Litigating on Your Own Behalf: How a Ground Breaker Breaks Career Barriers

Episode Notes

Transcript

Mic Robson:

Hello everyone and welcome to Litigation Radio. I’m your host Mic Robson. My background is in insurance litigation, but I’ve been in-house for many years. At this point, I am currently vice president at Skyward Specialty Insurance Company managing their national court bond practice, and I’m an expert in the litigation and fiduciary bonds that are often needed across the spectrum of litigation. On this show, we talk to the country’s top litigators and judges to stay abreast of developing trends in litigation and discover best practices and developing our careers and building a sustainable practice. If you’d like to stay up to date on future episodes, please be sure to subscribe to the podcast on your favorite podcasting app. This podcast is brought to you by the litigation section of the American Bar Association, which is where I make my home In the A BA. Not only is ABA Litigation Section an inviting and supportive community of highly talented litigators, it also provides litigators of all practice areas, the resources we need to be successful advocates for our clients.

You can learn more at ambar.org/litigation. Today’s guest is a lawyer who has not only made history, but has also fearlessly redefined herself throughout her career. Jill Wine-Banks first captured national attention is the only woman on the Watergate prosecution team where she famously cross-examined Rosemary Woods about the 18 and a half minute tape gap. If you’d like to read about it, you can get the full story in her book. The Watergate girl might fight for truth and justice against a criminal president, or you can get a briefer glimpse in her article in the winter 2025 anniversary edition of Litigation Journal, a publication of the a, a section of litigation. But being a Watergate special prosecutor was just the beginning for our intrepid guest. Since that time, she’s gone through numerous reinventions, leaving multiple shattered glass ceilings in her wake. Jill’s story is one of bold pivots resilience and a deep commitment to aligning work with values. In this episode, we talk about how she navigated those transitions and what it takes to break through inhibitions and expectations to carve a career path in the law that is both meaningful and satisfying, even if it’s not linear. Welcome, Jill.

Jill Wine-Banks:

Thank you very much. That’s a lovely introduction and I’m glad to get to know you.

Mic Robson:

Well, I’m just overjoyed that we can have you here today and in fairness, normally I would’ve provided more specifics in my opening bio, but your resume reads like something an auctioneer would need to call out and double time just to get through it all. Oh my

Jill Wine-Banks:

Gosh, you make me feel like Forrest Gump or one of those other characters who just keeps doing different things

Mic Robson:

And I mean maybe by the end of this episode we’ll have discovered that life is like a box of chocolates. Exactly. Well, I think we might get there. Let’s see. So by my count, you’ve worn at least 15 different hats and I’m going to try to go through them and you can correct me if I miss something. But you began as an organized crime prosecutor for the DOJ. Then you became the assistant assistant Watergate special Prosecutor. And I understand you were the only woman on the team, and were you the first, I mean, I think you were the first.

Jill Wine-Banks:

Well, if you’re the only, you have to be the first.

Mic Robson:

Well, you were the only one on the

Jill Wine-Banks:

Team. I dunno. There were other women lawyers in the Watergate prosecution staff, but none on the obstruction of Justice trial in the Courtroom or anywhere else.

Mic Robson:

And had a woman been named a special prosecutor previously?

Jill Wine-Banks:

Oh gosh, no. Of course not.

Mic Robson:

Okay. That was my thinking. So you were both the only woman on the team and the first to hold such a position,

Jill Wine-Banks:

I guess you’re right. I hadn’t thought of that.

Mic Robson:

And then after that, you went into private practice at Freed Frank Harris Shriver Andelman in DC until President Carter named you general counsel of the US Army. And again, you were the first woman to hold that position.

Jill Wine-Banks:

Yes.

Mic Robson:

After which you became a partner at General and Block where you handled litigation and immigration, and then you became Illinois’ First Solicitor General and then their first female Deputy Attorney General. Is that correct?

Jill Wine-Banks:

That’s all correct,

Mic Robson:

Yes. Incredible. After which, I mean we’re not even halfway done, right after which you became the executive VP and COO of the American Bar Association, and you were the first woman to hold that position. You transitioned from that to handling international business development for Motorola. Then you became vice president of Alliance Management for Maytag. And since then you’ve done a slew of things. You have been a consultant. You were CEO of a nonprofit that I believe you started called Winning Workplaces. You became Chief Officer of Career and Technical Education for Chicago Public Schools. That’s a fascinating pivot. I can’t wait to hear about it. You authored your autobiography, the Watergate Girl, and then you are the host of currently two. I believe previously it was three different podcasts or shows. You’ve got just the facts on YouTube. You do the hashtag Sisters-in-Law podcast and you used to do iGen politics, which was a very interesting premise. That was great.

Jill Wine-Banks:

It was great.

Mic Robson:

And now you’ve frequently serve as an M-S-N-B-C legal analyst and a commentator on radio and substack shows and other podcasts like this one. So you have really run the gamut in your career.

Jill Wine-Banks:

Yeah, and you forgot all the pre-law stuff. I mean, this is only since I became a lawyer. I took a year off of law school. My undergraduate degree is journalism, and that was my goal. I went to law school because I thought it would help me get a better job, a more hard news job if I had a law degree. And I thought, oh, this is law school is really a tough way to get to be a journalist. So I took a year leave of absence and worked as the assistant press and public relations director for an organization known as the Assembly of Captive European Nations, something that is quite in the news now given Russia’s attempt to recreate those captive nations in that role, it turns out that I actually probably worked for the CIA because in researching for my book, I found out that A CEN was actually funded by the CIA. So I don’t know, I’ll leave that to you to decide whether I worked for the CIA or not.

Mic Robson:

How fast, well, I’m going to go with yes because drama is fun. But what I find interesting is that it’s almost like you’ve come full circle. If your initial passion was journalism, you thought that law might be an interesting way to get into it, and you ended up effectively detouring into the law. And if you follow your trajectory, you have now in many ways ended up back in the journalistic world between the podcast, et cetera. So I think that’s really, really interesting and maybe we’ll come back to it because part of what I think I would love to discuss today and have as a through line is this idea of focusing on the things that you are passionate about and interested in. Many of us go into the law thinking it’s going to be one thing and end up doing something completely different, right? Or it just doesn’t look the way that we thought it would. You clearly don’t believe in sitting still. You follow your passion or the opportunities that are presented to you. So I’m curious, obviously you’ve had a very, very dynamic multi-layered career. What motivated your biggest career pivots?

Jill Wine-Banks:

I think you used the word earlier of opportunity and I think it’s just that I’m a risk taker. I hear about an opportunity, it sort of falls in my lap and I analyze would I like that job and could I do that job? Do I have the skills for it? And then I go like, okay. Yes. And I mean each one of my moves has been motivated by some different aspect. One of them, of course was because I moved from Chicago to Florida and then another because I moved back to Chicago after a year in Florida. But yeah, I mean I just have analyzed and one of the things I’ve learned along the way is that you should make an analysis of what are the things you like in your current job? What are the things you hate in your current job? What job would offer me the opportunity to maximize the things I like and to minimize the things I don’t like?

And I can give you some specifics as we go along on how I came to that conclusion, but I think that’s an important element is to what will I do when I get to the office in the morning? What are the actual things I will do and who will the people be that I work with? That’s very important to me is to and respect the people you work with, but it’s also the specific tasks you will perform. So I think those are things you have to consider in any potential job move and your own passions. What are you interested in?

Mic Robson:

What I think is interesting about what you just said is that you marry the unexpected, the opportunities or the challenges such as relocation, that many can see relocation as a challenge, right? An impediment to their career. And instead you take it as an opportunity to find something new. And what you do is you do it thoughtfully and you examine what it is that you want, what you’re interested in, and then use the opportunity, the change to implement that, to achieve that. Can you give us one concrete example of when you did that and how?

Jill Wine-Banks:

When I moved, my husband decided to move his business to Florida, and it was a joint decision. We had always wanted to live in Florida. He went to college there at FSU and we always loved hot weather, we loved fishing, we loved snorkeling, and so we thought it’d be a great place to retire to. And then one day we sort of said, if it’s going to be so great, why are we waiting till we’re old? Why don’t we go there now? And of course, for a lawyer, that means taking another bar exam. Florida does not have reciprocity. So that was a hurdle that we thought about, but I thought I could do that. It’s okay. And we moved to Florida. And in doing that, I talked to some search firms and one of them is the one who gave me the advice about think about what you like and what you don’t like in your past jobs.

I hated keeping 12 minute time segments, which meant private practice was less attractive, but it was sort of where I was heading when we moved there. And then because as I was looking, I started thinking about maybe now is the time for me to go back to my first love to journalism. So I prepared a resume that might help me get a journalism job. I got a headshot done that you would need for a television job. I was then exploring television, but I also thought I just was running the American Bar Association, and that’s like running a corporation. And I liked managing people. I liked managing budgets. I liked trying to figure out what products is the A offering, how do you manage the volunteers who are so crucial to the products of the A, B, A? And I thought maybe I would for the first time in my life, like a business job, I had never considered being an in-house console as you are, although I will address that later if you’re interested.

Because having gotten a business job at Motorola and working with the in-house lawyers, I realized how creative and exciting their roles are something that I would’ve never thought of when I was at a law firm. But being in-house can also be very exciting. It’s a question of being exposed to it and knowing what they do. But in any event, I prepared two different resumes. One to focus on my management skills. I had managed litigation teams, but that’s a paralegal and a couple of associates. That’s not a big deal. But then I had been the Deputy Attorney General and the solicitor general, and that was a large budget and a large staff. So although it’s obviously public service, it is still the management. And so I was able to, in my resume, highlight my management skills rather than the number of cases I had won, which was irrelevant for the job I was looking for.

And I started interviewing, and I did go on a corporate board while we still lived in Miami, but because we within a few months decided that we were moving back to Chicago, I did not take theBar exam. And so I did volunteer things in that year, but it only confirmed my desire to look for a corporate job when we came back to Chicago, and I will say it took me a year to get that position because everyone kept seeing me as a lawyer, even though my resume was not focused on my legal background, everybody kept saying, would you like to be our general counsel? And I was like, no, that’s not what I want. And so I worked hard and finally got to the CEO of Motorola who could see how my background could work in a corporate setting, offered me this international business development job, which was, I can’t tell you how much fun it was.

I couldn’t believe they actually paid me to do this job and to travel around the world, learn different languages, learn different cultures, and how to do business in these different countries. My first assignment was Pakistan. You can imagine how difficult that is for a woman. I loved it. It was an absolutely great job. And so that’s one specific example of how I sort of came to the conclusion that I really didn’t want to go back to private practice. I loved my government jobs, but private practice for me was not as exciting. And I’m not just comparing it to Watergate because that would be an unfair comparison. Nothing could top that, although you mentioned the Chicago public school. And honestly, there are some things I accomplished there that I think are as exciting as anything I did at Watergate. And the Army, oh my God, the army was fantastic.

There’s so much going on now that’s of great interest to me because of my experience in the Pentagon. The meeting that happened today as we’re talking with over 800 top generals being brought in for a lecture is of great interest to me. And the subjects that were discussed and the emphasis on downplaying the role of women, something that I worked very hard in the Pentagon to improve by eliminating the Women’s Army Corps so that women became part of the regular army. And by the way, women do have to meet the physical requirements for any job they take in the military. If you want to be an infantryman, your physical requirements are different than if you want to be a drone operator, as you might imagine. And so I don’t know why he’s emphasizing the physical requirements and that they have to be the same as the men they are for any job that you

Mic Robson:

Take. Well, I’m guessing that this may be a topic for your YouTube show in the future.

Jill Wine-Banks:

Yes, it might be.

Mic Robson:

But just to bring it back for a moment to, I mean, in thinking about that, I am still struck by the fact that you studied law in order to become a journalist, and that now that is fully coming to realization how many decades later that your familiarity, for example, with the Pentagon because you served as lead counsel for the Army, gives you an insight that allows you to engage in journalism on the topic that you would not have been able to do otherwise.

Jill Wine-Banks:

Absolutely.

Mic Robson:

So it really feels a little bit like a fairytale to me. And we can all aspire, right? There’s one of the chocolates in the box of chocolates.

Jill Wine-Banks:

Well, it does show you that you should be willing to take on risk. When I got that offer, I had two other offers in the administration. One was at justice, obviously I would’ve been very comfortable there. I had worked there, I knew it. I would feel very comfortable. The other was in the White House and it had a great title and I thought I’d love it, except when I said, what would I do when I get to my desk? And I thought, I don’t like any of those tasks. And then I thought, well, the Pentagon, I wouldn’t recognize a general if I tripped on one. And honestly, that’s true. And by the way, Pete ETH was a major, and I’m sure that he is loving being able to summon generals. Now, of course, he does have a civilian equivalent as the secretary, a four star.

So he does equate to them now, but I’m sure he still feels like the major he really is. And you’re right, I think every experience opens another door for you. If you just think about what have I learned, what have I gained, what could I bring to another task? When I was offered the job at CPS, obviously I have no education background, but Arnie Duncan, who was the superintendent in Chicago, went on to be Secretary of Education in the Obama administration, said, I don’t need someone who’s an educator. I need someone who understands corporate, who can create training for people that the corporations would hire and could recruit corporations to support our programs. And that was something that I knew I could do. I loved doing it. I’m a graduate of the Chicago Public School, so I was delighted to be able to do something to improve them.

Mic Robson:

And that was the other thing that struck me when you were talking about reinventing yourself on your return. Well, when considering your move to Florida and then your return to Chicago is effectively, you decided after making an analysis of what it is that you like and don’t like, what you enjoy, what it is that you want to be doing, you litigated on your own behalf. Every job that you applied to where they were seeing you as a GC instead of in the way that you wanted them to see you, which is painted with a broader brush, you had to litigate, right? You had to advocate, maybe not, litigate is not the right word, advocate is the right word, but what we are as litigators is advocates, right? We use it in the very specific arena, but we are advocates. It’s what we trained to do. And all that you’re saying is if you can figure out what it is that you enjoy, advocate for yourself until you are successful, until you achieve your goal.

Jill Wine-Banks:

That is such a good point. I’m not sure I would’ve thought of it in those exact words, but it is really true. Some of the training that you get in law school and that you hone and improve as you practice are communication skills, advocacy skills. I mean, every law student takes moot court and you might think, ah, I never want to be in court. But you always are in some way trying to convince someone, whether it’s your client or the opposition to negotiate a contract. It doesn’t have to be in a Courtroom. I think the advocacy skills, the analytic skills help you everywhere. And you’re right, I did try to, you might say I was marketing myself in a new way, but yeah, I think the law school training I had, and when you mentioned reinventing myself, something popped into my head, which is I was and still am, although people don’t believe it, a shy girl.

That’s how I was raised. I wanted to be active on campus when I got to college and I thought, I’ll go for an interview, but I’m going to have to be sort of an outgoing dynamic person. And so I sort of put on that act, and when I got the position, I thought, well, they expect that’s who I am. I’m going to have to act that way. And so acting as if I was that person, to some extent, I became that person. And I only learned later in college, I read a book by Erwin Goffman called Presentation of Self in Everyday Life. And that’s a strategy is that we do actually present ourselves and we make a conscious decision of how we’re presenting ourselves. It’s certainly true for trial lawyers, how you present yourself to a jury so that they will trust you, respect you, believe you. And the same thing is true with a client. You have to show that you are in charge so that they will respect your opinions. But I think that this idea of actually taking on and presenting yourself in a certain way has benefited me greatly. So I have invented myself to be that person and then reinvent the jobs in which I use those skills.

Mic Robson:

Exactly. Acting as if and imagining yourself where you want to be can help you actually get there. It’s funny because we think of it as play acting. It’s easy to say, well, it’s not real and I’m just deluding myself. But it actually makes an enormous difference, and I’ve experienced that in my own life where if I’ve been insecure and I just can’t afford to be right, if I need to be the decision maker, then I cannot afford. I can be open to hearing other ideas. But you have to project confidence, especially in fairness, just especially when you’re walking into a room full of men and you are the only woman which in the insurance industry has happened to me. You have to project confidence.

Jill Wine-Banks:

Absolutely. And one of the other things you learn as a lawyer is to ask the right questions. And I think that’s one of the skills that has enabled me to go into an education environment where I know nothing or into the Pentagon where I know nothing, but I know how to ask the right questions and how to analyze the truth of the answers, and that enables me to get the facts that I need to proceed to make good decisions.

Mic Robson:

I think that actually touches on a really interesting point about the transferable skills of lawyers. And we were talking, you were just saying the ability to be analytical, to assess situations, come up with the right questions and ultimately think through solutions or at least options. Many lawyers and possibly litigators in particular because it is a very specific field, can feel trapped in their careers because they cannot think outside the very specific box that they landed in. So beyond the analysis, beyond the advocacy, what skills or qualities do you think are most transferable across different legal and non-legal roles, and how can litigators think about presenting those skills if they want to broaden their horizons and think outside the narrow box of,

Jill Wine-Banks:

That’s a tough question, but aside from the two skills that we’ve talked about, it’s the general analytic abilities, the general communication abilities that you get from law school. And that’s not the specific topics. It’s not like, okay, I know what query clause and frigate is. Never thought I’d be able to use that in any way after law school. But it is that you’ve learned a way of reading, thinking, analyzing and somewhat teamwork, working with other people is important. And you kind of learned that in your study groups, not official part of law school, but it’s an important part. I think that if you can analyze your own interests and think about what you like going back to what are the things I like in my current job? What are the things I don’t like? What are my passions? I’ve always been passionate about the news.

I have been a news junkie since I was, well, certainly since college. And that was one of the reasons that I was interested in being a journalist and covering hard news and discrimination back then meant that my male classmates were getting offers to do hard news. I was getting offers to be on the woman’s page, and I read all that stuff. I just didn’t want to report on it. I wanted to do trials or foreign affairs, or I’m not sure exactly what, I did not want to report on recipes and social events. So I knew that, and I needed something that would make me stand out in a way, which is, as I said again in college, I read a book by Anthony Lewis, who was a New York Times columnist called Gideon’s Trumpet, and I remembered on the back jacket of the book and had said he had gone to Harvard Law School.

And I thought, oh, well, if he went to Harvard Law School and is this great writer, then maybe that would help me. What I didn’t know is that he went on a Neiman Fellowship after winning a Pulitzer Prize. So it was not at all how he got to be a great writer, but it was part of what made me think that this is how I could make the transition to being taken seriously. I didn’t expect it to take, what, 50 or more years for that to happen. Again, I have always tried to open doors for other women, and I’m very glad that Alpha Brady is now the staff leader of the A BA. I’m sorry, I took like 30 years after I left for her to be the second woman, but I’m glad that she is. So I think it’s just a question of analyzing what you want to do and why you want to do it.

What are your real interests? And a lot of times lawyers do it because they want to make the most money they can, and you probably can make more money as a lawyer in private practice than you can, for example, in government. But I wanted litigation, which is why I went to DOJ because I knew that I’d be trying cases much faster there than I would in a law firm. And of course that was true. I also knew that at Justice, at any government job, if you stay too long, you get too senior to be hired by a law firm. And so I was almost at the five-year mark, not quite when I started thinking it might be time to leave, and then Watergate happened and I thought, well, maybe I can leave DOJ and go to the special prosecutor. And I knew it would not be I thought and correctly so that it would not be a long-term position and it wasn’t. One of the things that your listeners may be very interested in is we were appointed at the end of May of 73, so less than a year after the burglary of June of 72. The trial ended on January 1st, 1975. So we’re talking about just over a year, year and a half from investigation, grand jury tapes, hearing Supreme Court arguments, trial verdict, all in that time period. Think about how fast that was compared to what any case is taking nowadays. But that’s a diversion from your topic. Sorry.

Mic Robson:

I mean, it’s fascinating. We could be here for hours, but it is because I really want our listeners to be able to benefit from your experiences in following your dream, your truth, your passions, and creating the career path that you wanted for yourself. And you say it took this long to get back into journalism, but you weren’t necessarily focused on that when you made your career choices. You were simply, if I’m understanding correctly, sort of taking a moment to examine what it was you were enjoying and what it was you were not, and asking yourself what you wanted to do next that would allow you to do more of what you enjoyed.

Jill Wine-Banks:

Let me stop you for a second, because most of my pivots, as you call them, were someone came to me with an opportunity. I wasn’t looking, I was extraordinarily happy in the Attorney General’s office. It was a fabulous group of lawyers, great camaraderie. The Attorney General Neil Hardigan was fantastic. I really was enjoying myself when I got a request from a search firm to talk about being the chief operating officer of the American Power Association. I was not interested, but I was on the Committee for Minorities in the Practice of Law led by Dennis Archer, who later went on to be the president of the A BA. And before that had been a defense lawyer in one of my very first trials in the organized crime section. So someone that I knew and then I served on his committee, people on that committee said, look, they’ll never hire you.

You’re a girl. They will never hire you, but you might be able to make the search committee aware that there are lawyers who don’t really have a home in the A, BA. And as a government lawyer, I knew that that was true. So when I started on the interview process, I thought, well, okay, I can make that point. I’m happy where I am. I don’t want to go anywhere, but okay, I’ll do that and I’ll let them know that as a government lawyer, I never felt welcome in the A BA, and that if we look at the number of lawyers who are government lawyers, that’s a huge number that don’t have a home. And so that was really my goal, that some are civil rights lawyers, some are prosecutors, some are defense lawyers. That was my reason for doing it. And then after my first interview, the search firm said, well, they didn’t think you were really interested in the job, but they’re inviting you back because of your experience.

They like your resume, but they didn’t think your interview was very good. Well, that was a challenge to me. I decided that I was going to prepare as if it was a Supreme Court, I argument. And so for the second round of interview, I really prepared, I mean, I was almost disgusting in how well prepared I was. And the search firm said, you get the award for the most improved performance I’ve ever seen. And the next thing I knew I was a finalist. And then I talked to the Attorney General and said, what should I do? He said, well, you could really make a difference at the A BA. I would hate to lose you, but it might be a good move and it could be helpful to me to have you there. And so I went forward and lo and behold got the offer and the final interview was in San Francisco during the annual meeting and they said, and you’ll stay. And of course I had only packed for a one day interview, but Carol Bellows, who almost was the first woman president of the A BA, was a good friend and I had her pick up some clothes at my house so that I could stay. And she very nicely did. And that

Mic Robson:

Was how you should know that that was the part of the story I was most concerned about is like, wait, you had to stay for three days and wear the same suit.

Jill Wine-Banks:

Right, exactly. Exactly. And there was also a shop in the hotel where I also was able to buy another thing. But anyway, that was that. And my greatest gift, by the way, to the A BA was my gender block secretary as we then called them, but she’s way more than that. Amy Eggert came with me to the ags office and came with me to the A BA. And Amy is still at the A BA. Oh, wow. She’s been there since, well, I came in 19, I think 87, so she’s been there almost 40 years. And she’s fantastic.

Mic Robson:

It’s funny because what I’m hearing is actually something that reminds me of something I did when I first graduated law school I was working in, it was a new tech building, it was the tech boom. There were a lot of startups, and I just started conducting what I called in my own head, the elevator interviews because everyone was just moving into the building. Nobody knew each other. And I am naturally friendly and outgoing. So I would just start talking to people in elevators and asking them what they did and how they ended up doing it. And as a rule, I mean the only ones who were doing what they planned on doing were the

Jill Wine-Banks:

Lawyers, really

Mic Robson:

Everyone else, really everyone else landed. I mean, whether it was through a friend or an opportunity or someone they met at a party or an event, whatever it was, people had just sort of landed in different positions that led them to where they were. And that was a really interesting lesson for me. And I think it’s probably one of the reasons today, because I interviewed for the company that I originally interviewed with for a legal position in their claims department. I had been doing insurance litigation. It seemed like a natural sort of segue, and they said, you’re actually overqualified for the position we’re looking for, but would you be interested in something that isn’t strictly legal? And I said, tell me more about it. I asked myself honestly, the same questions you were asking yourself, which is, can I do the job? And the answer was a resounding yes.

And then what I like to do the job and something I discovered as you were saying before is that being in-house actually offers opportunities for creativity that I didn’t expect either. I love marketing, I love connecting with my agents, I love educating the lawyers that I educate because the area in which I work is just not a very well-known area. I didn’t know much about it before starting it, but I knew more than anybody else might have because I had actually litigated. So it was a wonderful transition, but it was because of those elevator interviews because I already had in my mind the idea that sometimes things land in your lap opportunities that you don’t expect sometimes arising just out of a conversation with someone. And you can either stay in your lane or you can try to think outside the box and take the risk.

Jill Wine-Banks:

Well, as I said, my decision to try to get a business operations job was a definite. We had moved to Florida. I had some time that I could think and I started analyzing what do I want to do? And realized that I really did not particularly want to do a law firm that I really liked operational roles. So that was a specific decision where I actually went looking. Most of them have been things that either through networking have fallen my lap. In fact, most of my jobs have some networking connection, and it’s one of those skills that I think people don’t think enough about. But I ended up at Motorola because one of my best friends introduced me to the CEO of Motorola. I ended up at CPS because one of my other best friends who was a corporate officer was meeting with Arne Duncan and learned about this opportunity. He was asking her did she know any corporate execs who might consider this? And she said, I thought you would really like this. And I thought about it and thought, yeah, I think I would really like this. And I was at a point in the job I was in where I had accomplished every goal I had set for myself, and I was ready to move from that. So the timing was great, but it was networking that made it.

Mic Robson:

Well, we are nearing the end of our time, and what I’d love to do, I want to ask you one last question that I’m hoping might tie up our conversation into a tidy little packet. And I’m also pleased with the question. I like it. It’s if you could create a pivot playbook for lawyers, what would the first three chapters be titled?

Jill Wine-Banks:

Well, let me tell you, that is the hardest question because I’m really bad at titles. And I can tell you when I was writing my book and the publisher suggested the title Watergate Girl, I said, absolutely not. No book is going to say, girl that has my name on it. And my editor said to me, what captures the era better than that? And I went, oh, that is really true and I now love the title. And I do think it captures the era because the book is not just a Watergate memoir, it is a capturing the era at a time when women were less than 4% of the legal profession. Thank heavens we’ve moved beyond that. So I’m really bad at titles, but I think we’ve covered some of the topics that would be in it, which is the analysis of what you like and don’t like, and you can make a list of those things that no one else will see.

So you don’t have to be embarrassed to write down. The search person said to me, one of the things I like best about my job is that I know when I call, I’ll be the first call that anyone returns. And that’s probably true. So if that’s important to you knowing that your calls are going to get answered, that’s a good career. So I think that’s important. Networking is definitely part of pivoting. And how do you create a pivot playbook is you have to develop a network, which means you also have to give back so that for everyone who helps you, you have to help someone else. So that’s an important thing. And then being creative and analyzing what are your skills and how could they apply in a different environment and developing courage to say, I’m willing to try that because I think I would enjoy it in every case I’ve been in.

Let’s see, I did make one career move that was bad. Let me see if I can think of a way to synthesize what I learned from that. Corporate culture matters, and it’s very hard to determine as an outsider what it’s going to really be like to work in a place, but it’s worth researching before you enter into a new position or a new corporation what the leadership and your colleagues will be like. So that is an important consideration too, is to do the analysis of what the opportunity is and what your specific tasks will be and whether you’ll performing those tasks.

Mic Robson:

And the one thing that I think we should add, because it has been a theme that has floated, I think on the surface of everything you’ve said, which is not to limit your aspirations to the things that it’s like you said, you had no idea what working in a corporate environment could be how interesting and diverse and creative it could be. You need to, and that’s part of networking as well, is talking to people about what they do and finding out what’s actually involved. Because you may discover something that you would never have considered.

Jill Wine-Banks:

Two other things. One is when you’re talking about asking other people in networking, you don’t want to go to someone and say, I want to brainstorm with you. You want to go to them prepared and say, I see that you’re on the corporate board of X company and I know that there’s a job there that I am interested in. Could you just introduce me to somebody? And people are happy to do a specific task rather than to help you define your life. I mean, obviously if it’s a good friend, that’s one thing. And the other thing is risk taking is an important element of this. You have to be willing to take a risk. You have to make a calculated risk. You want to analyze what the job would be and whether you are interested in the task that it would do, and whether you have the skills to perform those tasks, then it’s worth taking the risk.

Mic Robson:

Well, I think that litigators are risk takers. If anything, we are the risk takers of the legal profession. We have to analyze our strategies, take the risks in court. So I don’t think it’s a stretch to ask litigators to assess the risks and then wisely choose which risks they should take.

Jill Wine-Banks:

And litigators are skilled to go into a lot of, not just different jobs, but different careers. Obviously you can do different jobs as a litigator, whether it’s in-house law, firm, government, but you also can be much more than a litigator. And I loved litigation. I would never have traded all my trial experiences for anything. It was fantastic. But I’ve also loved being general counsel of the army and being career and technical education chief for Chicago public schools. And my corporate experience was fantastic. So I’ve had a great life. I really have enjoyed every single thing I’ve done.

Mic Robson:

Jill, are you telling me that your life has been like a box of chocolates?

Jill Wine-Banks:

Yes,

Mic Robson:

I am. We did it. We brought it back. So fantastic. Well, we are at the end of our time, and I know you have to run because you’re also recording an episode of your YouTube show, just the fact later today, which I understand you’ll be discussing the problems of the Comey indictment. So I’m looking forward to that. Do you have any last thought you want to leave our listeners with before you go

Jill Wine-Banks:

For it? Do it now. I’m working on a young adult book right now, and that’s sort of part of the advice I’m giving to young adults is to do it. You can do it. If I could do this an ordinary girl, then so can anybody else. It’s just taking the effort to do it and don’t procrastinate. Do it now.

Mic Robson:

Thank you. I’m inspired. I don’t know what I’m going to go do now, but I’m going to find something.

Jill Wine-Banks:

Well, you have to promise to let me know.

Mic Robson:

Maybe I’ll sing in a jazz club.

Jill Wine-Banks:

Oh, man. Fabulous.

Mic Robson:

Thank you so, so much for sharing your remarkable journey with us. And I am going to say we’ve touched on it, but I just want to take one more moment to recognize that you charted your own career path in many situations where you were the first woman ever to do so. Like we had counted before there was at least four positions you’ve held where you were the very first woman ever to hold them. So for me, to you, I just want to say thank you for defying the difficulties and the indignities that I know we’re inherent in that journey so that those of us coming after you do not have to,

Jill Wine-Banks:

Could we please have another hour to talk about sexual discrimination in litigation? We could, I’m sure, share a lot of stories about the things we have encountered that are demeaning and horrible. And unfortunately, I fear we’re going back to an old era again, let’s not give up the fight.

Mic Robson:

Lessons from history would be a wonderful topic for another conversation. So I’m going to take you up on that.

Jill Wine-Banks:

Great.

Mic Robson:

Thanks again for being with us, Jill. Thanks. Thanks to the litigation section, premier sponsor Roundtable group for sponsoring this podcast. Roundtable Group was an expert witness search and referral service with decades of experience and a comprehensive array of academic and industry relationships, as well as access to proprietary tools that further enhance the expert search capabilities of attorneys with no upfront fees. You only pay if you retain an expert referred by Roundtable Group. Learn [email protected]. And now it’s time for a quick tip from the A BA litigation section’s mental health and Wellness committee. I’d like to welcome Pilar Kraman to the podcast. Pilar is a partner with Young Conaway in Wilmington, Delaware, and we serve together as co-chair of the Women Advocate Committee several years back. She’s currently a member of the Mental Health and Wellness Committee and has dropped by to drop some knowledge. Welcome to the show, Pilar, what’s your quick tip?

Pilar Kraman:

Thanks. So I’m here to talk about using this time fall instead of waiting till January, waiting till a new calendar year. That fall, as you might remember, after decades of school in and of itself is a new year and it’s a good time to reflect on current goals and maybe even start on a new path or set a new goal. So I’m here to just give you tips to do that. So whether it’s a specific area of your life that you’d like to focus on, that you’d like to focus on, it could be personal growth, career advancement, exploring new hobbies, whatever the goal might be. Setting clear and achievable goals can help you stay motivated and on track and can be a powerful way to turn what might just be a dream into reality. And so here are just a few steps to help you set and achieve your goals.

First thing that you want to do is reflect on your current situation. So take some time to think about where you are in your life right now. What are your strengths and weaknesses? Are there areas of your life that you’re satisfied with, areas that could use improvement, something that you’ve always been wanting to do but never have taken that leap? Reflect on your current situation. It doesn’t have to be in writing. I think it’s a good thing to do to write it down, but it doesn’t necessarily need to be in writing. But I personally like to write down my reflections because it’s helpful to look back on that. And then once you’ve reflected on your current situation, identify what the goals might be. What do you want to achieve? They can be related to career, personal growth, your health, mental or physical, your relationships or any other area of your life.

But the key here is to, and you’ve probably heard this before, identify smart goals and smart being an acronym that stands for specific, measurable, achievable, relevant, and time bound. So identify what those smart goals are and then break ’em down. Once you’ve identified them, you want to break them down into smaller, manageable steps so that it can make it easier to track your progress and stay motivated. So for example, if your goal is to start running, maybe step one is to buy running shoes. Or step one might be to buy running shoes and then start walking more. That could be step one and step two. So breaking your goal down into smaller manageable steps will help you stay on track and then create an action plan. Develop a plan for how you’re going to achieve the goals. That can include specific steps that you need to take, but could also include resources you’re going to need, people you might need to talk to or might need to bring in to help you.

Do you need an accountability partner, for example? Or you might need somebody’s help to achieve a goal and set a timeline. I like to set intermediate timelines. I do that at work, and I do that in my personal life too. I find it helps to stay on track setting. I call them fake deadlines or invisible deadlines that can help you avoid procrastination and help you stay on track and help you stay motivated. And then next step would be to stay committed, keep track of your progress. I love a good tracker and celebrate achievements along the way. I, like most people these days, use an Outlook calendar to stay on track in my life. But when it comes to goals, like for me, I started taking guitar lessons in January. I use a paper planner every month to keep track of my practice, and that helps me stay motivated.

And you can celebrate your achievements along the way for hitting your micro goals. Celebrating achievements are important way to stay committed and stay motivated. And then if you encounter obstacles, don’t get discouraged. Instead, find ways to overcome them and keep moving forward and give yourself some grace. This month I have a trial, so I’m going to give myself some grace. If I don’t practice my guitar every day, I have a trial and I need to pay the bills. So giving yourself some grace and then consider engaging somebody else in the process so they can help hold you accountable. That can be a friend, a relative, a therapist, a business coach, whoever that might be, your kids, your spouse, whoever that might be in your life that can help you stay motivated and hold you accountable. And then finally, review and adjust regularly, review your goals and your progress.

And if necessary, you can adjust your goals or your action plan to ensure that you stay on track. Maybe you bit off more than you could chew. Maybe as you were moving along the path to becoming a runner, for example, you realized that you might want to tweak that goal a little bit, or maybe you don’t enjoy running as much as you thought you would, but you discovered something else that you like to do more. So ensure that your plan is serving you, whatever that is, and that the goal is serving you. So whatever you choose to reflect on in your life, now, it’s important to do this periodically and fall is a great time to do it. But the thing to keep in mind is that it’s never too late to make a change. The windshield on a car is bigger than the rear mirror for a good reason.

So keep looking forward and looking ahead. And to wrap up, I just want to share a quote that has always been impactful to me, reminding me that the progress is what matters, not any missteps that I might make along the way. And so if you fall down as you’re trying to achieve your goals, cut yourself some slack. And as the Dalai Lama said, there are only two days in the year that nothing can be done. One is called yesterday, the other is called tomorrow. Today is the right day to love, believe, do, and mostly to live

Mic Robson:

Pilar. Thank you so much for sharing that and for being on the show today. And that’s all the time we have. I’d love to hear your thoughts about today’s episode. And if you have comments or questions you’d like for me to answer on an upcoming show, you can contact me at m [email protected] or connect with me on LinkedIn. You can also connect with the ABA Litigation Section on those platforms as well. But as much as I’d love to connect with you online, nothing beats meeting you in person at one of our next litigation section events. If you’re looking for the energy and inspiration to follow in Jill’s footsteps, I’d encourage you to join us at the 2026 Women and Litigation Conference, which is taking place this February 11th through 13th in Jersey City, New Jersey. It’s one of my favorite a BA conferences, and I always leave feeling inspired and reinvigorated.

For more information, please visit events dot american bar.org and search for women in litigation. If you like the show, please help spread the word by sharing a link to this episode with a friend or through a post on social and invite others to join the community. If you want to leave a review over at Apple Podcasts or a quick rating at Spotify, that’s incredibly helpful as well. And finally, I want to quickly thanks some folks who make this show possible. Thanks, to Michelle Oberts, who’s on staff for the litigation section. Thanks. Also goes out to the co-chairs of Litigation Section’s, audio contact committee, Haley Maple and Michael Steger. Thank you to the audio professionals from Legal Talk Network, and of course, thank you for listening. See you next time.

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