Jennifer Cona | How to Grow from Solo Practice to Award-Winning Boutique

Jennifer Cona, is the Founder and Managing Partner of Cona Elder Law, an award-winning elder law and estate planning firm located in Melville, New York. Celebrating 25 years in business, Cona Elder Law has been consistently ranked the number one elder law and trust in-estate firm on Long Island. Jennifer has won many awards, including the New York Law Journal Award for Top Women in Law.

She and her firm are committed to corporate social responsibility, and she has held roles on the board of trustees of the Long Island Alzheimer’s and Dementia Center, the United Way of Long Island, and the executive leadership team of the American Heart Association.

Jennifer has also been featured in many publications such as The New York Times and The Wall Street Journal, and has appeared on radio and TV. She also writes a monthly column for the Long Island Press called Power of Your Attorney. Jennifer Cona’s dedication to Elder Law and her impact on her community are a testament to her outstanding career.



Many lawyers dream of opening their own practice. It takes a lot, though, to go from working for someone else’s firm to starting your own, especially if you have no one with experience to guide you.

Jennifer Cona didn’t grow up in an entrepreneurial family who could show her the ropes. But going on guts, she managed to open an elder law practice and successfully grow it from a solo operation to a boutique. And even she will tell you it looked like she did it by the seat of her pants at times!

In this episode of The Lawyer’s Edge podcast, you’ll discover how Jennifer launched and grew a law firm while creating a culture built to last. She’ll also reveal how everyone at Cona Elder Law reinforces the core values of the firm, how they focus on the local community even outside of serving clients, and the challenges and opportunities presented by younger generations in the workplace and the advent of artificial intelligence.

2:16 – How Jennifer went from working at someone else’s firm to starting her own within five years of practicing law

5:26 – Why Jennifer felt the need to move her solo firm out of Manhattan to Long Island and expand to a 35-lawyer boutique

10:37 – Jennifer’s leadership style and how her firm focuses on corporate social responsibility

13:57 – How the core values of Jennifer’s practice are constantly reinforced and make it much easier to hire (or fire) people

16:42 – The generational issue Jennifer thinks is the greatest challenge these days

22:31 – How Jennifer uses AI now, how she plans to use it in the future, and why she’s excited about it when many others are wary

26:08 – The difficulty of growing a law firm (especially when you’re also trying to raise a family)

29:39 – Why you’re always answering to somebody even if you own a law practice


Cona Elder Law

“Power of Your Attorney” archives | Long Island Press

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Elise Holtzman: Hi, everyone. It's Elise Holtzman here, a former practicing lawyer and the host of The Lawyer's Edge Podcast, where I sit down with successful attorneys, legal marketing specialists, business leaders, and authors to talk about how lawyers and law firms can grow and sustain healthy, profitable businesses.

Today's episode is brought to you by The Coaching Team at The Lawyer's Edge, a training and coaching firm which has been focused exclusively on lawyers and law firms since 2008. Each member of The Lawyer's Edge Coaching Team is a trained, certified, and experienced professional coach and either a former practicing attorney or a former law firm marketing and business development professional.

Whatever your professional objectives, our coaches can help you achieve your goals more quickly, more easily, and with significantly less stress. To get connected with your coach, just email the team at

My guest today, Jennifer Cona, is the founder and managing partner of Cona Elder Law, an award-winning elder law and estate planning firm located in Melville, New York.

Celebrating 25 years in business, Cona Elder Law has been consistently ranked the number one elder law and trust in-estate firm on Long Island. Jennifer has won many awards, way too numerous to list, including the New York Law Journal Award for Top Women in Law.

She and her firm are committed to corporate social responsibility and she has held roles on the board of trustees of the Long Island Alzheimer's and Dementia Center, the United Way of Long Island, and the executive leadership team of the American Heart Association.

Jennifer has also been featured in many publications such as The New York Times and The Wall Street Journal and has appeared on radio and TV. She also writes a monthly column for the Long Island Press called Power of Your Attorney. Jennifer, welcome to The Lawyer's Edge.

Jennifer Cona: Thanks so much for having me, Elise. Great to see you.

Elise Holtzman: It's great to see you. I have so many questions to ask you today. I'd like to just start out with some background. If you could tell me a little bit about your background and how you came to start your own law firm.

Jennifer Cona: I was working like a dog for another law firm in Manhattan, pretty much working seven days a week, 16 to 18 hours a day, really enjoying what I was doing, working for that particular elder law firm.

Someone, a lawyer who was older and wiser than I was, said to me, "If you're working so hard for someone else, maybe you should think about working for yourself." Which was honestly not something that had ever occurred to me.

I just wasn't wired that way, wasn't surrounded by entrepreneurs, or grew up with them. But at that point in my life, I didn't have children, I didn't have a lot of responsibilities, honestly so I said, “All right, maybe I'll try that. If it doesn't work out, I can always get a job again as an attorney working for a firm. Maybe I'll give this a whirl.”

So I did. I set up shop downtown as a solo, really didn't have any sense of where I was going to get clients from. I had a friend help me design a website when websites were brand new, businesses didn't really have them, and certainly, attorneys didn't have them, but really on a wing and a prayer started networking and some clients from my prior firm reached out and found me and came with me and the rest just naturally, organically evolved from there.

Elise Holtzman: How long had you been practicing law when you hung out your own shingle?

Jennifer Cona: Probably about five years.

Elise Holtzman: Okay, so you weren't a particularly senior lawyer. To me, that takes a lot of confidence that you know what you're doing or at least that you're going to be able to figure it out if you don't know what you're doing.

Jennifer Cona: Yeah, absolutely. I had only practiced elder law and I didn't have a lot of mentorship, I was just thrown in. It was trial by fire and because I was working so much so quickly and really being self-taught largely, I was learning a ton very quickly.

I did have that confidence in all honesty because I was figuring everything out by myself anyway. Elder law at that time was very new and it was the wild West in terms of figuring out what you could do and not do and borrowing from other areas of the law since there was no body of law yet so it was very, very creative and groundbreaking at that time so it wasn't all that risky. It was I'm creating law as well as everybody else in the field, which was a very small field at that time in any of it.

Elise Holtzman: To the point of the gentleman who suggested to you that you were working super hard for somebody else, as you say, if you were going to work that hard, you may as well work for yourself. But it is a big leap to take for somebody who didn't grow up in an entrepreneurial family and never thought of herself that way.

What I did notice is that you said you started in Manhattan. You opened an office downtown, and yet I know that you've been on Long Island and you're well known for the work you do in Long Island. What made you decide to move your firm?

Jennifer Cona: A lot of my clients were out on the Island. I represent a lot of nursing homes. My first group of skilled nursing facilities were on the Island, on the Island, and in the Bronx. I was in court all the time on Long Island.

I lived in the city. I kept coming out to Long Island. I didn't have a car. It was a struggle for me to get around from the various courthouses, from the train station and whatnot, not having a car or motor transportation.

From those first relationships, I was developing more relationships, developing more clients out here on the Island. That was organically growing a client base on Long Island. You have to go where the business is, right? Eventually, it didn't make sense for me to have an office in the city so I brought my firm out here, learned about Long Island.

I'm not from here. I didn't even know how to navigate the island, but as I started developing more business and making connections, I started to learn even how to go east, west, north, south, and drive a car around here and all that kind of stuff. It just took off from there.

Elise Holtzman: It's funny to me. I love that you follow the clients there, but also for those listeners who do not live in the New York metropolitan area, the idea of you running from Manhattan to Long Island to the Bronx and especially going to Long Island without a car is just absolutely horrible.

It's a lot of wear and tear, a lot of hard work, a lot of delays, and probably not being sure you were going to get somewhere on time. That's a great story. You've grown your law firm from a solo practice with one paralegal, I think you said you started with, to a 35-lawyer boutique winning awards in your jurisdiction.

When you first started, is that something that you thought you wanted to do? Were you thinking to yourself, “Wow, I want to grow this into a decent-sized law firm that's well-known in this particular area,” or were you just flying by the seat of your pants at that point?

Jennifer Cona: I had no idea. I was just doing what I do, and the rest just followed. I love elder law, and I love trust in the States, really love it, really passionate about it, and passionate about helping the clients. I didn't really set out with any kind of intention. I just wanted to help people in this field of law.

What I did realize at a certain point though once I was out on Long Island was that I realized that I could be the best elder law attorney that there is, but if nobody knows about me, how am I going to help people?

I had met at one of these networking groups that I joined out here so I could start to meet people out here on Long Island. I had met someone who was in public relations just by happenstance and I was like, "Uh-huh, maybe I should be doing some PR in marketing."

Again, this was at a time when lawyers were not doing that and it was like, "Oh, lawyers don't do that." But I thought, "Well, maybe this is what I should be doing so that people can start to know what this field is all about and what I am doing." I ended up working with that particular person for the next 16 years until she retired from the business and she was amazing.

We had a great relationship and I really credit her with helping me grow this firm and again, it was just organic, it was just what I was doing. I didn't set out with any real intention other than to help people in practice in this area of law.

Elise Holtzman: Not many lawyers back there, as you point out, were thinking about marketing. They were not thinking about business development. It was kind of considered a little bit unseemly among some people.

Over the past 25 years, the legal marketing industry has exploded. For people who are more junior, they might not realize how different that was. The person that you hired, obviously, did a tremendously fabulous job for you.

As you say, you credit her with a lot of the success, but you had to be the one to make the decision that, “Hey, I'm going to do something different.” We know most lawyers aren't exactly risk-takers. Do you think you were a risk-taker?

I mean, you started your own practice after five years, you started getting into legal marketing before many people were in it. You say it's all grown organically, but do you think of yourself as a risk-taker?

Jennifer Cona: I do like to push the envelope and I've learned over time to follow my gut. A lot of people have told me over time, “Don't do this, don't do that.” They poo-poo what I want to do, but I've learned to trust myself and do what I think is best. I continue to do that. Maybe in the beginning I didn't really trust myself, but it panned out for me.

Elise Holtzman: Well, and you found yourself in a leadership role. You led yourself into starting the firm, but then over time you said it's grown organically, but you've had to make decisions along the way and then be in a position of piloting a firm of 35 people or 35 attorneys when it could have just been you.

How would you describe your leadership style and how has it evolved, if at all, over time?

Jennifer Cona: My leadership style is to lead by example and to walk the walk. That is just super important to me, that I would never ask someone to do something that I'm not going to do, that I'm here sometimes, the last person out the door. I'm kind of a workaholic and I expect people, I'm a perfectionist, I want people to do things the way I'm going to do things, so I just expect them to see what I'm doing and do it the same way.

I like to mentor people, I like to develop business, obviously, and I want people on the team that also are going to value that and people that are going to do the right thing. That's my style. My style is just walk the walk, talk the talk, and that's just basically being a person of integrity and commitment, but I don't have to shout that from the rafters.

That's just what I'm doing so you can see that, you can live that when you're here in the office and people who aren't that way fall out naturally because they just don't fit in and they can feel it and it works. It works itself out.

Elise Holtzman: When you look back at what you have created and the service that you've been able to deliver in the community doing the work that you do, what are are you most proud of or excited about?

Jennifer Cona: I am most proud of the focus that my firm has on corporate social responsibility. That is part of the fabric of this firm and that is really because that's how I was raised. By starting my own firm, I could have whatever kind of environment I wanted here and because that's so important to me personally, that's now important to everybody here, which is really great for me, but great for everybody here and great for our larger community.

We do so much to help not just older adults in the community, but we help the homeless, we help the hungry, we help people with special needs, and it is just so uplifting to all of us and uplifting to us that this is what we focus on with fundraising, with our spare time, with hands-on.

We don't just raise money or donate money, we dedicate our time because that, again, is something really important to me and it's about walking the walk also. We'll go to a farm and help plant vegetables or harvest vegetables for the hungry people on Long Island. Again, that's just really important and good for everyone here to spend a day doing that and getting our hands dirty literally. I think I'm most proud of that.

Elise Holtzman: Obviously, there's a certain set of values that permeates the firm or you wouldn't be doing this. It sounds like you're not just doing it as individuals although you're probably doing that as well but you're doing certain things together as a firm.

Does your firm have defined core values where everybody understands what the values are or is it just something that you think permeates the firm and people get the gist of?

Jennifer Cona: We have defined core values and we defined them together as a group actually. We hired an outside consultant to come in and work with us to do that. Our defined core values are in our community education center and we reinforce them often.

Because you can't just have them posted on a wall somewhere and then forget about it. You have to live them all the time and you have to remind each other all the time. We have a weekly huddle and we will give each other shout-outs of who exhibited what core value in what way this week.

People will tally them up throughout the week so that they can share them with everybody else because everybody else may not have witnessed it, recognized it, or what have you. So we make sure that we celebrate and acknowledge those core values every single week.

We absolutely live by them and they have really changed and made it much easier to hire people, to fire people. When someone's not working out, it's really easy to look at your core values and figure out if they're missing core values or what they're missing, and then you realize, “Oh my gosh, that's why they're not working out. They don't have teamwork, they don't have integrity, they're not committed,” or something like that.

It's really easy to say, “This is why they're not working out there, just not fitting in with everybody. They can be the smartest person in the world, but they're just not right for this firm.” Then you can hire slowly and fire quickly, as they say. It's really, really helped us. We've been dedicated to our core values for probably about 10 years, and it's been a real game-changer for us.

Elise Holtzman: It sounds like it really does impact how the firm is run. Would I be correct that everybody in the organization would be able to articulate the core values? They know what they are because you discuss them frequently enough?

Jennifer Cona: Yep, they know what they are. They're also part of our review process and on everyone's self-evaluation, they have to explain how they exhibited them, what they've done throughout the year to uphold the core values, and if they fall short, how and why. It's a constant reinforcement of the core values.

Elise Holtzman: What are some of the trends that you're seeing these days in the legal profession, in private practice, perhaps in your area of practice, and how do they impact your business, your audience, your outlook?

Obviously, a lot has changed in the last 25 years since you started your firm and we know that trends come and go. What are you seeing these days that either you're excited about or you consider to be a challenge or a concern?

Jennifer Cona: The biggest challenge that I'm seeing, and I'm sure it's not unique to me, is some of the generational issues. What I mean by that is the younger people that we're hiring that are coming into my field, and I'm sure all fields.

It's a challenge in terms of hiring the right people. We can hire people, but hiring the right people is difficult. What I'm finding in young lawyers is that they have more of a job approach than a career approach, which is very new for me as a managing partner, looking to hire, because obviously, we spend a lot of time mentoring people, dedicating time to grooming them in the way we would like them to be and all of that kind of stuff.

We don't want people who are going to hop around, but young people want to move around for whatever reason. They don't have the same kind of loyalty that we've seen in past people or past generations.

Obviously, the work-life balance is completely different. The younger generations don't value hard work, I think, as much as we all used to. That is difficult for someone like me to understand, in all honesty. Some of their older peers, it's hard for them to understand.

Yet they sometimes, the younger generations, don't understand why they haven't made partner yet. Which to people my age, I was like, “Well, are you kidding me?” Related to clients, it's hard for clients to understand the delivery of services.

If you have a younger generational person who's here, let's say, nine to five, nine to six, but clients are expecting 24/7 availability of their attorney because that's how it always was, you've got a real disconnect. Of course, again, as a managing partner, I have to manage that, I have to manage expectations on both ends, and it's a real challenge.

I used to always say, “I was going to retire before millennials fill up my office.” Well, they filled up my office by and large. But I have to navigate it. I don't have all the answers yet. It's difficult. Again, it's not unique to me.

Elise Holtzman: I do some work with generational differences and I was taught by somebody who is absolutely exceptional when it comes to generational differences. I think that what we can agree on is that since the time of the caveman and maybe before that, every generation has looked at the generation after them and a couple of generations after them and thought, “Oh, you young kids just don't get it and you don't do it the way we've done it. The way we've done it was the right way to do it.”

Then the younger generations look at the older generation who, by the way, are the ones that raised them, of course, and said, “Well, you're sticks in the mud and you're so old fashioned and why does it have to be that way?” So I think that in that sense, we're no different.

There are big generational differences, as we know, from Boomers to Gen X to Millennials to now Gen Z coming into the world as attorneys. They've been in the workplace for a while now, but now they're showing up as young lawyers.

I think that sometimes understanding, and that's why I do some of the work I do, sometimes understanding how they grew up, the things that they experienced in their lifetime, and why they think the way they do can be really illuminating and can help reduce some of the frustration.

At the same time, as you say, you've been doing it a certain way for a long time so it can be hard to change and hard to see the world differently, especially when you have clients who are used to it being done a certain way.

I think that I hear the challenges from the generations who are more around my stage, and then I also hear some of the challenges from the younger folks who feel the pressure from above them.

It's something that I hear a lot. I'm hearing it in virtually every law firm that I talk to. As you say, it's across the board. I think maybe for everybody learning more about why the generation shows up the way they do could be helpful.

Jennifer Cona: Yeah, absolutely. But I do think that if a person wants a nine-to-five job, they probably shouldn't go to law school.

Elise Holtzman: That is certainly a fair point. I don't know many lawyers at all who work a nine-to-five job. Even in-house, even in the government, I mean, there are people who talk about, "Oh, I'm going to go in-house," or “The government's going to be so much easier,” those folks are working very, very hard as well on long hours.

Jennifer Cona: Right. Same as medical school. If you want a nine-to-five job, don't go to medical school or law school. They should have their own expectations be realistic as well.

Elise Holtzman: Right.

Jennifer Cona: I think you're right. I think there should be some sit-down communication between all sides to get some perspective and understand each other.

Elise Holtzman: Yeah, I mean, I think the more that we talk to each other, the more that we communicate, the more we raise these issues and discuss them with one another, the easier it gets.

I think that goes along with almost anything that we see or any stereotypes that we may hold because again, we can all talk about the other generations. We know what the stereotypes are. Then with each individual person, it may not necessarily be that way.

Is there anything else that you're seeing these days that is either you see as a tremendous opportunity or has been a challenge?

Jennifer Cona: I think obviously, the opportunities that are coming down the pike are with AI. That's going to dramatically change the practice of law. I'm very excited about that. We use it in our marketing currently and we are looking at a couple of different areas that we practice in for rolling that out.

Elise Holtzman: Tell me a little bit about that because I think that many lawyers who are in your generation, I'm going to say our generation, are not quite as excited about AI as it sounds like you are.

Many of them are saying, "Oh, my God, the robots are taking over. What if it gets something wrong? We're all going to get ourselves in trouble. It's so dangerous." From your perch as the managing partner of a boutique law firm, what do you see as the opportunities? For example, how are you using it in marketing?

Jennifer Cona: We use it in marketing for idea generation, helping generate PowerPoints, kickstarting some copy, and then I will tweak it from there. Things like that. It's just really kind of a kickstarter. I added everything that goes out of this office from a marketing standpoint.

It has been a time saver because writing all the copy is a heavy lift in addition to everything else I have to do. If I've got a deadline of a half an hour from now on something I knew was due two weeks ago, but I never got around to it, it can just give me a little start of a couple of bullet points, even though I know in my head what I want to cover, if it can give me a little start, great. That's all I need sometimes.

My marketing team will use it. I can tell right away when they've used AI to get a kickstart versus something they've written themselves. It's just clear. It's more direct. It takes out a lot of fluff. It helps me edit. I appreciated it very much.

The first area that we're going to use AI in is to, we'll use a closed system, of course, but we're feeding it the work that we do in this particular area. It's going to learn the language that we use and how we like to couch things in some of our petitions, so that it can just be more efficient. Then we will be able to put in the facts of certain cases and whatnot.

We're not going to use it as a research tool where there is room for error. I shy away from it at this point in time for sure. But in terms of presenting the facts of the case and how we are doing it in typical cases that are often the same, but how we write as advocates, AI can learn. That's how we're starting to use it.

Elise Holtzman: Do you expect that to reduce lawyer headcount or do you think that it's just going to make all of us so much more efficient and organized that we can serve more clients and perhaps serve them more deeply than we have in the past?

Jennifer Cona: Yes, it's not going to reduce a headcount. Especially enough for lawyers because well, at least in my industry, we're client-facing all the time. Could it potentially reduce maybe some administrative staff or paralegal staff? That's a possibility. But not for some time, but it won't eliminate lawyers, at least not in my office.

I'm only speaking from my area of law, but we're meeting with clients all the time, we're on the phone all the time with clients, hand-holding all the time, AI is not replacing any of that.

Elise Holtzman: If you were talking to a younger version of yourself early on in the growth of your law firm, or you were to talk to somebody who wants to start a law firm but thinks it just sounds daunting and overwhelming and they too didn't come from entrepreneurs, what are some of the things that you might say?

Jennifer Cona: I would say don't do it unless you're prepared for a 24/7 job, including when you're on vacation, including when you have babies. You have to be prepared to do every single job in the office, such as being your receptionist, your bookkeeper, your photocopier, your marketer, your business developer. You have to wear all of those hats, and you will never ever stop worrying about your extra child, which is what your law firm will be.

Elise Holtzman: You mentioned children a couple of times in the beginning, you said you didn't have children at the time that you started your law firm. What was that like weaving together, having children, and having this extra child, as you say? Were there times that it just felt like it wasn't working or do you feel like you had it under control most of the time?

Jennifer Cona: Well, I never had it under control. Don't be fooled. It was really difficult. It was very, very hard to balance. I think people who say you can have it all, I've never met anyone who really kind of survived. Well, okay, so I survived it, but it was very difficult to grow a law firm and grow a couple of children at the same time.

It's just so hard to balance. I think for probably that five-year span of time, I was working on two hours of sleep at any given time. I would just drop my head when I had too much and then I'd have to get up at like four in the morning after nursing the kids and go back to work and look at the kitchen table.

It was just crazy, but I wouldn't trade it for the world. I have a ton of mental stamina, not a lot of physical stamina, but you also are trained for that in law school, you have to bust through a ton of work, studying for the bar also, all of that. I made it through.

I know if things ever get crazy around here, which they have, I know I can stay here all night long if I have to, to meet a deadline or to get something done, even in my old age.

Elise Holtzman: Well, I'm going back to the generational differences because you and I are similarly situated in that regard. That was kind of the bill of goods that they sold us as young women wanting to make our way in the legal profession when the generation before us hadn't been able to do that.

They did tell us that we could have it all and many of us tried to make it all happen. Some of us more successfully than others and some of us with more stress than others. But I think that it's good advice to at least make sure you understand what the expectations of the job are before you go into it.

Jennifer Cona: Yep, absolutely.

Elise Holtzman: Jen, as we wrap up our time here today, I want to ask you a question that I ask all of our guests at the end of the show. There is a phenomenon called the curse of knowledge where experts sometimes forget that what is so obvious and natural to them is not at all obvious to others.

You are absolutely an expert in starting and growing a law firm and developing a culture of a law firm that is designed to last and to make sure the clients are being served and that the right people are in the right seats.

When it comes to doing all of that, to successfully founding and growing a law firm, what's a principle or piece of advice that may seem obvious to you in your role and with your experience, but is important for people to hear?

Jennifer Cona: Never forget who you're serving. You're serving the clients. I know that sounds obvious but sometimes people lose their way. You always answer to the clients. Somebody said to me the other day, "Well, you don't have a boss. You are the boss." I said, "My boss is the client. Clients are my boss. I'm always answering to someone."

Elise Holtzman: It's great advice. For you, it sounds like you're particularly fortunate, and I hope all lawyers can be this fortunate that you absolutely love what I do, and that you continue to feel that you are delivering tremendous value to these clients and that there's a purpose there for you. So, great advice. Good thing to remember.

Thank you so much, Jennifer, for being here today and I'm going to thank our listeners for tuning in as well. If you've enjoyed today's show, please subscribe, rate, and review us at Apple Podcasts, Spotify, or your favorite podcast app. In the next meantime, be bold, take action, and make things happen. We'll see you next time.

Thank you for tuning in. If you've enjoyed today's show, please subscribe, rate, and review us at Apple Podcasts, Spotify, or your favorite podcast app. In the meantime, be bold, take action, and make things happen. We'll see you next time.

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