Sidley’s Yvette Ostolaza Says Stay-at-Home Moms ‘Rooted for Her’

It’s perfectly rational to me that women might not want to stay in Big Law. As anyone who knows the legal profession can attest, patriarchy still rules the roost at major law firms.

Yet some women not only stay in Big Law, but manage to rise to the tippy-top of leadership. Sidley Austin’s Yvette Ostolaza is a prime example. A highly-regarded litigator, she also stands out as the only Latina to lead a firm in the top 10 for gross revenue.

Yvette Ostolaza of Sidley Austin.

Ostolaza has a reputation for championing women. At Sidley, women comprise 30% of US partners, as well as practice area team leaders.

An unabashed extrovert, Ostolaza is known to be outspoken. Naturally, I was curious what she had to say about her vaulted position and the state of women in Big Law. Below is an edited version of our conversations.

You and eight other Weil Gotshal partners—mainly women—moved to Sidley in 2013 in what felt like a female revolt. Ten years later, you’re top of the heap at Sidley.
I was told that we were the largest group of female partners that moved from one big firm to another at the time. And every single client moved over with us.

Was it your plan to chair the management committee? Or is this a surprise?
My entire life is a surprise. I cannot say I foresaw any of this. It’s one of the great things about America. You can come from nothing—my parents are immigrants [from Cuba]; I’m the first in my family to go to college—and your daughter can be chair of a 150-year old firm.

That’s pretty cool. Now that you have power, does it feel different?
I’d call it a different level of responsibility. There are thousands of employees who are counting on you, which is humbling. And it’s something I think about 24/7.

Do you feel your gender influences your leadership style?
Who you are as a leader and human being is informed by your background, family, and experiences. We are informed by all facets of what we do in life. I focus on authenticity and transparency. I wouldn’t ask someone to do something that I wouldn’t do personally.

What do you mean by that?
I mean being a leader is to lead by example. So if you’re aiming for the highest quality in your employees, it’s important that the leader behaves in the same way by setting high standards. I also have an open-door policy. I do not believe in running an ivory tower.

Your firm—and maybe you—got grief for making bonuses conditional on the return to office. Did folks expect a female leader to be a stronger advocate for flexible work arrangements?
We were latecomers, based on client feedback and what our associates told us. We did this because clients are back in the office. I personally saw some mental health issues from being away from people for long periods of time. There’s something to being present and normalcy. Work is a good place to be!

Female leaders often cringe at the suggestion they do things differently because of their gender. But you say gender played a big role in your success as a rainmaker because women gave you business.
In the beginning, for sure. Certainly the rise of women in the in-house ranks gave more emphasis to diversity and changed business development activities. The presence of women has also been a complete game changer in the boardroom and the judiciary.

More clients are agnostic about gender these days. You don’t hear [male] clients saying, “I only want men on my pleadings,” which I remembered would happen 20 years ago.

Yet women still seem to have a much tougher time developing business. Why so?
It’s the sales aspect of Big Law that people find off-putting. But I see that with both men and women. I don’t think it’s gender-specific. Sales have always been part of it but it’s more so now than ever.

Well, I don’t think anyone would call you shy and retiring. Your career seems like a smooth trajectory. Did you have challenges?
I’m not a person who focuses on challenges. I move on. But if I had to name one it’s managing career and family. During my legal career, I worked around the clock, while managing a family and trying to take care of myself. I have three wonderful kids, and there were times I wondered whether I wanted to continue. Those were difficult times.

What kept you in the game?
I remember women in my neighborhood—who had quit their jobs—were rooting for me to keep working. I’d be complaining about how I didn’t have time to make organic baby food, and they’d say, “Are you crazy? What are you thinking?” I should have given myself more grace.

My husband, who’s a former partner at Baker Botts, was also supportive. When I was debating whether to make the change to Sidley, he said, “you need to do this.” You need all sorts of relationships—personal and work ones—so you can lean on them.

Yup, picking the right spouse is key. But it’s amazing that stay-at-home moms pushed you in your career. What else drove you to the top? What’s your superpower?
My personal superpower is my energy. I don’t know where it comes from. My other superpower is the ability to empathize, to look around the corner for trends, and to be authentic.

For example, I started our Build to Lead program with Northwestern and Columbia Business Schools to give associates an executive education. We’re investing in our associates, motivating them, and creating stickiness.

When they return from the program, they approach legal advice through the lens of business, and the clients see a difference. Over 200 [associates] have participated, and there’s another class coming up. People are giddy about this.

Big Law obviously clicks for you. But that’s not the case for many women, who leave major firms in much greater numbers than men. Is Big Law alienating women? Or is it a matter of finding the right firm?
Culture and diversity were important to me when I was looking to join Sidley. Women were on the executive committee and other top positions throughout the firm. Women were in leadership here—and it was real.