Flexibility and Innovation in Legal Tech

That was a very generous opening, so thank you for that.

Happy to because you're right. I love that picture of myself, which is why it's there. But I joke to my children. I say, that picture has to be a part of my celebration of life.

Right? Who gets an opportunity to do that? Right? I mean, for me, there was just so much joy in that entire event and the band and all of it.

So what had happened, frankly, was it was right before the pandemic, and a new partner had joined my former firm. And he is a guitarist and is a member of bands as well as being a tax attorney, which, you know, maybe sound like an oxymoron, but actually incredibly talented musicians in the law, FYI. So he had sent an email to the whole firm or, you know, to everyone in the California offices and had said, hey. I want to put together a band to play for nonprofits as part of fundraising.

I saw the email and I thought, oh my gosh. How cool. You know, I was a singer in high school. You know, I was in the choir, and I love to sing, and I love music.

I come from a very musical family. So that email really resonated with me, and I thought, oh, wow. What a great way to give back.

You know, it's a different way to give back to a lot of the organizations I already support in other ways. And so there were fewer people than I anticipated who signed up to join.

And so they eventually said, well, why don't you be the lead singer? And I was like, oh, okay.

Sure. Because I usually say yes, which occasionally is to my detriment, but I said yes.

But I also had this doubt through the entire time. Right? We're doing the practices. We're talking about the song set. And, eventually, at one of our practices, they put the microphone in front of me, and they said, okay. Go.

And I really truly asked, do you mean, like, by myself?

And it was just it's so funny because they were like, but you're the lead singer. I mean, I was so afraid. I was so afraid. And I speak on stage, and I present, and I write, and I put myself out there in those ways.

But singing, to me, was something incredibly vulnerable, and it was a much more personal kind of fear that I had. And while all of this has happened the pandemic happens, and so initially, we started with our band, and the fundraisers were not live because of the pandemic. So we did music videos. So that was a sort of softer entry into, you know, into performing and singing.

Those were a ton of fun. But then come twenty twenty two, we're allowed to actually perform live. You know, we've done these songs over and over again. We've practiced, and we're behind stage, and we're getting ready to go on stage.

And I am shaking with fear. I am so afraid.

And the drummer of our band, who's a professional musician, Scott, amazing person and personality and talented musician. And he looks at me and he says, Cynthia, you've got this.

Everyone in and I feel I've kind of moved telling this story. He said, everyone in that audience is rooting for you. They want you to kill it. And I was like, oh, okay.

You know, I still shook on stage, and I was afraid. But him telling me that and me looking at the audience in that way, having that view on the people who were, in fact, dancing and that whole experience, I can't even tell you how fabulous that was. And in full disclosure, the picture where I'm sure that picture was taken was me singing I fought the law, which is also a nod to maybe a few things, right, in my life and career, and also the fact that I love the clash. But so that's the other part. Then we did it again a few months later for a different organization, and I was so much more comfortable and so much more excited. And frankly, it's addictive to do that.

All the time. And you're so right. And I think especially as lawyers, there's so many things in that. Right? There's the desire to be perfect and to overthink. Right? And the fear paralysis.

There is the fact that sometimes not everyone is rooting for you. And sometimes it is a you win in order for you to win, someone else at least feels like they're losing. Lawyers tend to be very competitive.

And even for myself, that's a whole other mindset switch that I've really tried to work on in that way, trying to just be generous or more generous in the way that I look at the work I do. But, yes, I find myself reminding myself that I need to say that out loud to my team because it's demanding, and there's a lot on our plate, and we're thinking of a lot of things, we're trying to, you know, move forward really quickly. And I try to build in those opportunities to express that to them. Right? That, look.

I am rooting for you. We are all rooting for you, and we're a team. We are a team, and we all win together, and it makes a difference.

Thank you for saying that. I think sometimes my moves were, at the time, probably made under duress or stress, but there's an art to being able to take what is may an unfortunate situation and trying to turn it around at least, which is also something that I talk to my team, my students, or other young attorneys who ask me questions about that in particular. Everyone goes through ups and downs, and so being able to take the downs and at least at some point, maybe not immediately, right, turn them around into something that you can move into a better light or make work for you. But when I was in law school, I always knew I wanted to be a general counsel.

And I wasn't exactly sure of the path, but I always had that in mind. So moving into working in companies in house was always on the path. I just didn't know when necessarily.

And I always wanted to work in tech. And so, you know, those were my two guiding well, and internationally. Those were the three things. Right?

So I had sort of three overarching ambitions, let's say, for my career. So with that in mind, you know, going in house at whatever role, you know, that sort of made sense was right. And I started out at a software company doing tech transactions and really negotiating and understanding that role, which was instrumental. And I had a great boss.

He was a great mentor. Gave me a huge amount of rope and told me, go do it. There isn't anything that you do that we can't undo, so don't worry about it. And if you have a question, you push pause, and you come back and you ask me, and that's okay.

So with those two instructions, I was like, oh, are you kidding? I can do this. So but I think going back into big law was definitely a pivot that I had not anticipated for myself and frankly neither had my family. You know, they said, oh, are you kidding?

Is that really what you wanna do? You wanna go back? That was in twenty sixteen.

My role at the time was CEO and general counsel of Spectra seven Microsystems, and I had taken that company or the team. I really wanna emphasize it was a team effort. We had taken that company through a transition where the CEO passed away suddenly of a heart attack. I was part of the succession planning without knowing I mean, know, without knowing it in advance.

So we had been through, I would say, a rather traumatic event, and that was tough. I mean, I learned a lot. That was another opportunity that presented itself that I'm sure I always wanted to be CEO when I would never refuse a job again as a CEO, but it wasn't something that I was seeking outwardly. And so I think I wanted something kind of going through that after having been in house for thirteen years.

I wanted something different. And I felt like I had always had an interest in privacy.

And coming back to Silicon Valley in twenty fourteen, I had talked to a number of companies at the time about privacy issues, and they didn't seem very mature, let's say, on a lot of those issues. And so I really saw it going back into Affirm as an opportunity to build a practice that I thought the timing was right and that I could create a market for that type of tech transactions, privacy focused practice.

And I also felt like even if it didn't work, I would be fine.

Generally, my approach is we need to be flexible in how you look at there are certain, obviously, laws and rules where there is no flexibility. Right? But I tend to not be in those areas. I tend to be in the areas where there is a little more room for, let's say, creativity and how we look at issues and how we manage them.

I also ultimately am a humanist.

Right? I was an English major. I was a French minor. I moved to France, and, you know, I'm bilingual. I'm very focused on relationships, connection, human connection. So I think that's another point that I make with my clients all the time is that any tech, legal tech, any tech doesn't run itself.

And oftentimes, the biggest mistake I see is bringing on a new technology and then leaving it by itself and not having auditing and human sort of intervention or even just checking in, regular checking in. You know, that resonates with most of my clients. They know, and I know because I was in house. I know the budget constraints. I understand that oftentimes people are viewing the budget around legal tech as replacing humans.

But to me and I get it. There are some ways where maybe that works. But I think if that's your ultimate goal, then you will fail at doing what you set out to do.

I think this answers this question. We had a client come speak to our associates in the office earlier this week, and someone asked him, what is your expectation of your law firms? And especially knowing that the audience was really junior associate, people who are just starting out in practice, what is your expectation with respect to those individuals and the younger members of the team using AI or tech in how we manage your issues and just generally?

And, again, because of my bias, let's say, I loved his answer, which I won't, of course, be able to repeat exactly, but it was generally along the lines of junior attorneys need to understand the law, and they need to build on their own experience.

And the way that you get experience is not by asking a question, you know, of a tool and getting an answer. It's by doing the work and the research yourself. So his response was, my expectation is that the junior lawyers on your team are doing the work themselves like they've always done the work. You know, there are certain ways that we shorthand, you know, certain tasks, mundane tasks. I would expect you to be doing that, but I do not expect these tools to be replacing the fundamentals of research and writing and understanding and developing a profound knowledge base and experience.

Of course, I loved his answer because I feel the same way. I think that human experience, it's why I have been so fearless in so many of my decisions. I think the experience of making a mistake, of course, it's awful when it happens, but it's that experience that then allows me to be able to talk to clients authentically about, okay. If we experimented in this way or if we looked at it this way, here's the risk not from, like, an idea. It's a risk because I've probably experienced it in some way myself, or it resonates with them because maybe they've done the same thing. In my mind, we cannot shortcut.

I think that's what sometimes people are trying to do, gets back to this notion of perfectionism and risk paralysis ultimately, which sounds like it doesn't make sense. Right? Because using legal tech would seem to be risky, but I think that sometimes it comes from a space of thinking that using the tech is less risky ultimately because it takes the human and the human element of vulnerability out of the equation.

There's a great story about failure, and my dad was a big he worked for IBM for twenty six years, and he would always say stuff like, you know, you learn more from your mistakes. And remember, it's okay to be vulnerable in telling a story around mistakes because that's how people really latch on. Winning winning and being successful, people are usually like, great. She won.

It's not as relevant as actually I worked on a project where I had a bunch of files that were hidden in an archive and I couldn't get access because I didn't know the right password. Well, we had to hold off on our final production to the DOJ. And it was a mistake, and I learned. And I never did that thing again.

But the thing is that storytelling and that experience, like, intelligence is one thing, but I practice Buddhism for a lot of years and one of the ideas is to say, in the seeing is the doing. Like, you actually visualize your experiences before you actually do them and once you do that, you actually realize the actual outcome. One of the things that you guys are talking about, the adaption of technology and the acceptable use of technology. So so you're you're very much involved with AI governance, and there's lots of different changes not just within privacy, but acceptable use around what AI is, and we're hearing in Texas that it might be prohibited and all over the place we're hearing different ways in which people are gonna lock it down or actually provide better use cases.

Delicately.

Because you're right. That is the most difficult piece. And many in house legal teams know that people are violating the acceptable use policies that they've rolled out. And so you almost ask yourself, like, what's the point? You know, there's a point of diminishing returns.

And we talk about these things. And that's part of having a relationship with the clients that goes beyond just asking a question and me giving an answer. It's about providing guidance on these issues in other ways, providing benchmarking.

A lot of my work is saying, look. For these other client without naming names, you know, for these other clients, we did x y z. They had these issues. I think this is something that you could use as well, and it would be relevant. Or the way that they rolled this out even visually. This is something we've done with respect to acceptable use or even contracting guidelines because there's governance, but then there's also what is like you said, what does this mean in practice?

And this whole area, the amount of changes that I have seen in commercial transactions because of the use of these tools, the changes to indemnification, limitation of liability, you know, different aspects of all of these agreements, that has completely changed these agreements that hadn't changed for decades. Right? So those are the things that we talk about. And part of it is also approaching the way we get adoption inside the legal team, and there has to be a part of experimenting.

So one, you know, experimenting with the tools, experimenting, getting you know, asking, you know, what are you susceptible to use? What do you like? And then addressing it that way. And then I think it's also being able to pivot quickly.

Clients have gotten much better at this, and they should. You should be demanding of your outside counsel that they're providing you a regular cadence of updates. To me, that's the nuts and bolts of having a sustainable practice is being able to not just when the client is asking you questions, but are you regularly checking in with them and saying, hey. I saw this thing and this looks interesting.

What do you think about this? Or because oftentimes, if one client is having an issue, everyone is having the same issue. Right? But they just aren't able to knowledge share.

I don't think there's an easy answer, and I think that it's a question of finding what is the most important, really defining and going back and defining it again in a few months and not being static on that point. But it's defining what are we trying to solve for?

What is the risk? Right? And then going back to that over and over and over again. Because sometimes we get lost on a trail, creating a pause, going back, and asking over and over again, what are we really trying to solve for? What is the biggest risk here that we need to address? And that has to be the fundamental, and the rest of it, we can more or less let it go.

That is such a good question because it's really difficult. Because oftentimes, if we say there are different ways to do it. You can ask questions. You can ask more questions. You can say, hey. Can we take a look at this from another? But that may be viewed poorly.

So how do you put yourself in a position in the first place where when you say that, whoever you're saying that to takes it as a good thing and trusts that you're not doing that to stall.

Right? You're doing it because you have a good reason to do it. And I think so much of that goes back to building those relationships, understanding who you need to be building the relationships with.

This is something I talked to my team about as well is that and it sounds really stupid, but hello. How much energy do you spend trying to please people who, in fact, have actually no impact on whether you make a difference or ultimately what you're trying to do gets across the line. And so I think from a personal perspective, being able to answer those questions in your life, right, but in your job in particular, is key. Because then you can really focus on building the relationships that matter inside the organization so that when you ask the questions and you well, first of all, one, so that you're getting all of the information that you need.

Because sometimes I talk to clients, they don't even have all the information. So we're operating with maybe a third of the information that we really need. So we're out on a limb. One is putting yourself in a position where you're really getting the full information from the people who are making those decisions, building those relationships.

And then also, I think building into those relationships the cadence of questions. Right? So that it's not like you just always say yes. Yes.

Yes. Yes. And then all of a sudden you have a question or you wanna create a pause, and they're not used to that behavior from you. I don't know if that makes sense.

I think it's a part of how you set expectations of yourself. I mean, meaning the, I guess, the expectations that people have of you and what they would assume, you know, you would be asking. And I just think there are a lot of different ways to do that. It's not always easy.

You're not always in a position to do that. I mean, I get that. But if those are the things you have as you are building and sometimes you have no choice, and you just have to do it. And it just is what it is, and you take the information you've got, and you say yes, and you go, okay.

And you cross your fingers. And sometimes that's what you have to do if in the short term in order to, in the longer term, be able to have that opportunity.

So I think there, it's also perspective. I think the other thing that I see often with less experienced attorneys, frankly, sometimes more experienced attorneys, is the inability to see that risk is scalable.

Right? Not every risk has the same impact, and you need to be able to very quickly assess. You know, not every issue is of equal weight or equal problem or equal benefit. So being able to do that analysis and to be able to quickly isolate.

K. Here's a list of ten potential problems, but there's only two that really matter. So the rest of them, we're gonna put those aside and we're gonna focus on those two. And so what's the quickest way to get to a yes?

And that's not easy, and that's a learned skill. And that kinda goes back to, frankly, my client's point, you know, that I mentioned earlier, which is that's the kind of, I think, learned experience that you have to live through.

The only way I know how, which is being authentic and transparent. And I think we talked about this earlier, talking about vulnerability. You know, being open to say, guys, I'm not actually sure what this means. What do you think? You know, what does this look like to you? You can change your mind, but I think your principles and the way that you operate and the way that you build relationships and make connections, that needs to be consistent.

Because it's that consistency that then gives you credibility when you say, uh-oh. We need to change. We need to pivot. This was the wrong direction, or I took another look at this.

And I think that's where the human connection and the relationship building goes into that. And I think that as a lawyer, again, this was a very well known, just extremely talented general counsel friend of mine said about the general counsel role. And she had said in a different context, and she had said, the general counsel is the conscience of the company.

And I think that that means something different. That doesn't get applied across the board in the same way in every company. It doesn't mean the same thing to every individual. But I do think that you can absolutely be moving forward with all kinds of interesting, creative, innovative ways of doing things or bringing tech on board and still be principles focused and focused on understanding that you do need to be the one who maybe raises an issue that no one else in the room wants to raise because that is your role.

Yeah. Curiosity, I think, means a couple different things. I think one, it is being curious about yourself and self awareness.

And I think it also means being curious about other people.

I don't think that I have ever been a selfish person just, you know, generally.

But I will say that I have gone through a number of very personal in the last, let's say, decade, seven, eight years, very, very personal, very, very, very difficult moments or years, frankly.

And that actually, while extremely painful and I've heard people talk about how pain is ultimately a gift. And I don't think everyone always gets there and maybe because that the pain was too difficult. So I certainly don't mean this in a way to criticize. But for myself, being able to, one, be curious about that pain, just on a personal level, but then has also made me more curious fundamentally about other people and about where other people are coming to or how they are approaching issues and questions.

And and how this applies in my work is that it has ultimately, I think, given me a more generous posture. Because I think curiosity is generosity of asking questions to understand the other viewpoint in a way that where you are genuinely open and receptive to the answer without judgment.

It's very much about active listening and not looking for the answer that best suits your, you know, your preconceived notion of the outcome. It's a very humanistic thing to think about. Right? When we when we really talk about, like, my intended outcome, we think about starting with the outcome that we desire. But wait a minute.

Take care. Thank you so much.