Yvette Ostolaza grew up in an immigrant neighborhood in Miami, the daughter of parents who fled Cuba in the 1960s. She learned English from watching Sesame Street. As a young teenager, she lied about her age to get a job at Sears to make extra money for her family. When she announced that she wanted to be the first in the family to go to college, they told her she was crazy.
Four decades later, Ostolaza became the first Latina and first Dallas lawyer to lead a global corporate law firm — a position she has held since 2022 at Sidley Austin, a 2,300-lawyer firm with 21 offices and more than $3.7 billion in annual revenue.
“I have always been inspired by what my family overcame and the sacrifices they made in coming to this country as teenagers,” Ostolaza, who is chair of Sidley’s management committee, told The Texas Lawbook. “Throughout my life, my parents owned and operated small businesses from fence building to printing. They taught me that I needed to work to care for myself and others. The strong work ethic of my family and their involvement in the community taught me to learn new ways to support myself, to be entrepreneurial, to help others and to bet on myself.”
“As a result of seeing my parents start new businesses to support our family, I was not afraid to bet on myself by leaving my airline marketing career and attending law school,” she said. “Being a part of a community that was grateful to be in the United States, had a strong work ethic and was entrepreneurial has shaped me into the leader I am today.”
The Lawbook announced Thursday that it is awarding the first-ever Texas Lawbook Law Firm Leadership Award to Ostolaza.
The award will be presented to Ostolaza on Monday at the launch event of the Texas Lawbook Leadership Symposium, which is cohosted by the Association of Corporate Counsel’s DFW Chapter and The Lawbook and sponsored by Harvey.
“As The Lawbook launches the Leadership Symposium, we are honored to have a true trailblazer in Yvette as our first award recipient. She is an undeniable force, and her ascent to management committee chair at Sidley was a landmark moment for top law firm talent in Texas,” said Texas Lawbook publisher Brooks Igo.
Ostolaza will be one of the speakers — along with Jacobs General Counsel Chasity Henry, Keurig Dr Pepper Chief Legal Officer Anthony Shoemaker, Toyota America Managing Counsel Derek Lipscombe, Dallas Morning News Publisher Grant Moise and King & Spalding Dallas office managing partner Tom Melsheimer — at the event being held April 13 at The Dallas Morning News. For more information about the event, email Igo at brooks.igo@texaslawbook.net.
Kent Zimmermann, a law firm consultant, told The Lawbook in a 2022 interview that Sidley knew Ostolaza was a leader when they hired her in 2013.
“Yvette’s accession to the top at Sidley is a testament to her and her leadership abilities and to the increased role that Texas now plays in the future strategic planning of corporate law firms,” Zimmermann said. “Yvette is the first Texan to lead a global law firm, but you can bet she will not be the last. Yvette is the great American success story.”
A 1992 graduate of the University of Miami School of Law, Ostolaza did an interview with The Lawbook this week.
Texas Lawbook: Who are people in your life who were leaders who influenced you the most and who taught you leadership skills?
Yvette Ostolaza: First, my parents, who are true examples of strength, resiliency and determination. They provided a loving environment and helped me realize my goal of attending college. They continue to support my career and family to this day. I am also grateful to my late grandparents, who had the courage to send their children ahead from Cuba and who survived many hardships so we could live in the United States.
Throughout my legal career, I have had many mentors and role models. I am grateful to my first mentor, Ralph Miller. He is brilliant and taught me how to practice law while also allowing me to both thrive and fail as a young leader. And I certainly owe much to Larry Barden, whom I succeeded as management committee chair at Sidley. Larry has been a mentor for the past decade and is also a friend.
Mentorship comes from colleagues, too, including the several partners I have practiced law with for decades. They have inspired and encouraged me throughout the various stages of my career — through the ups and downs of life — and continue to support me today.
Lawbook: When did you first start feeling comfortable as a leader?
Ostolaza: Leadership comes from experience and the openness and willingness to seek feedback and continue to learn. I suppose the first leadership opportunity that I had was being in the student council of my grade school. Balancing the constituents in what the cafeteria should carry for lunch was quite challenging in a multicultural elementary school, but it taught me to listen, make a decision, then build consensus at a young age.
In law, I held leadership roles early in my career, such as associate committee leader that prepared me to be more comfortable with leading peers. Later, as a partner, I led practice groups and ultimately a global litigation group and served on management and executive committees. With each role, I attended programs, read books and studied leadership behavior. I observed what tactics worked for different leaders and applied them. I also focused on cultural and regional differences so I could be effective as a leader of global teams.
As I became a more experienced leader, I recognized that being comfortable is a recipe for failure. You always need to challenge yourself and make sure that you are not relying on the past to predict the future as it relates to leadership.
Today, I am more inclined to lean into experiences and seek feedback, but also pivot when I see a trend that requires an immediate change. I am also more willing to be a disruptor to ensure our firm is positioned to succeed.
Finally, I rely heavily on gathering feedback from a number of constituents, including the leadership of our firm, the management team and the executive committee. I also seek feedback from clients regularly. They are the main reason law firms exist.
However, you should never feel like you are completely comfortable as a leader. I believe you should continue to grow, always looking around corners to stay ahead of trends and lead through changing times by being creative.
Lawbook: What was your first leadership role as a lawyer?
Ostolaza: In terms of a significant role, I was a member of the management committee at my previous law firm, a global firm that I was with for 21 years, beginning as a summer associate. Since joining Sidley about 13 years ago, I have served in a variety of senior management roles.
Before becoming chair of Sidley’s management committee, I was a member of the management committee and the executive committee while maintaining a busy crisis management and litigation practice. I also co-chaired Sidley’s global litigation practice for several years, which is a $1 billion-plus practice.
Lawbook: What are the biggest challenges law firm leaders face today?
Ostolaza: One challenge law firm leaders continue to face is managing the law firm like a global business rather than a collection of individual practices. The firms that are succeeding are operating as integrated enterprises, aligning and retaining talent, technology and client strategy across offices and practices. Leadership today is about looking around corners for clients, anticipating risk and bringing the full platform to bear. It is not enough to be excellent in a silo. Breadth, collaboration, and disciplined investment are what separate firms from those chasing short-term gains and long-lasting firms like Sidley.
Another challenge is managing the adoption and use of rapidly changing AI. AI is reshaping how we work, how we serve clients, how we train and recruit our attorneys and how we lead our firms. The firms pulling ahead are embedding AI across research, drafting and knowledge management with strong governance and clear accountability. They also have the financial strength to invest in AI.
Lawbook: What has been your biggest success as a law firm leader?
Ostolaza: I hope that hasn’t happened yet!
All kidding aside, I am proud that the transition from the previous chair of the management committee was seamless through the efforts of the leadership team and the support that I received from the firm. It is no small task to co-lead a firm with a rich history of financial strength, top-tier talent and global clients through the pandemic, geopolitical risk and market downturns. I am humbled that our firm, as it celebrates its 160th anniversary this year, is stronger than ever. We have momentum. Our talent, client roster and financial performance reflect the efforts of our entire leadership team and partnership.
Lawbook: What roles should law firm leaders play in helping shape their communities?
Ostolaza: As lawyers, we have a unique opportunity to be involved in our communities by providing pro bono legal work to nonprofit organizations and individuals. Law firm leadership involves actively investing in local talent, educational opportunities and civic engagement through pro bono work, board service and training.
As a leader, I want to use the Sidley global platform to make a tangible impact in how we support and encourage Sidley lawyers and business professionals to use their talents to serve those in need in our communities through a variety of programs.
For example, we encourage our lawyers to reach beyond their legal expertise and lean into civic service. Through our Built to Lead® Civic Leadership Academy, we bring our lawyers together for hands-on community engagement. Most recently, we partnered with KABOOM! and Vanguard to build a new playground at a Spanish immersion school in East Dallas.These programs underscore our commitment to service, but more importantly, highlight our commitment to shaping the next generation of leaders through service and supporting teams both financially and through training to be able to dedicate the time to do so.
Lawbook: What skills are important to lead the law firm of the future?
Ostolaza: While there are many, I’ll offer a few skills that I think are becoming even more important to be a good leader.
First, be transparent with your team and invest in them — your reputation and your people are your legacy.
Second, cultivate relationships — they drive everything. This is a people business. Trust is built over time and wins in the end. Do not compromise your character. Ultimately, they will respect you through difficult times if you have led with authenticity, transparency and character.
And third, be relentlessly curious so you don’t get bored in your career and you are in the best position to learn and advise your clients accordingly.
Finally, I’ll offer this bonus: Find a way to have fun in your career. Prioritize balance to make the most out of your contributions to your work on a day-to-day basis and to achieve longevity. Great leaders should not have regrets.