Katya Jestin | Leading with Authenticity in High-Stakes Legal Environments

Elise Holtzman: Hi everyone, it's Elise Holtzman here, a former practicing lawyer and the host of The Lawyer’s Edge podcast. Welcome back for another episode. High-stakes legal work requires more than just intelligence and technical skill. Whether leading sensitive investigations, managing crises, or guiding a major law firm through periods of uncertainty, lawyers are often called upon to project judgment, steadiness and trust under pressure.

In this episode, we're going to explore what leadership really looks like in high-pressure legal environments. We'll talk about authenticity, mentorship, developing judgment over time and how lawyers can grow into leadership roles without losing themselves in the process. Before we dive in, 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 hello@thelawyersedge.com.

I am so excited to welcome my guest today, Katya Jestin, a partner at Jenner & Block and co-chair of the firm's investigations, compliance and defense practice. A former federal prosecutor, Katya represents companies, universities, executives and boards in high-stakes criminal, regulatory, congressional and internal investigations, particularly in sensitive and crisis-driven matters. From 2020 to 2024, which was a fraught time in history, we know that, she also served as Jenner & Block's co-managing partner, helping lead the firm during a period of significant change and uncertainty for the legal profession and the broader business world. Katya, welcome to The Lawyer’s Edge.

Katya Jestin: Hi, Elise. Thank you.

Elise Holtzman: I'm excited for you to be here. You have been in some very serious leadership roles, right? We know that Jenner & Block has 500 or more attorneys, in a number of offices around the US and the UK. And so that was a big job that you inhabited at a very difficult time. And now you are in a co-chair role for a practice group of the firm. Let's talk about that period from 2020 to 2024 for a few minutes, which, as we know, was just crazy generally for individuals, law firms, businesses generally. Talk to me a little bit about how the firm grew as a business during that time and how your leadership position shaped the way you approach strategic decision-making now.

Katya Jestin: First of all, thank you so much for having me. I'm very excited to be here with you. So I assumed the role of co-managing partner of Jenner & Block on January 1st of 2020, which was an interesting time to assume a leadership role of a large firm, to say the least. And I did it for five years. And it was a transformative experience for me. And looking back, I think the decisions we made in March of 2020 really shaped the future of the firm. And I really believe that those decisions have enabled us to flourish even today. I think they were so important. And I'm not saying that in a way that I'm not trying to be self-congratulatory at all. It was a learning experience. And I think the lessons that I would point to are when you are making difficult decisions, make them through your values. When COVID hit in March of 2020 and everyone was switching to work from home, especially in big law and in every business and in every household, there was so much anxiety. And a lot of belt tightening and fear of the future, complete uncertainty, in terms of what was around the corner. And we made a decision in March that unless we were in financial extremists, we were not going to fire anyone. And that was a decision we made through our values. Who are we? Who do we want to be? And we wanted to make sure our receptionists, our catering staff, everyone who was stuck at home and couldn't work, had a job. And we decided, you know, partners don't need to make as much money this year, you know, we don't all need a bonus or whatever it is, but we need to do the right thing. And that was a values-based decision that felt like it could have near-term economic consequences that, you know, negative near-term economic consequences. So it was a scary decision to make. But the lesson I took from that is if you make a values-based decision in the long-term, it will pay off. So that was the big lesson that I learned.

Elise Holtzman: Yeah, that's fascinating to me. And I think it's really important for people to remember, you know, I think that when we get super busy and when we get overwhelmed, there is a tendency to just react and act right, you're trying to survive. And so, you know, at the risk of stating the obvious, you didn't become managing partner, or co managing partner by accident, right. So when the decision was made, I imagine both you and other leaders in the firm recognized that you had all of these leadership qualities that they wanted and yet all of a sudden there you were, barely 10 weeks later or less, maybe it was nine weeks or something like that and crisis hit. It's kind of ironic to me that you do help your own clients through crisis and then there you were with your own crisis. You know, many, many firms and businesses, as you know, it's all like, OK, we're going to start with our values and we're going write our values down, on a piece of paper. And then what happens and I'm not critical necessarily, It's more an observation about human nature, as we tend to throw that piece of paper on a shelf somewhere with our values. And we don't necessarily live and act our values. So, you know, I love hearing that, because especially such a big organization, you could see how very quickly decisions could get made outside of those values to kind of try to preserve the economic stability of the firm, you know, at all cost to everything else.

Katya Jestin: I think that's right. And just based on my practice and experience, I think the worst decisions are made from a place of fear. And I think that making a decision that puts your people first, will never be the wrong decision. And COVID was an opportunity for Jenner. Jenner's always been a culture firm, always and reputationally and in reality. But during COVID, the emotional fabric of the firm really came into high relief. And I think because we were making decisions that were people-first, not money-first, that emotional fabric just became stronger and stronger. And we focused our energies, especially in those first few months, where people were so afraid and so rattled by this disease and what was happening, on trying to create an emotional ecosystem, where people felt safe and seen and part of a family. So every day we issued a newsletter and it was a ton of work, with pictures, people's pets, jokes. We had tons of town halls and I'm sure many businesses did this. But it really made a difference. And the other thing we did, just as a kind of practical decision-making point, is we decided that individualism was going to be in the rearview mirror. So many big law firms have a very strong individualist streak and you hear about the rainmaker. And we decided that we thrive with teams. And our expression is, teams crush individuals every time. So we looked at ways we could change our internal processes and procedures, when it comes to fee credit, staffing, whatever and really focus on teamwork. And it was the perfect time to do that, because people craved it, they needed it. And this all kind of evolved into a strategic plan that we rolled out over the five years I was in the role. And it's still kind of a, as strategic plans are, a living document today and really focused on teamwork. And that, I think, had a hugely beneficial effect for the firm and unlocked a lot of value.

Elise Holtzman: You mentioned that many law firms are very individualistic in terms of, you know, the individual matters and all of that sort of thing. And what strikes me is that that's also true of the American culture generally. I was just talking about this to someone the other day. Because one of the expressions we hear in the United States that's uniquely American, is “the squeaky wheel gets the oil”. It's like if you're the individual, stand up. You know, we talk about individual rights all the time and those sorts of things. And yet there are other cultures. There's another cultural expression, not from the American culture, that is the “nail that stands up gets hammered down”, right? It's this idea that we are a collective, we are more collaborative, we do care about the whole and the team more than the individual. And so what was that like for you personally, right? Was it a departure for how you normally would behave in the absence of a crisis like this? Do you think it was a departure for your partners? Because it sounds like it could be a very difficult shift to make and yet you were able to successfully make it. So I'm curious, you know, obviously without talking about individuals, or what showed up in the management committee, what that looks like. Like, do you feel like everybody went, oh yeah, we have to do this, or there was some real conversation that had to be had around, you know, what did the firm's values look like under pressure?

Katya Jestin: So I don't think it was simple or easy. I wouldn't say that. I would say my co-managing partner was Randy Mehrberg. He's still co-managing partner of the firm. And he's a wonderful, amazing leader and has a lot of experience in corporations. So he brought a strategic overlay to this whole thing, because he had just done strategic planning before, which I've always been a lawyer, not a strategic planner. So it was very helpful. And we did it together. And the power of two is something you know, not to underestimate. And it was really helpful. So he and I are very yin and yang. And we were able to, you know, I think persuade our policy committee that, you know, these changes we wanted to make made sense. But it was pushing against an open door, because we are culturally committed to that and it's just a cultural matter, that was a commitment that was there already. So it was just a question of making sure everybody was on the same team, rowing in the same direction, thinking about things the same way, understanding that credit is infinite and we should reward people for finding opportunities for others. And that's what grows your pie. That's what makes you an economically successful law firm. And just believing that and putting it into practice made a huge difference. And people feel like they're a part of things. And when people feel ownership, they give it their all. And, you know, one thing and I was thinking about this before we got together, we every year have an annual partners retreat, like every other law firm. And I think it was the first year we were back together, you know, post-pandemic or kind of in the middle of the pandemic. And we had a panel on vulnerability. And we had some of the most powerful partners in the firm, the chair of the firm, the head of the London office, the powerful partners in the firm on the dais, each talking about a screw-up. And it was really amazing and what they learned from it. So this is what I screwed up. This is what I learned from it. This is all of the things that came into play. And that panel and the evaluations after the retreat got the highest marks of anything else. And just being able to be vulnerable is so important. And so I think that that ethos and really promoting that also was very helpful in that respect.

Elise Holtzman: Yeah, so interesting, right? It's all about really being human. So one of the things that I know you do, as I said before, is that you are, you know, you are in a high stakes litigation kind of environment, right? High stakes litigations, high stakes investigations. And those things can be very traditional, very high pressure, very masculine. Tell me a little bit about your growth as a lawyer and a leader in those kinds of environments, right? You stepped into the managing partner role, after having done some of that work for a long time. And so again, stepped into kind of a crisis role in the pandemic. But what about in your everyday practice, right? Dealing with lawyers and judges and clients and investigators in a fast paced kind of traditionally male environment.

Katya Jestin: I grew up with a mother who's a lawyer. She was a trailblazer. She is a trailblazer. She is a force of nature. And I grew up in Dallas, Texas and I'm blonde. So I have been underestimated my entire life and stereotyped, as was she. We used to, I mean, we laugh to this day. She was always referred to as the lady lawyer. My whole life I heard that growing up. And we always talk about the power of being underestimated. And you know what? It's fine. You just have to be yourself. My two buzzwords are kindness and grit. I will never be unkind, because I think that it's a sign of weakness. And I will always approach things with all the grit I can bring. And that's it. That's who I am. And I think if you can, you know, feel good enough about the gifts that you're bringing to the table and just understand that that's why you're at the table, that's the most important thing. I am, I don't, I'm not a grievance collector. I don't think about, you know, all of the things that I could complain about, you know, in terms of the gender imbalance and all of that. I really just focus on, you know, getting the job done and trying to mentor women, staff them in big roles, give them speaking roles. I am very intentional about that in my mentorship of women. And I promote the power of underestimation. I think it's a superpower.

Elise Holtzman: So tell me a little bit more about that. How is that a superpower? It's like you sort of have a secret weapon. They don't know what's coming. Is that the kind of approach you're taking? Or what is it about underestimation that you think can be powerful for people?

Katya Jestin: I think it's disarming. I mean, I just think I have personally achieved the best outcomes by relationship building. And, you know, being myself and being disarming and not trying to put on a facade of being an intimidating, muscular litigator. And, you know, at the beginning of a relationship, if somebody thinks that I'm, you know, I'm not going to be formidable, that's fine with me, because at the end of the day, I'm secure enough in my abilities and my goals. I don't really worry about it. And ultimately, I think the way I approach things has worked for me. And you have to be yourself. If you're not yourself, it's not going to work. But I do think it's a little harder for women, because the signals are that's weak. All of the kind of female qualities, empathy, kindness, warmth, all of those things are considered to be weak and female. And so I think a lot of women worry about them. And the one thing I do say to my female mentees is don't apologize at work. Women apologize for everything. And that is some advice I give women generally, is be yourself completely. You just need to be yourself. But don't apologize. That's something that I think women do way too much.

Elise Holtzman: Right. And we're not born that way. Right. We were socialized to do that. We were socialized to believe that we should be smaller and, you know, we should make ourselves smaller to make other people more comfortable. I think that there's still a lot of that going on, although it's certainly gotten better. But some of those habits die hard. Right. Being socialized for perfection instead of being socialized for bravery. You know, like there's a book by Reshma Saujani called “Brave, Not Perfect”. And, you know, all of those sorts of things. So it is social programming. I don't think either men or women are born thinking these things, right? But society teaches us that these are the tried and true methods of behaving. And so what I'm hearing you talk about is being authentically you, which some people are afraid to do. And then I hear you approaching things with confidence. You said, look, I know what I'm capable of doing. And if other people don't think I'm capable of it just yet, I'll let them figure it out for themselves. What kinds of conversations do you have with people that would consider you a mentor, or a sponsor, where they don't necessarily show up with the same confidence that you did? It sounds like you grew up in an environment. where even though you grew up in a larger social environment, where we heard these messages, you grew up with a mom who was a role model for you and probably articulated some of these things to you. What are some of the conversations that you've had with people, male or female, who don't necessarily show up with the same kind of confidence and executive presence that you have?

Katya Jestin: I generally encourage my mentees to really confront and I hate all these buzzwordy, consultant-speak things like imposter syndrome or whatever, but the emperor has no clothes, or all of those things that we think about as kind of the metaphorical representation of how we feel. I really try to invite vulnerable discussions with my mentees and we have a lot of closed-door meetings about, you know, feeling like this is a safe space, my office. Come in, you know, I've got tissues, I've got whatever you need, you know, we could talk about whatever. But it's really about appreciating the fact that you're here for a reason. You're not here by accident. You didn't do well in law school and clerk for a federal judge, or whatever you did to get here. It's not an accident, and it's not a gift. No one gave you this opportunity. You earned it. And so take your seat. I have a picture behind me of Shirley Chisholm and it's a great picture of her. And she's wearing a skirt that has folding chairs all over the skirt. And it symbolizes, she used to say, if there isn't a seat at the table, I bring my own. And I just try to reinforce that there's a reason you're here and you're not, failure's not in your DNA. You wouldn't be here. So, you know, buck up and feel confident and be yourself.

Elise Holtzman: I know that in addition to you sharing advice and sharing your experience with people who are coming after you, let's say more junior to you, you said that you believe in mentoring through action, right? So the advice is fantastic and lots of people need it. And I have no doubt that the people you're mentoring get so much from hearing those words of advice. But what does that mean to you, this idea of mentoring through action and not just through offering words?

Katya Jestin: We have a women's forum. We have all sorts of different things like that where people can get together and talk about all these issues. And I think that's really important. But my focus really isn't on that stuff. I really try to focus on opportunities and looking for opportunities to help my female mentees get in front of clients, get the speaking role in court. And I'm very intentional about it. I really think about it. So when I'm handing out an opportunity on a case, or staffing a case, I very much try to help somebody kind of get to the next place they're trying to get to. So that's what I mean by action. I'm not a big sit-around-and-talk-about. I don't want to observe problems. I really, really don't. And one thing I learned when I was in the managing partner role was, if you're going to put something on my calendar to talk to me about a problem, come with a couple of solutions. Because problem observation is just not going to drive the bus forward. We're not going to get anywhere. So I'm all about solutions. And so I try to apply that ethic to my mentorship and hand out real opportunities as opposed to just words.

Elise Holtzman: Yes. So a couple of things there that I just want to point out, because I think these are such powerful things that you're doing and talking about. So one of them is this idea of people in a role like yours, people who have influence in the firm and have clients, right? They have juice. It's really what we could call sponsorship and not simply mentorship, right? Both of those are really important, but you're using your Rolodex, let's say and you're using your political capital to help other people achieve the goals that they want to achieve. That's what is so unique about sponsorship and that women and people of color, for example, didn't realize that they could potentially have access to. We didn't have a word for it until a number of years ago, when some books started getting written about it and people started talking about it. I think you deserve a lot of credit, I think, for doing that because a lot of people with influence are afraid to share it, in the sense that it might diminish their own cup. And I think that we know that that is really not what happens at all, right? Is that you wind up developing this group of really fantastic people, who are willing to run through walls for you, et cetera, right? You're not minimizing anybody's cup. It's like one plus one equals three. The other thing that you said that I think is really important and I think it's very important for people who are on their way up and maybe not already in significant leadership positions to hear, is this idea of coming to the table with solutions. At some point, this is actually a leadership skill. Right? In the beginning, you recognize problems, you're issue spotting, great. we teach young lawyers to issue spot. And you see the problem. But now, as you start to take on more important roles, or more complicated roles, which may just be from going from a junior associate to a mid-level associate, it doesn't have to come with a title, that leaders are looking for just what you said, Katya. Right? Don't just come to me with a problem. I'm not here to solve all of your problems for you. Part of your growth is learning to identify some solutions to problems.

Katya Jestin: That's right. And that was a lesson I learned early and it's really important. And going back to your cup analogy, that's kind of the micro example of the macro that we started with, is if you have fear and you're worried about losing land, you are going to make terrible decisions, period. Whether it's for an institution or for… whether it's for yourself and your own, you know, practice ecosystem or for an institution, you're going to make terrible, terrible decisions. You know, as I said earlier, credit really is infinite. And you find that you will actually grow the pie with your clients or whomever, when you try to expand it, when you invite people to join you. That's how relationships grow, whether it's the internal relationships of trust and, you know, being having great colleagues, or your relationships with your clients?

Elise Holtzman: In many ways, that's a modern way of looking at leadership and let's say rainmaking, as a good example of what goes on in law firms. Because we do know that in past times, you know, there were people with sharp elbows and you know, there's still some of those around and people with sharp elbows who may have a different approach to it. That being said, we know that the legal profession is evolving quickly in so many different ways. I mean, you know, a few months can go by and there's a big change. So it's evolving, particularly when it comes to expectations for leadership and culture and talent development. And I just came back from a conference of managing partners late last night. And these are the things that they're talking about, right? How are we growing the next generation of leaders at our firm? How are we making sure that this is the kind of culture that we want to operate in and that attracts the kinds of clients with whom we want to work? How are we developing our talent and making sure we retain these fantastic people in our organization? So you have very high standards. That's not a question, I know that you do. You wouldn't be at the firm that you're with or doing the kind of work you're doing, or in the leadership positions that you have occupied and that you continue to occupy, without those high standards. I think some lawyers think that if they embrace some of what younger generations are embracing, that somehow it's an either or game, that they have to give up standards, if they're going to adopt something new or try something new. So for you personally, just as a human being, but as a leader, how are you able to maintain those high standards and at the same time, adapt your leadership approach for a new generation, right? You did it so beautifully. I'm sure it was not easy at all, but you did it so beautifully throughout the pandemic. How do you continue to do that, you know, in the current landscape?

Katya Jestin: At the risk of sounding as old as I am.

Ellie Steinbrink: You and me both.

Katya Jestin: And, you know, I'm a mother of three, pretty much adult children. And, you know, I talk to them about this a lot. The thing I try to help solve for is, I think, narcissism. I worry, when people are too self-focused to really be institutionalists. And I think that happens. I think that's normal when you're growing up and you kind of are going through those growing pains in your 20s and whatever. I think trying to think about and I think this is where we go back to the importance of the teamwork piece, really trying to instill institutional values in the generation coming up, so that we can kind of try to chip away at and I don't know if it's social media or if it's COVID, I don't know what the cocktail of causes are, but that's just something I've observed. Not a lot. I mean, the associates here are amazing. But it's something I worry about and I talk to my kids about, because there is this very tendency on self-focus and this consumption with wellness and all of this stuff. And I'm not saying people should be unwell and I'm not saying people shouldn't take care of themselves and be healthy and fill their lives with joy. But I also, you know, people need to be good teammates and it's all about the team. And I learned that, I mean it when you're at the US Attorney's Office, if you're not a good team player, it's not going to work, it's just not going to work. It is so much ingrained in the way things work at US Attorney's Offices, it terms the way you try cases, investigate cases, work with the FBI, like if you are an individualist, it's just not going to work out for you, so those are great lessons. And if you haven't had the opportunity in your professional life to have them kind of beat into you, you have to learn them. And you have to realize that it's really important to think about your colleagues first. So, you know, if there's a broom and there's junk on the floor, sweep it up. I don't care if it's me, you know, the managing partner of the firm, or, you know, somebody, first year associate, you just have to instill those ethics into your younger colleagues, because for them, I think it's going to unlock their success in life and it's going to make them valued. And you are not going to be valued, if you don't value others and you don't think about, you know, the people on your team first. And so I really try to focus on those types of lessons, I guess, if you will, without, you know, sounding like an old grump. But I think it's really important.

Elise Holtzman: You mentioned this idea of teamwork. People should have wellness and joy, but teamwork is really important. And obviously, right, to your point, they're not mutually exclusive. You seem to be deriving tremendous wellness and joy from the teamwork that you exhibit and the people that you're developing and the teams that you've worked with. And so I think that's a really good lesson for people to remember and not just young people. I think we both know, I think we all know some people who have been around the block a few times more than others, who could remember that. Katya, there's some really great leadership lessons here and just personal growth lessons here. As we wrap up our time together today, I would like to ask you a question that I ask all of my guests at the end of the show. There's 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. When it comes to stepping with confidence into your own role as a leader, or developing leadership skills in others, what's a principle or piece of advice that may seem obvious to you, but you think is important for people to keep hearing?

Katya Jestin: I would say, do not be afraid to ask questions. I ask questions all the time. I ask what words mean. I don't care. If somebody thinks I'm stupid, because I don't know what a word means that somebody says in a conversation at work, that's fine. Always ask questions. That is how you learn and grow. And don't be afraid to raise your hand and ask what something means if you don't know what it means. You're not doing yourself a service by not doing that. You're not doing your clients a service. And it's just understanding that it's that confidence. You're smart. You're here for a reason. And there's no shame in asking a question and not understanding something, when you first hear it. So I ask lots of questions. I try to model that. I ask associates stuff all the time. And maybe internally they're thinking like, how does she not know that? That's fine. But I try to model it. I try to model that vulnerability, because I just want people to feel safe and kind of exercising it on their own, because it's just going to make them better lawyers.

Elise Holtzman: Yeah, love it. All right. Well, so much good stuff here for people to hear about today, Katya. Thank you so much for being here today. It's been really a pleasure speaking with you.

Katya Jestin: Thanks, Elise.

Elise Holtzman: And I'm going to thank our listeners for tuning in as well.

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