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CZ and Friends
CZ & Friends is a podcast about what it takes to lead and evolve legal in an era of exponential change. Hosted by Cecilia Ziniti, former General Counsel turned founder and CEO of GC AI, each episode features candid conversations with legal and business leaders who are building for scale, taking bold bets on technology, and leading with humanity. Whether you're a GC, operator, or in-house counsel, this podcast is your front-row seat to the future of legal.
CZ and Friends
Original by Design: Deepgram GC Holly Hogan on AI Guardrails and Leading with Authenticity
Holly Hogan has built her career leading through change, from nearly a decade scaling Automattic (WordPress.com, Tumblr, Day One) to her new role as General Counsel at Deepgram, a frontier voice AI company.
In this episode, she shares how to create AI guardrails that enable innovation, why “clear prompting reflects clear thinking,” and how small language shifts can transform how legal teams work and are perceived.
You’ll hear:
– What it means to be a “GC-in-Residence” at Mayer Brown and why firms need visibility into the in-house mindset (01:11–04:46)
– Automattic’s legal evolution from two lawyers to global scale (05:19–06:59)
– A nine-year free-expression case in Turkey that tested principle and perseverance (07:13–09:00)
– Building agile teams with “home bases” and embedding legal in the business (10:46–13:03)
– “Clear prompting reflects clear thinking” — why lawyers are built for the AI era (20:35–23:12)
– Using AI like a “supercharged thesaurus” to write, edit, and communicate better (23:12–24:04)
– How leadership language changes team culture (“We helped close the deal,” not “We cleared legal”) (24:33–26:35)
– Seeing legal as persuasion: “You’re selling to the lawyers on the other side” (27:53–28:55)
– Building responsibly in voice AI while embracing progress over fear (36:12–39:01)
– Why changing your mind is a leadership strength (41:01–42:14)
– Her career advice: Be original—both as a lawyer and as a leader (43:12–44:04)
Holly shows how curiosity, clarity, and originality can guide legal teams through any era of change, from open source to AI and beyond.
Follow Holly:
@Holly Hogan on LinkedIn
Books, Authors & Thinkers Mentioned:
– Decision Quality by Adam Grant
– To Sell Is Human by Daniel Pink
Other References:
– Automattic (WordPress.com, Tumblr, Day One, VIP)
– Mayer Brown GC-in-Residence Program
– Deepgram (Voice AI for the Enterprise)
– CDA 230 and Senator Ron Wyden
– AI Guardrails & Policy Frameworks
– “Clear prompting reflects clear thinking”
Follow us on all social platforms to get each new episode when it drops.
@Cecilia Ziniti on LinkedIn
@CeciliaZin on Twitter/X
@GC AI on LinkedIn
gc.ai website
Think being really open of saying we don't know what they are, and that's okay. But what we're gonna do is make the best judgments we have based on what we know. We've oh we have to shift, we have to shift. Thinking the worst risk here is standing still.
Cecilia Ziniti:Welcome to back to CZ and Friends, where we explore how legal leaders are shaping the future of business and beyond. I'm your host, Cecilia Ziniti. Today I'm joined by Holly Hogan, a legal executive known for helping innovative companies scale while navigating novel legal challenges. She spent nearly a decade leading legal at Automatic, guiding the company through global litigation, privacy, AI strategy, acquisitions, investment rounds. Most recently, she served as general counsel in residence at the law firm Mayor Brown, and now she's stepping into a new chapter, having just done her first week as general counsel at DeepGram, which is a frontier voice AI company. Something that I get kind of excited about for my Alexa work, so I can't wait to dive in. Holly is known for bringing originality to legal leadership, making strategy customer-obsessed, AI forward, and aligning with company values. She and I have known each other for gosh, maybe 10 years through L Suite and other things. So so excited to have you on the show. Holly, welcome to the show.
Holly Hogan:Yeah, thank you so much for having me, Cecilia. I'm really excited to see you. And we're having a virtual coffee this morning. It's one of my favorite things to do with people's.
Cecilia Ziniti:Oh, well, it's fall, so I'm doing I'm doing the pumpkin spice thing. I want, I think, I guess blue bottles got got it, got it with like some pepper in there. Delicious. Yeah. All right. So let's start with Mayor Brown. This GC and residence concept could be kind of interesting for our listeners. It's it's sort of like entrepreneurs and residents that VCs do. What was the goal of it? And what did you set out to do? And did you do it?
Holly Hogan:Yeah. So it was a great experience. So Mayor Brown started this program. I want to say, I think it was 2023. They're the first law firm to do it. And as you said, model after a VC and residence. And it's really an opportunity to come in. And I think of it a bit like immersive knowledge sharing. So I was able to take a step back, think about legal work from a different horizon of not just getting into it day-to-day, but really how law firms and in-house counsel work together. And so there's a couple of different things. Like I came in there really, I think, with the intent and what they wanted was to talk a lot and work with them on just what's the unique challenges that we face as tech companies. They're trying to be and are very AI forward, very innovative in how they approach legal services. And so really digging in on that. So I did a lot of different things. I worked with different practice groups on how to position themselves for what clients really need. I did a lot of one-on-one sessions with individual partners and some associates who sought me out, which I thought was amazing. I thought it was like, I was like, good for you. Oh, you're getting at it. Um and then working on some other AI initiatives. So it was a really, it was a really great time to be in that, in that role. And I loved it. And it's great people. They're really genuine. I've been fortunate both at my well for my practice ad as a litigator and here just to work with good genuine peoples. It was, it was a it was a great opportunity for for me and and and I and I I hope and think also for them.
Cecilia Ziniti:Do you um did it did you see anything about kind of like how the firm views clients or like was it what was it like to be on the other side again? Like because I feel like I mean, I love my outside counsel. Yeah. Like, you know, it's something that I think deeply about now with at GCAI is that you're using AI for some stuff, maybe going to count uh outside less for that counseling work. How does the firm view it? How did you view it? Was there ever a like, you know, did you have to change how you spoke because you're at a law firm now? Give us a little bit of a window into the experience.
Holly Hogan:No, I, you know, I didn't, I actually felt it, I felt in more sinless than expected. Although I definitely had to do the switch from uh I went from a law firm to in-house, went PC to Mac and then had to go back to PC back again, which was I was struggling. I couldn't find any buttons for three days. Like that part was hard. But in terms of how I spoke, actually not. Um, I, you know, I I felt like there was a lot of, I think a lot of curiosity and interest. Because when you think about it, and I I think my own experiences too, working with outside counsel, you're just so busy in the moment, which I think this program is a good one because you're just you're so busy. There's so much going on. I don't always have the time. I like to have to talk about our experiences and how it's different and how it's unique. And it feels so natural to us because we're just living it. Uh, but there's a there's like a window of visibility they don't have into what it means when gosh, every day you're bouncing around between employment law and and a product launch and some media inquiry and an HR issue and a regulator right shoe. And that that's like before lunch, right? And so having to move at that kind of velocity, like those kind of insights, I think, are things that they were really, I think it was like a real curiosity about what is your what is your day-to-day like and how can we better serve you and how can we be not just a subject matter expert, but actually real trusted advisor with you. So I think that that kind of curiosity really struck me as being interesting and just how much my role there was to expose some visibility that you just don't get sometimes in the day-to-day because everyone's just working through whatever, whatever thing is happening at the moment.
Cecilia Ziniti:Love that. No, I remember when I was an associate at Morrison Forester, we had bring your general counsel to lunch day or something like that to work day. And they brought in GCs doing exactly what you said. And at the time as a young associate, it was inspiring to see that. But you're right, homing in on this, like it's a different job, like right. And so being a general counsel, it's really just like a superset where you're, you know, your legal skills are are good, but the ability to do the employment, the securities matter, the privacy matter, the global matter all kind of before lunch. That's definitely uh been a theme throughout this show. So let's take us there. So let's take us back now to automatic. So what does Automatic do? How big is the company? And tell us a little bit about your journey there.
Holly Hogan:Sure. So automatic is probably best known as the Stewards of WordPress, which uh is the open source software that powers uh the about 40% of the web is using that to build a website. We had a hosted version of it called WordPress.com. We also have Tumblr, uh day one, a journaling app. There's VIP, which is a more enterprise version. So it's really, if you think about it, I describe as anyone from my mom to large media organizations can and NASA can can use work can use our services to build a website. It was a when I joined, gosh, there was a couple hundred people. And at our peak, we were going up to several thousand. We were up to 2,000 people. Went through just rapid change, just so much growth, so much change from the from the business perspective, and also launching into new things. I remember we went into a payments vertical. It's like, all right, I'm gonna learn payments law now, right? Or we acquired deeper. I gotta learn about messaging. So just a constant change in that trajectory. And then we went from a phase where the internet was was not regulated and I mean very, very lightly. And I think everyone thought it was lovely. And now there's just a lot more opinions around it and a lot more rules around it. And so growing up through that experience, uh, I came in as the second lawyer and then uh and then turned up, took over the team a little bit of time in there from there, and and just moving the team through that change, going, going from just the team growing, the company growing, the landscape, and everything around us changing. Yeah, it was a great ride. It was a it was a fun ride.
Cecilia Ziniti:So you were the second lawyer at this tech company. Yeah. Rose, it's powering you'd you say 60% or 40% of the internet.
Holly Hogan:So they get the open source software powers, yeah, powers 40%.
Cecilia Ziniti:Wow.
unknown:Wow.
Cecilia Ziniti:And so what what what stands out? I mean, what what are you most proud of from your time there?
Holly Hogan:It's a hard pick. There's a it's a really hard pick because we did a lot of really cool things. I I think I think see some of it is is the is moving things, is the whole aspect of growing things up. I would have to say one of things that actually the thing I think I'm most proud that the team did, and it's actually something I had nothing to do with, but I'm so I'm I'm comfortable, I think very comfortable and proud of, is there's a really uh big case against the the in Turkey trying to remove content that was critical of the government there. And over a very, very long time, it started before I even got there. And we continued to press it and go through. And it's really stood alongside our user, who was someone who was exposing a view around what they saw as inadequacies in their government and and things the government should be doing better. And it was, it was, it was taken, it was taken down and ordered to be taken down and fought and slogged through it for, I think it was it started before I got there. So I think it went on for nine years of really just standing behind, continuing to press, continue to ask, continuing to push through there and eventually got a victory, a really big victory of, I mean, it was, it was a long time coming, but being able to have a success of against all odds, really sticking through that. I think that's something that's really unique from you know from a legal perspective. But I'm also proud of, gosh, we launched really cool AI features. We we helped the business grow as a team. I think our team, I mean, every legal team says they're special. So I'm gonna, I'm gonna, I'm gonna, I'm gonna, I'm gonna brag on our team though, in that risk regard, of really being super business forward and being, I think actually really I got we get lots of comments that we were the best legal team folks I've ever worked with, that they felt like we were thought partners and not just lawyers. So I think that some of that, that too is a piece that I really appreciate. And I'm and I'm giving you two. It's hard for me to pick. I was there for so long, it's hard to no, no, look.
Cecilia Ziniti:I mean, I think we're proud that like some great themes to pull out there, which is like the ability to like really fight for what's right, it sounds like having company uh, you know, allow you to do that. So not only being at a company that that has that is on the right side of principle, but also giving the resources over, you know, almost a decade to actually stand up and do it. And then of course the legal issues, I'm sure were novel and interesting as well. Yeah, that's a great one. And then separately, the like just you know, growth of the team in general. So, what about leadership?
Holly Hogan:So you come in, did you come straight from a firm or like give us a little bit of the journey? Yeah, I did. So I came in, I was an IP litigator. If you look back at my my background, it both makes sense and makes completely no sense with what I'm doing. So I I was most recently before automatic an IP litigator. I was doing patent litigation. And I really enjoy my time at the firm. I enjoy being a, I think you were a litigator too. So you'll probably appreciate this. I liked it, but also didn't know it was something I wanted to do for the next 30 years and be fully committed to that. So I liked the the random questions from clients and they would call. I really like being on site with clients. And I thought, I think I'm gonna like being behind just one mission. So I came in at a time, there was just a few of us, and it was things would come in and it was who's who's available to jump on that football. That was that was who's who can catch this, who can crab this fire. And then moving into a place of wow, we have to actually be orderly about things because there's a there's a there's there's multiple of us, and there's a lot of people around the company, and we have structure and process. And the company was going through that too. You were moving from the place where you just knew that you know, Bob was the person to go to about something to we want to have some sort of structure around this, but we also don't want to be this very, you know, we're not a big company, right? You don't want to have like layers of bureaucracy. And so that pivot from just an organizational perspective is really fascinating to go through. Right.
Cecilia Ziniti:Okay. So so what are some of the structures? So a lot of our listeners are in this kind of scaling journey, or you know, maybe are new to in-house or things like that. What what would you say? So you said you got to put in the structure. So not everybody's calling Bob. I hear that. Bob, we love you, but like it's it's it's about scale. So what are what are the things that you did? Did you do like like just getting super brass tacks, like an ear system, or did you do like, do you like to assign kind of lawyers to business units, or like what what are your thoughts on kind of um uh legal team management? Yeah.
Holly Hogan:So we had a very, we have a complex had a complex business to automatic because there were so many different product lines and then there were so many different subject matters. So, and also we were a small agile team. So you could think of 30 positions that we could fill, but obviously that's not realistic and that's not what the company needs. And none of those people would be working full time. So what I tried to do was take an approach of thinking about what are the skills I need to hire for that I would describe as someone's home base. So, someone, we were going into payments, hiring somebody who knows a lot around fintech and those roles, because I don't know nothing, literally nothing about it. Um, but also having curiosity and agility and wanting to learn and grow and do different things. And I think that's the key, especially at a fast-paced company, is you've you're gonna need to hire like the person who knows this or knows that. But you also want people that are willing to grow and jump into things that are that are that they don't know absolutely nothing about too. And so having that, that kind of piece. I also would really tell the folks on the team, and we did do some, I think for for product and commercial, we would pair somebody on the team with the different business lines. And the way we approached it was you really should feel as much a part of that team as you are a part of the legal team. So you're going to their meetups, you are, you know, in the meetings, a lot of my one-on-ones with our team members wasn't just about the legal issues. It was about where's the business going? What are the metrics? What are they trying to hit? What are the challenges that they're facing? And so really being baked in and and part of it. Uh, and then and then I think because of our size, folks had to be managing a couple of different product lines, a couple of different business divisions. Um, but I think they like that agility, but also rooted in something that they that they were really, really good at and had a home base in.
Cecilia Ziniti:That's great. Yeah. I mean, we we've had that as an ongoing theme throughout the pod. It's like David's David Morris and I, uh, the ex GC of Snake, on his pod episode, he said kind of what he said, which is like you go to the meetups and you make it happen, get on a plane if you need to, or you know, virtually make sure you're in the Slack or whatever it is. And and we concluded, uh, this is funny that that uh my shining moment as product counsel was when the product management leadership had a uh like an off-site where they were going to uh one of these fake skydivings with a big big fan, whatever. And I got invited and I was like, I'm part of the team. And I'm like kind of like, you know, it really is helpful for the legal advice, right? Because you know exactly where the business is going to be going. You've got to your point their metrics. So you can say, all right, if we've got to hit, you know, why revenue, how do we uh revise our agreements to get there? Or if we've got, you know, uh a drag on on um you know, new signups, can we help um, you know, kind of streamline with some marketing campaigns and you know what what how can we uh make sure we get consent in a durable way to do that? So lots of lots of lots of fun examples. Any um, um, all right, so before we we leave automatic, any any any crazy stories or or or fun thing that that you would that you would want to relay? It's okay if you don't have anything.
Holly Hogan:No, I mean I think I mean my pop my crazy stories there is just ending up with this, I end up having dinner with the king and queen of Jordan with all these other tech companies, which was really which was very I mean, which I I I mean, I I remember walking in there and going, I have absolutely no no idea what you're supposed to call them, right? I'm walking in, like you say like, hi king or hi queen Ranya, like what do you um amazing? What an experience. Wow, great. Yeah, and just getting that they was they were doing, I think, an intention around working more with tech companies and and getting some visibility there. And also this at the time where there was a lot of concern around terrorist content online, and there was certainly a lot of coming out of Europe about how to handle that, and they wanted to have a voice and perspective and what that would look like. And so came all the way out here and met with folks and gave us a lot of information and perspective on things. But it was definitely a there's like this Frank Sinatra song where I think there's something some part of it where it's like I've dined with the king or something. I was like, oh, I've actually done that.
Cecilia Ziniti:Look at that. I love that. Yeah, you get these kind of like when you when you have these moments in your life where you're like, this is cool. That's amazing. Yeah. Um, all right. So uh, so on that note of like you said, okay, you didn't know, you didn't know how to address the the royalty. That's okay, I don't either. But you you've said on on in another context, you said sometimes we don't know all the answers, or we as lawyers don't have all the answers, and that's okay. So I agree with that. You know, you got to be able to look it up. Why is that mindset important generally? Um, and then now in this AI moment.
Holly Hogan:Yeah, yeah. And I I think especially doubling down on this in AI, and that's what really came up for me because I feel like there can be a hesitancy, not just on the legal team, but if the legal team it can it can spread out to the rest of the company if there's this sentiment of we don't know what the answers are, so therefore we don't know what to do, and therefore we stay still. That's there's like this worry. And I would, I was hearing a lot. I would, this is gosh, two years ago or so. I you know, be going to different events and just hearing a lot of lawyers saying, gosh, I don't want my team putting their code into this, and I don't want them using this, and we gotta, we gotta make sure there's protections that people don't know. And I'm thinking the the worst risk here is standing still and we don't know what the rules are. And I think being really open of saying we don't know what they are, and that's okay. But what we're gonna do is make the best judgments we have based on what we know. We've we have to shift, we have to shift, and that's fine. And that's I think, especially I think as the head of the legal team, as legal team of the whole, really conveying that message. So there's not this, I think a lot, I think there's a sometimes uh people don't appreciate the fact that for a lot of folks in business roles, you know, they worry about legal risk because they don't know what it is. They don't know how they don't, they don't have the different levels of comfort that we have. And so if we're conveying hesitancy or uncertainty in a negative way, that trickles down. And so I think it's more embracing the unknown and let's find a path through the fog. And if we come out and make good decisions, we'll be gonna come out on the other side in a in a great way. And if we have to adjust, we have to adjust, but it's probably just gonna be around the edges because we're gonna make good decisions to get there where we think things are going.
Cecilia Ziniti:I love that. I mean, I think it's like, you know, another another guest on the pod who's one of my favorite lawyers ever, Tina Patel, she's like, you gotta make the call. Like, you know, like take the information that you have and make and make the call, and you cannot shy away from from making that judgment. So that that's kind of kind of in line with what you said. So where did you end up going with with using, and then I mean, obviously you don't have to betray confidences, but in terms of what's your view now, obviously you're in an AI company, but AI coding or using AI to code is it's certainly a reason here at GCAI why we um were able to move so fast. We've got, you know, a less than 10 person engineering team supporting 700 odd customers, and we're able to do it because of AI. And if we had that hesitancy, we wouldn't be there. So I guess the question for you is like, where did you where did you end up? And then how did you guard against the risk? Because there is risk. Um but what did you do?
Holly Hogan:So what we found is we were getting a lot of questions from a lot of people in a lot of different areas. And that was also just process-wise, like, um, this is gonna be reactive and very slow if we keep doing that. So the approach that we took was was twofold. One is really thinking about not like subject matter, like privacy and IP and different pieces of it, but really how are our teams gonna be using it? Let's get them guardrails and what I would describe as laying down runways. Like let's like build the asphalt, let's lay it down, let's build runways they know they know where to go, they know they know the directions to take and how to move and get that plane and get rolling and make it really simple. So for coding, for example, we sat down with our engineering leads and instead of taking every single question, and certainly questions would come up, but we came up with something like two pages. Here's how to use it well, here's the things to stay away from, and making it very clean and easy and getting it out there for like the marketing folks, actually using AI for things that's just like don't put Mickey Mouse in your. I mean, it's not, it's not that much, it's not that different than than what you're doing already, and giving them so those permission space. And then on the places where we're using on the consumer facing where our users would be interacting with some AI tools, you're really thinking about there aren't rules yet about what kind of disclosures you need and what you need to say. But we could sit down as a team and think about consumer protection law is always about what does a user need to know. And if you think about like auto renewals, yes, there's like a lot of rules about that now, but it's really about what does someone need to know to make a good decision here about whether to buy a product. And so translating that to the AI space, what are things that users need to know to be able to use this well that we should let them know about? And so we sat down and worked through that and just got those pieces out. And then we did a marketing campaign. So we went around, talked to different teams, really got front and center and getting that guidance out there so people can move with it and move with it in a good way. And I think ended up in a spot where our company was very forward and embracing AI at a time where I think there was more hesitancy that I was seeing in other places.
Cecilia Ziniti:I love that.
Holly Hogan:All right.
Cecilia Ziniti:So switching gears a little bit, yeah. Let's go to just AI in general. And AI for lawyers. Yes. Are you using it? It's okay if you're not, right? This I really sponsored podcasts, just about the the fun of it. Are you using it? And then what you know, clear thinking, clear writing, clear prompting, all these things you've succeeded in your career from from that clarity. How do you how do you see that in a post-AI world?
Holly Hogan:So I I feel like there's for lawyers in particular, we're really good about asking questions because you're in a space, and maybe it starts with the um Socratic method in law school, and then it goes through trying to figure things out and really digging down the layers deeper to find solutions and and match things up. You'll appreciate, you know, when you do interrogatories and you're responding to it as a litigator, the quick response is probably not the actual response, right? You have to like really craft the like craft things well and work and ask a lot of questions on the inside to figure that out. I think that's actually a great skill that translate really, really translates really well to using AI because it's really a series of asking questions and having a dialogue with the technology to come up with the information that you need. And I've been thinking a lot about you know there's this idea, it's very classic, the clear, clear writing reflects clear thinking. I would venture to say the clear prompting reflects clear thinking, that you're really powering through how you how you just parse things and ask the right questions and get to the information that you need in the right way. So I think lawyers should be some of the best adopters of AI in using it for work. So that's number one. And in terms of how I'm using it on a practical level, kind of brass tacks, I tend to find the most success with things I either really, really don't like doing or things I really, really love doing. So I, you know, I think there's certainly grander plans of big structures that you can put around to make big projects faster, like absolutely. But I think if people are looking for places to start, I find, look, sometimes I have to send an email that I find to be uncomfortable. Um, and I'm like, I'll just put in, I'm writing this, I feel uncomfortable for this reason. Can you help address that? And it comes up with something sometimes that yeah, I'll, I'll work with, but you know, that's in a good space. And then on the side of things I really enjoy doing, I like making PowerPoints, but I don't like I'm terrible at moving the little pieces around. And so I'll use it for that. Or I'm I also will use a lot for editing. Always felt like as as a lit, when I was in my litigation days when you had 30 pages to say things, uh like three bullet points, that I was a much better editor than I was a first drafter. I I would like, I would remember, I would take my brief, I would go down to the coffee shop and I'd sit there and I'd like edit sentences and on and now I sit and I I I'll go through when I'm writing something. It's different because now it's a contract or something very short, but use it as feedback to almost like a supercharged, like hyped up thesaurus thesaurus to come up with a better draft of something. So those are those are just a couple of examples. But I think you have to you have to lean into it because it'll make your job, it's it's some work to figure it out. It's a totally new way of thinking about things. But in the end, it's going to make things a lot easier and better.
Cecilia Ziniti:I love that. I I've been thinking about nothing but AI and legal for two years. And I don't think I've heard anyone else so clearly articulate kind of that like the the management of AI is now what we're called to do, right? This like clear prompting, clear direction. You know, I even think about now the buzzword is like agents, right? Agents really is like people that you're asking to do things for you and you're SAS, you know, as a general counsel, managing a team, aligning people around ideas and around uh written communication, that that's gonna shift to AI, at least in some fashion. So yeah, I love that. And I love the the supercharged thesaurus. I do like, I do like super Google as well, but it's the supercharged thesaurus idea of like, I can make this piece of writing better, more clear, land my message, achieve the thing ultimately. Yeah. Yeah. That's that's great. And I I'm with you too on the craving the litigator days of just like really spending time, you and the draft and the doing and all this. But but I I think that's one of the things that I I think I guess how do you encourage on a team people to improve their draft? Right. So just like at leadership, like give us a little bit more. You give us a little bit of a window on leadership. But what do you do to bring up your team to that to the the level it sounds like you are? Not just with AI, but in general.
Holly Hogan:I think it's a lot of and this is personal to me in my own in my leadership sound what I found to be effective, but I think a lot of it is figuring out for each person what makes them tick, what makes them get up in the morning, what makes them excited, what kind of impact they want to have. But I think hiring for people that want impact, especially in tech, it's hard. You have to be resolute, you have to be able to work through challenge and ambiguity and hard things and fast paced. And so you want people that are drawn in by more than just this is like a fancy thing on name new site, right, and a shiny new thing, someone that really believes in what they're doing. And so I think starting there of giving people that, giving people a lot of autonomy and experience to be able to do things with the right amount of guidance. You got a safety net there if needed, but really letting people move in that space. And I think really a lot of it is leadership is just day-to-day habits of being someone who does things like don't say the business, we're gonna go talk to the business, like we are the business, don't say that. Um, talking about not, we we um we cleared legal disclosures for this product launch. No, no, no. We helped launch the product, right? We helped, we helped we helped our customers find clarity. We didn't do legal review for XYZ contracts, we helped close XYZ deals, like really language and how you talk and frame things and and really spending a lot of time that we would in our group meetings. I often found, especially when they got bigger, you get the question of like, what does everybody talk about? Like there's a lot of people doing different things, what's gonna be interesting? And we would spend a lot of time really talking about how we serve our fellow colleagues, how we make their lives better, how we help advance the mission of this company and really orienting it around that versus like, here's my three updates for the week. I mean, we also were a blogging company, so it helped a lot that you could write about ahead of time and and we have internal blogs to do those sort of things. But I think really spending, I think it's just like where you spend your focus and attention as a leader with the team and and spending it on those things and creating that kind of culture. It's just a lot of like little tiny things that over time build up.
Cecilia Ziniti:I love that. It's actually on theme of um we had done a like a career panel, and it turns out that things that are good for you as an individual attorney in your career, like expressing your wins as as business goals, are actually good for the company, good for the team at large too. Because you get this thing where, you know, I I remember one time one of my stakeholders was like adding legal to do the paperwork. And I was like, that's not the thing. And it's like, and that person, and I ended up speaking with them and saying, hey, look, you know, getting this deal done, like, you know, me and my team were helping you close this, you know, multi-million dollar thing. And it's gonna discourage the team to do that. And then I thought, you know, I want to make sure that my that the team has exactly the mindset you said, where it's like, you know, obviously you got to get the job done, but also do it in a way that reflects you understand that it's not just paperwork, that it is actually, you know, you're advancing the goals of the business. So yeah, I I love that. And I love also like doing it at the kind of the team meeting level, too, where words matter, right? Like this is we've been talking about this whole time that like, you know, clarity of thinking, clarity of thought. Like if you actually think that your job is the word red line, like yes, red line should be amazing. I'm super nerdy about it, you know, like we we do that, but it's like you're doing it with a purpose. I I I love that. That's yeah.
Holly Hogan:And I would actually say something that's struck me as a thought in the last year or so. This is, you know, the time in the GC and residence role and thinking, you know, thinking about the practice law in a different way, is in a lot of ways, your job as a lawyer on the commercial side in particular is you are selling to the lawyers on the other side of the deal. You have to have, I don't that doesn't mean that you give in on everything. And in the same way that our salespeople aren't gonna, I don't like make up a product that doesn't exist or put in, put in things that we're not gonna be able to do, right? But you wanna set up a situation in which you've got a reasonable set of terms that takes care of everybody and gets them what they need reasonably, gets us what we need. And if it's not clear, you have to think about different ways to to handle that. So in a lot of ways, you're you're actually selling to those folks. There is an audience for this who is the lawyers on the other side of the deal. And that is your sales counterpart in a way. So that's that's my latest thought experiment around this.
Cecilia Ziniti:I love that. I read a book called To Sell as Human sometime. Oh, interesting. And it makes that point that essentially everything we all do, including teaching. So obviously, I take classes, is like you're conveying knowledge to someone, and you have a goal, which is to move them, to influence them, to learn the thing, to do the thing. And is, you know, it's a psychology pop psychology type of thing from from more than 10 years ago, but it was very influential in my legal practice in thinking exactly as you explained, which is that ultimately all of us are in the influence business, whether we kind of like it or not. And so that's a really I I think that's a really astute, uh, astute point. Would you equate that with being customer obsessed? Any good examples that that jump out at you?
Holly Hogan:Yeah, I think so. I think it's another pivot off of that. I mean, one of the things, and this comes From I've been fortunate to work at companies that really care a lot about their customers and doing right by them and helping them succeed. And so that I think you have to take the company and their values and you have to really make that infuse how you work as a lawyer. So I uh a lot of times when we were even in daily practice, so there's from tactile things to big picture things, having that approach really changed how we did things. So some of the things you come across are more routine, like trying to do red lines, trying to put together a contract, doing, if you're on the consumer side, doing disclosures. If you're thinking about what does the customer need to know here that I need to help make sense to them, that makes a lot of it easier. Instead of, you know, if you've got some sign-up flow where you've like wedged in some like sounds like a prescription drug ad, right? Like just like a of disclosures, like that's not even like fulfilling the point of what the whole the law is about, which is like you're supposed to understand that they're gonna get billed and how often they're gonna get billed and these different things about it, right? So I think putting that perspective. And then times where you have tough decisions and it's like, gosh, we could go this way or that way. And what's gonna be the thing that decides it for us? A lot of times I feel like, especially in a legal context, if you go with what's gonna be best for the user and what's gonna support their experience with your company in the right way, I think that's that's what gets you there. That's what helped us when we were fighting this case in in Turkey for a long time and on the automatic side of really thinking about this is what's best for the user. And this is, I think, good for our platform as a whole and and our users, our users in their entirety. So let's keep going on this. And when we were doing things in in other spaces and opening up opportunities, where we were EPR and how we did privacy compliance and the things that we made available to our users, a lot of that was driven by what do we think is going to be useful and resourceful to them.
Cecilia Ziniti:Love that, the customer obsession. See it in lots, lots of jobs. So on that topic, uh, you recently started a new role. Tell us about the new gig.
Holly Hogan:Yes, yes. I've been here two weeks. Uh, so this is the end of my second week at DeepGram, which is a voice AI company for the enterprise. They do a lot of really exciting work to enable businesses to use voice AI in their own applications and and working through their own service with their own end customers. So I was really drawn in, obviously, as you could probably tell from that I have a lot of affinity towards AI and see it as the future and really wanted to get closest I could get to where the action is happening. And being at a company, building a model was the place to do that. Uh, I was also drawn into the fact that they're solving the really hard challenges of voice, which is just, it's just another layer of complexity. And the more you dig in, the more you realize all of these little finer points around how do you know when someone's done speaking? How do you know when someone's asking a question versus saying a statement? How do you, how do you know what what language someone's in coming like all like the little finite, minute things you have to do? How do you get the pacing right so that there's not these weird, awkward pauses, but it's also not too short, too long. So I just I love the technical challenge and the really hard things that they're doing, doing in the space. So I'm very excited about it. And I also just feel like voice is a place where it's there's a lot. I mean, this is true of all AI, certainly. So it's, but especially in voice, there's just there's so, there's so much more to go. We're so early and early innings of what we can, what we can do there. So I'm really excited about it. It's a great team. It's remote, like automatic was. So I'm I'm able to kind of flex into that muscle again. Uh so just a lot of a lot of things that excited me. And I'm I'm I think in a great spot to to jump back in.
Cecilia Ziniti:Awesome. Voice privacy is my um, I was uh product counsel on Alexa and these issues around literally like what you described, pointing of like when does it know you're not talking anymore? Because it's natural, like, you know, and and even in a remote context, being able to tell, am I done speaking? Am I not? I always tell this story that I my my spouse, so I'm Italian chucker, uh we we talk a lot and we talk loud and we talk at the same time. But it was funny when I first visited my uh my now spouse's family, I'm like, it was like they they had the talking stick. It was like, I'm done talking now. Would you like to speak? And it was like for Alexa or these voice devices, that's a much more natural or you know, it's much easier to tell in that environment. But like for us, we're talking all the time. And it's just it'll be interesting to see how these kind of like human constructs and go with AI. So I'm like, I'm I'm on the deep gram website website, and it says something like model design for conversation, not transcription. So it's just literally, are we are are we talking to bots? What what are we doing with the deep gram products?
Holly Hogan:Yeah, yeah, yeah. So there's it's it's building in these layers. You could think of it as in some ways, it's putting in all of that, like there's this really stomach called Flux, which we're really excited about and which handles some of these really complicated things like interruptions and like all of this like pacing and moving through things in a way that's really, really dug in on those really hard, challenging problems. So it's so those, those things, like all of that around speech, is is where a lot of their technology is at and where the focus is at, and where I actually think a lot of the promises. Really, if you want to make voice agents pass the audio Turing test, uh, which our founder says you could you could talk to for five minutes and not realize that it's that it's a that it's an you know, that it's a rope, that's that's not human. Because you could say you could get away with it. He was speaking as you could get with like like 30 seconds um if you went to the full minute.
Cecilia Ziniti:Is that you know you said five minutes?
Holly Hogan:Five minutes. Like that's that's the goal of like moving towards that. You know, it is that is the peak of the mountain. You've got to handle all of this nuance. And the idea behind the technology is to make it so that it feels conversational and natural and helpful. And also the the part that I think is just from a user perspective really fascinating is how this might change our just interaction with technology. Because for a long time we've been, we've been doing a lot of this and a lot of typing and tapping, but voice and the things that we're doing now and just talking, that's really that's the most innate way that we've always communicated as humans. And not that the screens and the clicks are just like going away, but what does that look like in the future? You know, I I often wonder are lawyers gonna get back to dictating, right?
Cecilia Ziniti:Because my family always makes fun of me that I'm like obsessed with voice dictating in Siria, I'll be like in an elevator and talking. Yeah. An elevator thinks that I'm talking on that and I'm talking my phone. But I agree, I think we're gonna get there. I am like a obsessed. So not every lawyer is gonna lean into that because obviously privacy issues, legal issues. So I gotta ask you like there's the Elvis Act, um, the Federal Take It Down Act, people are worried about voice cloning. Obviously, Scarlett Johansson had a claim against OpenAI, which I think was a was a good one because it was very clear that, well, I don't know how very clear. I don't want to editorialize too much, but the claim was that OpenAI had used another actor to recreate a voice very similar to Scarjoe. And well, I open AI didn't help its case when Sam Altman tweeted her when they launched this voice model. So, with all that background, I guess with all these laws, the aim at voice clone and deep fake, how do you see that evolving if your company is hard charging towards five minutes of passing the Turing test? Which again, for listeners, that means for five minutes you are talking with an AI and you do not know you believe it is a human. That is, that is the future. So with that being where your company's going, the law being what the law is, what what's gonna happen? Give give us some predictions or or give us some like you know, way to think about that.
Holly Hogan:Yeah, I think about that a lot. And I think you know, in some ways, it's interesting because right now folks get so deceived by text, right? I mean, like phishing, I mean, I don't know if it's the number one way that that that cybersecurity events happen, if if it's phishing or not, but it's definitely like up there. And so there's, I think it's it's been a challenge that's in some ways always existed, right? Sort of know something's accurate or not and coming in different different spheres. Like certainly it's it's another vector and it's and it's more dimensional. And so there's there's different risks there, but it's also a thing that I think like building responsibly and and moving and moving along in that space. I have a lot of confidence in the fact that when the technologies uh, you know, you've got this like embrace of like new and form of technologies that that those things get worked out and worked out responsibly and figured out. So I um I actually, in some ways, I'm a little bit more focused on a lot of like the opportunity there and the way to do things, in the way to do things differently. So obviously I want to be mindful of the risks too and all of that. Um but it is it is a place where there's there's just been a history of technology of working through those risks and doing it responsibly. And I think that's a lot of of I think what the part you come at it from a legal point of view of having that just lens of wanting to be and build responsibly. And it's good to be at companies that you know that want to build and be responsibly, which is I've always been really fortunate to be a part of.
Cecilia Ziniti:So um I yeah, I I that's I think that's my overall view on it. I love it. I love it. So I'm gonna hold you to that. I'm gonna I'm gonna send you a podcast invite for five years from now. Yeah, and we'll see if it if it's AI Chilea and AI Holly, and and we'll go at it. I love that. Like this new technology, there's always been more and better ways. Like fraud, fraudsters and bad people have always been at the forefront of technology, including email, right? And I mean, that's more of the original, you know, with spam and all that. So I uh I love that point that we'll get there. You've had some memorable moments. We already talked about dining with uh the king and queen of Jordan. Apparently, Senator Wyden came to a talk of yours. You didn't know uh that he was there. What what happened and who's Senator Wyden?
Holly Hogan:So he, you know, is the is the the the the the person the the government, you know, he and and and representative cox, you know, putting together CDA 230, which was just the the law that embarked the embarked the internet. So it was during COVID and I was doing a an online presentation and I realized about halfway through that he was on the thing, was on the line watching it, uh, which first of all I almost fell on my chair. Um, but I was just so honored. But also I think it reflected how cool is it that this is someone who cared so much. I mean, just certainly obviously was his signature, one of his signature bills, so certainly he does. But what are we, 25 years later, and he's still going to talks about this issue that are that are, you know, it's not it wasn't some amazingly large event or anything, but he's still going to, I was like, that's just really special. That's really cool that somebody cares that much about the internet and technology and moving forward. I just um, you know, sometimes people feel like the government doesn't get it and there's a lot of regulation that can be very difficult. And it I think it's also nice to see the side of it of people who care and are trying to support innovation and continue like believe in it that strongly that that that that long later they'll they'll go listen to some general counsel at a company talk about their CDA limitations.
Cecilia Ziniti:So like you know, yeah, give her give give yourself some credit. That's an incredible story. All right, let's move on to the lightning round. What's up, the podcast, or article that has shaped how you think about leadership?
Holly Hogan:So very recently I've been reading decision, I think it's called Decision Quality by Adam Grant, who I think folks know is an organizational psychologist. And he has a point that actually you should be changing your mind more often than you think you should be. And he bases it in looking at science and scientific research and how they build a lot around like hypotheses that they test out and change. And I like one of my favorite things has always been to change my mind about something. I feel like you learn something new, you grow and develop. And I'm really big on my teams of telling people that you part of your job is to disagree with me and help us come to better decisions. So I've certainly changed my mind on things over time. And so I think having an openness to that, I think, especially being at a tech company where you're always challenging assumptions and you're challenging the way things have always been, even the thing that you think was so great and awesome you did as a legal team in 2018 at a tech company that might not be relevant anymore, right? It probably isn't actually in the age of AI, especially. Everything's changing. So be having that piece, um, I think is is is agility, right?
Cecilia Ziniti:But it's like agility plus humility. I love that. Yeah. Any advice for for for listeners? It could be early career or maybe their first general counsel role. What's your advice?
Holly Hogan:Yeah. I would say to think a lot about putting yourself in positions, especially if you're early in your career, if you're at a law firm, think about how you can help people and how you can solve problems and put everything through that lens. I think when you're there's, I think the fascination of legal issues is obviously important and it's part of what drives the intellectual stimulation for the job. But I think really, really, really keying in on that because there's that's so much of what the job is ultimately. You're helping people solve problems and that translates into business development, that translates into networking, that translates in doing well at your job. So really putting everything in that, in that context. Think about things from that point of view.
Cecilia Ziniti:Holly, if somebody listens to this conversation as a window to you and how you lead, any one principle you want them to take away?
Holly Hogan:Yeah. I think I used to say be a creative lawyer, but then I think that has a bad, that's sometimes a kind of like a weird connotation. So I would say be an original one. Like think about originality. Think about, I mean, this is at a personal level, what makes you you and be that? I can say this now with age and experience. You sort of realize that actually being who you are and leaning into the best part of yourself is really important. Don't try to be anybody else. But also from a meta level at your company, what's unique and different about your company and how can you how can you put that into practice in what you do for your legal team? How can you reflect those values? I mean, I was if you're an open source company, be really transparent, be really open because that's that's that's the mode and the model of what the company is. Really reflecting that and finding new and different ways to do things that are unique and original to your company. I think it makes the job a lot more fun too. Much less cookie cutter and more and much more uh much more simulation and better job at the end.
Cecilia Ziniti:Thanks for sharing your perspective. Where can listeners connect with you?
Holly Hogan:I'm on LinkedIn. Uh I am, you can find me there, Holly Hogan, I think through a Google search, and that's probably the best place to reach me.
Cecilia Ziniti:That was my conversation with Holly Hogan. She's reminding us that we can be who we are as lawyers, that tech can be a force for good, that you can stand up for what it's right. And she gave us lots of great leadership nuggets, including a fun one that all of us lawyers are actually in sales. If you're thinking about how to bring AI into your practice, whether through experiments, cultural change, new systems, taking a new role, I hope this episode sparked ideas for you and your team. You can follow CZ and Friends wherever you get your podcasts and subscribe to our newsletter at gc.ai/newsletter for more conversations, tools, and takeaways for legal and business leaders and beyond. Thank you for listening.