Episode 71: Ann Kappler
Executive Vice President and General Counsel at Prudential Financial
00:54:05
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Show Notes
Ann Kappler, Executive Vice President and General Counsel at Prudential Financial, sits down with host MC Sungaila to discuss her career journey from a law clerk at the U.S. Supreme Court to BigLaw and a key member of the executive leadership team at a Fortune 100 company.
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Ann Kappler
As executive vice president and general counsel at Prudential Financial, Ann Kappler is the head of Law, Compliance, Business Ethics and External Affairs and a member of the Executive Leadership Team. She was appointed in September 2020 after serving as the company’s deputy general counsel and head of External Affairs for six years. In that role, Kappler oversaw Prudential’s corporate legal functions, including M&A, litigation, regulatory law and corporate investigations. She also led the company’s public policy advocacy, managing all federal, state and international government affairs activities.
Prior to joining Prudential in 2009, Kappler was a partner at Wilmer Cutler Pickering Hale and Dorr in Washington, D.C., where she focused on emerging issues at the intersection of regulation, legislation and litigation. Her previous roles included litigation partner at Jenner & Block and general counsel at Fannie Mae.
Kappler serves on the boards of directors of the Pro Bono Partnership (treasurer) and the National Health Law Program (chair), and serves as program co-chair for the Georgetown Law Corporate Counsel Institute. She is a member of the Board of Visitors of the Dartmouth College Rockefeller Center for Public Policy. Kappler has served on the boards of the Washington Lawyers Committee for Civil Rights and Urban Affairs, Appleseed Foundation, and Global Rights, and was a longtime member of the board of trustees of the Lowell School in Washington, D.C., where she served as chair. She has earned several awards such as 2018 Executive Women of New Jersey Policymakers honoree and was recognized on NJBIZ ’s 2021 Law Power 50 list. She is a frequent speaker on topics such as legal and compliance best practices and diversity.
Kappler graduated from Dartmouth College, magna cum laude, and received her law degree from New York University School of Law, where she was editor-in-chief of the Law Review. She clerked for Judge Abner Mikva of the U.S. Court of Appeals for the D.C. Circuit and U.S. Supreme Court Associate Justice Harry Blackmun.
Transcript
I'm very pleased to have join us in the show, Ann Kappler, the General Counsel of Prudential Financial. Welcome, Ann.
Thank you very much. I’m glad to be here.
Thank you so much for being here. You have in your background something close to my heart in terms of appellate litigation and being an appellate lawyer also. You had a wonderful journey in-house moving internally up to the general counsel position so I thought that journey would be of interest to those who might be considering going in-house. Also, what do you need to consider in moving towards the general counsel role and what does that role include? That will be very informative for those who are reading but first, I wanted to start with how you decided that you wanted to become a lawyer or go to law school, to begin with. What was the spark that caused you to want to do that?
The spark was I realized I wasn't going to be an actress because that's what I wanted to be or thought when I came out of college. I got a job in New York as a paralegal. I had no idea what a paralegal was but I had a friend whose sister had a job as a paralegal at Skadden, Arps. This was in the very early ‘80s. He said, “If you went to a good school, they'll hire you.” I thought, “That sounds better than waiting tables.” That was my introduction to the law.
After four years of being a paralegal, I realized I'm not going to be an actress so I thought I'll go to law school. My plan still was to stay in the arts. I was going to do a Law degree and a Master of Fine Arts and Arts Administration but then I fell in love with the law when I went to law school. I love the analytical thinking, problem-solving and advocacy part of it. I found it incredibly intellectual and stimulating. That was the beginning of my journey and I've been on it ever since.
What caused you to think you're not going to be an actress? Whether it was just too tough a road or life or you weren't committed enough to it?
It’s all of the above, to tell you the truth. Frankly, I was too ambitious to give it what's supposed to be a seven-year try. I can't wait for that. It's very different to be cast in roles when you're in college than it is to be in New York with a huge pond and you're only a little fish.
In New York, the caliber of people, even in the category of extras, the chorus or something like that is amazing and how many people are there. It's very competitive. I had a similar experience. Originally, when I was younger, I thought I wanted to be a poet. My particular reason why I didn't end up doing that was I had a vision of myself starving in a garret. I thought I probably should do something where you could get a roof over your head and things like that. As it turns out, I'm a professional writer of the persuasive type as an appellate lawyer so it all fits together.
That's how I feel. I’m still in the problem-solving. I very often have an audience so you need to persuade. There are skillsets there that you bring to bear.
That's so interesting that you came into the law sideways in that regard because you're like, “Paralegal sounds good while I'm pursuing the acting.” It then turns out, “I liked the analytical side, the rigor of the analysis and all of that.” Some people have the desire from the very beginning when they're quite young to enter the law and others discover it along the way but that's great that you love the law itself and you enjoyed that.
It's interesting because part of it is if you come up from a family who has lawyers or you've seen lawyers, then you understand what the practice is. I didn't come from a family of lawyers.
I didn't have any either. I had no idea what the beast was or what I was going into. It can be so different. They're very different even as you've seen in your career between working in a law firm and working in-house. Those are very different roles that you're playing and enjoyed that role in-house. How is that different for you? What about that appeals to you?
It’s not that I didn't love working in a law firm because I did. I love being part of a shared enterprise where you're all doing the law and frankly, you're a revenue generator, not just a cost center, which is what you are. It’s also a different kind of pressure. There are two pieces of it that I enjoy or probably more than that but the ones that distinguish it from being in a law firm. One is that you're part of a business. You're not only doing the legal part. You're asked to bring much more for the bear than just your legal acumen, especially in the companies I've worked in. They have this expectation. You're bringing all of your gray matter, judgment and experience to bear. I liked that part of it. It’s understanding where the law fits and it can advance the company's strategic objectives.
The second part is I found much to my surprise that I liked the talent management part of it and developing people, thinking about how to put effective teams together and how you motivate people. It's not as if there isn't a piece of that when you're in a law firm but it isn't as big a piece. Most law firms are often almost like entrepreneurial pockets that are brought together as opposed to thinking about it as a shared enterprise. Both of those things, that part of satisfaction and what I like out of a job, I found uniquely offered by working in-house.
That talent management piece is an interesting one. That's one that Joanne Caruso mentioned. It's also one of Sheila Murphy’s favorite things who used to be in-house at a large company. Having that role, being responsible for developing talent and seeing people grow and how rewarding that was.
You not only can feel but you can help people with their development. Whether they stay in the law or don't stay in the law, whether they stay in your company or not stay in your company, it's very satisfying if you help.
I get a little bit of that with my associates and law students because I also teach in a law school clinic. For me, when I see the students graduate and they have their appellate argument and all of this and you see how much they've grown over that year, you're like, “I contributed to this person's expansion of their skills.” Whatever they end up doing next is great but there are some good building blocks and I may have played some small role in those. It's nice to see it.
Young folks trying to think through how to make decisions, what's possible, and what's not, it's very helpful to just talk to many people.
We have a 1L program. We bring in a small group of students who are 1Ls and they spend their summer with us. I also do a fair amount of stuff with my college and talk to women in particular who are trying to navigate their careers. Being on the outside, you're not necessarily right next to them so it's a safe space for them to have conversations and explore. I first was asked, “How did you do it with your career? What do you have to offer to somebody else's, your narrow path or whatever it was?”
Giving advice to people or young folks who are trying to think through how to make decisions, what's possible and what's not is very helpful. What I urge people is to talk to lots of people about why they took it, what worked, what didn't work and what you should ask yourself, all those things. I wish somebody had done it for me when I was in college because I had one idea with no plan B.
One of the things about this show is that as you're moving along, it’s like this mosaic. You can't tell how all these pieces fit together that they make sense. When you look back at it, you say, “Yes, it makes sense now. All of those different pieces were necessary to build the skills to where I am. This is where I'm at because it's a culmination of everything,” but along the path, it's way muddier.
Sometimes you ask questions like, “It would be helpful to talk to people or be more intentional about things but sometimes we're not.” I hope that that's one of the things too of the show that people will be able to maybe get different nuggets from different people in terms of how they've thought about their career, whether it's thinking about asking people questions about how they did things if they're interested in that position or even if they just respect someone like, “How did this happen? How did you get to where you are?”
Also, inspire them to think outside the box a little bit more in terms of not having only one path. There are a lot of paths, things to do for a law degree, ways to lead and different roles to play in that regard. You didn't ask questions and you wish you had. Are there particular things that you're like, “If I were starting in law school or my legal career, I would do X?” Is there something that you have in mind?
I had an assumption that I was going to be a litigator because I had been a paralegal for the litigation group. I liked the advocacy part of it. I made a conscious decision in my 2L to go to a law firm where I could do some transactional work so I didn't feel that I shut that door but I didn't even realize I'd chosen a firm that had a very narrow transactional practice. Even though I had exposure, paralegal to transactional lawyers ask, “What is it like? What do you like about the job?” It's not as if I regret anything I've done but the question is, “Were there other things I would have liked to have done?”
I don't know about you but I’m assuming when you were in law school, there's a path you take and if you're doing well, you get on the board. You should apply for a clerkship and then go with a big firm. That's what you should think about. There are many other paths. There weren't a whole lot of clinics when I was there although in law school, I wished I had done some but I did not, to have some practical experience and understand what it is to have a client you're working with. I didn't get that until after my clerkships. Some of the most meaningful were through pro bono work, which frankly I could have gotten as doing clinic work. It would have been the same kind of work. It’s those kinds of things.
As you were pointing out, there are many paths to go down. My advice to anybody is if the door looks like it's cracking open, open it up and see what it looks like. Don't be afraid to do it. There's nothing that's a big risk and there is certainly nothing that's going to slam behind you and you can't take another tick or tack. Don't have assumptions going into things about what success looks like or what's going to be satisfying for you. Be open to the experience and open to trying things.
You are right about the path. When you've done this and law school says, “These are the next things to do, the clerkships or whatever it is.” Also, private firms or maybe the government but that's it. Having more clinics is helpful. There weren't that many when I was in school and certainly there weren't any appellate clinics. They were just getting started. Now, there are so many opportunities and many schools require at least one clinic before graduation. That's a good way of trying something that you may not have thought about at all and seeing what it's like to represent someone and do a different kind of law. If you want to do public interest or something else, maybe there’s some opportunity that you haven't seen before.
I also think that other than litigation, it's hard to figure out what else there is to do in law school because that seems to be where everybody goes to the firm and litigation. It’s because you're reading cases, discussing them and doing moot court but there's not a lot of transactional or negotiating. There was only one negotiation and mediation clinic that had started that class that I had taken in law school. Other than that, it isn't oriented towards that. If you have opportunities for other things to explore to see what's out there, take it so you can see. Maybe it's something you like to do that you never knew existed or you would like.
That's true that sometimes your skills in different areas translate to new practice areas that you never would have imagined were as they are. Tina Byrd who sits on the LA Superior Court, for example, in an interview for the show said, “I had all this experience as a US Attorney and a prosecutor doing financial crimes and things like that so I understood my way around a spreadsheet. I then get on the court and I'm appointed to family law. It never occurred to me that financial knowledge is super important because you're looking at spreadsheets, dividing money and doing accounting.” She's like, “It translated well to this area of the law,” but if you'd asked me, I would've said, “No, please. Maybe not that part of the calendar or something else because I don't know anything about it.” You never know if there's a good fit.
There’s going to be a temptation early on in your career and feel like, “I've got to be an X and learn X and Y.” I purposely chose a firm. The first firm I went to is Jenner & Block for my clerkships where I was doing litigation. I wanted to concentrate on appellate litigation but I didn't want to be locked into a practice group. Everybody's a general litigator, which I always think of as the best way to be a renaissance person in the world. You had to learn the new business, a new area of law or whatever it was you were working into.
Eventually, with your clients or the way the firm is structured, you end up concentrating. I ended up concentrating on financial services. If you had told me that's where I’ll end up, I would have said, “No way.” I avoided anything that looked like economics but I was an undergraduate. I loved the way of thinking about it and where it sat in society and the role it plays in societies. It’s why I liked both in-house jobs I've had at Fannie Mae and then at Prudential.
It’s the role that it plays for individuals and the purpose-driven aspect of it. It's important for people to understand, to your point, what have you learned? What are you good at? Also, what do you like? Do you like the advocacy part, writing and financial problem-solving? What do you like that you want to get out of a job that is going to make it more satisfying for you?
I think of it as three intersecting circles which are your skills. What are you naturally good at that you could get more training to be even better at and then where can you apply that? The other part is the meaning. What kind of purpose or meaning, which you alluded to when you're at Fannie Mae and your current role does all that fit together or am I orienting those skills in a way that's meaningful to me or whatever that is?
You feel good about it. You want to get up everybody, go and put your energy in there.
I have a couple of questions. I'll start with mentors and sponsors in terms both in the law firm setting but also in-house. I assume that you've had some of those and probably served as those for others also. Do you have any suggestions for those who are newer? Everybody always says, “You need a mentor or sponsor.” People will start looking around and going, “What is that? How does that work?”
I was very fortunate in my first law firm where I had two partners in particular. They were former Supreme Court clerks. They'd helped recruit me into the practice, looked for opportunities and advocated for me. They helped me when I was struggling with how to work through the law firm. I was quite fortunate there. When I left the firm to go in-house at Fannie Mae, one of the reasons I left is because I wanted to work for the woman who was then the General Counsel of Fannie Mae, Stasia Kelly.
It would have been the first time I had somebody who was a woman as my direct boss I could work with. Jamie Gorelick was the Vice Chair at the time. I also wanted to have an opportunity to work with her because I knew people had worked with her when she was working for Janet Reno as Deputy Attorney General. They are amazing people and mentors.
Both of them have been lifelong mentors to me. Since then, beyond advice and behind the scenes, they’re mentioning me to other people. They will tell me that but I have a sense that it goes on. They were meaningful to me and helped me figure out where I want to go, get opportunities and see where my strengths were and where things were that I needed to work on.
That's an interesting decision in terms of not only the organization having some meaning and purpose for you but also saying, “There are some leaders at these places that I want the opportunity to learn from and work with.” That's a unique mindset. I haven't heard anyone say that specifically yet.
To me, that was one of the biggest draws. I never thought about going in-house. I was on this track and I would've loved frankly someday to become a judge but I didn't live my early life thinking in those terms. It might not work out but there was an opportunity and I was tapped. Through my conversations, I thought, “I need to try this.” I knew nothing about what it would be like to be in-house. I didn't know the business, whether it was a mortgage or securitization business. The only thing I knew about it was my mortgage. It was a great learning experience.
I will tell you what I've found. I liked to be challenged and be in a learning environment where I'm constantly learning. That was a big leap, especially because Stasia Kelly left seven weeks after I was there to go and be a General Counsel at Sears. I then became Acting General Counsel, talking about drinking from a fire hose. There were lots of learning opportunities.
I wanted to also talk a little bit about your Supreme Court clerkship because federal clerkships are special in themselves but clerking on the Supreme Court is pretty neat. How do you feel that may have impacted what you thought you might do next or even that relationship with your justice and the clerking community that comes out of that?
I clerked in '87 and '88, which was the year after Justice Powell retired. That summer was when Judge Bork had his hearings and people recalled. The court had eight justices for half of the term and then Justice Kennedy came on. You had always this risk that they would have cases that were divided by having an equally divided court. Like in any clerkship, you learn to be a quick study because you get so much to figure out what's important and what's not.
It’s incredibly valuable and I am thankful that both of my clerkships were in courts where all of the chambers were together. We weren't isolated in some ways like the DC Circuit, which meant you had a body of clerks that you could bounce ideas off of and talk through problems. It was fabulous. I knew that's an environment I wanted to replicate in terms of what my practice would look like.
I knew by the time I came out of there that I surely want to do the appellate practice. That's what I'd like. I like thinking about not just your good argument but what are the arguments going to resonate with the judge you're talking to, which is one of the biggest learnings. It is a lot of justice’s general strategic thinking. If you're a negotiator, it’s important in life. It's a good thing to learn.
On the appellate level, there isn't just one judge that you're persuading either. It's the collection of judges who are on the panel, their interactions and persuasion with each other and things like that. That's all part of it. There are lots of layers to it.
I enjoyed the strategy part of it.
There are extra layers of strategies. I can imagine clerking on the Supreme Court and not thinking, “Appellate work would be cool.”
The majority seem to go off to become professors.
There are a lot of academics from that setting.
I feel as if I had anything to teach. I didn't feel as if I had enough experience to teach anybody so I went off to practice.
I love that you were drawn to particular people for their leadership and what you might learn from them. That's a great takeaway for people in terms of thinking about where they might go next or reasons to move to a different position.
It is important to have that mindset to be in a teaching mode even when it doesn't feel like you're directly teaching.
That has been important to me in my career when I've made career moves. When I left Fannie Mae and went back to a law firm, I went to a practice where I knew I could learn from the partners I'd be working with. I went to WilmerHale for a couple of years and then came back in with Prudential. First of all, I knew I was going to learn a lot from the environment and the company. All the lawyers that were in the corporate center are going to report to me and I report up to the general counsel.
It's the relationship with the general counsel and there is a woman, Susan Blount, whom I knew I could learn a lot from. Who is the management you're going to work with? Can you learn from them? Can you learn from the folks who are in the senior management that you're going to be partnering with? At least from my perspective, if I'm in a place where it's stagnant, I don't think I give my best in that environment, to be honest.
I made one particular move in my career. When I decided to focus on appellate law, I said I'm going to go somewhere where people know it well. I want to be trained by some of the best lawyers. I don't want to be the only 1 or 1 of 2 or something like that. From that clerkship thing too, I like a group where we can brainstorm and work together on things. I never thought of it that way but there was one choice where I made that decision in part based on who I could learn from.
It's a good takeaway for people because that also is more of business-minded decision-making. I don't know that necessarily people within law firms think that way or law school trains us that way to think about how can I grow within the team of people that I'm working with, as opposed to what kind of work I'm going to be doing and how I can learn to do more complex work.
It's important if you're going into a law firm to understand what they do to train you to build your skillsets and who are the people you're going to be interacting with. As you get further along in your career, it is constantly a good thing to remind yourself that you are teaching all the time by your behavior. People are learning either good things or bad things. Having that mindset of you're in a teaching mode even when it doesn't feel like you're fully teaching is important.
It's so true. You think about it in families too. The kids emulate whatever they see you doing. You're like, “I do that. I need to change that.” Some of what people have been concerned about during the pandemic is that you're not around each other as much so you can't have that. If you ask someone, “How do you do X,” if they've done X for a long time, they may forget certain steps in the process because they know it and they don't think about telling anyone to do that. Watching someone do something and having someone explain what they do is very different. You get more soak up stuff by being around people and watching them do what they do.
That's true too. We've been virtually entirely remote. We're coming back to the office and some people come back in. Although, for the lawyers in particular and the compliance people, there hasn't been a huge need. With us, we're remote but weren't all centered in one place. What I have found is it's a great equalizer. Everybody's in the same size box on the screen. It can be more inclusive than what’s necessarily the case outside of that setting. In that sense, if you're less experienced or you're newer to the environment, there's a huge opportunity to dive in because you don't have to wait to be asked. You're part of the conversation right away. I agree with you that you need to lose some of that practicum part of it.
It's hard to figure out how to replicate that and be conscious of it. It’s when you're like, “I explained this to someone.” You're like, “There may have been something you didn't explain that you do.” To be conscious about that to say, “Maybe I missed some part of this.” I need to go back and say, “Also, this. You don’t think about this part.”
You know how I translate that and see that in the in-house setting if there's somebody and you're trying to problem solve, try to urge them to get them to explain how they thought through a problem. You're like, “Where did you start? What facts did you think were important? What did you bring to bear? How do you think about its impact on the business?” You're not just telling them what to do. You're coaching them through the thought process to get where you need to get and give whatever advice you're going to give to the client.
The process part is true. That's how I've done it too in terms of thinking, “I see this answer.” Then say, “When you did this, did you also look here and think about this? Tell me what you were thinking.” There might be a missing piece. You’re like, “You might want to go back and think about this too.” There is a way. You only need to be more intentional about it.
That's far more effective in training a person to be the best they can do than telling them no.
There are some benefits to it as well but it requires more openness to discuss and have a dialogue, instead of thinking that someone's going to watch you do things. They'll soak it up and it'll all come out. You remained remote. It's interesting in terms of the inclusion piece that you mentioned that people are either more comfortable speaking up or you get a wider variety of insights from a broader amount of people in meetings.
To your point, you do have to be intentional about it because you're not bumping into people and pulling people together on the fly. I miss that part. I'm looking forward to being back in the office.
Some things are serendipitous that end up working out well for the client and business. You’re discussing some aspect of something they're working on like, “I know something about that. Here's something you should consider.” Maybe no one would know that they should have asked you about that. Also, there's more willingness to have more hybrid of people being in and outside the office.
I agree. Although I'll tell you, in our office, we're not well-practiced at it. Who's talking to whom? Who's very big on the screen. Everybody recognized that's the world we're going into and we have to get better. It's a skillset we will have to develop.
People got comfortable with the other ways of operating and it should be comfortable to integrate it with in-person ways also. It is a way to help people whether you need to concentrate on a piece of work for a particular day and you're better off being at home in the office, which can be the case or whether it's like, “I don't have to commute that day, which would make it easier for me to take care of my parents or do something else with the family.” That's helpful. You then want to continue to support people in being able to do that.
For things like this with our conversation and journal engagement, I've been able to be more engaged in a broader range of things than I ever could've done if I were dependent upon having to travel, stay someplace and be offline from work for days. It makes a huge difference.
I was wondering about that, whether it's been with the new in-person conferences happening again, which is nice. It's very refreshing to see people and do that but a lot of people have rethought that in terms of if that was the only way to see people or to engage externally, then you would go to a lot more conferences but if there are other options to have an in-person meeting with people once a year or every other year and then have something else in between, then you might do that.
What we're trying to move towards internally with our teams is to be very intentional about when you're bringing people together and what's the purpose for bringing everybody together but otherwise be much more flexible in terms of, to your point, a hybrid if not fully, even if not remote.
I've seen some companies having like, “We might breathe the hybrid or remote but then we're going to come together for esprit de corps meeting for a week in one particular location. I've seen that too. I don't know how that's working but it's an interesting idea to say, “We're going to be intentional about this point in time when everyone's going to be together.” When people are working hybrid, it can be hard to have the stars aligned when everybody's in the office. That's one of the things coming in like, “Bob's not here and I want to talk to him. He's coming on Thursday and it's Wednesday.”
That also becomes a vicious circle. People don't want to come in because when they go in, no one's in but then they don't go in. To be able to do that, you do have to be intentional about it. That's what we're finding.
It’s because you go and you're like, “Why did I come in? There are only five people. What was I doing here? 5 plus I is 6. It's not the people I wanted to talk to.” You may need to organize that a little bit so people come in on the same day. What advice would you give to those who are considering in-house or let's say their in-house and they'd say, “One day I'd like to be general counsel somewhere?”
Let's start with the latter one. If you're thinking that you might be an in-house general counsel, first of all, think about what do you like about the job you want to do? What I've found is the more you get to be more senior, the less it feels like you're practicing law sometimes. For a management job, you've got to exercise your judgment on the hot legal issues that you got to be able to discern when you need to get involved and when you don't need to get involved. In general, you shouldn't be involved unless you're in a very small shop. You shouldn't be involved in a whole lot of other things. A lot of what you're doing is working with senior management wearing your legal hat. You're advising on that but you're also a part of senior management deciding business-related issues.
You got to run your department and know how to run a budget. There's a lot that feels very different than practicing law if you're not in a more senior position. At least my experience has been in and the way we've been thinking about it with our teams too is the more experience you can get inside whatever company you're working on so that you're not feeling that you’re not just going up a ladder that looks like it's going like this, take advantage of lateral moves if you can get it so you can learn a new part of the business or a different part of a law or get exposure to different groups of management.
Broadening your experience is very important. Leadership skills are paramount. You can't advance if you don't have leadership skills. Also, honing in on those and taking opportunities for when can you learn them and figuring out the conversation we were having before, looking for people who you think are good leaders, are you recognized as good leaders in the organization with and how do you learn from them? All of those things are important in terms of how you do that and being intellectually curious. Express that curiosity that includes keeping up on things but also asking questions and understanding the business. All those things are important in-house.
I've seen the first part that you're talking about in terms of a lot of lateral moves within the company that even business is facing different business units so that you have a much broader base of understanding of the company itself and the business issues that it's facing. Also, the objectives that the different aspects of the company have. That means that more people across the company in leadership positions who have heard of you wouldn't feel uncomfortable working with you at a strategic level.
I've seen that. I don't think that a lot of lawyers think of that necessarily because it's getting to know the organization and the people in the organization kind of question. That's helpful but then also I've seen where if you can't get it, people will move laterally. They'll move to another company in-house because they said, “I want more leadership training or whatever it is but I'm not able to find that same lateral move within the company that I'm at.”
Keeping yourself open to that is important to do. I hate losing people, especially people who we think have high potential and are talented but there's only one general counsel. There aren't always opportunities and often, you got to wait for your turn. I take pride. If we’ve developed somebody who we think is strong and some other company finds them to be attractive and they can successfully move there, I wouldn't like it but everybody does that.
You should say, “This is great. Here’s somebody who's acknowledged as being a leader and having opportunities we couldn't afford them.” That switch from being in a law firm and going in-house. Some people can do that very easily and it's an easy transition. For some people, it's a rough transition. Frankly, some people find that they don't like it. They want to go back to law. You are part of the business and they're your client. You’re in a service organization that is serving your client.
You've got to persuade them to do the right thing. You can't say, “I'm an outside counsel. This is what I said. Do it. This is what I said and then you don't talk to me,” because you don't know whether they did it or not. You're part of the organization and invest in it. You have to know the business to be effective. That can feel very different than what it's like to be in a law firm in terms of the role that the lawyer plays and what you're doing a lot of the time.
In terms of the term persuasion, there's an influence and persuasion component to it that is way more subtle than an outside counsel has. You say, “We've done the analysis. Here's it. This is the best way to go or how legally we think things should proceed.” There are a lot more considerations to the business itself about how it does proceed. When you're internal, you're not the only one that's making that decision. You have to talk to others and stand up.
There are some other considerations we have to keep in mind. Also, when you're in a law firm, very often, you're dealing with an in-house lawyer. You're not dealing directly with the business. It’s not always true. There isn't that filter when you're in-house.
You have to have that conversation directly with the business folks who are saying, “No, we want to do X for a particular business reason.” I could see where some people would not feel comfortable with that.
“This is going to be too costly. We got to figure out some other way to do it. What's another alternative? I'm willing to take more risks to trade off the reward.” For some lawyers, that's an uncomfortable place to be and say, “I can give you guidance but in the end, it's a business judgment as to what risk you're going to take.”
Learn as much as possible about the company you're interested in. Learn from the lawyers in that environment.
That’s true but it’s the law rules like, “It allows one consideration.” The law is not as black and white in many cases so you're talking about a gradation of risks and other components. That is not something that you generally encounter as outside counsel. Oddly enough, on the appellate side, I see a fair amount of it because we're helping select cases like, “Is this the case you want to go to the mat for in terms of making law? Is not the rate case?” It's that strategy across cases, the whole battle instead of a particular war and then what is the overall goal not just legally but in terms of other aspects and for the company institutionally. We see a little window into that when we're counseling along those lines.
That's the best outside counsel, “Why does she walk you through that?” I can think of a broader transaction or matter.
That’s advice for people who are in-house and want to be general counsel. Do you have any tips or considerations for people? We've talked about a little bit whether there's anything beyond, “It's very different. Be aware of that.” If you would have to be from the outside to going in-house.
Learn as much as you can about the company you are interested in. Learn from the lawyers who are in the environment and what it's like. The role that a lawyer plays can be very different in different kinds of companies. If you're on a financial committee, we're not making widgets. We've got contracts and security. It's built on a legal construct and heavily regulated. Lawyers are fundamental to business operation.
That's not true in a lot of operations. You need to understand where you're going to sit and you are comfortable with that. Are you somebody that gets called up? Are you there at the table at the very beginning? Are you somebody who gets called when we're about to close the deal and we need you to check off on something?
I've always thought about the difference between outside counsel and in-house counsel and how you're integrated more into the business but you're right. What kind of business it is? What role the law plays for that business can inform what in-house legal role is or how soon you're called in to participate in the strategy. Are you okay with coming in at the end maybe or have things come to you and go, “We have a big mess. We need help,” instead of being proactive. That does matter on how integral that is to whatever the company does.
I have a son who works for Lockheed Martin. If you're an engineering shop, I can guarantee you that he doesn't deal with any lawyers. Their product development is all about the engineering product but if you're in a financial institution, the product is a regulated product that has to be legally sound right from the very beginning. It's understanding the role of the lawyer where it fits. Some of that is industry-specific or what the company's businesses. Some of it is like, “What's the culture of the company?”
Also, the cultural aspect of how they roll in terms of how they operate internally but also in terms of their level of risk too. Those are the component. They’re like, “No, we're good. We take a lot of risks and then mop it up later,” or whatever it is. It's a different perspective. Culture, which people would probably think of but also this more fundamental question of, “It's integrated into the business but what would that look like in terms of how integrated you are?” I'm like you. I would rather be at the table in the beginning in terms of strategizing and working things out if that makes sense or is necessary.
That is what's attractive to me.
I do have friends in-house. We're triaging a bunch of stuff. Fires come to us and we wish they had come earlier and then you have to change the culture towards people integrating legal into the decision-making earlier but still, that's different from what you're talking about. Even if you can adjust the culture in that regard to integrate the legal questions and the strategy earlier. If it still is inherent either because of regulations or the product itself, then it's still going to be different.
That's great advice because that's about a way of thinking about a question, which you can translate to a lot of different things. Thinking about this and you're like, “Let me look at this through a different lens.” I haven't heard even my friends who have gone in-house think about it that way or express that as one of their decision-making. I hope that's helpful to folks. It was interesting to me. I wanted to wrap up with a few rapid-fire questions. My lightning round questions are what I call them. Which talent would you most like to have but don't?
Jewelry making. There were great little workshops in college. I never took advantage of it. This is my bucket list for when I retire.
Particularly, what kinds of jewelry?
It’s not high-end jewelry.
I was like, “That could be a very expensive hobby.” That's what I was thinking. My mom does some of that too. She's self-taught in that regard. When she would travel, she would pick up various beads or things like that and then use those. Travel and those experiences are together in the design. She doesn't use super expensive things either but it's a fun thing to do. What is the trait you most deplore in yourself and then what is the trait you most deplore in others? It might be the same thing or different.
Deplore is a strong word. One thing I constantly disappoint myself in is that I am a procrastinator. I wish I were not such a procrastinator because it creates stress. For other people, I'd say lack of authenticity. I find it harder and harder to tolerate it, quite honestly.
Who are your favorite writers? They don't have to be legal writers.
I read a lot, although I'm not a repeat reader. If you put a gun to my head, I’d probably say somebody like Shakespeare although that feels like a cop-out. I like reading all different kinds of things.
Do you have a wide array of things? I’m that smorgasbord kind of reader. I like all different kinds of things, whether it's fiction or nonfiction. Anything where I'm learning something new or somebody is a good writer in different ways, that's what I enjoy. A well-turned phrase with a little different style is very enjoyable to read.
I love beautiful or interesting writing. It's different. I remember Wolf Hall and it's from a different perspective. I remember reading and it was extraordinary reading. I forget what the story is because it's all that great story about the Anne Boleyn period but the way it was written was interesting. If you'd stacked up my books, the highest stack is probably historical fiction.
I was wondering based on your comments, “Historical fiction, I'll bet.”
I lean heavily that way. It can be trashy. I'm fine with that too.
Who is your hero in real life?
I'm not sure what a hero is but I'd say who I admire. There are lots of women I admire. One is Maya Angelou. She's inspirational. She's been through so much in her life. To your point, she changed the way you think about things. That's on my list.
For what in your life do you feel most grateful?
My family. I have a hugely supportive family and I've learned a huge amount from them. I’ve grown because of them. I’m very grateful.
Given the choice of anyone in the world, who would you invite to a dinner party? It could be more than one person if you want to have a group.
One person would be Abraham Lincoln because he's such a fascinating person where he ended up. To your point, speech writing is extraordinary when you read it. What he navigated in terms of the country, the way he worked with a team of rivals but made them work, I’d love to hear him talk about the way he talks, thinks and moves.
The leadership aspect would be very interesting to you in terms of the group he had. He wanted people who had different perspectives.
It would challenge him.
I often think about how he and a few others are the right people at the right time in history for the country or whatever purpose. They rise to the particular occasion. We're grateful and lucky for them to have done that.
I can't help but think. Given the environment, we're operating in the United States where it feels like everybody has a rival with somebody else. We could use some of those skillsets.
I was thinking about that. If we can harness that moving in a certain direction as he did, that would be great when you have those skills because it doesn't seem that is going to end anytime soon so it would be nice if someone could harness that. The last question is what is your motto if you have one?
“Be kind to everyone because you don't know what they're going through.” I've been doing a lot of work on mental health and mental awareness. It's something that was instilled in me in a lot of ways. I realized from my parents, my mother in particular, that it doesn't matter how smart you are. If you're not kind, you're not worth much. It’s the way I was brought up. It's been brought home. Being in a leadership role, you got to care for your people. Have the empathy that enables you to be a good nonjudgmental listener.
Be kind to everyone because you don’t know what they’re going through.
I always find that's a fine line. I want people to be able to maintain their privacy. If they don't want to discuss things or if it's too much information, you also want to be sensitive to the point of, “You don't know what's going on in that person's family or whatever else is going on in their life at that point in time.” The best way to be sensitive to that is to be generally kind and try to be patient. If people go off the handle a little bit, you're like, “A lot of other things may have happened before that person walked in the door for work.”
It's not always easy. It takes a lot of practice but it's worthwhile.
It's a lifelong practice in terms of the patience part, for sure, but it's good to keep it in mind in that way so that you can always come back to it and say, “Am I doing this?” You may need to remind yourself of that. Thank you so very much, Ann, for joining the show and having this discussion. I learned a lot of different ways of thinking about decision-making and growth opportunities. You've had such a remarkable path yourself in leadership. I appreciate you joining this episode.
Thank you, MC. It was a delight talking to you. Frankly, your questions and our conversation helped me think through myself.
I learned a lot and I'm going to implement it in decision-making going forward. It made a difference to me. I appreciate it, Ann.
It’s great to talk with you.