S5 #2 Legal unicorns: Bridging law and technology in the digital age

S5 #2 Legal unicorns: Bridging law and technology in the digital age

S5 #2 Legal unicorns: Bridging law and technology in the digital age

Olga V. Mack

Olga V. Mack

Olga V. Mack is a Fellow at CodeX, The Stanford Center for Legal Informatics, and a Generative AI Editor at law.MIT and CEO, founder, award-winning general counsel, operations specialist, and tech startup advisor who encourages lawyers to embrace disruptive technologies that make the law more functional and accessible. A three-time TEDx presenter with an exceptional blend of legal, technological, and business expertise, Olga is one of today’s top speakers and thought leaders. Find her latest insights at Above the Law, Forbes, Bloomberg Law, ACC Docket, law.MIT Computational Law Report, Newsweek, Venture Beat, and her podcast, Notes to My (Legal) Self. As a Berkeley Law lecturer and a fellow of the College of Law Practice Management, Olga is confident the law’s future is secure in the hands of innovators. Olga’s numerous awards include the Silicon Valley Women of Influence, ABA Women in Legal Tech, Make Your Mark, Corporate Counsel of the Year, and Women Leaders in Technology Law. In examining how disruptive technologies impact laws, society, business, and commerce, Olga authored Blockchain Value: Transforming Business Models, Society, and Communities and co-authored Fundamentals of Smart Contract Security. She is working on her three books: Visual IQ for Lawyers (ABA 2024), The Rise of Product Lawyers: An Analytical Framework to Systematically Advise Your Clients Throughout the Product Lifecycle (Globe Law and Business 2024), and Legal Operations in the Age of AI and Data (Globe Law and Business 2024).

In this episode, Kristina delves into the increasingly critical nexus of legal expertise and technological acumen, highlighting the emergence of "legal unicorns" - professionals who are not only adept at navigating the complexities of the law but also possess a profound understanding of technology. Guest Olga V. Mack, a lawyer with an extensive background in digital technology, discusses her journey and the growing trend of digitally savvy lawyers, including in-house legal teams, law firms, and government agencies.

law and technology, legal innovation, digital transformation, tech policy and compliance, legal and tech leadership, emerging technologies, AI and law, digital operations, legal education and technology, risk management in tech, general counsel role, legal advice in digital age, legal professional development
Episode number:
Date Published:
February 7, 2024

[00:00:00] KRISTINA: What are the unseen forces shaping our tech-driven future? How do we redefine the boundaries between technology, ethics, and policy? And most importantly, perhaps, how can you and your in-house legal counsel become best and fast friends in deploying emerging technologies?

[00:00:17] INTRO: Welcome to The Power of Digital Pol Policy episodeicy, a show that helps digital marketers, online communications directors, and others throughout the organization balance out risks and opportunities created by using digital channels. Here's your host, Kristina Podnar.

[00:00:35] KRISTINA: Welcome to today's Power of Digital. We're deep-diving into the digital future guided by none other than Olga Mack. Olga is a fellow at Codex, the Stanford Center for Legal Informatics, and a generative AI editor at law.MIT and CEO, founder, and award-winning general counsel. She's also an operations specialist and tech startup advisor who encourages lawyers to embrace disruptive technologies that make the law more functional and accessible. I could go on about her accolades for probably most of the next hour, but to me, I think she's an accessible lawyer who can shed an interesting perspective on how we become friends with our office of general counsel and how we ensure that new and emerging technologies are well placed in the enterprise? Olga, welcome. It's great to have you. You're one of those rare people.

[00:01:24] OLGA: Thank you for having me, Kristina. I am really excited to have this conversation. And thank you for calling me rare. I'd like to believe that we're all rare in our own ways, so I think it's just right.

[00:01:37] KRISTINA: We are very rare, I think, in our own individual ways, but you're very rare. I always refer to you when I'm out and about, in the world talking to folks. I always say, you know what, there are these sort of unicorns out there, and thankfully I'm seeing more and more of them. But I often say that you're a purple unicorn because not only are you a lawyer and you understand the law, but you actually understand the technology, and that combination and having that digital nativeness is, or used to be, very rare, especially when we look inside of the office of the general counsel. So, I think you're rare, but are you seeing more people like you these days?

[00:02:11] OLGA: I definitely think that there are more digitally savvy and digitally versed lawyers generally. Yes, in-house, yes, in law firms, yes, in governments, yes, in our institutions of legal education; it is partially because of folks who grew up with technology like myself. I basically don't really remember time without email. I went to college using email. I didn't use it in high school, but I basically used it always since college. I think that's part of it. I think we have also been through a number of changes. I don't want to call them disruptions. I really think they're more of evolutions. They could be disruptions if you're not prepared for them or do not like change, but they're just natural changes in the world due to technology and frankly other things like social changes and you know, environmental kinds of things. So this is kind of happening more frequently. And, all those changes. And they coincide with technology. So it's a combination of digital and native folks coming to the workforce. Also having folks who have been around and actually experiencing changes. And now, you know, having a plan or at least appreciation that it's possible to get on the other side.

[00:03:39] KRISTINA: So, as we're thinking about digital operations teams and digital being a critical word, I think I'd probably use technology instead because there can be an array, as you said, not necessarily thinking about it as disruptions, but really an array and evolution of technologies, new things coming at us continuously. How should these digital operations or technical operation stewards instead of enterprises approach the development of the technology, the adoption of technology. And how do you really see the role of the lawyer, whether it's in-house counsel or outside counsel? How can they actually help enable the enterprise from a business perspective?

[00:04:19] OLGA: I really see lawyers as a very good flight attendant. I do. Because when you're on a flight and you experience turbulence, you don't usually go to a lawyer unless you're expecting a bad thing or it's happening to you, really. That's really why you go see a lawyer. So when you go to a lawyer, it's a vulnerable conversation, it's a vulnerable event. That's why I think comparing it to a flight attendant is a really good analogy. You are flying and everything's fine, and you're watching a video, reading, or sleeping, and then there's unexpected turbulence. At the point of turbulence, you're going to look for your flight attendant, their reaction. Do they have their stuff in order? Are they worried? Or are they smiling, giving you peanuts? Or whatever your snack of choice or drink and continuing was applied, telling him to buckle up and giving you a few more instructions on whether or not you can continue using lavatories, for example. So, I think that's, it's not a one-to-one analogy, as any analogy has many flaws. But that illustrates what I think is the role of the Office of General Counsel. It's really there to one if we have catastrophic events, like the kind of event that basically will obliterate your company and the value of your share, whether it's a public company or private company. And then, really, you are a business professional who understands risks and laws so well that you can, in the process, also contribute to the bottom line. I think that's the role of the general counsel generally. And you build relationships, in turbulence, and then you build on top of that relationships during the good fight.

[00:06:10] KRISTINA: What is the best way in your experience for folks to start approaching their general counsel regarding AI or other emerging technologies? How do you think that that relationship can best be formed?

[00:06:24] OLGA: I think it's with any interaction, whether it's with your CEO or your general counsel, it's kind of important to know who that person is, who that leader is. Is this, a person who is digitally savvy? Did they grow up with technology? Are they on social media? Are they experimenting? Do they use modern tools? I think it's just understanding who that person is is very important. With CEOs, for example, I always ask, are they more like numbers person or are they more like hearts and people person? It's you almost never get somebody who's equal as fit; you will get a CEO or a leader who often has their numbers first or warm-feeling people first. And I think you really need leaders to do both, but primarily when you look at the folks you're interacting with, I think it's helpful to kind of bucket them in that way. So that's going to be your leading argument, really. The question is, what's your opening line given your audience, how do you get their attention? And then the third item I think I would notice about the Office of General Counsel is that independent of their peculiarities, most lawyers are what I would describe as life-learners. Becoming a lawyer is really adventurous in accepting the learning as a lifestyle. Practicing law is really an exercise in learning every day, so that approach to, hey, let me educate you about things that you need to be educated about, and I'm very clear about it. Which you may not fully appreciate. I've seen very effectively done with the Office of General Counsel; from leader to the junior legal person on the team; I see a lot of open-mindedness and eagerness to learn. And if you approach it from that point of view, not with an agenda and not with an angle, but a neutrality and how that fits into the business, then let's work together to make the right decisions or create the right policies or reforms or outcomes. I think you will score a lot of points with the office of the general counsel.

[00:08:41] KRISTINA: It sounds like a little bit of a dance. And so I'm wondering, when we start a dance, somebody has to lead. In your experience, and when we're thinking about AI policy or any other emerging technology policy, who should be leading? Is that the role of the business? Is it in marketing? Is it IT? Is it general counsel? Does anybody need to take the lead?

[00:09:03] OLGA: Yeah, it's really interesting. In our culture, we overestimate the importance of a leader and underestimate the importance of a follower. And I'd like you to sort of think a little bit about it because If there are no followers, there's no need for leadership, so, and I think, so my first observation is that lawyers tend to be, especially if they're involved professionals who succeeded in their careers, they're usually equally competent in leading and following. And being a good leader is as much of a skill as being a good follower. In fact, that would go as far as saying being a good follower is a more important skill, and some, and honestly assessing whether it's your place to lead or follow requires advanced EQ skills. That, to me, is assigned with true professionalism. But that aside, I think your specific question with respect to who should be like, this is the CLO, the chief legal officer or CMO, chief marketing officer, or who, who is, I think that will vary greatly on the industry, on the size of the company, on the profile of the executive teams, on the goals and all kinds of things. Sometimes, it is the right place for the CLO to be a leader, especially when they have a really great rapport with all the members of the executive team, the CEO, and the board, because sometimes you really need a lawyer who is not necessarily driven by revenue to neutrally advise and lead. And sometimes for other reasons, or the same reasons, other members are maybe better suited. It's less about a title, it's again sort of understanding who the members of the executive cabinet are and who is in the best position to lead and who's in the best position to support. And I will conclude by saying that never underestimate the importance of your followers.

[00:11:19] KRISTINA: I find that really, really poignant advice, especially because you're not just a lawyer, right? You've played a multitude really of roles, as I mentioned in your introduction. And you've also been a CEO, so you have this multitude of perspectives. When you wear your CEO hat instead of your OGC hat, how do you see tech policy challenges and solutions evolving inside of the enterprise? And is there a specific way that you think we should be shaping culture, especially to foster innovation and also minimize risk?

[00:11:55] OLGA: Those are two different goals: innovation and risks. Are two different goals. And depending, they're almost never equally important at any given time. And depending on which one is more important, you go to a different leader. Yes, I've worn different hats, and as the general council, you have certain ethical professional obligations and job descriptions, and as a CEO, you do as well. I generally see CEOs sort of essentially chief sellers. And really because every CEO conversation I witnessed or been part of always revolved around revenue, whether it's sort of a positive conversation of, hey, how are we going to make more money coming in or sort of more negative conversation of how we reduce costs to make sure that we don't have a kickback and often both. I've always understood that theoretical difference. between the office of general counsel, who often also have business roles and are business-minded and all that, but the primary function is very different, and it's interesting when I transitioned from in the house council legal leader to CEO, it was amazing how overnight primarily started to focus almost entirely on revenue because that's all the conversations I have with my board really and my executives. And I, I think in the process, I've realized two things, and one is that I should not be giving myself legal advice because all of a sudden, nothing looked risky, or at least not nearly as risky as not having revenue. So, it is not a place where you want to get legal advice. And two, I've understood very well why some of my legal advice was ignored. Because even if the business-minded and business savvy in-house lawyer focused on revenue, their big, if not the primary function, depending on the industry and size and job, is a risk. Not revenue. And I realized, when people just sort of like, yeah, yeah, yeah, bye. I realized why I had some of those interactions with the lawyer where I would go above and beyond to share how their life would be improved by managing risks. And they couldn't get rid of me faster now because they really had a bigger problem from their perspective, which is revenue. And so very different jobs, very different focuses, whether it's, if it's innovation CEO, maybe the right person, maybe not, depending how innovative that CEO is, it could be general counsel, perhaps if it is a legal sort of product type of business. And if it is risk, again, it could be your CEO because in some industries, like financial industries, everybody's looking for the CEO's reaction. And sometimes, often, it is the Office of General Counsel because they, you know, the General Counsel, sometimes, often, is the effect of consciousness. of the place, the publicly visible executive that embodies the consciousness of the company. And sometimes, it's helpful to have that person as a leader. Again, depending on the goals and skills and circumstances.

[00:15:31] KRISTINA: I love how you put that into the word consciousness, that role potentially because I think it's so. appropriate with a lot of the emerging technologies that we're facing that aren't regulated yet, right? We really need to have some boundaries. My theory is that if you create a framework and tell people this is your framework, it's almost like having children telling them they can play in the backyard. I always used to say to my son, do whatever you want in the backyard because I knew he was safe, right? Your kids aren't going to go and run into the road and get hit by a car that he might get a bruise or even break an arm, but those things aren't life-threatening, so you kind of know the backyard is pretty safe. Go out there, get creative, get innovative, do crazy. Be in the backyard. Don't leave the backyard. It's the same thing I think of when we go into emerging tech; I think, you know what? If your buddy in legal, if the OGC or outside council says, here's your framework. Don't go outside of this framework. I believe it fosters innovation and creativity. But has that been your experience? Because you've had so many more hours of this.

[00:16:32] OLGA: Do I think sort of compliance fosters innovation? I actually think increasingly, yes, I think we started with sort of move fast and break things, right? This is sort of classic, Mr. Zuckerberg says, and I think at that time when the innovation was not actually nearly as fast-paced. And frankly, not nearly as high risk social media is a risk, but it's not nearly as risky as things in the medical field or financial sector, which can bankrupt like countries; all of this is relative. So we're moving much faster, and we're putting increasingly bigger bets. In that type of environment, what I've seen over time as a practitioner is this switch from, hey, we'll ask for forgiveness. We'll send Olga, and Olga is an adult in the room. She's been a practicing lawyer, member of the bar, like young company and regulated, she will explain for, you know, ask for forgiveness, maybe we'll pay some penalties and agree to a go-forward plan. To something more like what I would describe as compliance as a competitive strategy. Because in a world that moves much faster with increasingly higher bets, compliance is actually becoming the reason why you get partnerships. Why do you befriend regulators? Why do you win trust? so, yes, compliance could foster innovation. And by the way, there's a lot of room in compliance to innovate as well. In the recent hearing about AI, various regulators, including FTC, very much sort of have this undertone from not only how we move from moving fast and breaking things to something like compliance by design, but this undertone that we need to be innovating the way I to the compliance is an innovation reach experience. Are you as leader? must be doing that too. If you find yourself that complying is prohibitive, then you have not for you to be in business then you have not been innovative enough as a compliance leader. I think we should really ponder on that experience.

[00:19:02] KRISTINA: What emerging tech trends do you believe will pose the biggest challenges or even opportunities for lawyers looking to help their organizations get digital policy and compliance right for the coming years? Because there's just so much, I think, happening right now.

[00:19:19] OLGA: A lot is happening. There's probably a lot more noise that's happening, but yes, a lot is happening. I think to answer your question, which tech trend will be defining, I think it's undoubtedly going to be AI. I think hands down. If you have to pick one, you shouldn't be picking one. The thing about those new technologies, disruptive or not, Is that they actually like to couple up. They 're lonely by themselves. Being powerful alone is not nearly as fun as being powerful together. Because that's when you get one plus one equals more than two effects. And so, yes, if I have to pick one, it's going to be AI. But remember, they're going to couple up. And that's when you're really going to feel it. So your AI will be coupling up with your VR. And you likely crypto depending on how it's regulated and all kinds of other stuff. So I don't think, I don't think choosing one is the way to go, but for the purposes of analytical conversation, yeah, it's AI, it's most definitely AI.

[00:20:32] KRISTINA: So I'm going to ask you your favorite question of the day, which I know you asked, which is how do you stay updated with the constantly evolving legal landscape? How do you ensure that you understand what's happening today and can kind of look at a crystal ball and understand possibly what's going to happen in the future?

[00:20:49] OLGA: Yeah, I've been doing it my entire career. I think at this point I've developed sort of a methodology to do that. It probably has, let's just say, three steps, but please don't be surprised if I end up with four. It's not because I'm bad at math, it's because I do not have a canned answer. But step one I think original sources. I think original sources are important, especially when the field is evolving. So you now have the EU AI Act with all this legislative history and all that. You also have FTC guidance and new powers. In various workshops that it's conducting asking folks for feedback and input and working group and all of that, being part of the original source of information, and I don't mean just original four corners of the documents, I mean, the actual being, being in the kitchen, understanding why they use that word choice, what did they think was the catastrophic event that they really wanted to avoid? Who was really shaping that agenda and why all of that is super important. And being involved in making that, that sausage, no matter how ugly that process is very critical. The second thing, I would say your peer groups, you know, your peer groups doing exactly the same thing I just described with the original sources will have reactions. Shortcuts. Insights. And it turns out that when you go through hard times with others, it's just much more fun, and you're much more likely to get to a better decision, or at least a decision, that is defendable, so that conversation with your peers and growing with them, and then as peer group influencing regulators back in feedback, I think it's a very powerful place to learn and struggle together and grow professionally. And then I will say, this is, I think, one and two are sort of, one is an obvious thing, the two is advanced tip, and here's what I think is a ninja tip. The ninja tip is shared on various platforms, and I don't necessarily mean, yes, social media, but, you know, forums, like World Economic Forum, or Association of Corporate Council. As shared as knowledge and request for feedback and insights and information. And sometimes it will come in public form. Sometimes you will decide to share, learn, and challenge each other collectively. In not just like with people you're comfortable with, but with people in other industries or other regions outside of your country. That definitely will extend the limits of your imagination. And will really give you what I call ninja powers to be a better advisor to your company and your stakeholders.

[00:24:05] KRISTINA: That's great advice. And for listeners who are just starting to understand the importance of digital AI policy, appreciate the fact that there are many unknowns you have to talk them through. What would be the one thing you'd want them to do differently if there is anything that they should be doing differently going forward?

[00:24:25] OLGA: With any undertaking your why is more important than what or who and definitely not new as important as how, and what I mean by that is that anytime you do anything, especially something new, it's important to have a vision. Why we're setting out to do this is that because we are trying to avoid certain catastrophic outcomes, or is it something else? And I think that vision, it's something, you know, occasionally that importance of vision is occasionally taught in business school. It's almost never taught outside of business school, but I think that that's super important because if you're putting a policy on something that is still evolving, you need to anchor it in, in why, because every decision could be right or wrong, depending on whether or not it contributes to your why, and I find that policies that are sort of written as articles, They don't have a larger vision, they're sort of written to communicate. They're really not as powerful as policies that sort of have a definite purpose that is agreed on. And if you have a vision, you're far more likely to actually, you will not succeed at everything, but you will succeed at the vision more likely than not. You will get there more efficient with faster, cheaper, in the kind of more in the way without making enemies in the process and you will build unity on a team around the shared vision. You may have a disagreement between sales and legal or sales and marketing, but provided we all agree on our why, the outcome is much easier to reach. So I do find that something we almost never started with and ignore as not just as lawyers, but as professionals generally. Your why, your vision, vision is the most important thing.

[00:26:55] KRISTINA: I appreciate that advice. I hope everybody listening will as well, but I think I'm going to print out these huge font letters on a piece of paper that say, understand why it sounds like sound and sage advice, not just for emerging technologies, but how we go about our day to day jobs. So understand your why! Olga, this has been so much fun. Thank you so much for giving us your perspective. As we all go forward with understanding our why better, as well as all of the insights you shared, we're very grateful. Thank you.

[00:27:26] OUTRO: Thank you for joining the Power of Digital Policy; to sign up for our newsletter, get access to policy checklists, detailed information on policies, and other helpful resources, head over to the power of digital policy.com. If you get a moment, please leave a review on iTunes to help your digital colleagues find out about the podcast.

You can reply to this podcast here: