How to Build Board Trust as a General Counsel or CLO

Anirma Gupta0:00
AI can help you gather facts and information and synthesize it. But I think the real value add for us lawyers is at the judgment layer. It's being able to take that information, understanding the business context, understanding your risk profile, and being able to help the company make tough decisions.

Cecilia Ziniti0:25
Welcome back to CZ and Friends, where we talk with legal leaders, operators, and technologists shaping how modern companies work. I'm your host, Cecilia Ziniti. Today I'm joined by Anirma Gupta. Anirma is a growth company executive who spent more than three decades operating in technology, law, and leadership. Most recently, she was the chief legal officer at Unity during a period of intense growth and change. Before that, she built and led legal teams in cybersecurity, AI, data privacy, SaaS, and advanced technology. What I appreciate about Anirma is how clearly she thinks about leadership. She thinks about designing an environment where attorneys and others on her team can thrive and move with grace under pressure. She has a grounded principled view on judgment that I know you're gonna enjoy. Let's dive in. Anirma, welcome to the show.

Anirma Gupta1:11
Thanks for having me.

Cecilia Ziniti1:13
You said something that stuck with me recently. You said that leadership is about creating the conditions where you can make good decisions consistently. And I've heard others say, you know, your job as an executive is to make three good decisions a quarter, which I feel is like not high enough.

Anirma Gupta1:29
But how do you think about that and what shaped your view? That does seem like a low number to me. I think in terms of what shaped my view was a combination of early in my career observing what I thought worked and didn't work for other leaders. And then quite honestly, learning through trial and error in my own career. Early in my leadership journey, I think I was transitioning from doing everything to leading and probably made some mistakes along the way. Over time, figuring out what works.

Cecilia Ziniti1:57
So you've had some really incredible roles, GC of public company, private company, just progressive legal experience.

Anirma Gupta2:05
What stands out as the most fun? I think the most fun part of it is learning at every single company that I've gone to. It's because it's been an opportunity to learn something new, whether it's the technology or the industry or the challenging regulatory or legal problems that I've had to deal with, that's been a motivator for me throughout my career.

Cecilia Ziniti2:26
Any particular law or new law that came out, so it looks like timing-wise, you know, CVAA or some of the uh the SEC rule changes, or even SOCS maybe was early in your career. Any particular like legal or regulatory change that you worked on that stands out?

Anirma Gupta2:46
There's probably two that come top of mind. One was, of course, GDPR. I think I was at Tanium at the time that GDPR was going into effect. And it was something, you know, people didn't know what it was. It was the first time that people really had to think about privacy. So we were fortunate that, you know, we were able to put ourselves in a really good position and be compliant in time for GDPR implementation. And the other was um, I think about a year and a half ago, was when the SEC had its um cybersecurity reporting rules come out. So again, it's thinking about what are the processes that you have in place, not just within legal, but coordinating with finance and IT and others to make sure that you have the right infrastructure in place in case something does happen and you have to think about whether or not you have to make uh an SEC report.

Cecilia Ziniti3:43
So with the SEC change in particular, the rule comes out, put us in your shoes. You're literally like, all right, I'm gonna need, you know, a corporate counsel to do this, I'm gonna need this to do that. What do you do at the beginning to make sure it's successful? And, you know, if you can tell us if it was successful, I'm assuming it was. You know, it is it a like like what can you do the planning to to to thank yourself later? I always tell the team, do things where you're thank yourself later.

Anirma Gupta4:11
So what was an example there? You start with the basics, you understand what the law is and what what needs to be done, but I think more importantly, it's making sure you have the right people working on it. So selecting uh a leader within your organization or an up-and-coming leader within your organization to drive the effort. And then it's understanding who are the stakeholders. I mentioned finance and IT uh earlier. Um, it might be internal audit as well and comms. So it's really understanding who are the people who are going to have to be involved should something happen. And then getting a lean tiger team together to figure out what are the roles and responsibilities going to be? How do you scenario plan if something does happen so that when it does happen, happen, um to get the team together, it's seamless and you can you can navigate through what might be a challenging situation without scrambling or having to figure out who does what.

Cecilia Ziniti5:11
So um was there any kind of turning point in that project? Did the person you select, you know, step up or you know, uh compared with GDPR? Like was it smoother? And any color to add for listeners?

Anirma Gupta5:26
Well, I was fortunate in both cases to have um an individual who really stepped up, did an amazing job. And from my perspective, it was pretty seamless. In both cases, the attorneys were really good at just taking ownership, figuring out who needed to be involved, creating a framework, and just executing.

Cecilia Ziniti5:47
Did um the stakeholders notice?

Anirma Gupta5:49
Yes, they did. I got positive feedback in both cases. And I think that's part of like having um a successful legal organization. It's about the people. And when you have people who are enabled to do their best work, they often step up and and actually do a great job. And then the business notices it.

Cecilia Ziniti6:09
So when you say enabled, what is what does that mean? So um is it like the the actual like legal learning? Is it leadership? Is it do you kind of pre-view with the business stakeholders, hey, you know, this person's gonna run this project, you know, that they're still learning. Like, like what do I, like, like how do you, what are the things that you thank yourself later for with respect to to leadership and enabling those conditions?

Anirma Gupta6:35
Sure. I think it depends on the situation, the people, and what you're trying to solve for. So with the SEC cybersecurity rules example, we knew we had someone who was, I think, two levels down for me who was really smart and wanting to step up and wanting to do more. So it was pretty clear to us that um they were the right person. And it's figuring out what is, you know, helping them determine what is the end game, what is it, the end result that we want from this project, making sure that they have the support that they need, being there as a sounding board and as a resource uh through checkpoints along the project to make sure, you know, is the direction they're going in the right direction? Are they hitting any roadblocks? Do they need any further support? Um, are they getting pushback from anybody else on the executive team? And, you know, you know, do I need to go have a conversation with someone? So to me, those are all elements of enabling.

Cecilia Ziniti7:37
Your company had a number of kind of leadership changes and you know, this is public that, you know, might be considered crises at the time. Two questions from that. One is do you ever have days where you're like, hey, I I don't, I don't feel like being an enabler and a really good manager? And just like, and what do you what do you do on those days?

Anirma Gupta7:59
So there are probably days when I was more tired than others, but it's it's part of the job. You need to be there for the company, you need to be there for the team. And you always put your game face on um and and help others. It's it's working with the business to solve the business problems. It's working with your team to make sure that they have the resources and the backing that they need to be able to support the business. Uh so whatever's going on inside, you gotta have the game face on.

Cecilia Ziniti8:29
I love that. Yeah. So my uh one of my idols is Taylor Swift, and she she talks about, you know, you I get tired, but I never get tired of it. It's like, and that kind of kind of feels feels that way. Do you have any kind of mentors or or outlets that help you to show up with a game face?

Anirma Gupta8:47
I have a wonderful group of GC peers. I think you've probably interviewed many of them or are about to. So being able to talk to people who go through similar issues is a great outlet in terms of release. I exercise every day. So making sure that I can start the day with a clear head and be able to release the tension is essential for me.

Cecilia Ziniti9:08
Have you gotten feedback that you are kind of the grounded one? And has that been part of your success?

Anirma Gupta9:14
I I have actually. I've had multiple board members um talk about me being calm and grounded. And uh I think that again is part of the role and part of how we need to show up as GCs and CLOs.

Cecilia Ziniti9:28
Let's talk about uh relationship with the board. So you've been uh a general counsel for for a long time, worked with different boards. When boards work really, really well, what is happening both in the meeting and outside of it?

Anirma Gupta9:41
I think when boards work really well, the board members understand the business. They understand the role of the board, which is to be there as an advisor and they ask questions. So whether it's strategy, your board members typically are well versed in the industry and understand what's going on at other companies in the industry or um in the world at large. So asking those critical questions that allows management to think further about their strategy, I think is essential.

Cecilia Ziniti10:14
So you've worked at uh a number of companies. You've been a CLO for a lot of years, work with different boards through CEO transitions, through crises, international, new regulatory, SEC roles. As a CLO, how do you make your relationship with the board more effective? And, you know, what are the what's the impact of that when you do?

Anirma Gupta10:35
I think it's all about building relationships with each of the board members, understanding what they care about, where they're coming from, and what their perspective is. And then quite honestly, it's about working through issues as they come up and showing up as your best CLO, demonstrating that you are engaged, that you also understand the issues and understand where they're coming from and are responsive and able to solve problems with them.

Cecilia Ziniti11:04
Anything like so a lot of our listeners like to get kind of pretty breath tacks. I think, you know, obviously you can't give specifics of situations, but you know, literally like pragmatic advice like do you text the board, do you call them separately? How do you kind of like plant the breadcrumbs to develop that relationship, as you said?

Anirma Gupta11:23
Usually it's with specific issues when they come up because the board members are often very busy people. They might be operators themselves or they might be on multiple boards. So I think it's um key to use a bit of judgment on when to engage. But when the issues come up, I think it's important to first of all exercise judgment about when do you need to engage with the board or not. And then secondly, if it is something that you need to engage with the board on, be ready to articulate very crisply what you think the issue is, why you think the board member needs to know about it, and then have a couple of solutions ready as well so that the discussion can be very focused on problem solving and you're respectful of the board members' time as well.

Cecilia Ziniti12:10
One of our um guests, Rebecca Fike, uh, who's now at Reed Smith, she has a uh a white-collar crime and uh defense uh uh fraud investigation practice. And as part of that, she frequently works with board members where there's been some kind of crisis. And she said something to the effect of like, I don't really want them to be my friend. Like, I'm pretty clear that like here's the situation and you know, and then ultimately they end up having higher trust from that. What would be your reaction to that, to that statement? And is it different with her being outside counsel versus a CLO?

Anirma Gupta12:50
I think it is different outside versus inside. I think inside you have more context and are able to have, I think, deeper discussions about the business and the people if needed. So I think certainly my job is not to be a friend to the board member, although I have developed friendships with board members in the past, but being laser focused on what the issue is and what you're trying to solve for, um, and doing that consistently and time and time again is how you build trust over time.

Cecilia Ziniti13:22
Is um on that point, is consistency a superpower? Would you say?

Anirma Gupta13:27
I think so. I think consistency and calm.

Cecilia Ziniti13:30
You've said before that an important way to use power is to actually develop people under you, and that having a a group of folks who are effective is is obviously better than the the sum of its parts. Um, how do you do that? So again, back to Danielle Shear's episode. You all are, you have if you haven't met, you gotta meet because you you remind me of each other a lot. But she said something to the effect of like she literally has like a development plan for everyone on her team. And it's just like the incredible satisfaction when they sort of step up. So you talked about this SEC example, but in the in terms of actual like literal management, what do you do? And a bonus question, how do you deal with the the parts of the lawyer personality that tend to anxiety? Um, and if you've seen that on your team members, if at all ever.

Anirma Gupta14:16
So I think it's it's vital as a leader that you spend time developing your people. And as a CLO, you tend to have very senior people as your direct reports, VPs, senior directors, and the like. So these are all people who are subject matter experts. And your job is to help them improve their game. I think even as CLOs, we have an opportunity to improve our game. Uh, but that's your role as in terms of helping others. So whether that's through development plans or creating opportunities for them to take on more responsibility, giving them exposure to management, I view it as my role to make all of those happen. And then, you know, I think you have leaders sometimes who always want to be the face of the organization, always want to be the one interacting with management or the board, but that doesn't do your team any good and doesn't help them develop. So part of my philosophy is to create those opportunities where my leaders can interact with management and interact with the board, because that's how they're going to learn. And then I need to be there initially by their side, brainstorming on the side, helping them think through the issues, think through how they're going to present something, and then let them handle the situation with me by them by their side and over time handle situations on their own. And then dealing with uh, you called it lawyer anxiety. Yeah. Um, it's, you know, it I like to be a safe space. So I tell them, you know, it's okay to be nervous. Tell me what you're worried about. Let's talk through what the what potential solutions might be to the issue that's causing you worry. So if you address it up front, then it's less likely to show up when it counts.

Cecilia Ziniti16:07
So slightly sensitive. I remember one of my mentors at at the big uh at the big technology company that I worked at, they kept tissues in their office. And I was like, well, I mean, okay, whatever, if you cold season, whatever, but it was clear that it was because people get pretty upset in those moments. Have you ever have you had a moment like that? And and and and what do you do?

Anirma Gupta16:30
I have had moments where people have gotten upset. And it's, I think at that point it's important to listen, to understand what might be causing that upset. And then, you know, it's whether it's air cover or support or advice, um, I try to help navigate, help them navigate through whatever is causing them that angst.

Cecilia Ziniti16:52
Let's talk a little bit about kind of budgeting and planning and all the kind of like big old CLO stuff.

Anirma Gupta16:59
So stuff.

Cecilia Ziniti17:00
Exactly, exactly. Now, I mean, like I said, we get super pragmatic, right? So that's obviously not everyone's strengths. Do you have any kind of like big success from doing that right? Or, you know, any just like, okay, imagine our listeners listening and they're gonna like, they're gonna bookmark this part. Any any hard lessons you've learned on sort of the the tactics around managing a legal team?

Anirma Gupta17:25
So in terms of budget specifically, I think it's you just have to figure it out. It's being willing to roll up your sleeves, dig into the various parts of your budget, having oversight. I've had finance people who've probably been frustrated with me because I want separate cost centers for each of the practice groups, but that's how you understand what's going on. If everything rolls up into one lump sum, you really can't figure out where you might have overages or underage, underspend and where your levers are. So it's figuring out the mechanisms that you can put in place to understand where your spend is, how it's being spent, and where your levers might be to make some changes.

Cecilia Ziniti18:13
Do you see a relationship between spend and level of legal protection? And how do you turn that dial if there is one?

Anirma Gupta18:19
I mean, I'm sure there's some correlation, but it's probably indirect. To me, the level of legal protection is really dependent on kind of what your business is, what regulations you are subject to, what level of risk you're willing to tolerate because every business is different. And then making sure that you are dialing your efforts to align with that risk tolerance. And to me, the best way that happens is when your in-house people are making those decisions. And that's um headcount spend for sure, um, and less about outside counsel spend.

Cecilia Ziniti19:01
Do you see a shift in how legal operates with AI?

Anirma Gupta19:04
Absolutely. Um, I think AI is having a huge impact on legal departments in terms of being able to digest more information. We all get all of those news alerts from law firms when something, some new regulation comes down, and it's impossible to keep up with all of them. And with AI, you can digest all of that in a very succinct way and be able to move more quickly to support the business. AI is also a huge opportunity for efficiency, whether it be drafting or creating agents to automate some of the more routine or rote work that a legal department does.

Cecilia Ziniti19:46
How will being a lawyer change in that environment?

Anirma Gupta19:49
I think it is going to put even more emphasis on the judgment aspect of being a lawyer. Because AI can help you gather facts and information and synthesize it. But I think the real value add for us lawyers is at the judgment layer. It's being able to take that information, understanding the business context, understanding your risk profile, and being able to help the company make tough decisions.

Cecilia Ziniti20:16
So, how do I develop that? I mean, this is the question that comes up. I I see the same game as you're seeing. I absolutely see more legal work going in-house. I absolutely see AI elevating everyone to the judgment layer. But then I'm like, you know, I'm talking with Anirma, and you're this 25-year attorney that's been through global crisis, security stuff, you know, every everything in the book. And so you have that judgment. How are people going to develop it? What's it, what's your what's your prediction?

Anirma Gupta20:43
I worry that it's going to be harder, but I think it puts more of an onus on us as leaders to help people develop that judgment. To, you know, ourselves work with our leaders and have our leaders work with their people to coach them through situations so that they develop that judgment. Because I think the way you develop judgment is through experience. So going back to sort of an apprentice apprenticeship type of model.

Cecilia Ziniti21:11
It's let's say it's five years from now and you're on the pod again. Give us some wild predictions.

Anirma Gupta21:16
I think legal departments are going to be smaller and I think law firms are going to be smaller. I worry about uh, you know, the future of the legal career or people who want to go into it. I think there's going to be fewer opportunities for people. But for those who are willing to put in the effort to develop those judgment skills, I think there's a lot of opportunity.

Cecilia Ziniti21:41
How do you going back to the breast tack? So AI has pretty let's let's get a scenario here. AI has you're you're working an issue, let's say, uh let's say an employment matter, and AI has served you up. Okay, all the communications between the parties, the person's review, giving you An analysis and the answer is basically like, yeah, there might have been some hint twin hinge of discrimination, but there were it was legit, they were legitimately performance managed. Um when you actually frame that risk now, like you're having that call, you mentioned, okay, it's issue dependent. Are you, do you start up front with like, all right, we're gonna defend this? Like that call of when to settle and when to fight, that is something that for me in my transition from you know IP litigator, then in-house and being like, litigation is freaking awful. Just pay them. And now as CEO, where I'm like, what the heck? We should not pay this person or whatever, whatever, whatever the situation is. We had a vendor dispute and it was actually over fraud. And I'm like, this is ridiculous. We should not pay this. Dude, I never want to see them again in my life. Like very kind of emotional driven. A lot of setup, but how do you, in an AI world where you've got all the facts, there, the facts are pretty clear. What are you saying when you when you make that call to the board member, the CEO, the VP, whoever it is you're advising?

Anirma Gupta23:07
Yeah. So um, I'm gonna give you the lawyer's answer if it depends. Of course, it always depends. So I think it is going to depend on sort of what is the state of the business? How much do we care about this particular issue? How much of a distraction is it gonna cause if we do litigate? There are times where the cost, uh, not just the monetary cost, but um if it's a litigation, who's going to be deposed? How long will they be deposed? Where is the case? How much will it take out of the company to defend the case? And then when you look at that bigger picture, sometimes it is worth settling. There are other cases, for example, when you're dealing with patent trolls and you've got a well-known plaintiff's law firm that if you settle with them once, they're gonna come after you 10 more times. In that case, you absolutely are gonna fight it because you don't want to be setting yourself up for having to pay again and again. So it is fact-dependent.

Cecilia Ziniti24:08
That's fascinating. We just had Mallun Yen on the podcast. And in her case, that exact scenario of you've got a bunch of patent trolls coming after you, her solution was like, all right, found a company, in her case, RPX, to fight it. And so it's actually literally that I think it proves your point even more that it is, it is basically the ability to see the bigger picture, do the probabilistic analysis. Yeah, but also just the emotion. Like it it is shocking to me when I when I had a litigation in my first big litigation I managed as a GC, how much it was emotion. It was like, it was one of these, like it made me want to go back and read, you know, Lincioni and the influence books and all these things about that. And anything to say on that? And are you uh are you a natural litigator? Did you litigate before before you went in house?

Anirma Gupta25:01
I started my career as an IP litigator. So I've been there. And to your point about emotions, I've had situations over my career where somebody wanted to make a decision because of the emotion. They were angry or frustrated. And part of my job is to talk through, okay, I hear you. If you want to litigate, here's what it's going to look like. Here's what it's going to take. Is that what you are ready to sign up for? Um, and if the answer is yes, let's go. But I'd say more than half the time the answer is, oh, I didn't realize, you know, I'm gonna have to sit for a day for deposition prep and then another day for depositions, and you know, a bunch of other people are going to have to go through the same. So maybe we should settle for a nominal amount. So that's again part of the job.

Cecilia Ziniti25:50
Yeah, I it's been interesting. The the the kind of other side I have had from being a GC, I've had a bunch of other executive friends call me actually debating whether they should sue their company. I almost always tell them no, even though it's like my my my uh you know, the sense of justice I think is hard. Um, I remember, I think I've told this story before, but in that big litigation um that was very emotion-driven. You know, we were in uh basically a mediation, and the judge said, um you know, I I said, This is not right, this is unjust. And what do I tell my students? Because at the time I was teaching, what do I tell my students about this? And the judge said, Well, you tell them that sometimes you pay money to get crazy people out of your life. And I was like, Oh my God, like that is so unjust. And I like I literally was like, my kind of like 21-year-old or 22-year-old law school self was like, What the hell is this? Like, why are we doing this? But do you I mean, how do you? I think what's her name talks about. Um, there's an executive, this Dun Blue, the CEO of Ancestry, talks about uh forgiveness as a business value.

Anirma Gupta27:04
Um, would you agree with that? I've never thought about forgiveness as a business value. I think probably the way I look at it is being pragmatic. And are there situations where it's just not worth your time, energy, or effort and you need to move on and not think about it anymore because you've got a business to run? Or is this something that's going to impact the future of your business and you need to dig in and deal with it? So I view it more as pragmatism.

Cecilia Ziniti27:30
I love that. I love that. One of our guests recently said that he wanted to dispel a myth, which is that he felt like recently there's been a trend, and and I would agree with this, and I've been part of this kind of movement, that you know, GCs and legal leaders needed to be more business forward and business partners and all these things. And he said, and and he was a former federal clerk, and and I mean Matt Gipple in his episode's paying, you should listen to it. But he said at the end of the episode, something I've been thinking about since, which is he's like, No, we're not business partners. We are lawyers. And, you know, our job is to like understand the law and to advise on it. And I think, in his view, the being business forward was uh was almost like a crutch. And it got me thinking, but in this kind of post-AI world where the legal answers are, you know, maybe served up to you, uh, is he right?

Anirma Gupta28:28
I think we absolutely are business partners. But when you're in-house counsel, you're working for a corporation that's trying to make money. So your job is to enable the business to be successful. Um, but yes, you are also lawyers. You need to think about what, you know, your legal and compliance obligations are. Um, but you're not going to do that in isolation. You have to understand the business. You have to be embedded in the business. You have to be part of it. And I think the best legal departments are working side by side with the business, and it's seamless. It's not like, oh, legal is an afterthought and, you know, scrambling to figure out what's going on. You know, some of the best places I've worked, we've had product lawyers embedded with the product groups. And they are working, you know, they're they're sitting with the product groups. They are thinking about the legal issues with the product groups as the product is being defined. Um, and that's that's optimal. So we absolutely are business partners.

Cecilia Ziniti29:32
I love it. I love it. Yeah. No, maybe he didn't go, he didn't go quite that far. So maybe, Matt, if you're listening to this, um, I don't mean that. But and he similarly said that that embedded aspect made a huge difference. Yes. And he actually pointed out that he thought that people who are not lawyers, the the the you know, engineers or the product managers or you know, the marketing people, whoever it is, um, tended to actually be able to think out the side of the box a little bit more on how to solve something. Has that been your experience as well?

Anirma Gupta30:00
Yeah, I've seen that happen for sure, you know, on both sides. And when you have the product people embedded with the business, it becomes sort of a dialogue. And the best conversations are the brainstorming conversations where you leverage each other and uh, you know, come up with solutions together.

Cecilia Ziniti30:17
I love that. I love that. All right, let's go to the lightning round. So, what's a myth about leadership or being a CLO that you would love to debunk?

Anirma Gupta30:28
I I think a myth is that um great leaders always have to have answers. I think uh the best leader leaders often have the best questions and exercise really good judgment.

Cecilia Ziniti30:38
What's a value or idea, mentor, or book that has shaped how you lead?

Anirma Gupta30:46
I think for me it's a value. And the number one is integrity, because when you're under pressure, relying on integrity will allow you, I think, to make the best decisions for the company. Um, and then those are decisions that you can live with as a person too.

Cecilia Ziniti31:03
And a piece of advice you would give your early career self.

Anirma Gupta31:07
I think uh to our earlier conversation, being able to develop judgment alongside getting to the answer is really important.

Cecilia Ziniti31:15
So you've led through growth, change, pressure, you know, uh new laws, new regulations, shifts in technology. If you could leave our listeners with one thought um about leadership or let's broaden it to life, what would it be, Anirma?

Anirma Gupta31:32
I think uh leadership today, again, is about judgment, not just speed. It's about values and not just outcomes. And it's about building organizations that can move quickly without losing trust.

Cecilia Ziniti31:44
Thank you, Anirma. This is such a thoughtful and grounded conversation. I am so happy we had the chance to catch up. Thank you for being on the show. Thank you for having me, Cecilia. This has been lovely. That was my conversation with Anirma Gupta, a leader who reminds us that judgment, values, and intentionality and speed are actually not trade-offs, that we can be effective leaders and CLOs, exercising judgment and values and integrity and just a delightful conversation. Follow CZ and Friends wherever you get your podcast. To learn how legal teams are using AI to work smarter and hear more about the change and the future coming that Anirma described, visit gc.ai. Thanks for listening. We'll see you next time.