At The Table

Client-Focused, With a Collaborative Spirit

Yvette Ostolaza, chair-elect of Sidley Austin’s management committee, discusses her leadership style, what she looks for in lawyers for her team, and the best career advice she’s ever received.

Yvette Ostolaza, chair-elect of Sidley Austin’s management committee, discusses her leadership style, what she looks for in lawyers for her team, and the best career advice she’s ever received.

CCBJ: What led you to join Sidley?

Yvette Ostolaza: What originally attracted me to Sidley was the global reach of the firm, its premier brand, and the strength of the firm’s leadership team. I was very impressed with Larry Barden and others I met early in the process. Larry is the current chair of the firm’s management committee, whose giant shoes I’ll be filling as I transition into this role. One of our early meetings was over dinner and I was struck by the fact that Larry and his wife joined us. That spoke volumes to me and is something I’ve referred to as a “triple scrabble points” with my team. In business and in life, it’s about seizing opportunities to be genuine and human because that is what people react to in various settings, including at the office. Authenticity is very important to me.

As I learned more about Sidley’s collaborative culture, its global client base, diverse leadership, and the vision that management had for the firm, I became intrigued.

For example, Sidley already had women in meaningful leadership positions running large groups and offices. I was impressed by the firm’s track record of diversity. It became clear to me that the firm was motivated by attracting and retaining talent that reflects the clients’ priorities. Sometimes it really is as simple as giving clients exactly what they want.

At the time, I was also referring a significant amount of business to firms in Southern California and Chicago. As my practice grew, I found myself needing talent in markets where Sidley already had significant strengths and strong ties to local business communities. The firm’s practice depth, including transactional, litigation, and regulatory work, along with its regional strengths make for a potent combination that I knew I could leverage and build upon. The team of lawyers who worked with me for two decades and joined the firm with me felt the same way, which made it easy for me to pick Sidley over other firms.

Please tell us about your leadership style, and who or what has influenced it.

I try to focus on making sure we get the best out of all of our talent, as well as understanding that leading an organization is not one size fits all, especially when you are working with professionals in different parts of the world who have different practices and cultural norms. I apply a flexible leadership style that focuses on the individual while also trying to look around the corner for trends that others may be missing in the marketplace, so that we can be at the forefront of providing the best legal work and value for our clients.

I try to remember that this is a talent business first and lead with that in mind. I also work hard to instill an understanding within my teams that a career is a marathon, not a sprint. There will be times in their career where they need to focus on their children, other times perhaps on their parents, and always on themselves in addition to their day-to-day client responsibilities that we have as professionals in a law firm. I try to empathize with those shifting priorities as much as possible.

My approach to leadership was shaped early in my upbringing in a middle-class Cuban family in Miami. I played a lot of different roles in various family businesses but was always reminded of what was truly important – family and community. I also understood clients are the reason we had a business. I work hard to incorporate that understanding into my leadership approach daily. I think a balanced approach plays a key role in attracting the industry’s top talent, who want a platform to practice at the highest level, but also a winning team.

Mentoring is also very important to me and I have learned a great deal in my career. As a leader, I value and encourage mentoring and long-term relationships.

What qualities do you look for when hiring new people for your team?

There are many good lawyers out there. Because of Sidley’s strength in the market, we have plenty of opportunities to bring top lawyers to the firm. I try to take a long term, holistic approach with individuals. They obviously have to have a proven track record of client service and legal acumen, but I’m also looking for attorneys who have common sense and will integrate well into Sidley’s collaborative culture.

I want attorneys who work well in teams. There’s no room for sharp elbows. We “hunt in packs,” and want smart people who enjoy learning from others. You have to be willing to ask questions and know how to observe in order to be a life-long learner. That inquisitive nature and intellectual curiosity is a trait that I’m always looking for in all employees.

Additionally, now more than ever, we are looking for leaders that can appreciate and seize the informal training and mentoring moments with their teams. The value of those opportunities has been made clear as we’ve adapted to this remote style of work during the pandemic. The informal mentorship opportunities have been missing; we want leaders who recognize that and are able to adjust accordingly.

Can you describe the culture of your organization?

The American Lawyer described our team as “Built to Win.” We’re looking to win for our clients, whether it’s in a transaction or in litigation. We value diverse, collaborative teams. Our clients represent society at large and are looking for a diverse range of experience and advice so they can make the best decisions for their business. And that’s at every level of the organization. Our wonderful staff all have to be client-driven and flexible. I don’t think the world is very linear nowadays, so individuals who are entrepreneurial, client-driven, service-oriented, at every level of the organization – that’s ultimately what we look for at Sidley.

What’s the best career advice you’ve received?

One of the best pieces of advice I’ve received was when I was working in corporate America, in marketing, before I went to law school. Our corporation had gone through a reorganization and the leader had lost his job. He had spent his entire career with the company. His advice to me was to go to law school. He said, “You know, the great thing about lawyers is that as long as you keep your clients happy, you always have a job at the end of the day and can hang a shingle with your name.”

My parents always had their own businesses, and I remember thinking that working in a large organization would provide less risk, but now I was seeing the ebbs and flows of business that made me realize the benefits of being independent. I’m so grateful for that advice and have held onto it throughout my career. I feel fortunate to not only have found a profession that I love but also a firm in Sidley that challenges me as a leader and offers me significant opportunities to provide top-tier legal work for clients.

What changes would you like to see within the legal profession?

I believe it’s important to ensure that diverse teams are tied together at every level to address client needs and reflect our communities – whether it’s in terms of gender, ethnic background, religion, or socioeconomic status. Our profession should continue to focus on making sure our talent is reflective of the needs in our communities. Our profession is making great strides in that area, but we still need to continually evaluate what we’re doing and make sure that we’re at the forefront in recruiting and retaining diverse employees. The serious manner in which Sidley approaches its commitment to diversity, equity and inclusion is a big part of what attracted me to Sidley in the first place and continues to inspire and motivate me as a leader.

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