In legal leadership, credibility is key. In this episode, we’ll discuss the importance of earning and maintaining influence. Lisa Keith, General Counsel for Steve Madden, emphasizes aligning legal counsel with your business’ goals, and how legal professionals can effectively take part in business decisions.
In legal leadership, credibility is key. In this episode, we’ll discuss the importance of earning and maintaining influence. Lisa Keith, General Counsel for Steve Madden, emphasizes aligning legal counsel with your business’ goals, and how legal professionals can effectively take part in business decisions. Tune in to gain practical advice on enhancing influence within your organization, balancing business and legal perspectives, and building crucial relationships with key stakeholders.
Steven Madden, Ltd. is globally recognized as a leading company in the fashion industry. What began as a modest $1100 investment in 1990 has developed into one of the most iconic brands in footwear.
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"I would say that you really need to pick your battles… I think you have to figure out the right advice to give within the confines of the business you work for and what is realistic, you know? And so I think if you come up with something that is palatable to the business. Then they will hopefully listen to you."
"I often try to think of my job as kind of like the moral and ethical center of the company. And I think to be a general counsel, you have to have a very strong sense of values… I'm not saying you have to be like a goody two shoes, but you have to kind of have a good sense of what you think is right and wrong and you have to let that guide you and your decision making. So sometimes it's not even about the legal, it's just about your instincts of morality."
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01:13 - Question of the Day
02:49 - Jim’s journey
06:47 - Lisa’s journey
10:31 - How to influence business
15:16 - GC/CEO relationships
25:54 - Acting with integrity
36:28 - Keep or redline?
41:14 - Find Lisa Keith on LinkedIn
41:54 - Final takeaways
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Find Jessica Nguyen on LinkedIn
Find Jim Shaughnessy on LinkedIn
More about Docusign
[00:00:00] Jessica: Hello, everyone. Welcome to In House. The podcast for in house legal by in house legal. I'm Jessica Nguyen,n, Deputy General Counsel at DocuSign. So this is an exciting episode y'all, because this is the very first time I'm hosting a podcast. So folks, go easy on me. Even though I'm a tad nervous, my nerves are eased because I have a wonderful co host today. My co host also happens to be a wonderful leader and my boss, Jim Shaughnessy, Chief Legal Officer of DocuSign. Hi Jim, thanks for joining me.
[00:00:37] Jim: Hello, Jessica.
[00:00:39] Jessica: How are you doing? Are you ready to podcast with me?
[00:00:41] Jim: I am, I am really ready. Uh, I have a confession. This is my first video podcast too. So we're a couple of rookies and, uh, but we'll have to do the best we can.
[00:00:52] Jessica: You'll do great. We'll do great. I have belief in us. And I couldn't think of a more special guest than you and our customer guest, Lisa, coming up very soon on this very important topic that, frankly, is one of the hardest parts of being an in house legal professional. So folks, the question of the day is how does an in house legal professional earn and maintain influence. Jim, does this, does this resonate with you, this question?
[00:01:23] Jim: Absolutely. It is the thing that matters most in our jobs. And it's really the thing that makes our jobs fun, uh, is being able to influence decisions and, and our company's direction. So it is the most important thing that we can do and pay attention to.
[00:01:40] Jessica: I love that you call it fun. Sometimes there are moments in my day that I'm like, I don't know if this is fun, but it is definitely harder than legal work, if I'm going to be very honest. Uh, when I think about folks, Influence. I think it is the second hardest part of our job. In addition to being basically a leader and a people manager, folks are nodding their head, yes, it's really hard to be a leader.
[00:02:02] I think one of the challenges is our role. It's not, it's not about how smart or capable we are. It's about, we are boxed in a legal lane. So a lot of folks in sales, marketing, CEOs, board members, often Misperceived that the only value that we as legal leaders bring to the table is our legal expertise, but you two know more, more than I do, how much more we can bring to the table and offer in perspective.
[00:02:30] Jim, tell us, you know, you have an amazing in house legal career, your general counsels of several companies, Workday, Orbitz, and many others. And what have you learned from your experience of what it means to be influential? And tell us about, tell us about that.
[00:02:46] Jim: Thanks. I've actually, I was thinking about this this morning, but I've actually been the GC or CLO of five companies. Uh, the first was, uh, PeopleSoft and it's a big part of my career. I won't count the actual number of years because then it's a lot. But, um, the first was PeopleSoft, uh, enterprise software company.
[00:03:07] The second was, uh, Was Lenovo, uh, uh, the PC company, and this was just after Lenovo had bought the IBM PC business.
[00:03:15] The third was Orbit, uh, online travel business that had just been purchased by private equity. Uh, then fourth, uh, my former PeopleSoft colleagues asked me to join Workday, which at that time was a very small company. It's a very big company now. And I
[00:03:28] Jessica: It is.
[00:03:29] Jim: The great privilege of joining early on and contributing to the growth and going from being, you know, lawyer number four to building a part department of about 140 people.
[00:03:39] And then I had a chance to join DocuSign a couple of years ago. And when it wasn't, uh, really my goal to be a GC again of a different company, but the opportunity was just way too compelling to, to let pass by. So I've. I've done it for a long time and I've seen it from the perspective of many different companies.
[00:04:00] Jessica: Yeah. I hope you can teach myself and all of our listeners here today about how to, the tactics and tips and how to gain influence because it is so hard, Jim, as you know. And so much, what some of the lessons you've learned, but it's not going to just be me and you, Joe. We have a very special guest today, folks.
[00:04:20] I'd like to introduce you to Lisa Keith, the general counsel of Steve Madden. Hi, Lisa. How are you doing?
[00:04:27] Lisa: I'm good. I'm good. Excited to be here.
[00:04:29] Jessica: Ready to talk about influence?
[00:04:31] Lisa: I guess so.
[00:04:32] Jim: thrilled to have Lisa here because her company sells a product that is by definition, cool. You know, it's like software,
[00:04:39] Lisa: Yes.
[00:04:40] Jim: People like it, like what they do, travel. It gives them good experiences, but it's basically, you know, getting on a plane, going someplace, going to a hotel or some experiences. But Steve Madden's products are really, really cool.
[00:04:51] And so I'm sure being cool was an important part of, of her recruitment there. And so I'm, I'm
[00:04:58] Lisa: you got to have good shoes. You have to have good
[00:05:00] Jim: can choose.
[00:05:01] Lisa: know, but I probably use DocuSign more than I buy shoes.
[00:05:05] Jessica: Oh, well, I was cool. Lisa, you'll be, I had a lot of Steve Madden shoes. I think I picked coolness when I had the, The flat, the platforms, the, the iconic black platforms.
[00:05:16] Lisa: slinky,
[00:05:17] Jessica: Yes. Is that what it's called from the late nineties or
[00:05:20] Lisa: yes. It makes that good noise when you walk.
[00:05:23] Jessica: Yes. Do they still sell those model.
[00:05:25] Lisa: They do. We had a 30th anniversary slinky that came out a couple of years ago. And, uh, they do it in all sorts of cool colors, neon, yep, still a big shoe.
[00:05:34] Jessica: Well, I bet a lot of our listeners here today have worn those shoes. And actually I think I'm going to buy them after this,
[00:05:40] Jim: Yeah, I was going to say, Lisa, if they haven't worn them or they're not now wearing them, where can they find Steve Madden shoes?
[00:05:46] Lisa: They can find them at SteveMadden. com and obviously we are very big with a lot of wholesale customers.
[00:05:51] Yeah, you know, it's the best gift to give is a Slinky.
[00:05:54] Jessica: All right. Well, Jim, I wear a size eight, eight and a half. So just, you know, a little hint there, if you're looking for a Christmas gift for me.
[00:06:01] Lisa: I'm the sample size, so that's pretty much why I have to stay here.
[00:06:05] Jessica: Alright, being influential. Well, Lisa, I'm really glad to have you here joining Jim and I, because as you can see, our backgrounds are very technology or less technology. Cool company focused, unlike shoes and Steve Madden, but you bring a lot of diverse perspective because you work with different types of personalities,
[00:06:21] Lisa: Oh, yes.
[00:06:22] Jessica: oh yeah, in the fashion industry, I can only imagine the challenges and, or sorry, opportunities, I like to say, trying to influence creative types in the fashion and folks in the fashion industry.
[00:06:35] So Lisa, Uh, you've been at Steve Madden for how many years now? Tell us about your background.
[00:06:41] Lisa: Yeah, seven and a half years.
[00:06:42] Jessica: and before Steve Madden, you were at a law firm. That's correct?
[00:06:46] Lisa: I was at two law firms. Yep.
[00:06:47] Jessica: Okay. Two law firms. Tell us about over the past seven years, what you have learned to be, um, a successful, uh, influencing the business and the fashion industry.
[00:07:00] Lisa: I mean, a lot of people now actually do go straight to in house and I think that's fine. But I think it's also very good to have the law firm background.
[00:07:06] But I think overall, the skills that you need to succeed in each environment are different, and, you know, there are rare people that can be in house and then later on go back and become partner at a law firm. But for me, I, I don't see them as very compatible careers. I think it's different skills that you need at each.
[00:07:25] And so I think for me, I had to kind of take what I had learned being in a law firm, but learn how to think more like a business person. And that is what helped me to succeed in my career in house. So, um, whereas in law firms you can be very deliberative, sort of slow, very thoughtful, um, very precise, you know, I think in house you have to be a bit quicker, a bit more pragmatic, um, you have to be willing to take in a lot of information but then come to a decision.
[00:07:52] The biggest thing for me was I really had to work on my decision making skills and become comfortable with making a decision even if it might be wrong.
[00:08:00] Jessica: Interesting. Jim, have you experienced the same lessons and learnings yourself as you've based in your in house career?
[00:08:07] Jim: Absolutely. They, you know, value, particularly in the senior legal position comes from the counseling that you do for clients and really the opportunities you have for, for leadership. And let me tell you what I mean by those two things with counseling, you know, you're often asked a question and the answer is, this is what I think we should do.
[00:08:26] It's not necessarily, this is what the law says or this is these are our chances of, you know, winning. If it's a dispute or something else, it's, this is what I think we should do. This is why, and this is what we might accomplish. This is what we have to worry about. And, and that's, uh, It's a really different exercise than when you're in a law firm. In a law firm, you're handling a legal matter, or maybe you're giving an opinion on a topic, and it's, um, you get a chance to dig into the legal issues and really kind of focus on, you know, the, the beauty and the majesty of the law, as they used to teach us in law school, well, for us, it's about being a lot more pragmatic and including, uh, counseling about what it is the company should do, even when there's a lot of uncertainty, because oftentimes you just, you, you have, um, time constrained decisions and you, you're not able to know Um, everything you might, if you're going to do a, uh, you know, complete and thorough analysis of a question, you just don't have time or, um, and so you, you, you need to, to share your best judgment.
[00:09:29] Your ability to do that well, and your willingness to, to do it and not kind of, uh, retreat is a part of what earns your influence over time.
[00:09:37] Jessica: Yeah. So oftentimes we are giving those recommendations, concur with both of what you've said. We need to have a point of view. We need to provide direction, a clear direction and recommendation and course of action because the business wants to move. They want an answer and they want to, and to move and act.
[00:09:56] But the challenges I've seen though, is how do we actually get the business to listen to our sound advice. If, if, if our advice creates some friction or makes things more complicated or the business perceives it as a less growth or revenue generating path, how do we influence the business to, you know, do the right thing?
[00:10:17] Lisa, do you want to kick it off? Yeah.
[00:10:19] Lisa: It helps to be right a couple times first. So I find that like maybe the first time you give your advice. Maybe they don't take it right. And then, and then things blow up, and then you don't gloat about it. You know, but you
[00:10:34] Jessica: Well, I told you, No, no.
[00:10:40] Lisa: Not to do that. You know? And then I think you have credibility after that because you said something, no one listened to it, it went wrong, and now you have some credibility. So now the next time you say something, you know. Maybe they're going to view it differently.
[00:10:54] So that's just one way I think is you have to kind of be right, but it's painful to get there because somebody else has to be wrong first, you know, or it has to kind of go the way you said it would go. And then people are like, oh, maybe I should listen, you know. But I would say also that you really need to pick your battles. And so I think the benefit of being somewhere seven years, and I'm sure Jim could speak to this having been at a lot of different places, is like you get to really understand your company. And so even if I know that like, okay, this is really what they should do, if I know they're never going to do that, I'm not even going to suggest it. You know what I mean? Like I have to kind of work within the confines of, of where I work and they're, you know, we're a very risk tolerant company. So if I were to say something ridiculous, like we just shouldn't do that or whatever, it's just, it's not going to be considered.
[00:11:41] So I think you have to figure out the right advice to give within the confines of the business you work for and what is realistic, you know? And so I think if you come up with something that is palatable to the business. Then they will hopefully listen to you. Mm
[00:11:56] Jessica: So I love that. Earn credibility and then also be wise about picking your battles and chime in really where it really matters. Jim, anything you'd like to add from
[00:12:06] Jim: I agree a hundred percent. A lot of fast growing companies in particular have this mantra of, you know, debate, disagree, but then commit. And one of the things that we as lawyers need to do is recognize that as counselors in particular, that, you know, that the, the matter doesn't end.
[00:12:26] Our involvement doesn't end when we give our counsel and then You know, disagree if it's not taken and then, you know, kind of go off and wait for the next question. We're there, we have to be part of the team, have to know we're part of the team, and do to help in, you know, celebrating the successes and learn if the course of action that was taken, you know, that might be not right in line with our advice proves to be, uh, successful.
[00:12:51] And then if it's not, as Lisa said, you're not gloating over it. You just, everyone's learning and figuring out how to make a better decision next time around. And, and that's how you build trust in, to trust and to be trusted. And that's a big part of, of the relationships and the kind of, um, emotional capital account that, that, uh, results in influence.
[00:13:12] Jessica: Yeah, one of the most powerful moments of, my aha moments of my career was back in 2017 or 2016 when everyone was freaking out about this new privacy, privacy law called GDPR. And, Uh, what really worked to influence the product and engineering org to follow my advice was I did a ton of competitive and product research.
[00:13:40] And so to influence the engineering org of Office and Outlook to properly collect privacy consent, Is I actually did a presentation of the user experience for all of these competing email products and said, Hey, look at this proposal that I'm proposing. It is a better user experience than this email provider and that email provider.
[00:14:03] And that really resonated. So. So folks, in addition to the fantastic advice that Lisa and Jim have shared, think about who your audience is and who you're trying to influence, what motivates them. And in my case, when I was at Microsoft, it was motivating an email engineering organization that was very competitive about gaining users and user adoption with other email providers. So folks, I think a lot of folks here are very curious about how to influence not just general business folks and sales, marketing, engineers, but really gaining the trust of a CEO. So Lisa, where have you, like, what have you seen worked of you becoming that trusted CEO? Did advisor to A CEO so that they don't just call you or reach out to you when there's a legal problem,
[00:14:51] They really just seek your advice day to day. Like, Hey Lisa, what do you think? This is a general business issue that is like the gold standard or goal. So many general counsels and legal leaders that I, that I chat with
[00:15:04] Lisa: Mm hmm. Well, I think that projecting confidence and competence is important. And so I remember like one of my first interactions with the CEO, actually when I was here but before I was general counsel, was we had a litigation that everybody had a strong point of view about. And they felt that it was a very weak case for the other side and that we were going to be able to settle it very inexpensively and that we shouldn't really worry about it too much.
[00:15:29] And I had been a commercial litigator at my first firm. And when I took a look at the case, I didn't feel the same way. And so even though they were like two years into this case, I came in with sort of a contrary point of view and had sort of the backup documents to show why I felt differently. And it sort of changed the whole strategy of the case.
[00:15:48] And I think that was the first time that anybody sort of realized that I. Kind of knew what I was talking about. So I think it's good when you have, you know, those kinds of moments. But it was a gamble because had I been wrong, you know, I don't think it would've been a very good first impression. Um, but I think you have to sort of know what you're, what you're talking about.
[00:16:05] And I think you have to have, uh, the ability to deal with lots of different types of personalities and adapt. Like, I'm very different when I'm talking to our CEO than I am when I'm talking to Steve Madden.
[00:16:17] And I think being able to adapt to different, uh, audiences is, is a helpful skill and I don't think you really have to exercise that skill so much when you're at a law firm because you're just surrounded by like total, you know, brainiac lawyers all day
[00:16:32] Jessica: Right. Oftentimes your contact is a in house counsel or another lawyer. So you don't have to adjust your communication stuff. So tell us, cause you know, Jim and I, again, work in tech, not cool company. What is it like, like, what are some, uh, advice of effectively communicating with a, a visionary creative type, like a Steve Madden?
[00:16:54] Lisa: Well, you know, the first few times I met him I was sort of like starstruck because I, I wore the, I've been wearing the brand my whole life, you know, since I was like a preteen and I knew, I knew he was a person. I knew who he was. I had heard when I was interviewing that he still comes into the office a bunch and I might meet him at my interview, but I didn't think I actually would.
[00:17:15] I didn't interview with him, I So, I just ran into him when I was here. But the first few times I just kind of was very quiet. And I will say that one thing that was interesting was I started at the company. I really didn't have much to do with Steve. I had met him briefly at my interview. I was starstruck.
[00:17:31] I don't think he remembered me at all. And then, uh, when I started, I started working with a lot of different business people and a lot of product people. And just sort of trying to make a good impression and get to know everybody.
[00:17:42] Like we have a lot of people that have been here a long time. So I started to really get to know the long timers. And I guess it created a little bit of a buzz about me. So then when I ran into Steve a couple weeks later in the hall, he's like, Oh, you're that new lawyer everybody's talking about. And so sometimes I think you can create a good impression without ever actually interacting with the person that you're trying to create a good impression with.
[00:18:04] Um, and I just, you know, I thought that was interesting that it really wasn't anything I did with Steve in the beginning. It was more the way I interacted with other people and then they said things to Steve. And I think it is better sometimes for other people to say good things about you than for you to just constantly be trying to impress and make people feel a certain way about you.
[00:18:21] So I think that's what sort of opened the door for me and Steve to have a relationship. But over time, I would say I just sort of, from the minute I met him, I understood him, I felt. Um. And, and so we've always just been able to sort of get along. We have a lot of things in common. And, uh, we actually spoke together at Cardozo.
[00:18:43] Um, he comes with me sometimes. I, my, my friend Barbara runs their program. They're called the Fame Program. And he came and did like a little night event with me there. It was like an evening with Steve Madden and we did a Q and A for all like the law students and it's very nice.
[00:18:56] Jessica: That is, you brought Steve Madden to the law school? That is such an amazing opportunity for law students and like, not just lawyers, but you know, these visionaries, these iconic brands.
[00:19:11] Lisa: It was great and he was giving advice to lawyers and he took pictures of everyone, we gave out his book, even if you're not going to be an entrepreneur or a business person, I think all, everybody can learn from everybody.
[00:19:23] Jessica: Yes, absolutely.
[00:19:24] Lisa: Mm
[00:19:25] Jessica: So, Jim, I, I actually, when we first met and I actually didn't have a job yet at DocuSign, we had coffee at a conference and one of the things that really struck me, and I didn't tell you this, Jim, uh, when I was deciding whether or not to join DocuSign was, I love that you had a text based relationship with Alan, DocuSign's CEO cEO, and that you were giving insight to Alan, but was more than just giving him legal advice on something. So that really struck me as important because for me, it's important that the CEO values their chief legal officer or general counsel as more than just a legal advisor. So Jim, given that you have earned those types of relationships with CEOs, any advice for our listeners here? How do we get that? We want that.
[00:20:12] Jim: Well, I was, I was fortunate, um, with Alan in that I was here when he was hired and I was supporting the board during his recruitment. So it was like I was imprinted on him a little bit as someone who could help him find it, find his way.
[00:20:28] But. But, um, that wasn't guaranteed to last forever. And so I think, uh, what helped is that I'm, you know, genuinely interested in our business. I'm genuine, genuinely interested in his role in running our business, understanding things from his perspective and trying to. Uh, engage with him and, and with others so that when issues, um, get raised to him, that we're, we're looking at it from the CEO's perspective.
[00:21:01] So when you CEO, you're responsible for optimizing a lot, a lot, a lot of really, Divergent considerations and you have to find the best solution and you can rarely, uh, really say, I'm, I'm going to do the best, uh, thing that, uh, um, sort of solves the legal equation.
[00:21:21] They're like, uh, whatever I do, I want to make sure that I get the legally best outcome that I can. No, it's, it's, it's a, it has to be acceptable from a legal perspective. It also has to work for customers. It has to work for suppliers. It has to work for other employees. It has to work for, um, from a budgetary perspective, a business model perspective, and so I try to make sure that, that I'm looking at it from as close to his perspective as I can, yet providing, you know, my Uh, domain expertise and, and then, and really encourage others to do that as well and, and make sure that, that he understands, not because I tell him, but because I show him through the, how I approach these problems, that I'm really there looking at the world the way he, he is, with my many, many years of, of legal experience and that's helped form, um, you know, a good relationship.
[00:22:12] And we need to help them build on their strengths, compensate for their weaknesses and, and, uh, and just, you kind of attend to the personal relationship as well, as well as the professional relationship.
[00:22:25] Jessica: I love
[00:22:26] Jim: Yeah,
[00:22:26] Jessica: You have so much empathy for the CEO role. It's a hard job. It's a really, really hard job, uh, because all the things you just said, and there's going to be good and bad days and no one is perfect, but it's also very isolating job as well for, for many, in many respects.
[00:22:43] So the next segment, I would like to talk about some real world events where a company has, um, had a suboptimal outcome and probably didn't listen to their general counsel or legal advice from their in house counsel. So, a couple events come to mind. Actually, just today, a very popular food delivery company, which shall not be named, was fined 25 million for deceptive and unlawful business practices.
[00:23:14] Jim, this may resonate with you because one of the practices that this company was fined For was all of this add on junk fees.
[00:23:22] I see that there was probably along the journey, an in house legal professional that advise the business, Hey, maybe we should do something different because these are the risk of taking those coercive actions.
[00:23:37] Any, any like lessons that we could learn from this and advice that we have for the listeners here who may be running into friction with a business who says we need to show up as the lowest cost provider. Because our competition is cheaper. Even if that means six clicks through a user will then be proceed, you know, then get the real cost of something, or really the, the delivery person will then realize they're underpaid.
[00:24:04] But we were advertising that this is their hourly pay. That was one of the other violations as well. Jim, any thoughts on that? Like, what
[00:24:12] you really want to, um, get them to see like preaching about what's right or not right. It's probably not going to be what's most effective under those circumstances, what you want them to do is step outside the situation and look at it and, and, and look at it from a number of different perspectives, like what are the customers really going to think about this, how, how would, how would, uh, the CEO defend this if it was raised in a, in a sharp, uh, interview, how would, uh, the CEO respond if there were, um, an expose, uh, talking about these fees and, and just how they raise the price to, to customers and whether that's the ground with which we want to operate, despite the fact that others are, others are there.
[00:25:01] Jim: if you decided that for competitive or other reasons that we had to do that, I would say, well, what is our exit strategy? How will we be the first to the exit if this goes wrong?
[00:25:11] Jessica: Yeah, I love that. So what I took away from that, Jim, is taking a customer first approach because the reality is there are several different food delivery service providers. And by positioning that this is not just a right or wrong issue. This is a customer experience issue. And so if we have consistently bad customer experiences, our customers are going to go to our competitors.
[00:25:33] For a better experience. I love that. Lisa, any thoughts on approach here? Because you also work for a consumer brand and you're very customer focused, which I love.
[00:25:43] Lisa: I often try to think of my job as kind of like the moral and ethical center of the company. Right? And I think you have to, to be a general counsel, I think you have to have a very strong sense of values.
[00:25:56] I'm not saying you have to be like a goody two shoes, but you have to kind of have a good sense of what you think is right and wrong and you have to let that guide you and your decision making. So sometimes it's not even about the legal, it's just about your instincts of morality. And so I think if you feel there's like a shady practice going on, you need to call it out.
[00:26:15] if I feel something's not right, I'll, I'll discuss it. Now I might start with the business person. Maybe I don't even start with the president of the division. Maybe I just start with the person that I think is responsible. And then if I don't get a good response, I escalate it to the president of that division.
[00:26:29] And then I sort of pick what I take to the CEO. But if I feel it's an important enough issue, I'll take it to the CEO. If I lose at that point, then I feel I've done, I've done what I can, but I try to always be guided by very strong moral principles, and I think as long as the company is aligned, you know, not that I control things, but if I feel like where the company is going is aligned with my moral principles, then it's, then it's easy to do the job.
[00:26:57] You know, there's things that maybe you wouldn't do or would do differently, but, but you can live with them. You know, and then there's things that you feel like you can't live with. And those are the things that you, you go to the top for. So that's one thing, but I think what's even scarier than someone not taking your advice and then it goes wrong and blows up is that no one even knows to ask you your advice to
[00:27:17] Jessica: Oh, yeah.
[00:27:18] Lisa: And I think that, you know, we definitely have parts of our business that maybe they're like, Oh, I never thought I had to show that to legal. I didn't realize that was like regulated or that there's rules about that. So I think that's where you have to be a constant present. You know, you have to really put yourself out there.
[00:27:35] It's easier for me because we're in an in person environment. I think it probably is harder when you're remote. But I'm always walking around. I'm always trying to meet people. I'm always trying to be informed about what's going on. I'm always reading legal news and articles to see what are the emerging areas that maybe I need to take a look at.
[00:27:54] I have moles. And, you know, then you can kind of figure out how to insert yourself and say, actually, yeah, this is something I wish you guys had shown us, but, you know, and you can solve a lot of problems and, and you can add a lot of value that maybe isn't even really your job when you sort of try to get involved in things that maybe at first seem beyond your scope.
[00:28:18] Jim: The CEOs oftentimes really want you to weigh in because they, they're part of, part of the balance they need to strike is they don't want to try to start doing everybody else's job because the company can't scale.
[00:28:32] If every decision has to come to the CEO or if people are just waiting to see, well, what does the CEO think about this? And so sometimes, ideas get floated that aren't necessarily great ideas, but the CEO doesn't want to be the person to once again, you know, be the person criticizing it. And I had a situation once many years ago where after our marketing person made a big branding presentation, I said, the CEO, well, I don't really think this is very strong.
[00:28:58] I don't think it's going to turn out like we want it to. And he justifiably and appropriately jumped all over me and said, well, why didn't you raise that during the meeting? That's what we rely on you to raise. We're not just looking for you to tell us what the law is. That's important. Your judgment on this is good.
[00:29:15] And, and now we have to go back and revisit this whole thing because I agree with you, but I was, I didn't want to just impose. My own point of view on this. I was waiting to see what others thought and you didn't share what you thought. And you know, basically saying you didn't do your job today, which is, which is true.
[00:29:30] It's 100 percent true. They're looking for that and I've gotten, you know, positive feedback when I've weighed in on things that, other people would think aren't anywhere close to the legal remit, and the CEOs will say thank you for raising that point. So, they're really looking for us to be guided by what Lisa talked about. Sort of our sense of what's right, what's wrong, what we can be proud of as a company.
[00:29:53] Lisa: Cause you know, we're one of the few divisions that like, we're only motivated by what is best for the company and what is best for the CEO. You know, everybody else sort of has their own interest in mind, you know, like their, their compensation is based on the performance of their division. And people are self motivated and, and maybe they're, they're motivated by good intentions, but it might not be what's best for the company overall. It might be best for this sub brand, but not best for that brand. You know, we, we are in a position of sort of having a view of the whole thing. And so that's where we have to be comfortable exerting our influence.
[00:30:30] Jessica: I love that because that is so spot on, Lisa, that legal is one of the few departments of really the unbiased, the, our only goal is the success and longevity of the company, and is very much aligned with the CEO. For folks who are listening, what advice would you give to them to make sure that when they're interviewing for a role or interviewing with a CEO, to make sure, because something you said earlier, Lisa, that really stuck with me was alignment with your moral compass or your moral principles.
[00:31:00] So to make sure there was a alignment of values between you and your CEO partner or the overall business, like what, uh, Would you look for in the profile of the CEO or what questions would you ask in the interview to make sure that there is that alignment, at least do I kick it off?
[00:31:18] Lisa: Well, I'm thinking back to my own interview with the CEO many years ago, and I probably would have done it differently because I kind of violated a lot of my cardinal rules.
[00:31:29] Jessica: What would you do now? Yes.
[00:31:32] Lisa: Well, I was just very, I was informal. I um, I didn't have like a, an agenda of like what I was trying to say. And I think within 10 minutes I brought up my son who was three at the time and that he had pink eye, which a is just gross. And also like I had promised myself that I wouldn't mention like children ever on a job interview because I've had bad experiences
[00:31:57] Jessica: Oh,
[00:31:57] Lisa: in my prior life, pregnant and another, you know, So, I was in the United States and it's, it never has worked out for me, so usually you bring up your kid and then you never hear from anybody again.
[00:32:05] Um, so it actually was a good sign to me that despite doing nothing right, we still hit it off and I came here. There was a period of time and I think it's gotten better where everybody that I was interviewing, there was a lot of kind of like, well what can you do for me? And, like, how many days do you need me in the office and, um, you know, is there a free lunch or whatever it might, I'm sure, you know, working for DocuSign, you guys have all of that.
[00:32:31] You know, I, my husband's worked in tech and I, it's just a different, you know, world. And I'm not saying that employee benefits and perks aren't important and that people shouldn't be rewarded and, and feel valued in, like, their jobs. But I think in an interview, what you're trying to get across is what you can do for the person.
[00:32:47] Not what they can do for you. And so I've seen that kind of go back now, I think, to the way that I think it should be. But there was a period of time where I was like, I don't even want to interview. You know, I, I feel like I'm the one being interviewed. There is some of that, you know, to some extent, it's like, you have to show your Why you're going to be a good person to work for.
[00:33:07] Like, I think that being a good manager is important. It's not just that someone's there to serve you and you have no role to play, but I think that when you're interviewing, you do need to figure out what your value proposition is to the company.
[00:33:19] Jim: when you're interviewing for a general counsel's job, the CEO's not trying to assess whether you're capable of writing a law review article or whether you could write a Supreme Court brief or, or how brilliant the contracts are that you, you write that, that, uh, they'll draw inferences or, or get secondary evidence from, you know, others about your legal acumen.
[00:33:42] They wanna know is, is it someone I can talk to? Is it someone I can have a wide ranging discussion on? Is it someone who will be able to keep up with me and with the other members of the team intellectually? Is it someone who's interested in our business and engaged? Is it someone who will You know, that, that people will like to be around because people on management teams are around each other a lot.
[00:34:04] They don't need to be best friends, but they need to be able to tolerate, do better than tolerate each other. They need to be able to, to engage and feel good about being, uh, being there together. And, and those are the sorts of things that, that, um, the CEO and other members of the team will be assessing.
[00:34:20] And the kind of things that, you know, that, uh, candidate needs to assess as well. I mean, there is really no point in taking a job where we'd say, well, this, I think this company is great and they're going to pay me a lot of money, but I'd be miserable working here. I mean, that life is way too short to take that job.
[00:34:36] Lisa: That's right.
[00:34:37] Jessica: Yeah.
[00:34:38] Lisa: Now, I think a lot about COVID because I went through COVID here and, you know, it's like, who do you want to be in the trenches with? Like the day you shut down all of your stores nationwide, who do you want to be working with to figure this out? You know, when you have to furlough your employees, when you have to lay off people, when you have to figure out vaccine mandates or whatever else, but I mean, every single thing happens, right? And who do you want to be making those decisions with?
[00:35:02] It was a bonding experience for all of us, I would say.
[00:35:05] Jessica: I love that the people connection and is a core part of that. Actually, one of my favorite stories, uh, was when I was interviewing to be the general counsel of Payscale, this is back in 2017, I believe, uh, the recruiters made note that I was odd candidate because I showed up, uh, About 30 to 45 minutes early, and I just sat in the kitchen area working, but also observing.
[00:35:32] And what I was observing was what the employees look like and the energy level when they came into the office. Were they excited to show up to work? Did they seem energized and motivated? So that to me was a signal of the culture more than What an executive may say to me, what they think is the values and the morale of the company.
[00:35:54] I wanted to see for myself before I took the leap of joining this company because I was leaving a great job at Microsoft. Alright, for our final segment, we're going to do something fun, Lisa. Are you ready?
[00:36:05] Lisa: Yes.
[00:36:06] Jessica: All right, so as you know, Lisa, and as we first met, because you are a user of DocuSign's agreement technology, I am a nerd when it comes to all things agreements.
[00:36:16] So for our last segment, it's going to be called, what would you keep or what would you redline out? All right, are you ready? And I want you to answer quickly. I want this, I want you to go. With your gut feeling. Okay. Like that's where the truth comes out. So to kick it off,
[00:36:35] pineapple on pizza.
[00:36:37] Lisa: Redline.
[00:36:38] Jessica: Oh, thank you. I'm from Hawaii. So that really speaks to me. All right. Because Hawaiians, we don't eat pineapple on pizza, by the way. That's not a thing.
[00:36:46] But I, I don't, like, everyone always wants, like, salami on their pizza. I mean, I'm okay with it, but I, I, I'm fine with just cheese, all cheese, or cheese and a little bit of fresh, you know, tomato. I'm good. All these other things, it's too much.
[00:36:59] Jim: now. Now, if you would ask the question, You know, Deep Dish or Thin Crust, we would be, we're both East Coasters in New York. Definitely Thin, definitely Thin, right? And I spent time in Chicago too in the Midwest, but it's definitely Thin.
[00:37:14] Lisa: Yeah. Then it's better. Then it's
[00:37:15] Jim: is
[00:37:15] Jessica: It is better. It is better. Okay. Two more questions for you. And this is because you're in the fashion industry, Lisa. Number one, athleisure as work attire. Oh,
[00:37:27] Lisa: Okay. So if I did not wear athleisure as work attire, I would have nothing to wear to work. So that's probably like the main reason I say here is they just leave me alone when I'm wearing my leggings. Yeah.
[00:37:39] Jessica: um, well, one, I love that. Well, one, I can only fit moomoos and leggings right now. But even if I wasn't pregnant, I'd be wearing leggings and moomoos. But also I was surprised because the fashion industry,
[00:37:49] Lisa: Well, so it's funny, when I got the job, I went out and bought all these, like, cool clothes, and I wore them for, like, the first year, and then about a year in, I got pregnant with my daughter, and then I had to switch to leggings, and then I just kind of never went back. And, um, it's worked for me, you know, we have a lot of great sneakers, um, so I do wear our, you know, the most important thing here is wearing the shoes.
[00:38:10] So I always am wearing Steve Madden shoes, and we have other brands too, by the way. We own Dolce Vita, we own Betsy Johnson. Um, so we have, we have a, we have a bunch of cool brands that we own. So there's some options.
[00:38:22] So I probably do need to like up my game, but I think when you're making the hard decisions, you need to be comfortable. You need to be able to breathe.
[00:38:30] Jessica: All right. Alright. Um, all right. Last question, but not least, this is more substantive for our listeners out there, is the GC reporting to A CFO.
[00:38:43] Lisa: Red
[00:38:43] Jessica: Oh, it was a quick red line. That was a
[00:38:45] Lisa: Red line, red line. I mean, I don't know. I look, I'm sure sometimes it works, but I think you're going to be very budget driven if
[00:38:56] Jessica: Mm-hmm.
[00:38:57] Lisa: to a CFO. And I think that you need to be able to make your own decisions about your legal spend. People do not understand how expensive outside counsel is.
[00:39:08] And I would not want to be micromanaged on that. And, uh, I just think it shows something about how the position is viewed within the company. If the person reports to the CFO, you're, you're not viewing them as part of management, in my opinion. But, but there could be times it really works.
[00:39:26] Jessica: Jim, I'm sure you have a lot of thoughts on this topic too, but reporting structure,
[00:39:30] Jim: I don't like it. I've, I've a couple times been asked to do it and I've agreed. Uh, somewhat reluctantly, but I made sure that I maintained my direct relationships with the board, direct relationships with, with the CEO and that, uh, you know, the CFO understood that, you know, That there wasn't an opportunity to manage down the legal budget, right?
[00:39:56] Like it wasn't going to treat me any differently on budget issues than any of our other peers. Um, and it was just a convenience because of the CEO's kind of focus on other issues. And as I said, I didn't like it. I agreed to it. Did what I did despite it. Uh, but I, I wouldn't, I wouldn't recommend it.
[00:40:17] Lisa: I, I think that the GC CFO is an extremely important relationship. Um, and I think they have to work very closely together and there has to be a mutual respect and I think that it's an extremely important position, but I think that it works best when you're not reporting to that person. I think, you know, we have a very good working relationship, uh, me and our CFO, but that relationship would be different if he was my boss.
[00:40:41] But I understand sometimes CEOs do have sort of focus areas and they just don't have the bandwidth to oversee legal. And so it has to be the way it is, but I, I, it's a red flag for me.
[00:40:52] Jessica: Mm.
[00:40:53] Jim: I agree.
[00:40:54] Jessica: It's a red flag for many folks who are evaluating in house or general counsel roles.
[00:40:59] Lisa: So for folks here who want to listen and listening and would love to connect with you, Lisa, is LinkedIn the best way to connect with you?
[00:41:05] Yep. Yes. I'm on
[00:41:07] Jessica: And any recommended conferences for, cause you mentioned you'd like to reconnect with your lawyer roots after spending all day with designers and fashionistas.
[00:41:16] Lisa: So I was just at the Luxury Law Summit and next up on my list, um, the National, yeah, it was, it was cool. Um, and then the next thing on my list is National Retail Federation does a big event in January at the Javits Center.
[00:41:28] Jessica: Lisa, it was such a pleasure to have you join Jim and I on our very first DocuSign podcast. Thank you for joining us.
[00:41:36] Lisa: It was great. DocuSign seems awesome and, uh, must be very fun to work there. And I, I'm a big user.
[00:41:42] Jessica: I'm so glad we got a chance to have this conversation with Lisa and get the perspective of someone who works at a cool shoe company, Jim.
[00:41:49] Jim: lot of things we have in common and there are a lot of differences as well. It was, it was great to explore both of those and she's such a, you know, wonderful and warm and, and, uh, you know, down to earth person. It was, it was just a great conversation.
[00:42:02] Jessica: You know, Jim, we work in tech and Lisa's in the fashion industry, there was still a lot of patterns. of what it means to be an influential in house leader.
[00:42:13] What I learned from Lisa is the importance of, especially when you work in the fashion industry, where everyone's hyper focused on creating the next great new shoe or clothing item, is you have to really earn credibility. That also translates to To the tech world as well. What are some things you learned, Jim?
[00:42:33] Jim: Well, one of the things I realized we had in common, and it wouldn't have occurred to me beforehand, is how companies in both industries tend to really be founder influenced and founder driven, even when the founders are no longer involved.
[00:42:49] The DocuSign founders haven't been actively involved.
[00:42:53] For, um, a long time, although some of our directors have been with the company for a very long time since it was small, but we still have, um, you know, they still put their mold on the company and there while Steve Madden is not, is no longer the CEO, he's still, he's still there. And obviously he's a creative force and a, um, You know, source of, of culture and, and direction for them. And, and that's something that we had in common and I wouldn't have appreciated that.
[00:43:21] Jessica: Actually didn't realize that even for a more mature technology company, that the founder vision, influence, culture still permeates throughout an organization. Cause Jim, as you know, I've worked at a lot of early stage technology companies as well and wholeheartedly agree, Jim, that if you want influence with a founder or CEO of an earlier stage technology company, where I've seen success to help influence those leaders is to show that I care just as much as they do about the company, the brand, and its success.
[00:43:55] So I think that translates to more mature companies, fashion companies, technology companies.
[00:44:02] Jim: Show you care. It's important that every day you show up, you show you care. You care about your colleagues, you care about the company, you care about the business success, you care about, um, you know, the CE o's success. You care about the board success and, and, um, that builds a lot of goodwill. And, and those days that you occasionally make mistakes which happen, uh, which definitely, which definitely
[00:44:27] Jessica: Oh yes,
[00:44:28] Jim: Then showing you care, uh, gives you that, that, um, sort of, uh, that reputational capital that lets you survive to the next day.
[00:44:38] Jessica: So folks, the takeaway here is show you care. If that's one thing you need to learn is show you care about other people's interest, goals, the organization, and you'll find that that will lead to great success and influence. Thanks for joining us.
[00:44:51] Jim: Thanks for having me, Jessica.