#66 - So you wanna be a GC?
15 Apr 2025 · 48 min
This is a podcast episode (#66) in which Mary O'Carroll interviews Ann Kerwin Payne (founder/managing director of Kirwan Associates) about what makes an outstanding general counsel and how organizations hire legal leaders. Core takeaways: exceptional judgment, presence/communication, leadership and mentoring, and ability to scale teams matter more than pure technical legal depth; recruiters vet both candidates and hiring organizations (including backdoor referencing); career strategy involves tradeoffs between big-company infrastructure experience and being first-in-house at smaller firms; gaps and lateral moves can be explained positively if framed well; compensation mixes (base, bonus, equity) and geo-based pay adjustments have shifted post-COVID; hybrid work is now most common though many senior candidates miss in-office social capital; legal ops/tech awareness and AI adoption are increasingly important. The episode also describes a soft-skill-focused hiring market influenced by growth experience and current macro hiring pauses.
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Hello everyone and welcome to Pearls on Gloves Off. I'm Mary o', Carroll, your host and chief operating officer at Goodwin. Today's guest is someone who is a household name in the world of legal leadership, Ann Kerwin Payne. Ann is the founder and managing director of Kirwan Associates, one of the most trusted executive search firms for legal compliance and regulatory leaders. With over 30 years of experience, Ann has built a reputation as the go to advisor and for both high growth companies looking to hire their first GC and Fortune 500 searching for their next legal leader. Her client roster includes some of the most innovative, fast moving organizations in the world. And the lawyers she's placed have gone on to shape the future of the profession. In this conversation we get into what companies are really looking for in their legal hires today. What looks good on a resume? What are the most important qualities to have that go beyond the resume of experience, like leadership skills, what CEOs and boards are looking for in their new hires and and what makes a legal candidate stand out in this competitive market. Ann also shares her perspective on the future of in house legal teams, the importance of telling your story well and why the best recruiters know how to read people. So whether you're an aspiring general counsel, a seasoned legal leader, or just curious about what makes great legal talent, you'll get so much out of this episode. So let's get into it from AI to M and a change is accelerating.
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Our data driven insights. Hey Anne, how are you? Hey Mary, how are you doing? I'm doing great.
It's such a pleasure. I'm so excited actually for this conversation because you have placed some of the most respected general counsels out there in their current roles or their past roles. So you have so much wisdom to share. Maybe we jump right in. What are the qualities that set apart, you know, the great ones?
I've had a great opportunity to learn and work for just amazing leaders and I would say that the number one thing in a great leader is probably outstanding judgment. And that is a really the trusted advisor outstanding judgment that individuals have. And it's such a nebulous thing to like quantify and it's a million dollar question like how do you vet for outstanding? You know, that's one of the many things I think that it's leadership, it's presence, it's mentoring and scaling a great team. You bring A following. You've got a breadth of substantive knowledge, and if you don't know the answer, you're unflappable in finding it. Those are a few of the qualities, I'd say, that makes a great leader.
Yeah, it's so interesting. I mean, I've been doing this podcast for a while and talking to GCS coaches, all sorts of folks in our space. And that's the answer that always rises to the top on what, you know, what makes someone successful. It's not the depth, you know, of their legal expertise or how much experience they've had arguing certain things in court. It comes down to all these qualities that are just general leadership qualities. Right.
I really think it does. And I think one of the things that is interesting is communication style also. And in the boardroom, around the table, does the candidate or the leader meet the bar of the communication that they need? Like people who are long winded, people who can't give the straight answer, make the tough judgment calls? I think CEOs and leaders have a tough time with. They're relying on these individuals to say, which avenue should we take? So it's a commitment, it's an ownership, it is very nuanced. And a lot of these great leaders, when they speak, everyone listens, right? They don't have to say a lot, but they command the room in a very subtle and profitable way. I think one of the things that candidates on the flip side and leaders, when they go out to look for roles they don't often understand is management teams and CEOs, Mary. They have so much rational on them. They go to hire and they're looking for all these qualities. They've got an answer to a board and they've got to answer to their VCs. So candidates will come to me and say, you know, I can't believe I didn't get that job. I didn't get an interview. And there's so much that goes into it. But it took me a long time to realize that these leaders under all this pressure, whether it's in series A or a public company, have to take this general counsel, have to say to their people, look who we hired. And we hired this person for whatever reason. And that took me a long time. It actually took me a long time in my career to realize, okay, I get it now. Like, it's not just that this person wasn't the right fit, there's a broader thing going on here.
It's so true. And that makes it so hard and probably why your role is so Valuable. It's not just finding someone who has the right background and experience and pedigree, you know, that fits in with the right resume that you're looking for. But all this other stuff you have to vet as well, and you probably can't pick up on any of that from a piece of paper. Do you agree you have to kind of do that in person, face to face or on video.
Yeah. I mean, there's no question that you can vet for substantive pretty easily. Like, someone's taken a company public. They haven't. They made by the company. But it's really the pieces and the pain points of listening to the client and them saying, ian, we've got this issue with unions. We've got an issue with whatever it is, and making sure that when you're meeting and vetting the candidates, that you are listening what everyone on the client side and everything about their business, you've learned. And that candidate is meeting those pain points in a lot of ways. And so it's all about more of the soft skills. The other thing, Mary, that's really interesting is you hire a search firm to run a process, and it's to get to the passive talent. Right. So our job is not to post a job and get inbound. It's who do we know? What relationships do we have? Let's get to the passive talent and let's market this team. Let's market Mary Carol's legal ops team to. To everyone that needs to know about it so that our client knows we've done that. Right. We've uncovered every rock. So it's really running a process. But through that process and talking to candidates, they show their true colors. It's a very interesting thing that happens, how they respond, what they say to a third party, you know, I want more money. And we can be very helpful from that information we gather, we already know many of these candidates. But through the process, it's kind of like buying a house. When anyone goes to buy a house and they go through that process, it's stressful. They show their true colors, and you learn so much from them. So that's helpful in meeting the pain points for the client, if that makes sense. Yeah.
Are you doing that on both sides? You know, sort of like vetting the company, the organization themselves, you know, the CEO, I guess, who's hiring the general counsel, in addition to the candidates who are being vetted?
Yes, it's a. Studying that we do. It's also like the facts of the company. But also I will tend to, you know, look at all the YouTube videos of the leaders. Where did the management team come from? What is the story behind this organization? Did they hire a lot of people from Google? What are they apt to do? Where's their board from? And a lot of times it's really learning like how they value the legal function, which as a leader in legal ops or general counsel, you know, like how important it is. How these teams value the legal function is also going to help who you bring to the mix. And so just really vetting on the nuances of these people who would work well with them. I'm working with the founder right now. Super high energy, quick talker and I'm like, okay, what is the right fit? Is it who's more calm and unflappable that compliments? Or is it going to be the same type? And through giving him people, I'm kind of getting my answer right in terms of the way he's responding to the market.
Yeah, I can totally see that. I can totally see that. What about the need to be business minded and strategic? Has that changed? Is that becoming more and more part of the job description for gcs?
Yeah, these people are supposed to be superhuman, but what's happened with lawyers and general counsels is they have proven to be superhuman. They are so, well, business minded and some of them are so good that they give them, you know, they become chief administrative officers, they become CEOs, there's this general counsel plus in the marketplace that I think because lawyers are so business minded and been trained and learned over time. I mean, when I started in this business, you know, many, many years ago, the general counsel or people in house were really just more like law firm lawyers in house right now it's different. I just had a CEO to me like, and is this person commercially minded enough? And I'm like, look, all of these leaders are really business people that sit around the table, are strategic minded, but they have a jd, they're building companies from the legal perspective, the compliance perspective and whatever else they have on their plate.
Yeah, my last guest was the CLO of Intel, April Miller Boyle. She was saying that the, you know, best general counselors or clos are really business people first who just happen to have a JD or happen to be lawyers. So I think that's exactly right. So I'm assuming that the CEOs want someone with that business mind of people with the jd, not necessarily the type that, you know, I think want to run it like a law firm or run it like a very, very risk averse sort of legal department?
Yeah, definitely. I mean really, it's, it's someone who's going to meet them intellectually, whatever, and have chemistry with them. But generally the first thing that they want as a leader is someone who thinks strategically, right, understands their product, understands business models, but has a jd. I think one of the things that's also been really interesting in the searches we've driven is that CEOs and founder led organizations, they want to hire people who've seen a lot of growth. And that's tough because a lot of these places haven't grown, not by fault of their own, just by the macro economy, but they want to hire someone who's seen growth, seen a lot of complex problems and they're very focused on where these people come from and they have opinions about companies. It's very interesting. They know the ecosystem so well that you bring up a company and they're like, no, I won't look at that company. They had X, Y or Z problem. So that's one thing I think candidates don't understand. They're like, why won't they look at me? And it's either they might be at too big of an organization or they've never really seen the growth. And it's hard because these people are absolute rock stars. They're good at what they do, but their company just hasn't grown. They haven't seen revenues go from 100 million to 600 million. And that's what a lot of these leaders look for too.
And as you're hiring GCs, are they looking for people who have led that or maybe have just been like the deputy general counsel in, in that kind of hyper growth or just kind of lived through that experience and that how do you get to the top if you have to lead in something you haven't done before?
Question. Because there's so many DGCs and up and comers and agencies who are just so smart and so talented and they've seen a lot of growth. So they will like if someone has sat in one of these companies and they've seen a lot of growth, it's really great. But you know, I've been dealing with this where we've dealt with this on a couple searches, where we brought a number two in that has seen a lot of growth and there's so much pressure from the management side. They're like, we need someone who's been in the seat, we need someone who's had a couple tours of duty as a general counsel. And again, it goes back to what they have to say to their board, their management team. But it's also because if you sit at the helm, you know what it's like to make the tough calls. You have that seat at the table and a DGC may not. A lot of them do. A lot of these corporate lawyers are in boardrooms. They've seen a lot, they're trusted advisors to their CLO's. But it's just a little bit of this juxtaposition of before. People are trying to get to the GC level, but then the hiring entities are like we need someone who's done a tour to duty, so they've just got to get in and then their career will go from there.
So interesting. So I guess if you're trying to make a decision between, let's say going to a big company where you're number two or number three versus going to a tiny company where you're number one, does one look better than the other or it really just depends on who's hiring and what they're looking for?
That's a tough question. A lot of times if you look at the careers of these great leaders, they've had a stint at a large company as a leader of a team and the one thing that's wonderful about that is like anyone's time at Google, at Amazon, at even a smaller mid sized legal department, they see the infrastructure of how a good team is run and they bring that with them. They don't even know what they know, but they see a legal ops team, they see how a great GC has set up a legal department. Here's my product, commercial, corporate. And they bring that infrastructure knowledge on top of everything else to a smaller organization so they know how to scale it. But then there are the times where if you stay at that big company too long, it's hard to get out. And you might have to go to a small place to get that head of legal or GC title because then to sell yourself to, then go on as a gc. If someone wants to be a public company gc, you know the steps to get there.
Yeah, let's talk about that for a second. Is there such a thing as staying too long in one place and does it get to the point where it raises questions or does that look good to have continuity? And I'm hiring a ton right now. And so it's actually this is a really interesting conversation because I like to see a lot of different experiences or at least different roles that you've played within the same organization.
It's Such a great question. Okay, so years ago, I've been doing this a long time. I mean, 25 years ago, leaders or anyone hiring would be like, I love the longevity of this company.
Yeah, exactly.
Right. I love it. I love that they've learned. It's like, you look at the Yahoo lawyers that would move around. They stay there a long time. The way of the world now is, why have they been there so long?
Yeah.
You know, there are reasons why people stay. And I have to say to these people, like, look, they need to feed their family. They've gotten different titles, They've gotten different jobs. They bumped up. They've seen the trajectory. Right. They've scaled a company, but if it's too long, they're like, no, didn't learn it out, didn't jump out. So it's a really tough thing because you can't jump out of these organizations for just anything when you have such a wonderful place to work.
Yeah.
And everything else.
Golden handcuffs, as they call them, Right?
Yeah, it's very much the golden handcuffs. But I have to say, in my career, taking a lot of people out of the golden handcuffs situation and really marry, what it's about is they get to a point where they're saying to me, ann, I'm so bored. I need to learn. I need to grow. And I know at this point in my career, I've got to leave this money on the table to move on. And they take the risk. And generally that risk pays off. And they. They love it because they'll learn more and they'll grow. But it is challenging to do that generally.
Yeah. It's so interesting because before in the old days, you'd see someone jumping around a lot, and the question's like, why can't they stay at a job? Why? You know, why have they only been there for three to five years in every single job? And now it's sort of the opposite, where you look at someone and you say, yeah, why have they stayed so long and are they still learning and, you know, has the role changed? Those are all valid questions. Now.
I think the short stints really show. Sometimes you have to vent for why they made the moves. Companies get acquired, different things happen, but there's still a concern. On the flip side, that same leader that's saying, why did this person stay so long will look and say, wow, lots of job moves. You know, what's going on here? And then they will question, decide decisions that people make. Right. Like, people have gone to companies in a series of places that haven't done well or they've kept the same title. They'll question like, why did they go from this company to that company? Like, I don't get why anyone and the candidates sometimes don't have a choice. I had a CEO say to me, why did this candidate who had been at some pretty hot Companies jump in 2023 to this company that wasn't so hot? And I was like, well, I can answer that. I don't even need to ask. That candidate is because they were there at the last place for seven years, they go to look, it's 2023. There were not a lot of opportunities. They got a GC title at a lower rung company and they took it. And he's like, that makes sense. So a lot of it is, what does the ecosystem in the hiring market look like for these people? It's not always great. Right. You have to take what you can get sometimes.
What about gaps? How do gaps look and how do you explain some of those?
Yeah, I think gaps have gotten so much better in terms of a positive. Like some of these people who've scaled legal teams, taking companies public, bankruptcy, whatever it is. Yeah, they need a break.
Yeah.
And they're going to be better people if they take a break. Or people who take six months off to travel. I think it used to be like, no, no one took gaps. Like you just didn't take, you know, you didn't look for a job when you didn't have a job.
Right.
Now I think sometimes for really for high level individuals, they need to stop off the freight train because you can't even think. In some of these jobs you've got so much demand and time and pressure that you just get into your job. What is the next best step for me, Let me take a breather. And then to really do a job search right at a higher level, you need to really be able to study a market. You know, it shouldn't be just what is on LinkedIn that's available. It should be a really thoughtful process. From a candidate's perspective.
Is it different if you're like a mid level person versus, you know, someone who's led through M and A and bankruptcy and public markets? I mean, those are grueling, you know, years. But if you're a normal middle level person, does that gap look different?
Yeah, I think it does. I think it does look a little different because there's this expectation that people want to hire candidates who are hungry and that are on a mission and that work and so a big gap. I Just represented a candidate on a search who had a near gap. It was interesting. And he said, I want to explain the gap. And he had taken care of two very ill family members, and it required a move. And I explained it to the leader. Okay, that's great. I get it right. You know, it was okay. But sometimes I think there's a different expectation on the younger generation.
Yeah, I guess that's probably true. What advice would you give to that younger generation as they aspire to be, you know, a general counsel? Should they get involved in special projects like M and A and IPOs or sometimes that's not really available. If you're in a steady state company, there's no high growth. What can you do proactively to showcase yourself or to get yourself ready?
Yeah, I think there's many things you can do. I think you have to think about career trajectory, whether you're at a law firm or not. You go into a bigger company, you might be more siloed. Then it's thinking about, how do I broaden my practice? How do I take on other projects? Maybe so I could talk about the fact that I've done some transactions if I'm a corporate lawyer. So it's broadening, attempting to broaden the practice. I also think this is not something lawyers were used to doing many years ago, but a lot more better at it. Looking at the market, meeting people, networking, what's going on out there, and really thinking about, what am I passionate about? Like I always say to candidates, you know what? Okay, you're looking for your next move. What are the top five things you want in the next world? Did you get three to five of them? I think you're doing well. But I think what a lot of times these candidates in this generation don't realize is it's not all about title. A lot of times it's like putting your head down, working hard, and the money and the title will come. And it's a little bit more of a reward generation.
Yeah.
It shouldn't be rewarded. So I would say, you know, broadening your practice. What is the end goal if you want to be a public company? Gc. What are the steps you need to take to get there? Being able to sell yourself, which is just such a hard thing, and learning how to do that at an early age in a very humble way, kind of convey that you solve complex problems and what your value ADD is. And I think that's really hard for all of us to talk about ourselves in a subtle way. What are we really good at and coming across with Twitter, this younger generation, that's what people want to hire. They want to hire lifelong learners, hungry people.
I totally agree with that. I mean I mentioned I'm hiring a ton right now and that's, that's exactly the quality I'm looking for someone who's hungry to get after it and like still make a mark here. Not someone who's just trying to punch it in, you know, day in and day out. It's like you want someone who wants to make their mark at the next organization. Does it sometimes mean taking a step back or step down to get the right different experiences? You know, going to a different organization, does it look okay to do that?
I think if you can tell a story of why you made that move. Like a lot of people say to me, and I don't want to do that, that's the lateral move for me. But if you are in a sinking ship. Yep. And you can go to a company that's grilling and you can add a lot of value there, build a team, do something different. I'm all for the lateral moon. I mean it's the story you tell. It's a title generation. I think it's calming down a bit. But it used to not be like the early lawyers at Google's went in as, you know, 2001. Those people went in there as counsel but they didn't care. But I think what happened in the in house legal market just to be fair to the candidates is a lot of times these candidates get stuck like corporate counsel, senior corporate counsel, they get stuck there. They can't move up and they're doing great work, but it's the environment. There's nowhere for them to go.
There's just not, there's not a spot.
So I get why they don't want to make a lateral move. Like I, I've been burned here. So I don't want to go be another senior corporate counsel. Yeah. I have frankly had to counsel a lot of clients on this issue. Like you cannot call a 13 year lawyer who's doing commercial contracts a senior corporate counsel and think you're going to hire great talent. I've asked clients, sometimes I've talked to like comp leaders. They've had me talk to conversation people about how do they level them. Can we add a layer like an assistant GC below or above an associate GC so that you can recruit talent? Because in fairness to these candidates, they're deserving of a higher title.
Yeah, yeah, yeah. I couldn't agree more. The story that you tell has to be crafted and will make sense if you can tell it right of why that move was the right one. You do need to gain new experiences and continue to learn. And the compensation piece, at least my view is kind of the same. If you're getting more learning, sort of okay. To take that lateral step down to get exposure to something totally new.
I think compensation, that is like a ten hour conversation.
Yep.
But compensation, a lot of times you have to take two steps back. Like we said, leave money on the table to learn, to take four steps forward. People go to private companies, they have no upside, they take a lot of equity that they may never realize. If you have a senior corporate counsel who's moving for the same compensation, you know, that's tough. But a lot of these people could be even overpaid at that level.
Totally. Yeah.
I have a problem when it's all about money or anyone. Like if it's all about money or title, first question is, what's the column? What's the title? Can I get this title? I'm like, no. Because the best candidates, Mary, you know, from hiring all these years, that are passionate and connected to what they're doing.
Yeah, right.
I mean, I, I love what I do and I'm passionate about it. And that's what I want to see. I want candidates who are like, oh my God, they're doing this help tapping. That is so interesting to me. Let me tell you. My parents were doctors. This speaks to me. And you just feel this connection to the mission.
Yeah.
And it's not all about the comp, and it's not all about the title.
When people fixate on the title or the comp, it's a bit of a red flag, I think I have to say, as a hiring manager, because you just, you know there's going to be other things that they fixate on that's not appropriate or not the right things on the compensation. Have you seen the compensation packages? The mix changed over the years for in house and general counsel and in house.
So, I mean, I think that companies had to raise their game from initially when I started doing in house work because they were paying like lawyers, 160 to 180 base bonus. The call of packages in house have come a long way, but it kind of goes with the tide. Like in 2021, when the market was on fire, the comps were higher to acquire the talent. And now like 2023, they're pushing it down. Right. They're taking advantage of candidates, they're pushing Pump down. I think, you know, I just got off the phone today with the CLO who's look, you know, I've done well on equity, but if I make a move, I've got to have the cash. You know, equity is equity. And so while people really, it's important what they negotiate at every level on equity, a lot of people in the last few years because the equity hasn't done well, they want cash, they need cash to live their family. And so what is a base and bonus going to look like? And many of these venture backed companies do not have bonuses in place. So if you're trying to move someone from a public company and or even a company that has a bonus and it's a significant part of comp, it's very hard to make the transition. What has really changed with COVID and it's really hard to navigate is this location based home. If you're in Texas, North Carolina, should you make less than the lawyer sitting in New York?
Yeah.
And a lot of these companies think they should and a lot of the candidates think they shouldn't. So they might have moved out of New York, they might have moved out of the Bay Area and moved to a lower cost living during COVID and they're like, no, I want to make what my counterparts making and I get it. But there is an argument, and I think these companies have an argument and they all do it, that look, the cost of living is less. We're going to adjust your comp based on it. So it frustrates candidates, but it's kind of the way of the world. And from a recruiting perspective, it's constantly being able to know, okay, this person's sitting in Ohio, that's why they're being paid that and having these conversations, are you okay with they're going to pay you less because you're located there.
That's surprising. I actually thought that was more the norm, that there were sort of like bans of geolocation compensation. But when Covid hit and everybody went remote and everyone's got dispersed, a lot of folks went with their existing, let's say San Francisco Bay Area salary and then moved to a much lower cost area and just had no adjustment. So did that. Do you think that had an effect?
That's what happened. That was the biggest effect. And so these people are then sitting there and then these companies like we're going to adjust you. You don't live 70 miles from this. And all the red tape. And so I think candidates were really bitter about it, you know I think also with Kola, what has happened is or did happen for a while is, you know, to be in an office, you had to pay more to attract the talent. And I think that's settling out a bit. You know, I'm hearing from candidates, like very Senior level candidates, GCs, DGCs, they miss being in an office if they've been working remotely for three years. I'm like, I don't want to go into an office five days a week, but I miss the social capital, the relationship building from being in an office as a leader. And I have zoom fatigue. I'm on zooms from 7am, have a break, maybe at dinner and then internationally at night. So I think I am hearing more about being in an office and clients want people back in an office. But then myriad, it's surprising. All of a sudden you'll talk to a company and they're like, oh, we're fully remote. So it's just interesting.
Yeah, I'm surprised you said that. Wouldn't have expected so many of the candidates to want to be in the office. And are there a lot less remote or even hybrid jobs? And where does hybrid fit in? Is it, you know, is that the most common or what are you seeing? And I guess. Yes. Does remote still exist?
Remote still exists. It does, but I think hybrid is the most common now. I really do. I think people want people to be together. And I get it. I mean, I think it's important for the younger generation to, you know, think about when you were at a larger company running legal ops, the people your team that got to witness you. There's a lot they learned from just hearing you talk, meet with other people. There's. The social capital that these younger people are missing out on is really sad. By working from home, you know, in. The ironic thing is they're the ones that want to work from home.
Yes, that's true. It's true. They're the ones because they didn't experience, you know, the grind, you know, to your point of the. I don't know, the earlier days in my career where we were there eating dinner together, because you're just grinding from morning, noon and night together, working hard, and you're with these people much more than your own family that, you know, day in and day out, how do you not come out? Forever friends, you know, forever bonded.
And I really think that has affected why you see people leaving companies. Because I think when you and I work together and we have that more of a relationship as a trusted counterpart and we're Working together. It's harder to leave a company when you have really great colleagues. And I hear it a lot, people who have great management teams, they're like, I know I need to leave, but I have such a great relationship. My team is like my family.
Yes.
So the younger generation is missing out a little bit by not having witnessed that.
Yeah. And missing out a lot. I mean, what we talked about at the beginning of this podcast was what makes a great general counsel. The qualities that set you apart are all these soft skills and all these leadership skills and reading a room and having that high EQ and, you know, storytelling. Storytelling. And all these things that you absolutely learn from the leadership around you and that, you know, the people that you're working with and for, and seeing how they lead meetings and seeing how they speak and hold themselves and if you're not physically together, I mean, I just think that's. How do you get that? How do you teach this next generation to be able to do those things?
I don't know. It's an interesting time. I think we're going to see a crop of a generation that can't read the room because they just don't get it. They haven't seen what it's like to be in an office. You don't interrupt people like the nuances, everything that you learn. So it's going to be challenging. I also think it's an interesting time married with AI and the law because it used to be years ago that you didn't go in house as a lawyer until you were six to eight years free. And it was a decision either I'm going to go for a partner or I'm going to jump in house. Then as we moved forward, companies started hiring like three year, four year lawyers. HP and other big companies had recruiting people right out of law school, had these great programs. Now, you know, with AI in these legal teams, when it's adopted more and more, which is happening, what is going to happen with the junior lawyers that third year that might have came over from Lakeville and had got to witness everyone? How do you become business minded to be a great leader? I feel like they're going to have to stay in a law firm longer and they're not going to make that transition early to get all those skills on the business side to make these people great leaders? Because AI is going to be doing that work.
Yeah, that's a really interesting observation.
It's a total speculation, but I'm like, where are they going to learn?
Yeah, because they won't Be ready with that judgment.
And I think it's tbd. I think we're really just at the infancy of what's going to happen here with AI and legal. But it's making a mark for sure.
As you're hiring or helping to hire for in house legal leaders is technology awareness, AI literacy, is that like legal ops, you know, knowing how to do a tech stack, is that becoming part of the equation? Is that even being asked about by I guess boards and CEOs at this point?
They don't necessarily put it that way, but they are asking like someone who's seen and can put process in place. But it's more on my side when I'm vetting talent. One of the first questions will say, so who's your legal ops person? What have you done? How do you work with them? And so I'm vetting for that to help my client because I know it's important. If they're going to go into a lean legal team, they need to know how to put process in place. And if I can have them ask them about their legal ops hire, ask them what they've done individually, I can share that with my client as a value add. And a lot of general counsels and leaders, even DGC's heads of commercial, will go into these things where they will share what they've done as far as technology and what they've built and what they've brought in, how tightly aligned they are with their legal ops partner. You know, there's no question that what's going on with legal tech and is just, you cannot afford for these legal teams to not have legal ops specialists in a legal team. You just can't.
Yeah. I mean that's the future.
Yeah. And if you, if they don't, you wonder like, do they value the function? Do they understand? So in a lot of the building and the venture backed companies, we've done searches for and placed the gc, one of their first or second hires and maybe a revenue person or a product lawyer is a legal ops individual. So. Because they know they need it.
Yeah, absolutely.
Which is great.
You're speaking my language, Ann. I like you.
Yeah.
The other thing I wanted to dig into was, you know when you said the most important skill set of quality that sets people apart is the judgment and it's so hard to vet. You must be really good at reading people and asking the right interview questions. How do you vet for judgment?
Yeah, that's a really good question. I think that, you know, one of the things that's Hard about selling yourself as a search professional is I think there is a level of intuition that you've developed and you have otherwise 100%.
Yeah.
So, and so it's hard to sell yourself like why are you good? Why are you different from someone else? So you can ask a lot of questions around. I think about it like putting a bow on it, asking questions all the way around this person's life, getting to know them, decisions they've made, what they're saying to me, how they've negotiated, how they talk about pump like the judgment. I can kind of summarize it and share with my client like what I see, you know, from what you do that a lot of these places are using a lot of prompts and they will then have a lot of heart to hearts with these candidates, leaders, CEOs, CEOs and vet for judgment as well. So it's a lot of asking questions but I would say it's a lot more listening. Listening and watching behavior. How they talk about why they left companies, what they did around certain issues. It's really interesting. People are fascinating. You know, that's why I love what I do because they are so fascinating. But it is really looking at everything and kind of putting a ribbon on it in the end. Sometimes candidates won't share that they've moved and you're like, why wouldn't you share that? Or they finally share something and you're like, that was odd. So there's a lot of summation that goes on. And Most of these CEOs do have high EQ. They call it out too. They see it.
Yeah.
So it's interesting.
Yeah, I think part of it is experience. I mean you call it intuition, but I think you've just done so many reps, you know that you're, you see patterns and you can pick things up. I know in my early days at Google when I was interviewing folks, I made a bunch of hires. I made a lot of mistakes, you know, hiring the wrong people. And then we went through hypergrowth and I was, I think I got some award or recognition for being like one of the top interviewers, not the best interviewers, but in terms of volume because I was very as legal ops, like everyone's cross functional with the legal. I was like the, not the person in your practice area. So I interviewed so many, I mean probably 500 people in a year. And what I had learned is and we had a ton of coaching on interviewing when I had the same list of questions for every single candidate on let's say A certain role and I would ask the same questions over and over rather than just like having a free flowing conversation. I started to see, you know, what someone who could answer those questions in a really solid way or all those things that you're kind of like the intangibles that you mentioned of how they responded, what they responded with, what stories they told and brought up, what they chose from their history to share, what they didn't share. Those little nuances when I had the same list of questions just became so much more apparent as I was comparing person A and person B versus Ah, I like them both. I had a really good conversation with both. I feel like they could both do the job. When you have the same questions, I just felt like one would definitely pop over the other.
Yeah, I think you're right. And I have a set, I do have like sets of interview questions and for searches with the pain points I will build out those interview questions. And also we build interview loops here as a part of our backend and what even clients so that they're not asking the same questions but what they're going to test for.
Yep.
So it is helpful. But you know, even with everything you do, people make mistakes. One thing Mary talked about which is very interesting that's gone on in hiring is this backdoor referencing.
Oh yes.
You know, when I started in doing law firm work in the late 80s, which is so frightening, and then in house work, never in my wildest dreams would you think that, you know, I would call Sally over at Roback and say, Sally, what would she like to work with while they were looking for a job. But a lot of these in house leaders, they want to know that someone worked for someone they know or that someone could vouch for them. And I don't blame them because when you've made mistakes, I get it. It's not easy to get rid of people. And in a smaller team, one bad egg can ruin everything.
Absolutely, I get it.
But it is, it's really like the way the world now going to do a back door on you and it's just crazy.
I mean I am one of those people. I can't imagine not doing a backdoor on someone or at least trying because references are great but of course you're going to choose the best people who are going to give you positive references. And if you want to hear the real story and you have that now that the world is so connected and you have LinkedIn, you can absolutely see who's worked with that person and who might have some Experience. So it's. I almost feel like it would be irresponsible not to try and do a check, you know, discreetly. Discreetly.
I actually have to say part of my job that I love is checking references. Because I think that one of the things that is a part of the whole judgment Rick and I talked about is who they give as references. So some people like, I'll just get off food. Why would they give me this person as a reference? Like they were super monotone and flat and didn't have a lot to say. And you're like, okay, you want to pick people who are going to be, you know, they're going to tell the truth. What are the concerns? What does this person need to work on but has a personality. I can't tell you how many times in this office someone will not give you their direct report. And you are like, why? And there's thing that goes this circle of energy around why from the client, from us and me having to go back to the candidate, try to suss out why not. But it can go to judgment. Right on. Pick that pick. And it is fascinating and I just love hearing people talk about in these references the energy they exude. So when people, when you pick your reference list, pick the right people. Right. That are going to speak really well of you as a leader or a client that speaks well. A problem that someone solved.
Yeah.
Or why you're the best gc. Like one of the questions I always ask is, who's the best lawyer you've ever worked with? And how would you rank this person? Making sure that your reference is going to really share that you're a star in a meaningful way.
So I love that point. What do you think are the right people to get? And I asked because when I was once asked for my references, I was told someone above you, someone who is a direct report and then maybe a stakeholder or client. And I thought that's a nice rounded out group. Is that what you would recommend?
Yeah, that's what I'd recommend. Yeah. And I think one of the things that's interesting because we are not a large search firm and one of our value adds is that we work for people. We do searches for people who report to gcs.
Yeah.
And close. So we hear a lot about what these people are like to work with. And for talking to someone or doing a backdoor for someone who's really worked for someone is really invaluable because as you know, Mary, because you've been at big places, a lot of people Manage up incredibly well. But they don't treat people very well below them and they aren't great managers and mentors and, you know, these people aren't superhuman. It's not an easy job they have, but it is important.
And I also think it's a great sign if you've stayed in touch and left on good terms with those people and that they would follow. Follow you. The people who are like, oh, I could bring a whole team tomorrow, that's a good sign. People would want to follow you to another job.
That is a really great point you bring up because one of the things when I'm doing pitch for business and people or CEOs are hammering on me about what they need, what they should do is my advice to them is bring someone who brings a following.
Yes.
That people want to work for. Yes. That have done great things, but just treat people really well and have developed great talent. You look at some of the exceptional leaders across the nation that have built legal teams and their direct reports that go along to BGCs or CLOs or business people. The really great leaders are like, I love that someone that worked for me, they brag about it.
Totally.
They brag about it. The other people that are, you know, five stim control people, they don't want to develop their talent because they're a little afraid or paranoid or not confident enough in their own abilities.
Right.
So bringing a following is really important. And that goes to somewhat of the backdoor referencing, I think, too. Yeah.
It's all these things that you can't tell from a piece of paper.
No, you can't. It's very interesting. Yeah. I think it's been just a little bit about the market. It's been tough on people. Mary. I think this has been a tough time. I've been through four downturns. This is my fourth, I would say. And usually they last about 18 months. And so June of 22, like with crypto and fintech kind of hitting the wall, you know, it started, the layoff started. I just talked to someone yesterday that got laid off recently. So it's just been this bleeding. And at the beginning of the year, I would say that we were very optimistic. Wow. This legal market is starting to feel like it's on fire. Just totally helped. And then the administration making these changes, doing what they're doing is people feel very stalled.
That's a lot of uncertainty.
Feeling like the uncertainty is there again. And so that doesn't mean that there's not a lot going on. And the disruption is still happening and people need good talent, but it's just. It hasn't taken off, you know, and we needed to take off a little bit more to help everyone out. And it's out of work. People move around so that people around and open up jobs.
Definitely. Well, you see a lot of companies, early stage companies start to hire general counsel for the first time when they think they're going to get ready to go public or do some sort of exit. So, yeah, there probably is some stalling on that.
They're definitely. Yeah, the IPO market is probably going to stall again. When we thought it was going to pick up where I said. One of the most impressive things about dealing with anyone in leemall throughout my career is the resiliency of these people and what they've been through. Whether it's a challenging work environment, a challenging company. I just look at this talent and how they come out the other side, even when they've had a rough period. And it's pretty amazing. I mean, people are very resilient and it's really impressive to watch.
Yeah, this is great. It's been such a pleasure. You've bring so much wisdom. I think you are have the finger on the pulse on this world and that was a really fun conversation for me. So thanks for being here.
Thank you, Mary, for having me. Nice to see you again.
You too.
Thanks so much.
All right, thanks everyone for listening.
Take care.