have two other veteran attorneys on the team. I have an of counsel who started out as my intern and is a strong lawyer. We've got one or two people who are on the horizon of joining us as lawyers. So they can actually make the appearances, they can go argue cases, and advocate for our clients and I'm here all the time.

Now that doesn't mean that it makes it any easier, cause you're still seeing and hearing a lot of things that are very disturbing. But to my point, many days I don't hear any of that because as I said earlier, political asylum and the related areas, protecting victims of violence, et cetera, is only a portion of what we do. We also handle what I refer to as the more vanilla work. So, say Sigalle long ago when she was right outta school, called me up and said, I fell in love with somebody from a foreign country and they need a green card. You know, you get a lot of that too, which is wonderful work as well, because you're bringing people together and you're helping them get legal status. 

But to your point when it is traumatizing and it is stressful to some people in our field, you get into a whole host of strategies that you need to employ. Back to the original question from a few minutes ago. Why do you need to do the mental and physical exercise every day? Because you've got a lot of potential stressors on you. And I'll check in with my people, some of my attorneys on my team who handle a lot of victims of violence, people who are applying under the Violence Against Women Act, people who are filing for asylum. I'll ask them, Hey, how are you with this? Is your caseload bogging you down, not merely from a volume standpoint, but are you emotionally drained from having to talk to people at much greater length than I do in the initial intake process. But at the end of the day, yeah, it's not easy, but you just have to remind yourself that all you can do is work one case at a time and you do, and you keep your eye on the outcome.


On How His Work Comes Full Circle

A Surprise Visit from an Appreciative Client


You know, a woman who was brutally assaulted many years ago and didn't speak a word of English, literally came into my office. This is kind of embarrassing, but it's worth telling. Many years later, now fluent in English. And somehow she found out from one of my people it was my birthday and she appeared in my waiting area and started singing happy birthday to me in English in the most beautiful singing voice. And this was a lady who, I had to try her case and I had to retry it cause whatever there was some procedural issues in a matter, but we won asylum for her and she had a terrible, awful traumatizing experience in her home country. And here she is years later singing happy birthday to me in English. 

One of those weird moments where you step back and you go, is this really happening in my life? Or is this something that like I'm seeing in a movie or a TV show, but that was a real thing. 


On the Importance of Checking In

Know About Your Team’s Personal Lives and Ask How They’re Doing


Pretty early on. I mean, you get to be close to people who you work with in a boutique practice where it's not 90 or 9,000 people working here. We've got like more or less, counting the law student interns, 14, 15 people here. So you do see each other on a pretty regular basis where everybody's one or two or three doors down from you and you know one another. You know how their families are doing, you know how their children are doing. You ask one another how their lives are. You certainly want to know if anybody's dealing with anything, whether it's outside the practice or from within, because something is happening with a case or more than one case that might be impacting them from an emotional or psychological standpoint. 

I don't know. It just comes naturally. I just think it's important. A great thing about immigration law, Sigalle, is that we tend to be empathetic people to begin with, not to exclude lawyers in a lot of other industries or subspecialties, but it's part and parcel of being a good immigration lawyer. So it only would follow naturally, I think, that you would also wanna make sure that the people on your team are in good shape and are able to function at a high level. And I don't mean it just from the standpoint of winning cases, but just that they're able to cope, that they're able to manage. 


On Respecting Your Team and Clients

Be Patient and Empathetic


I wrote about this when I did the book, Three Degrees of Law, back in around 2015, where I did a section called Never Scream or Yell, or something like that. And we all know as attorneys that there was a time and a place, and it may still exist to some extent in a legal profession, where it was completely acceptable for a partner or a person in high authority to yell.

And number one, it's bad for business. If you yell at your clients, cause who wants to pay a lawyer, who's gonna yell at them. It's not only bad for business with the clients and bad for business with the people who work for you (cause they're not gonna be very happy showing up every day). It sounds like such common sense, but you hear all these horror stories. People walking in here all the time saying to me, I don't like my current attorney and they'll tell me all the different reasons why and one of them is the lawyer has no patience for me, they yell at me and this and that. Look, we're human. I'm not saying everybody's gonna keep all their emotions in check all the time, but I feel like it sounds again like such obvious commentary. And I just fervently believe. Get away from that, not to mention it's bad for your health. We were been staying with that topic throughout our discussion. I feel like, you know, what could be worse for your well being than to be yelling and screaming? We know what that does to your cardiovascular system among other things.


On What Leadership in Law Means

Finding Strong Lawyers and Letting Them Succeed


I always talk about success. I always talk about dedication. I always talk about freedom. There's a Warren Buffet saying that goes something like get people who are more talented and smarter than you, and then get out of their way. And you'll discover that you're a lot smarter and more talented. I'm paraphrasing, obviously. So that's a big thing with me. Leadership has a lot to do with finding really strong people to put on your team and not micromanaging. I hate meetings.

A lot of us are fans of the sitcom The Office and I always feel like whatever, Michael Scott does, the opposite. You know, like don't have meetings, don't go to the conference room for 10 minutes. The disdain I have for meetings is at such a high level and we see it all the time now like, these memes about that expression you get, when you realize that meeting could have just been done in an email. I've been doing that forever. I mean, I very rarely have meetings. I don't think they're necessary for the most part. So that's just an example of my mindset. When it comes to leadership, get out of their way, let them do their jobs, they’re grownups, you don't need to micromanage them or treat them like children.


On Aligning With His Team

Delegating Tasks and Playing to Individual Strengths


I think the best thing to do is have a really strong infrastructure. So I noted earlier that about the 15th year of my career, I determined that it was no longer the best use of my time to appear at immigration courts and immigration service offices anymore. I needed to be here all the time. So I started delegating. My perspective was find strong lawyers and then I align with them by saying to them, okay, you're my partner, for example, in charge of figuring out how the actual legal work will be assigned and delegated, and which attorneys are a good fit for which kinds of cases, which paralegals then will be good at assisting them, which legal assistance will then be a good et cetera, et cetera.

So I spent a year on a national practice management committee among immigration lawyers, which was a very valuable experience about a decade ago. And we would cover these sorts of topics all the time, like how to be a good leader and how to align as you say. And I think a lot of that is just like play to people's strengths. 

There's an old bit from like the 1950s or so where the ventriloquist, I wanna say it was Charlie McCarthy, I'm getting really dated now with this reference. This is from like our grandparents' time. But I heard it, it sampled on a hiphop record in the eighties or nineties: He's dumb, but he knows he's dumb and that makes him smart. That's been a big mantra of mine throughout my career. 

Why would I take on work with my people? That would be my weakest area, if you will. Find the people who are better at that stuff. To the sports analogy, find a good relief pitcher who could come outta the bullpen in the eighth inning. It works just the same in our field and it could be any analogy. It doesn't have to be athletics, but you get my point. 


On Leaving Litigating to Manage His Team and Firm

Building a New Infrastructure to Remain Successful


Standing around waiting for the cases to be called and saying to myself, I can't make enough money here in order to support this firm. I can't make enough money here to pay the people who are on the team. I can't make enough money here to do what I wanna do. It's just a matter of using your time properly. If you're standing around waiting for your cases to be called, how can you also be in your office seeing potential clients? How can you be in the jail seeing a client who's locked up in the court in front of the judge and simultaneously being able to see potential clients. 

So I made a new infrastructure. It wasn't rocket science. I just figured out that if we could find the right people who were the strongest in each individual area. So we've got one lawyer in my office who's good at Violence Against Women Act cases, better than anyone else. We've got another lawyer in my office who's really strong at the criminal immigration, what we've referred to as "crimmigration" work, et cetera. You know, one of our lawyers who's very good at working on some of the corporate stuff. Everybody's capable of handling all the other stuff, too. You just start finding people who are sort of keen on doing some kinds of work, they're more interested in it and / or they're stronger in those areas.

And I just walked outta the building at the end of my case. And while other lawyers, and I don't mean to criticize my colleagues, went to the cafeteria and started spending time sitting around a table, having coffee and complaining about the law not being fair or that judge being a jerk or that immigration officer being unreasonable. I was like, I gotta get back to the office and see people. So I just became kind of singularly focused. That's how it kind of happened. 


On His Experience on a National Practice Management Committee

How Conferences Helped Him Build and Maintain His Practice


It was the National Practice Management Committee of the American Immigration Lawyers Association. I spent a year on that committee with some excellent lawyers from all over the United States. Some of whom managed practices with only one lawyer, some of whom managed practices over a hundred lawyers. And we would have Zoom meetings when Zoom was still a new thing. Like, I don't know, 10 years ago or whatever, and we would share ideas and we would do different topics and it was great. Because I would go to these conferences on immigration and other areas of law. A quick example, in 1997, I was at a national immigration lawyers conference when I was a very young lawyer starting out. And there were maybe 3,000 people there and only 30 people showed up for this one seminar that a lawyer was doing on marketing. And I'm going, okay so 1% of the attorneys in attendance at this conference thought it was important to go to the marketing seminar? I mean, how are you building your practice? Again, I wanna reiterate, I'm not criticizing anyone else who practices in my or any other field. But this is so crucial in order to maintain, let alone in the first part, which is to build the practice, but also to maintain the practice.

I started going to conferences where I was the only lawyer there, and there were 5,000 people there from new media and communications and on breaks they'd be like, well, what are you doing here? I'm like, well, I'm trying to get more customers, you know. It makes sense. I'd go see Seth Godin speak. Gary Vaynerchuk speak. These are gurus in the marketing world. And I applied a lot of the principles that they wrote about and they spoke about because they were, to a word you used earlier, authentic.


On Recruiting Talent

Law Schools Recruiting, Enthusiasm, and Luck


Some of it is just luck. When I think about the three people who have been with me the longest, one thing, I guess, to answer your question that I've done differently is reaching out to law schools. 

We posted for our summer law students online for 20 law schools. We got probably a hundred resumes from law students. Many law student interns who have a good relationship with our practice and enjoy being mentored and getting that internship experience with us have gone on to longer term projects and in a few cases became attorneys here, including my partner and my of counsel. So two of the four lawyers who work with me day to day started out as law student interns. All of these folks are coming at me through a very simple posting. Everybody's looking to fill so many roles. And I feel like the first place to look is the law schools. 

You're looking at enthusiasm. To me, that's a biggie. It's super important. My of counsel, who's in Charlotte, North Carolina, and works down there and runs her own practice, but is also of counsel to our firm. Again, started out as a first year law student with us. She was like one of the most enthusiastic people we ever met. She was so passionate about her function as a law student and then eventually an attorney. And everyone here has that sort of mentality. You can see it very early on when you interview people. 

Seth Godin used to always tell people at his seminars and lectures, don't immediately disqualify a candidate who makes a typographical error, for example, on their resume. If when you interview them, they turn out to be the cream of the crop. And I like that sort of mentality. Sometimes people get so focused on what's supposed to be what they're looking for.


On One Thing to Improve about the Legal Industry

More Focus on Specialization


The best thing that people can do in the law is pick a specialty and stick to it. I see too many people who have general practices. A colleague of mine who only does white collar criminal defense, a former US Attorney - is very good at what he does, once said to me, general practice is malpractice. And unfortunately, a lot of people will decide to put up a shingle or couple together a few lawyers and put up that shingle together and they'll do everything under one roof. And I have a saying here: we've got five lawyers right now who do one thing. How comfortable do you feel as our client versus going to one lawyer who does five things? 

I'm sure there's a few outlier geniuses who can do it, but for the most part, if you're trying to do under one roof, bankruptcy, divorce, criminal defense, real estate and immigration, and you're one attorney? And that goes on an awful lot. I mean, that is a big, big problem.

And 30% anecdotally of the work that my law firm takes on is fixing messes that were created not by the government, which is a whole other discussion in the context of immigration law. But because the people ended up in the wrong office with folks who just didn't do the proper work on the case. 

I think I would follow the lead of medicine. I think in medicine, as we know, in order to become a specialist, you have to undergo some sort of formalized training and licensure. If you wanna do heart surgery or what have you, you can't just get a medical degree and become a cardiologist also. I really think the best lawyers stick to one area and practice in that one area. All the best lawyers I know are specialists. 

I've been saying that forever. You wouldn't want me to do your real estate closing. You wouldn't want me to do your divorce. You wouldn't want me to defend you if you were charged with a crime, I could give you three people or 30 people in each of those three areas who I'd be very comfortable referring you to. But I wouldn't be comfortable sending you to a general practitioner who decides anything that comes in, I'm gonna take. Because frankly, how good can they be? Immigration law, which is what I know, changes on a minute to minute basis. How can I possibly be capable of handling work in any other area of law? Once in a blue moon, you'll get, like I said, a unicorn who might be able to handle one or two or three things, but those are definitely like the equivalent of the five tool players in baseball or whatever, or like when Dion Sanders was in the NFL and major league baseball at the same time. Occasionally you get these people who are just like so incredibly brilliant that they're managing to be highly skilled in more than one specialty, but they are absolutely the exception, not the rule.


On the Importance of Playing to People’s Strengths

Treat Every Experience Like a Learning Experience


This is gonna sound really funny, but you know, one of the things that's helped me maintain my mental health in the last two years during COVID is watching professional wrestling. I'm a big fan of it.

 I'll give you a quick story that I remember reading about the industry of pro wrestling. One of the very successful promoters of professional wrestling said a long time ago. If you get somebody who's six foot eight and 300 pounds, he's probably not gonna jump off the top rope. You play to people's strengths and you hide their weaknesses. And when I say hide their weaknesses, that doesn't mean that you do something unethical or unprofessional. It means you stick to what you're good at. So you don't jump off the top rope. And you do stick to being that big, strong immovable force, like a real life version of some superhero, like the Incredible Hulk or whatever. And I make this point, realistically, all kidding aside, because it's a billion dollar industry that I'm using as an analogy to immigration law. I mean, a publicly traded corporation, like WWE, for example, they know what they're doing. They know to play to strengths and they know to play to weaknesses. 

Everything in life for me is an experience. When my kids were little and we went to the Harry Potter amusement park in Orlando, Florida, everybody else is walking around going, wow, this is an incredible place. And I was too, it looked exactly like being on this set of one of the Harry Potter films, cause it was like a cold morning in Florida and it was kind of misty and even felt like England. But the whole time I'm walking around going, what are they doing here that's appealing to the people in the park that I could bring back to my law practice that would make our clients and potential clients feel better about our environment. I never stop thinking about this stuff. I'm always thinking about playing the strengths and avoiding weaknesses. 


On a Piece Of Practical Advice to Leaders And Future Leaders In Law

Focus on Mental Wellness and Gratitude in your Practice


I think you started this whole podcast by asking me about gratitude. So I think that's a good place to conclude. What helped me keep my mental health in year one of the pandemic was buying this enormous biography about Rockefeller. Which was written by the same author who wrote the book on Hamilton for which the Broadway play is based. And I was reading, I think for months it was like every day I'd read 10 pages and it was like bench pressing 500 pounds mentally, cause the book is so heavy, literally and figuratively.

And I kept reading about how Rockefeller managed to go through depressions and civil wars and all these times and lived to be almost a hundred years old and become the world's first billionaire, but the same message I kept writing down in my notes. I was actually marking up the book while I read it. Gratitude and I kept writing courage and I kept writing luck where some of us might say Chutzpah and Mazel, but it's really, really important to be grateful and to maintain your, uh, intestinal fortitude, as they say. So gratitude. I really think it's keeping us from focusing on the other side of gratitude, which is that part I mentioned earlier that everybody loves to complain about things that we can dangerously fall into if we're not too careful. And, of course, you gotta be lucky. 


Lawyers Who Lead is a weekly podcast that celebrates lawyers who are making powerful changes through extraordinary leadership. Each week, Lawline’s Chief Storyteller, Sigalle Barness, interviews a lawyer who is driving meaningful change in the legal industry. Guests represent a diverse and exciting range of experiences but with one common thread, the pursuit of bettering the legal profession. 

Each episode explores the guest’s journey to leadership, the underlying principles that helped them make an impact, and devises ways listeners can apply these concepts in their own lives.

Subscribe or follow on Apple Podcasts, Spotify, Google Podcasts, Audible, or anywhere you listen to your favorite podcasts. You can also follow @lawyerswholead on Linkedin, and Twitter. Let's celebrate and continue to build a community of leaders in law together.

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About the Author

Written by Sigalle Barness

Sigalle champions and grows Lawline’s brand awareness through impactful stories that are authentic, meaningful, and thought provoking. She designs communications strategies that underscore the why and how behind Lawline's work. Sigalle is an avid lover of music, video games, blogging, asking questions and all things food. She is also fluent in Hebrew and enjoys writing fiction, traveling and scuba diving.


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