GC Sidebar: Carolyn Herzog, Chief Legal Officer at Elastic

In this GC Sidebar Season 2 episode, Paragon Legal CEO Trista Engel speaks with Carolyn Herzog, Chief Legal Officer at Elastic, about translating legal complexity for non-legal leadership, leading with confidence, and evolving legal organizations in the age of AI.

Carolyn shares how the GC role shifts when reporting to a boss who’s never practiced law—success isn’t about explaining every legal issue, but translating complexity into business language and helping leadership focus on what matters most. She reflects on the career advice that reshaped her approach to leadership: a CEO reminding her that she was hired for what she knows, not what she doesn’t, which shifted her focus from eliminating weaknesses to building on strengths and creating complementary teams.

She also discusses the emotional impact AI is having on legal teams, how legal leaders should rethink resourcing as the technology evolves, and why organizational design is part art, part science.

Full episode now available.

Read the Full Conversation

Prefer reading over watching? Below is the complete transcript from our GC Sidebar interview with Carolyn Herzog, Chief Legal Officer at Elastic.

Trista Engel: Welcome to GC Sidebar, a short and sharp conversation series with leading general counsels about the decisions, the reflections, and the people behind the title.

I’m Trista Engel, CEO of Paragon Legal, and today I’m joined by Carolyn Herzog, Chief Legal Officer at Elastic, the search AI company used by more than 50% of the Fortune 500 that helps organizations find answers in real time across all their data. Carolyn has been at the center of many of tech’s major legal moments, having led more than 30 acquisitions and divestitures over the course of her career, including Arm’s proposed $40 billion sale to NVIDIA. She also brings a distinctly international lens to her work, having lived and practiced law across the U.S. and UK. Carolyn, I’m so glad to have you here. Thank you so much for joining me.

Carolyn Herzog: Thanks so much for having me.

Trista Engel: Alright, let’s dive in. What’s one issue facing legal teams right now that isn’t getting enough attention?

Carolyn Herzog: One issue that I think isn’t getting enough attention is the emotional impact of what’s happening with AI. We’re all thinking about how AI is changing our legal practice and the tools we’re using to become more efficient, but there’s also a massive shift happening across the entire legal industry—rising outside counsel costs, tools that create both opportunity and risk. It’s fundamentally changing the way we work in a way we’ve never experienced in our lifetime.

We’ve had transformations before—moving to cloud services versus on-premise software—but we’d plan an entire year for that kind of transformation. The concept of transformation now is a completely different dynamic. We used to fix things while the plane was still on the runway or taking off; now we’re building the plane while it’s in the air. That’s frightening for a lot of people, though some are really leaning in and excited about it.

We also have to think, cognitively, about whether we could get lazy very quickly by using AI tools. What’s our obligation to get things done quickly and still have the judgment and oversight we need? How do we train junior people to build that judgment while they’re becoming more comfortable with the technology? So I think there’s an emotional impact, a fear impact, and something we’re all living through in real time that we need to address as we think about transforming the work we do.

Trista Engel: That’s such a great point. I was just reading something the other day about how humans aren’t meant to be operating at 100% for eight hours a day. When we think about AI and the benefits it’s going to bring—lawyers being able to do more high-value strategic work—we’re not really thinking about that cognitive load, and what the emotional and mental impacts and limitations might be on the people doing the work, setting aside efficiency and speed and all the other benefits.

Carolyn Herzog: Right. I think there’ll be some areas where AI creates more time, but other areas where we’re really just speeding up—doing things much faster, and that’s how the time gets filled. So there’s a risk of missing something, of not having time to reflect, or to ask somebody what they think. We could be missing out on those collaborative opportunities, because so much of what we do is based on judgment—do you think this is a good idea, how would this be perceived, is this within the remit of the law or outside the lines, is it blurry, and how do you decipher the blurry from the pure dark line?

Trista Engel: Yeah, you’re right, and the speed at which this is moving is limiting our ability to manage and prepare for that change.

Carolyn Herzog: Absolutely.

Trista Engel: What’s something that has surprised you about the GC role?

Carolyn Herzog: One thing that surprised me when I first became a GC is how different it is to report to somebody who has no experience doing what you do. Throughout your entire career—in school, studying topics with people who share your interests, maybe even traveling to places tied to that shared interest—there’s a throughline. But so much of being a GC is about making things not interesting for your boss and everyone else on the leadership team. The more you can keep away from them, the more noise you filter out, the more successful you are.

People think in a very different way when they’re not trained as legal professionals, so the language you need to use is very different. We learn, as we progress in our careers, to have different conversations with people at an executive level versus people who need more detail. But when you’re really trying to communicate the value of legal—what people need to know and what they don’t—you have to have a different kind of conversation.

Trista Engel: Yeah, there’s a lot of talk about how, as you progress in your legal career, your clients change. But you’re making the point that your boss changes too—and maybe this is the first time in your legal career your boss isn’t a lawyer.

Carolyn Herzog: Yeah, usually not. It would be quite rare for the CEO to be a lawyer these days.

Trista Engel: Right, but even coming up in-house, at a law firm, even in law school—even without a boss—the person you’re reporting to is still a lawyer. But as the GC—

Carolyn Herzog: That mindset.

Trista Engel: It’s not. Yeah, that’s a great point. What’s the best career advice you’ve received or given?

Carolyn Herzog: There are always a few points in my career that come to mind, but I thought I’d share something a little different that ties into the last question. When I first became a general counsel—early in my career, and I joke that it was because everybody else left, more a matter of timing than being fully prepared—that was my first real GC job at a big company, and it was also the first time I was reporting to somebody who wasn’t a lawyer, wasn’t another general counsel.

I remember my first annual review. I did a whole self-assessment, sent it to my CEO, and the first thing he said to me was, “I hired you for all the things that you know, not the things that you don’t know.” My self-review had been fully self-deprecating, analyzing everything I didn’t know—I’d also switched industries, moving into semiconductor rather than cybersecurity and software, so I’d basically written a review of how terrible I was and all the things I didn’t know.

Thankfully, I had a really supportive boss who pointed that out and reminded me I was there for a reason. So often we go into a new place—and we all like to learn, we all like to try new things, especially in technology, where everything changes so much and there’s so much that’s new—but it takes a good boss to point out the things you do really well, and where you have opportunities to grow. We’re such high achievers that we compare ourselves to others and want to do everything perfectly, and when you throw yourself into a new environment, it’s very easy to just look at everything you don’t know.

Trista Engel: I love that. That’s such great advice, both for people thinking about their own career and performance, and for people managers—a reminder to see through others’ self-deprecating tendencies, and to help remind them of everything they’re really good at. That’s how you want to be as a manager.

Carolyn Herzog: Yeah, everyone has a special sauce, I say. If you’re a good manager, you look for those opportunities. We all have gaps too—things we don’t do as well—and we have to be open to that kind of feedback, but we can’t necessarily fix everything we don’t do well. You can amplify the things you do very well, and fill in the gaps with partnership, collaboration, and management in the areas where you’re less strong.

Trista Engel: Yeah, I love that. GCs today have a wide range of resourcing options beyond FTEs and outside counsel. What’s your approach to resourcing your legal team?

Carolyn Herzog: My approach today, in this age of AI, isn’t necessarily what it would have been in the past—it’s part of that rethinking of how we do our work and what we really need to move the ball forward. I do try to think about organizational design—part art, part science, going back to that last question. You look for the strengths on your team where you can amplify and use more of those strengths. How do you help people continue to grow?

I always think about organizational design and resourcing with a mindset toward the talents on my team—what people are doing really well—and how I map that to where the business needs to go. I like to think about looking around corners, and I encourage my team to do the same: what’s coming next, how do we make sure we’re prepared for that, how do we train people up for it? And particularly now, in the age of AI—what are the areas that are low-risk and repeatable? I’m sure this is a broken record in every AI conversation, but it’s so much more important now to think about how we get that work out of our hands. We’re thinking about risk in a completely different way—where do you really need a human in the loop, and where is it a commercial risk that’s just not worth our time going forward?

Trista Engel: Yeah, everyone’s talking about it, but it’s so important to think about how the work is getting done, and where. Now we have so many more options with AI—outside counsel, your in-house team, flex talent—so many different ways to get the work done, and it really forces critical thinking around where this sits, who should do it, what makes it efficient, what makes it cost-effective. And what you’re describing also requires a degree of nimbleness—being able to shift as you see a new risk coming around the corner, and adjust your team and resources to get the work done quickly and efficiently.

Carolyn Herzog: Yeah, I think we’re all thinking more about whether there are alternative service providers for task-oriented work versus purely going to outside counsel. What tools are we going to use to do research differently? And when you need amplified resources for a period of time, is that a permanent hire, or can you bring in a contractor—somebody with a special skill, or the capacity to manage that flexibility? Capacity, which I think is really important.

Trista Engel: Yeah, absolutely. If you weren’t an attorney, Carolyn, what would you be?

Carolyn Herzog: I would be a jazz diva—and I say “diva” with particularity, because I don’t have the gumption to be on stage and be that kind of person, but it’s my fantasy. I’d want to be Fitzgerald or Sarah Vaughan, have that talent, and just live that dreamy lifestyle.

Trista Engel: Oh my gosh, that sounds glorious. My secret dream is to be a musical singer, and I have absolutely no talent and no gumption either, but we can dream.

Carolyn Herzog: A girl can dream. And it’s true.

Trista Engel: Never too late, right? Maybe we have a second act. And the bonus question—Paragon turns 20 this year. What’s one memory from 20 years ago that still stands out to you?

Carolyn Herzog: Well, before we started chatting, I told you I have a 23-year-old and a 21-year-old. At this stage in my life, I have colleagues and friends who are just starting out, having babies, with really young kids, and gosh, I swoon over them—it all seems so romantic and wonderful, because I have such happy memories of my kids at that age.

We actually moved to London when my youngest was three years old—she’s 21 now. It’s amazing. I like to think about that time as—in some ways you’re so tired you don’t know what time it is, and in other ways time really slows down, because a toddler captures your attention in a way an adult doesn’t. You can tell an adult you can’t talk right now because you’re speaking with someone, but you can’t tell a one-year-old or a three-year-old “not right now, we’re busy.” There’s a kind of magic in being so focused on raising a little human being.

Trista Engel: That is beautiful—a lovely reflection and reminder for those of us in the thick of it. I have a three-year-old and a seven- and eight-year-old, and sometimes you wish they wouldn’t capture your attention so persistently, but it’s a good reminder to see the joy in it.

I love that. Well, this was so fun, Carolyn. Thank you so much for sharing your stories and your journey with us.

Carolyn Herzog: It’s absolutely my pleasure. Thanks for having me.

Trista Engel: Alright, that’s a wrap on today’s episode of GC Sidebar. Catch more great conversations on our website at paragonlegal.com. Thanks for tuning in.