Yvette Ostolaza | Chair-Elect of Sidley Austin’s Management Committee
Enjoying What you Do | An American Story | Maintaining an Active Docket | Journalism & Sales | 3 Trends | Band 1 Chambers USA | Valuable Board & Attorney Advice | DE&I Positioning | Family and a Love for Texas
I interviewed Yvette Ostolaza | Chair-Elect of Sidley Austin’s Management Committee on Tuesday, August 17th, 2021.
We began the episode with Yvette sharing how her story is an American Story, of how her parents immigrated to the US from Cuba, and the opportunities afforded to her by coming to this country. We discussed how her focus on journalism and her experience in sales served her as a litigator. She shared how she met her husband and settled in Texas. We discussed her work as a litigator and recognition of her superb skills by Chambers USA. She shared about her leadership journey and how she was part of a large group of Dallas attorneys that lateralled to Sidley Austin. She shared an overview of Sidley Austin and how they were ahead of the curve with DE&I. We discussed her new role and how she’ll continue actively litigating. She shared 3 trends she sees as a result of COVID and the changing legal landscape. She provided advice for attorneys that want to be a partner in BigLaw or who want to join boards in public companies. We talked about her leadership philosophy and rounded out the conversation with her sharing about her family, road trips, and her love for Texas.
Here are some highlights of my interview with Yvette Ostolaza:
I loved every minute of law school. I’m one of those weird ones. Going back to law school and just focusing on studying, working, and having intellectual debates was a whole lot of fun.
With the benefit of hindsight, the immigrant experience, growing up with Spanish as my first language, and being very observant of human nature and people, plus being a consensus builder, but also not being afraid to constantly ask questions has been really good for my legal career.
I’ve always been very happy to work with other people and was happy if I got the leadership position or if I didn’t. I would work with whoever the leader was to make sure that we succeeded.
If you get a career where you enjoy what you do, you make a great living out of it, and it’s challenging intellectually and every day is not exactly the same, you’re a very fortunate person.
The firms that are going to be winners are going to be representative of their communities and able to attract talent, independent of their gender, their socioeconomic status, their race, where they’re from, the LGBTQ community, etc.
More and more the well-rounded lawyer is what clients are looking for, as AI takes over many of the tasks, some of them menial, some of them not so menial that we did as lawyers.
Many of our clients in many industries are in the office, and they are concerned about distracted lawyers that are not focusing.
Invest in reading books on business and the business of law so you understand how to read a P&L and can speak the language of your clients. Look at things through the lens of a business person.
When you’re younger, invest the time in your career. Consider it like you’re still in school, but now you’re getting paid. There is no shortcut to spending the time learning your trade.
People will say you made a mistake here or there, but leaders are paid to get information and make a decision.
Links referred to in this episode:
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Greetings, friends. This is Chris Batz, your host of The Law Firm Leadership Podcast.
In today’s episode, I spoke with the elected female leader of an AmLaw10 law firm. We discussed her journey to the top, her passion for the practice of law, advice for board opportunities, her love for Texas and so much more.
If you haven’t already, please subscribe to this podcast and leave a review on iTunes. We interview corporate defense law firm leaders, partners, general counsel, and legal consultants.
You’re listening to Episode 59 of The Law Firm Leadership Podcast.
Chris: Welcome to The Law Firm Leadership Podcast. I’m your host, Chris Batz, with The Lion Group.
Today, I have the pleasure of speaking with Yvette Ostolaza, Chair-Elect of Sidley Austin’s Management Committee. Yvette is also a member of Sidley’s Executive Committee, the Managing Partner of the Dallas office, and the Global Co-Leader of the Litigation practice. Yvette has developed a national reputation as a versatile lawyer who excels in all aspects of complex multi-jurisdictional disputes and investigations. Prior to Sidley, she led the complex commercial litigation group and was a member of another management committee. Yvette currently serves on the Board of Directors of Lionsgate in LA. She also served as the Vice-Chair of Ethics and Investigations subcommittee of the ABA Corporate Governance Committee, and also served on the Board of the Directors of the State Bar Association of Texas. Of the many accolades that follow her, I’ll mention just a few. Since 2009, Yvette has been ranked as a leading general commercial litigator by Chambers USA and is also a band 1 lawyer. She was recently named to the “2020 Texas Trailblazers List” by Texas Lawyer. She was also selected as one of 20 “Women of Excellence” honored nationwide by Hispanic Business magazine. Yvette received her law degree from the University of Miami.
Welcome, Yvette, to The Law Firm Leadership Podcast. It’s great to have you on the show.
Yvette: Thanks, Chris. It’s great to be here.
An American Story
Chris: Yvette, can we jump right in with the amazing story of being the child of Cuban immigrants and “Operation Peter Pan”?
Yvette: My parents met in the United States. Many Cubans sent their children before the revolution, and during that period of time, they stayed in other people’s homes. My mother stayed with family members and my grandmother arranged for my dad to stay with someone she knew. They met in the United States and got married at a very young age. My mom had me when she was 18.
Chris: So, you were raised and lived your whole life in Miami before you graduated from law school, correct?
Yvette: Absolutely. I’m a Miami native and a Floridian. I’ve now been in Texas since 1991, but I come back and forth between Florida and Texas.
Chris: Did you always know that you were going to go to the University of Miami for college?
Yvette: No, I certainly did not even expect to go to college when I first started. My story is a traditional American story. What makes our country so great is that it offers people opportunities. In my family’s case, fleeing from a communist regime, coming to America, starting their own business, and doing the things that immigrants have done for centuries in our great country. As I grew up, I was not expecting to go to college because it didn’t seem like something that I could do or afford. I was fortunate that the University of Miami gave me an academic scholarship because of my class ranking in high school and my SAT score. I ended up going to college and graduated early, in three years, while also working throughout my studies there.
Chris: Did you stay local in Miami because of the importance of family?
Yvette: Yes. Between undergrad and law school, I took a break and worked in the airline industry in marketing and sales. I sold the computer systems that at the time Eastern Airlines and later Continental had. I worked in different territories like Latin America and stayed in South Florida. When it became time to go to law school, I applied to a couple of schools, got in, and was grateful again that the University of Miami gave me a wonderful academic scholarship. I decided to stay as a Cane and was also able to work during my time in law school because I was going to school during the day.
Sales & Journalism
Chris: What caused you to want to become a lawyer?
Yvette: Well, it happened organically. I worked as a summer intern for Miller Brewing Company in Milwaukee, because I was a Miller campus rep back when they had those in high school. During that summer in Milwaukee, I saw what an in-house lawyer did like advising on advertising or on compliance with the law. I thought that was interesting because I didn’t know there were lawyers, as unsophisticated as that sounds, in companies. After that, when I started working in the airline business, I got to know more lawyers in corporate America and in the community. I really enjoyed a class that I had taken in journalism. My undergraduate was in communication and marketing with an emphasis in journalism. In my classes, there was an intersection between constitutional law and journalism, defamation, and libel. I did well in that class and I loved it. It piqued my interest in the legal world, so I decided to apply to law school, and the rest is history.
I loved every minute of law school. I’m one of those weird ones. I’m a legal geek and I loved it. I went back to law school and focusing on studying, working, and having intellectual debates was a whole lot of fun. I also enjoyed getting to be with a peer group, doing mock trials, court writing, and publishing. During that period of my life, I thought it was just the best thing I could do.
Chris: It’s interesting to see the emphasis in journalism compliment the career that you’ve had in litigation where communication is so critical. Do you feel that crafted your journey in becoming a litigator?
Yvette: The background in journalism, writing, interviewing people, and keeping it simple has been an extreme positive in my legal career. In particular, it’s a benefit in litigation because so much of it is writing briefs or spending time deposing people or interviewing them in connection with an internal review. That skill set that I learned in undergraduate certainly translated quite well to being a lawyer. The other thing that translated is the experience in marketing and sales. I did quite a bit of cold calling, and that translated so well to the business of law, understanding P&L, understanding sales, and understanding the way that business people think.
The Texas Market
Chris: Where did you end up for your first job?
Yvette: I started in Dallas, Texas. I met my husband as a summer associate. He did not start at the same firm I did, but he interned at a firm. He was a Texan. It was 1991. He was a year ahead of me in law school, and he already had a permanent job, so I decided to interview in the Dallas market thinking that I would be here for three or four years. From a legal standpoint, the Texas market was so strong that we decided to build our family and stay here and have been here ever since. I’m admitted both in Texas and New York. My husband was born in New York, but he’s been in Texas since he was a little boy so he’s a Texan.
Named Band 1 in Chambers USA
Chris: As I look at Chambers USA and the comments of third parties speaking about you and your abilities in the courtroom and in the boardroom event, it is extraordinary. Talk to me about your journey as a litigator and helping your clients navigate very sticky situations.
Yvette: I’m honored and I’m humbled by the comments that I see. I read them and I can’t believe the girl from Miami is getting comments like that. If you had told me that when I was in middle school or high school, I would have said you were crazy. But looking back with the benefit of hindsight, the immigrant experience, growing up with Spanish as my first language, and being very observant of human nature and people translated in sales. Being a consensus builder, but also not being afraid to constantly ask questions has been really good for me. And in terms of negotiating skills that I learned in sales, they’ve been wonderful in negotiating on behalf of my clients.
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Enjoying What You Do
Chris: Clearly, you have this extraordinary career of leadership roles. Have leadership roles always come to you?
Yvette: Yes, and I never really asked for it. I like to tell people to just act like a leader and the title will come. I didn’t realize that’s what I was doing. I was just trying to do the best at anything that I did, and to work with other people, and to help them. I was always surprised when somebody would ask me to take a leadership role. It really was that way all the way until I was selected to be the chair. I’ve always been very happy to work with other people and was happy if I got the leadership position or if I didn’t. I would work with whoever the leader was to make sure that we succeeded. For me, it’s about winning for my clients. I don’t mean winning from a litigation standpoint. I mean winning as an organization, however you define that win and I tell my clients and colleagues that. We talk about what a win is in different contexts. I take pride in being able to be in an organization where that’s the focus while also having fun. Part of life is enjoying what you do. If you get a career where you enjoy what you do, you make a great living out of it, and it’s challenging intellectually and every day is not exactly the same, you’re a very fortunate person. I have landed on a career where those things have happened, and I’m very grateful for it. I’m a big salesperson for the practice of law in big law, because I do think that it offers the opportunity to be an owner, to be creative, to not do the same things day in day out, and also to be very involved in your community.
A Lateral Move that felt like Home
Chris: Yvette, you made a lateral move within the partner world in Dallas about eight years ago. Was the move something that was planned or unexpected?
Yvette: Completely unexpected. I was surprised that I made the move. I’m a very loyal person, and I don’t like a lot of change when it comes to the people I interact with day in and day out. I had been with the same firm for 21 years since I was a summer associate. I’ve now been at Sidley for eight years, and I’m so grateful that I made the move. It was one of those things where I wasn’t looking, but through chance and circumstance, I ended up taking a meeting through mutual friends, and then the rest is history.
What attracted me to Sidley, in addition to being around 150 years, was the vision that the leadership had for the firm. What they wanted it to be was very attractive to me. It was roughly double the size in terms of revenue of the firm that I was in, and I like the challenge of growing and developing a business. I also saw that there were a lot of female role models throughout the firm that I really enjoyed meeting. It was just an opportunity that I couldn’t pass up. I also ended up moving with about 50 of my colleagues, so it still felt like home when I moved.
Chris: It was a very historic move that caused ripples in the Texas market. I was recruiting at the time and can remember the day it was announced.
Sidley Austin LLP
Yvette, would you share with my audience who is Sidley Austin?
Yvette: Sidley is a firm with a rich tradition. As I said, it’s been around for over 150 years. What I love about the firm is the focus not only on talent and results for our client but teamwork. It’s a very collaborative firm. It started as you know, in the Midwest, and I think it has that Midwestern friendliness, hard work ethic, and it’s expanded. There was a merger with a New York firm, and I love the balance. It’s a good portfolio. We have all the right offices in the right size and they’re all in major cities. We’re not a firm with one big office and small satellite offices. It creates a great advantage for us worldwide, but also within the US. It was a very attractive platform for me and for my clients.
We are a top-six firm in terms of revenue across the AmLaw firms. The other thing that I love about Sidley is, when you have a firm of that sheer size and diversity of geography, it makes for a great balanced portfolio where you can represent clients from across the globe and do that really well without having to refer a lot of work. Prior to joining Sidley, I was having to refer a lot of work in certain markets where we did not have offices, in particular, Chicago and southern California. From a diversity perspective, I felt like Sidley was a step ahead and very committed to DE&I. I met so many female leaders and that was pretty unique at the time when I was looking at top firms.
Chris: Diversity, equity, and inclusion is front and center now, but you are talking about eight years ago. Would you share your thoughts on the legal profession as it relates to DE&I?
Yvette: We’re a licensed profession. Part of the honor of being licensed is you have to also make sure that you’re representative of the communities that you serve. The profession is making great strides in this area, though sometimes I’d like it to move faster. But at the end of the day, because of the birth rates of people going to college and how that has lessened, the firms that are going to be winners are going to be firms that are representative of their communities who are able to attract talent, independent of their gender, their socio-economic status, their race, where they’re from, the LGBTQ community, etc. Sidley’s very well positioned. In particular, the pandemic has been an interesting time for all of us that are running professional services firms because the world has opened up in terms of where you can recruit. The winners are going to be people that recruit a wide spectrum of talent. DE&I, in addition to just doing what’s right in making sure we’re representing the communities we serve, it’s going to be a gamechanger for the firms that do it right.
Taking the Helm in April
Chris: Would you share with our audience the role you’ll assume next April and what you’re up to right now?
Yvette: In addition to working on succession planning for the Dallas office, I’m very proud of what’s been accomplished over our 25 years in Dallas. The growth of the office has been phenomenal which I’ll share more on in the future. I’ll be engaging in succession planning in October. Right now I’m working on a listening tour in our offices developing the vision with Larry, Mike, and the Management Committee for the roaring 20s. It’s been a great year, and it’s hopefully going to continue to be that way, but developing what the firm is going to be in the 20s and 30s is our focus. We’re listening, not only to our internal constituencies, but also our clients, and how the clients view the future of the legal profession. What I will say is more and more the well-rounded lawyer is what clients are looking for, as AI takes over many of the tasks, some of them menial, some of them not so menial that we did as lawyers. I say this in terms of giving not only legal but business advice for the clients that we represent, which normally in our firm are businesses or individuals involved with businesses.
Maintaining an Active Docket
Chris: You are currently the head of litigation. Will you maintain an active docket while you’re running the firm?
Yvette: People ask me how I do all this, but yes, I’ll have an active docket for clients. I won’t be running the office in Dallas, but more importantly, I have three kids, the last one is going off to Northwestern (Go Wildcats!). I’m an empty nester and being a mother and not doing all the things that you’re supposed to do with your kid’s school anymore will give me so much free time that it’s going to be easy.
I do think that to be a good lawyer, a good leader, and a good owner, you have to continue working. And I do board reviews, internal reviews, and investigations. I advise directors and I do litigation. But there are some of the other roles that I’m not going to have to do anymore that will free me up. It’s important as a chair to always keep in touch with what it is to practice law.
As a Result of the Pandemic
Chris: Yvette, how has COVID affected the future of law as a firm?
Yvette: During the pandemic, we’ve done what every other firm has done by using Zoom and WebEx to make sure that we do whatever was necessary to make sure that our clients are being serviced. This includes the remote work policies with providing computers and having cybersecurity measures. Most of the large firms have done that.
What I find more interesting is what is going to remain as a result of the pandemic. We know there are some clients that have said, “We’re done with Zoom meetings, and we expect lawyers to be in the office.” We’ve seen those articles. We need to be responsive to clients. Many of our clients in many industries are in the office, and they are concerned about distracted lawyers that are not focusing. That’s something that we’re going to have to pay close attention to in the court systems. In litigation, I did a live trial the other day. Both sides wanted it to be live and did not feel comfortable doing it differently. It was good to be back in the courtroom in a very professional setting. I have done things remote in arbitration and other areas and that has worked well too for our clients. I find it fascinating that people will be more and more able to remotely do some of the litigation work and hearings, which are more status conferences and things where clients paid a lot of money, but a lot of time is just spent waiting in the courtroom. We’ll be interested in doing so remotely if the courts will allow it.
3 Trends To Watch
Chris: What future trends do you think will come to the practice of law?
Yvette: One of the trends obviously, is the issue of how much we are going to allow people not to be in the office who maybe have never even met the client in person. Every firm is still focusing on what’s in the best interest of the clients, and balancing what’s in the best interest of training attorneys to make sure they’re great lawyers. I don’t think we’re going to go back to the everyday work week in most companies or in most firms, because it just won’t be competitive. People will want to save the money from the real estate and have gotten used to saving some money from people not being in the office. A trend that I see in the legal world is there is a separation between the haves and the have nots in terms of law firms. The reason that’s happening is multifaceted. One, the fixed cost of a lawyer has become the same in terms of things like cybersecurity, whether you’re a very big firm or a midsize firm. It’s hard to expect people in smaller firms to absorb that cost. So, you’re seeing more and more firms having to merge to succeed. Second, the war for talent continues to be crazy. What people don’t realize about it is that it’s not that people don’t want to go to law school, it’s that they don’t exist. Many of our law schools have gotten smaller because the people weren’t born during those periods of time to then go to law school and have the social economic interest. There are less folks out there to hire, especially when you’re narrowing it to the top of the class. Third, AI will continue to be a pressure. Many of the tasks that we do have changed, even in the last five years, whether it’s a document review that an algorithm is doing very quickly, a transactional document, or looking at an analysis of a document and saying this is where all the changes need to be. AI has changed the way that we practice day in day out, and I think that will continue to accelerate exponentially. In the future, I think it’s going to be more about judgment and more about a different caliber of lawyer and training of that lawyer that will be expected by clients.
Valuable Advice for Aspiring Law Partners
Chris: Yvette, what advice would you give to folks that aspire to be a law partner within a large corporate firm?
Yvette: I always tell people to act like an owner from the first day you walk into an office. Think of it through the lens of an owner. How can you make the job of the leader easier? It’s so easy nowadays to add value to clients with social media, with Google, being able to sit down and say, let me learn everything there is about the company. Don’t stop learning because you graduated from law school. When I first moved to Texas, since I had not gone to law school in Texas, I took the Texas Rules of Procedure, and over the weekend, I read them, came back, and annotated them. After that process, I came back and I felt like I knew them. People to me and said, “Oh my gosh, I can’t believe you did that. That’s so impressive.” And I thought I’m a professional. I couldn’t believe that people thought reading a 200-page little book on procedure was that impressive, but it just goes to show you that many people think that they no longer need to learn. Invest in reading books on business and the business of law so you understand how to read a P&L and can speak the language of your clients. Look at things through the lens of a business person. That is a challenge for many people who focus on simply being a lawyer and only offering legal advice. Of course the legal advice should be there, but it has to be through the lens of business and practical advice.
Another tip is to practice public speaking. If you’re not taking courses on how to do public speaking, at any level, whether you’re a transactional lawyer, tax lawyer, or litigator it is important. We are communicators that generally get paid to speak and therefore being articulate, and making sure that we’re making our points in a way that a business person or a jury can understand is extremely important. Those are the skill sets that I think are important to develop at a young age. Be a lifelong learner. Work hard. The time that you invest in working hard in your career pays off. If you are a first-year lawyer that bills 1600 hours and another associate bills 2000 hours, that person has 400 hours of knowledge on you. If in the second year, you bill 1800 and the other person bills 2000, they now have another 200 hours of knowledge on you. It’s back to that book that talks about the 10,000-hour rule. The faster you get to that experience level makes it’s almost impossible for people to catch up. When you’re younger, invest the time in your career. Consider it like you’re still in school, but now you’re getting paid, and you’ll be very happy about it. Nobody will ever be able to catch up with you because you will have run the marathon five times, and they’re just catching up. There is no shortcut to spending the time learning your trade.
People Want Leaders to Lead
Chris: How do you define leadership?
Yvette: I don’t have a definition, but RBG had a great quote that went along the lines of lead in a way that other people want to naturally join you. I try to lead in a way that others want to just naturally join me. I try to persuade people sometimes, and there are definitely times you have to fight for things that you care about. Other times, you have to make tough decisions. People want leaders to lead. You may make mistakes. Sometimes, you will receive input from many constituencies, and sometimes you’ll have to make a hard decision. It is important to make a decision, especially during difficult times, like the pandemic. There were decisions that had to be made by all of us in the firm. People will say you made a mistake here or there, but leaders are paid to get information and make a decision.
P&L Experience is Key
Chris: Would you share advice for attorneys who aspire to be members of the boards for public companies?
Yvette: You’re not going to be naturally attractive just because you’re a lawyer. Although, there are many lawyers that have started companies, are on boards, or have pivoted. Most boards are looking for people that understand P&L. If you have been a leader or you’ve been on the Management Committee of your firm, or manage P&L of an office or of a firm, that can be extremely helpful. You need to understand more than the law because you’re not going to be practicing law on a board. Understanding things like the HR aspects of running a business, or basically being a CEO type within your organization, will give you a higher chance of getting selected. If you are someone that has been a board advisor to a client, and they’ve seen you in that room, you may be naturally attractive to some of the clients that you’ve been advising day in day out. For me, it has been my background in governance, internal investigations, and nominating and governance committees that have gotten me most of the calls about being on boards. There are a couple of ways to add those things to your resume. Obviously, there are audit committees and nominating and governance committees within the nonprofit world. Many of the folks on the nonprofit boards are also people that run companies. So, if you are truly interested in that, in addition to taking coursework that focuses on areas that add value to a board that is public, it’s really about having those experiences. By the time a headhunter gives a call, you can say, I’ve been on the audit committee of these nonprofits or I’ve been a trustee of a university.
Love for Texas
Chris: Let’s pivot to family. Did your parents follow you to Texas?
Yvette: Yes, they live in Texas now. It took some persuading and it helped that I was the only child but my parents have now lived here for two decades and it’s been great. My aunt and my grandmother, who has since passed away, also moved here too.
Chris: I know you’re a big Texas fan and that Texas and Miami have varied backgrounds when it comes to Spanish-speaking people. Care to share what you love about Texas and the differences you’ve noticed?
Yvette: What I love about Texas is the can-do spirit. This is a place where people got here and there was no reason to stay. But they built this unbelievably thriving economy in Houston, Dallas, San Antonio, etc. These are top 10 cities! When you look at the gross product of what they did, it’s amazing. There’s a little bit of an indoctrination that happens in Texas. From the moment your kids are born, they’re learning 22 Texas songs. I don’t know a Florida song. Nobody taught me those. What my parents most missed about Florida was the Cuban food and not having it in every corner. Whenever I connect through Miami, I have to bring my box of pastelitos for the parents. In terms of the Hispanic community here in Texas, although it’s not Cuban, it’s as diverse as it was in Miami. It’s been really fun not only to use my language skills in Spanish but also to develop a wonderful appreciation for Mexican food and Tex Mex food, which I can’t live without now.
Chris: I know your youngest is headed to Northwestern, but are your other kids staying close to home?
Yvette: My oldest graduated from college already, and started a business. He’s single and has a little office in New York. My middle son is at Georgetown and is double majoring in Government and in Spanish. He intends to go to law school after getting his Master’s degree this coming spring. My daughter wants to be a doctor, and we’ll be dropping her off at Northwestern in mid-September.
We love traveling. It has been really fun during COVID to take road trips. I’m not a big road trip person, but my daughter said the other day to me. “When did we become National Park people?” In the last year, we’ve been to Yellowstone, the Grand Tetons, and we’ve been to Zion. It’s been really fun to do that. I’m a foodie. I enjoy good food. I also enjoy reading and gardening. Those are fun things that I do. But mostly I enjoy being around my family and doing things with them.
Chris: Last question, what is the kindest thing anyone has ever done for you?
Yvette: I’ve been the beneficiary of so much kindness in my life that it would be hard to isolate just one. I would not be here without so many different things that people have done that have been kind to me, since I was a child. It’s hard for me to isolate one thing, but what I will say is there have been times in my life, like in everybody’s life, where you need support. It could be that you’re a new mother, it could be that your mother’s going through breast cancer, which I had at a young age, and people came around and supported our family. That has been an incredible experience.
What I would say is my parents have probably done the kindest thing to support me in my life. They moved from Miami to help with raising our three kids so that I could pursue my career and my dreams. It was a challenge when I was a young mother to imagine doing it all, but my parents came in and supported us and I would not be who I am without that support from my parents and from my husband.
Chris: It’s been an honor and a pleasure today. Thank you for your time.
Yvette: Well, thank you so much, Chris, it has been too. I really appreciate you taking the time to interview me and look forward to talking to you in the future.
Thank you to everyone who listened to this episode of The Law Firm Leadership Podcast.