#71 Stop with the AI generated cover letters! Hiring Legal Ops in 2025

Hello everyone and welcome to Pearls on Gloves Off. I'm your host, Mary o', Carroll and today we're diving into a topic that so many of our listeners care deeply, careers in legal operations. More specifically, we're talking about in house legal operations. Not to be confused with law firm operations, which in my view is what I do now. So it's a very different world altogether. Legal ops as a term is what we use to describe running the corporate legal department like a business. And it has become one of the most essential and strategic functions inside modern legal teams. Legal ops professionals usually report to the general counsel and do all sorts of work related to project management, budgeting, finances, technology, knowledge management, process improvement, practice management, you name it. Now, on the law firm side, it is a little bit different, at least in my role. Operations for a law firm encompasses running the actual business side of the law firm, which includes all the functional areas in addition to helping operations related to the delivery of legal services or the practice of law. So today I am excited to welcome back Anne Kerwin Payne to the show. If you've been with us for a while, you remember Ann from an earlier episode, 66 to be exact, where we talked about the role of the general counsel and what it takes to become one and what companies are really looking for. Today though, she's back to focus on the other side of modern legal departments and what legal operations is all about. For years I found myself playing matchmaker between GCs and legal ops professionals, trying to help GCs understand what they actually needed and helping these candidates position themselves for roles that weren't often well defined. And that's because there simply weren't recruiting firms who truly understood but both sides of that equation. So much education continues to be needed on both sides and this is an industry, a profession that is changing in real time. That is why I'm so grateful for Ann and her team at Kirwan Associates. They've stepped into this gap and are now helping to shape how legal ops roles are defined, hired for and set up for success. Ann brings decades of experience in legal recruiting and has become a trusted advisor to some of the most forward thinking legal departments and ops leaders out there. Today we're going to unpack where the market is headed, what makes a candidate stand out, why some legal ops roles are thriving, how companies can evolve in this fast changing landscape, what companies should be looking for and a lot more. So let's get right into it.

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And welcome back.

Thank you for having me again.

Of course we had you just a few episodes before because we all know that you are absolutely the person to go to when it comes to recruiting tech GCs in Silicon Valley. But I was also so happy to learn that your firm also tackles the ever important legal operations role. And just for some background, I've been begging headhunters to get smart about this role for years. I have spent too much time in the last few years playing a middleman, I think between the people who are like looking for roles and giving the GCS counsel about what they should be looking for. So really happy to hear that someone professional has taken this spot. How did this even come to you guys and how did it become a specialty for you?

You know, I think in about 2009, Mary, we started to do a lot of work and we were probably one of the only search firms focusing on contract managers. And so we built this and a recruiter in my office where like built this contract management arm. And through that, as people started to evolve into legal ops, that was one path. The other path, to be honest with you, is Sun Microsystems was a client. Okay. And Mike Dillon, the general counsel at the time, and Damien Eastwood, they literally had this idea that each team should have like a chief business officer of legal. And that was Jeff Franke, who was one of the original founders of Clock. And I had recruited for that team and he shared this vision and that was the birth of it. And so we started those searches then and then went from there with Connie and Jeff and different roles that they had. And then it evolved.

Amazing. That's a long time ago. Have you seen the legal ops function evolve as we all know it has?

Yeah, it's crazy. I think that as you very well know, Mary, it was like started out of these legal functions and now I think if you don't have a legal ops person on your team and you wonder if there's an, there's something, there's an issue with the team. I would say that these leaders or these legal ops professionals are much more strategic, they're much more cross functional, business savvy. You see these people coming from everywhere. It's just, you know, it's grown into a must have and an integral part of the legal function, the in house legal function. And the firm and firms too. Yeah.

And in the early days, by the way, it was only at these big companies, right, These big financial services or tech companies that had, you know, like over 50 to over 100 people in those legal departments. But now of course we see it like as the second hire in legal. There's no group that's almost too small for this function.

Right. I think that what we see, we do a lot of work for venture backed companies and they might hire a head of legal, a general counsel, and then immediately the second or third hire will be a legal ops, you know, depending on the level. But they know they need to have that person to really help them run everything effectively and efficiently.

Even though it's been around for a while now, I feel like we are still in a world where nobody understands what the role is and we're all still trying to explain it. And frankly, you know, if you ask five people, you're going to get five answers and five people structure it all differently at their companies. You know, what's important to know in how you define or structure the role for success?

I think that one thing is on the company side or the law firm side being very clear about what the pain points are. What are the needs? Is it, you know, that you need someone to help you on the sales side? Is it that you need to help, you know, more with budgets? Is it the e billing, the 12 pillars of cloth that you have? If you read these job descriptions of what these people are, I just read a bunch of job descriptions just to, to refresh myself. It's a little bit overwhelming everything they can do. But I think it's important for companies to say, okay, this is the level we need, these are the pain points and go after that hire. You know, it is true, I think, Mary, that I think one of the biggest challenges with legal ops is the definition of what they do because they can do so much that it is very challenging. It's challenging even for candidates to, to describe what they do. And a lot of the legal, a lot of legal and a lot of HR and a lot of people that are hiring these legal ops, they don't really understand what legal ops people can do. So that's challenging. It's an education from the candidate and it's just the companies really knowing what it is they want and what problems they need solved.

I think that's exactly right. Even when we went and tried to create this clock, Core 12, which is the scope of role that could possibly fit into a legal ops function, and as we both know, not, not everyone does all those things. In fact, most people don't do all 12 things in their day jobs. You know, you probably have some segment of those, but we wanted to create that as like the full scope of possibilities for people, whether you're hiring for it or whether you're going into this function. So you're absolutely right, because I talk to folks all the time that know that they need legal ops. And what they really need right now may be that they have so much litigation and they need an ediscovery expert or they have so many contracts that they need a contracts person or their outside counsel. Management is out of control. And so they need E billing and, you know, someone who's got some budget and financial acumen, or they have a lot of projects and they need project managers. So it's exactly that. It's like figuring out what do you need right now in the short term and hiring for that skill set. And for sure, that role will evolve because your. Your organization, your legal department, your function will change. And then the hope is that you've hired someone who has that ability to grow into the role or with the role.

Yes, definitely. I think that there are so many strong people who've gotten into these roles that might be number twos or number threes. Right. That are doing just because they don't have it all. But how do you get to that next level? So I think that's a pain point for a lot of legal operations professionals is just how do you get to be the head person if you're more junior and you've been given the opportunity? And it's a big role. When you look at just the 12 pillars or you look at even the E billing piece, it's so large, it's like becoming a gc. You have to have all of these substantive skills, but you also have to have the soft skills. And so how do you get there? And I think what I hear from clients a lot of times is they really need to hire people who are intellectually curious, adaptable, and strategic. And the strategic piece, you hear that over and over again. And I think candidates can really do themselves a service to really hone their elevator pitch in terms of why they are strategic and what they've done and use examples. I think one of the most challenging thing in vetting this talent is the way that legal ops professionals explain what they do. You cannot assume that anyone understands what you do day in and day out, because it is fairly new. Sometimes I'm listening to people and I'm not getting it. I don't do this every day. And so I'm Thinking about heads of talent, I'm thinking about paralegals, I'm thinking about operations, people that are interviewing Legal Ops professionals and going, I don't get what they're saying. So you really need to almost. It's almost like that lawyer talking in non legalese. It's like having that mindfulness to talk to people in layman's terms. Let me share with you what I did and go into specifics so that people can touch it.

Yeah, I couldn't agree more. And Aaron from Snowflake and I were just talking about how every time you speak to someone, they just, they use the words like efficiency and technology and enable. It's wait, what do you actually do? And we do have to remember that most GCs are hiring this role for the first time. So to your point, they maybe have not worked with this in a past job. They maybe, you know, don't have a lot of ideas about what this role is, but they've heard great things or they know that they need it in concept. But when they're interviewing. Yeah, you really have to be outcome focused or impact focused in your delivery of who you are and what you do and this tell the stories about what you did and it, you know, how that reduced time, cycle time, how that reduced hours, how it reduced expenses. But if you're not giving contract examples, it's hard for these folks. And you know, probably you in the early days, there's other recruiters that are trying to get into this space and they're not clear on what you do. So you really have to speak in their language.

Yeah, it's really sharing your value. Add on the candidate side, when Legal Ops individuals are looking to either get into Legal Ops, make a move, make a transition, I think it's really important for them to do some soul searching in terms of what they know, why they want to do it, what their leveling is, and really just take that time to understand, you know, what is their end goal. Do they want to be ahead of Legal Ops? Just talked to someone recently who was like, I just love emailing. I want to do emailing. And I'm like, okay, how about it? You really need to do that. You need to have your resume and your LinkedIn buttoned up. And I was thinking about the fact also you need to send your resume to your friends and have them look at it and print it out. Because sometimes I feel like people use these systems or whatever they do to use resumes, and then I get it and it comes across, it looks funky, it doesn't look as professional as it should. And of course your LinkedIn should be detailed on what you do and maybe share your value add too. And then I think really what's most important is there's all these roles out there, there's these job descriptions. It's like there's no one that can do it all. Right, there's no one that can do it all. But what's really important is to understand the mindset of the leadership. When you're thinking about legal ops, if you're more junior and you're looking to work on Mary Carol's team or sun leads team, you know, what is the history of that person, what have their teams look like, what have the people on their teams thought on to do so you can find out what kind of a mentor leader they are. If it's a gc, I would look at who has been their head of legal ops before. You can really put together a little bit of story to see are you a fit for that given what you know, these people have done. Just don't look at the paper anyway. I also think one thing that I've heard a lot recently with regard to hiring is that when you have the opportunity to be at a large company or even a medium sized company and you build these relationships with even a five person legal department, those five lawyers move on. Their team is looking for a legal ops person. If you've done a great job for them, that's the first name they're giving to their gc. And so the networking piece of the relationship build not only amongst your. There's so much pressure in legal ops. You really need to know your colleagues in the space because you learn so much from each other. But it's really just making sure that you're creating great relationships and leaving a mark on the attorneys you work with.

Yeah, and you. And with the world being so small now with LinkedIn being able to see who knows who, you better believe we are all back channeling information about who's worked with you before and can you actually deliver the work. We're also seeing, at least I know people who are in these legal operations roles. They move around a lot and part of that is because there are so many new opportunities and shiny new things and I can get more money or I can get more scope of role and more responsibility if I just jump around the. But I think you're right that there's also a bit of a challenge in moving from these mid level roles into that head role and people are hitting that ceiling within their own companies and wanting to move around. I feel like I've seen a change in what people are looking for from like a tactical perspective to more strategic. You touched on that as well. Are you seeing that trend and is it continuing? I got a little discouraged, you know, in the last year or so when I saw less sort of high level strategic roles. But I guess let's talk through as a mid level person, like how do you get to that head? Has the role changed? Do you need to leave your company to do that and so on?

No, it is, it's interesting. I think there has been less leadership roles which has been indicative of the market in the downturn and a lot of restructurings. You have a lot of innovation going on, a lot of hiring in the AI space. But at the same time you are having this market is very strange in the sense that there's a lot of hiring. People are having a tough time finding people but at the same time they're letting people go. The administration has thrown some things and you know, stalling in the market. But I think it's going to, you know, I've seen a lot more roles recently and I think it's going to open up as people move around in the market opens up. But I think that is the biggest question is how do you get to the next level? You know, I was working on a search for a head of legal operations and I was looking at those number twos and threes and these teams to be the head for this company. And I was thinking about the search. We drove and it was interesting. I think some people, some candidates didn't come across super strategic and super like taking initiative and sharing. Some people didn't share their value add. There was one candidate who absolutely hit a home run but had not managed. And so the management piece, it really, the GC couldn't get over the fact that she hadn't managed. She had a lovely personality. She could have easily managed. She just had been burned. So she wanted someone who could manage a team of four. So I think you really have to think about honing your skills and selling the strategic nature of what you've done and who you are. Some of you, I think hiring an executive coach to help you present to share your story. And it's a tenacious game, just getting there, just interviewing a lot, talking to people, making sure people understand you're ready for it. Because a lot of people, they can do it.

Yeah.

And they can make a change.

It's not just the management skills but that leadership mentality and showing up. Right. Because so many people will say, I get great reviews, everyone loves me, I get everything done. And you may be really good at like project management or change management or getting the work done, but can you show up as a leader for the department? Can you show up, you know, at the leadership team table and have that sort of ability to influence and get people around your ideas and add a voice to the leadership team table? Many of these general counsel are getting much smarter about what they need to do on technology and operations and how to run things efficiently and what data they should be looking at. And so the expectation that they have for that right hand has, has also gone up. And they want people who are smarter than them on these things. And so there's this need to be proactive and this need to take initiative to a know what's happening in the market, know what all the tech players are, know what other people are doing and just basically have a perspective on the direction that department or that organization should be going.

Yeah, it's a lot. And you think about the real leaders. You know, there's the soft skills like you're talking about, Mary. Like these jobs are so cross functional world. Yes. And you're talking to the CEO, the cfo, the head of sales. It's crazy what these individuals are doing. And so you've got to have that presence. I think you've got to have this unflappable leadership style. And then, you know, you've got to have these people on your team to help you. Because I think it's overwhelming the pressure on these people to understand all the tech that's out there. There's a race in the legal technology world to AI. Right. And to understand all these products. And what do we do then? Legal ops people aren't just feeling the pressure. The GCs are more than ever because they're just like, what do I need to do to get my department running on technology? And they're feeling the pressure. And thus the legal ops people are feeling the pressure. So you don't have. When you think about legal ops and everything that they do or their teams do and then all of the soft skills, it's a lot. And so just being aware of the adaptable leadership way you have to have about yourself is pretty important.

It is AI and technology and the explosion there data, you know, the GC getting smarter. Is that shaping the profile of who gets hired?

I think so. Do you think about the fact that legal ops may have come out even a sales, commercial lawyer. Right. Or a Contracts manager and was just outstanding of what they did or a paralegal. And now you fast forward, it's almost like everyone, every person on that team has to be much more technology focused and that's really the difference, probably the main difference I've seen, you know, over the years on. It's a lot for them to understand. And you know, I really, sometimes I sit there and say how do, how are these head of legal ops supposed to understand like all of this technology that's being developed and look at it all and make informed decisions and then sell it to their people to use it? Yeah, well there's a way that legal ops people are in a way like leadership, subtle influencers.

Totally. And I don't think you necessarily have to like deeply understand the technology but you have to be naturally curious about it and have an interest in it such you're diving in and understand how it can be used and what the limitations are and you know who you should be talking to. So I do think that at least interest in technology and AI is becoming much more important. What about the need for a legal degree, a jd? Because there's been the ongoing ever going debate about whether you need a JD to do this job or not and we continue to see job descriptions that are like you need a JD and 10 years of legal experience and this doesn't exist.

Yeah, I think sometimes it's a little bit like who else would say they need, you know, contract manager with a jd? They're thinking that they're going to get a different level of candidate. I don't think that you necessarily have to have a jd. I think if you've been an in house lawyer and you've worked around a legal team, you've seen the scaling, you've seen the infrastructure, you've seen what best in class legal ops is and then you become a legal ops. That's great. But I think it's more important that you're operationally minded. A lot of lawyers have become more operationally minded than they used to be. You see general counsels taking on, you know, four different pieces of companies. It's just the way lawyers have evolved over the years to be just business people with jds. These successful legal ops people come from all walks of life and it's really come from technology. They come from MBA backgrounds, they come from finance, Some just fall into it and do incredibly well. There's a variety of places and people can do really well with what they know and what they learn.

Yeah, how have you seen that affect compensation? Or the trends in compensation. Right now with legal Ops, it's interesting.

I was looking at everything, reviewing everything a legal ops leader does, and I was thinking, wow, they don't pay these people enough. Because it's a lot. It's a lot. So I do think that if you're going to hire someone with a JD or someone who's scaled a team, your comp, you know, scale the team, been in legal Ops for a significant amount of time, the comp is a lot higher. The average range, I think the medium range you see in legal ops is like maybe 240 to 260 base. And companies, you know, when you see on a JD sometimes ahead of legal ops at 175 to 185 or lower range, you can gauge from the compensation, maybe the level of hire they're looking for. And if you flip it, with all the budget pressures that legal is under these days, people will say to me, man, I can do that job. They really need someone more senior. And I get it. They do. But they've got the pressure of I can only. I only have this much budget. So it drives the level of hire. And that's something that, you know, legal ops professionals, when they're looking, they really need to be mindful of. And that's not it. You know, you don't want to talk about comp right away. You don't want to waste people's time either. It. It's going to be so low that you're not going to be interested. So it is something that should be vetted up front because there is such a range.

Yeah.

What legal ops professionals make and what.

They do, what I struggle with. And again, I talk to so many people hiring and creating these roles that if it's the first time, so much of what they need is cleanup and heavy lifting and getting things in order. And you need someone who's willing to roll up their sleeves. And so they. They don't want that sort of strategic leader yet because there's so much. I don't know what the. I don't want to say grunt work, but just getting things in order first, that's very tactical. And so you want to hire someone a little bit more junior who has room to grow. And hopefully as the department and the function matures, then there's headroom. But I think that's the key is if this is the first role and they're hiring you, how do you assess as the candidate whether or not there is going to be headroom? And, you know, is this a GC that's committed to a path to directorship or head of something at some point. Or do they always see you in this role?

Yeah, it's true. I think many of these people will hire. I call it the block and tackle. They just need the block and tackle someone to come in, start the function. Those roles can be very fun for junior Legal Ops professionals. I call it the hub of the wheel. Sometimes where a startup company has three to five lawyers, this comes in. They're like the cheerleader for the department. They're in the weeds. And you know what a great role to learn.

Yeah.

And to grow from, to be in that position, to be the right arm of the GC of many high level people really go after the chief of staff, legal operations roles and those are coveted. Just having being the true right arm of the GC and not that other head of legal. And sometimes it's just semantics because head of Legal Ops can be the chief of staff as well.

Totally.

Yeah.

In fact, I think ideally it does play both the COO and the chief of staff role to the general counsel.

Yeah. So back to your point. I was on a panel at Legal Operators and I think it was Elizabeth Miller and KD who were at Legal Ops were talking about hiring and when they talked about their teams, they're like the most. The word they use was curiosity, intellectual curiosity. We mean we need to hire people that are curious how can we do it better? And they're going to go after it. And so I think if candidates can really share more about that and what they've done in their elevator pitch, that's helpful as well.

Yeah. Because when you're first starting out and creating the function, you actually don't know what you're going to uncover and need to get smart on and learn to fix and work on. So that is something. If you're going to grow into a role that's going to be really important. Looking at the GC side or the hiring manager side, what are some tips you would give to them or even what are some things that have gone wrong in the hiring process As a gc, what should they be looking for? What are they looking out for?

I think when you say what's gone wrong? I would say I think that GC sometimes can be shortsighted in the sense that they just want more the block and tackle. They don't want to go after the super seasoned person because they're almost afraid. They don't. They think they're going to want too much from the role. And I Think they could hire more senior than they do oftentimes and it's going to just, in the end add more value. But I think Most of the GCs, unless they don't understand what the function is, they're pretty good at saying, here are the pain points, here's what I need. And I think they learned through the process, Mary, that really it's the chemistry piece. This is a little bit like when you're doing a search for a GC and they're looking for their first, their number two, let's say, growing venture back. That hire is incredibly important because the chemistry, if they get that wrong, it just doesn't go well. Like you've got to make that first hire and make sure there's the right chemistry. So you're the team driving this place. Yeah, the Legal Ops is just as important. And so I think it's making sure that they find the chemistry and that it's not. This person's going to sit over here and meet with me once a month. It's got to be more of a partner. And so I think many have learned that and many haven't. Otherwise, I think they're evolving. And Most of these GCs know they need these people. They cannot do it all.

When you talk about needing to hire someone more senior or at the level and they're slightly afraid of it, I do find that gcs tell me I don't know what this person will do beyond the initial project that I have in mind for them. And they worry that, like you said, they may not have a concrete enough idea of if I meet with this person once a week and what am I going to tell them to work on. I have often said if that's the way it's working, you've hired the wrong person. Right. This Legal Ops person should actually be identifying areas of opportunity and strategy for you and telling you what the opportunities are and what the priorities are that they should be going after and making sure that they're aligned with your vision and direction. And so in that way, it's not someone for you to manage, it's actually someone to help you do better and make your department look better.

Yeah, that's really the answer to the number two. Becoming the lead is like that initiative. You should be taking the initiative to sit down on your one on ones and say, here are the things we're doing and here's what I see that we need to be doing and really driving and educating that leader, your team on what needs to be done, what other people are Doing and maybe not just legal, other parts of the company as well. The better your legal ops person is, the better the general counsel is going to shine because this department is running like a business and is super efficient. Their attorney, contracts, whatever it is, it shows. And so sometimes I think it's really short sighted not to get the right level or not to hire at all and not these people in place.

Yeah. And by the way, just as a side note, we're not seeing that many hybrid roles anymore. You know, we used to see a lot of I need a contracts manager slash legal ops, or I needed a commercial attorney slash legal ops. But they're much more pure play now. Is that correct?

They are much more pure play. I think that, yeah. You don't you see more the contracts manager, you do see them more sitting in the sales side of legal.

More that.

But legal ops is its own thing now generally. So I do think that a lot of companies have used the legal ops words to elevate candidates as paralegals and contracts manager to keep them and have them do some of that. But it's rare these days.

Yeah. And those are the folks you know that I think end up having to leave their organizations to become ahead. Because despite how good they can be, I often find if you're working with the same people, it's hard for them to see you differently than what you were for the last 10 years. You know, how you worked closely with them and all of a sudden you have a different hat on. But they're used to working with you in a certain context.

And I think, Mary, you touched upon it like some of these candidates in the contract, not, I'm sorry, legal op space, they've moved a lot. They've moved around a lot. And I think that what you're seeing and you're finding it used to be obviously that you had to be, you stayed with the company for seven to 10 years and now you move companies to be for that reason because you want to learn and grow or you want more money or you're going to be seen as X and do that. And so there's more movement which becomes a little bit more challenging in terms of recruiting because people will say, why so many job moves when you have to get back these candidates, like why did you move from A to B to C? And they'll explain it. And there are reasons for these moves. Now if someone's with a company for seven to nine years, clients will say to us, why? Why have they stayed at this place for so long? And you Know, I'm working with a candidate right now, has been at one place for 11 years and I'm getting that question. But the candidate, if the candidate can say, look, I started out as a paralegal, then I became Legal Ops, then I went to this and I built this massive team. But they have a Thor to share it. But otherwise, that's why you see the job moves. And to another point that I think Legal Ops professionals really need to be aware of is because their backgrounds are so varied, this backdoor referencing is really paramount. And you know, when I started in this business, you would never ever get on the phone and call someone that had worked with someone. It's so confidential. And now it's so common that GCs, CEOs even, they won't hire a GC as GC won't hire a head of Legal Ops unless they know that track record and they can call a couple friends to verify that person was outstanding.

Totally. Well, and there's so many platforms in Legal Ops for people to become public speakers on webinars, on podcasts, on social media and posting their thoughts. And you can portray yourself as being very knowledgeable, you know, but sometimes you have to, as a hiring manager, be really careful and do your diligence and find out, you know, they can talk the talk, but can they actually deliver the work and do those back channel references?

It is true, I think the whole social media and being able to speak doesn't necessarily equate to how good you are day in and day out. And so you do need to that that talent. It's a little bit. I remember a GC saying to me, I need a privacy lawyer, but I don't want the one that just speaks all the time as like what, you know, just is out there speaking. I need someone who can build it, build the function and do the tractable work. But at the same time, I really do see the value of these conferences and Legal Ops knowing, being out there, speaking, learning, because of what these people do. You really need to touch on a lot of things.

Yeah, yeah, very true. And you know, you said recruiting is really hard in this space. Many folks who are hiring managers, general counsel, who are looking for this role are almost afraid to put a job description out. And sometimes they tell me, oh my God, Mary, I put something out. And within, you know, two days, I got 700 resumes for one job. And it's overwhelming to your point, because people are coming from all sorts of backgrounds, interesting backgrounds, relevant backgrounds. 10 years of experience never touched legal. Like all These different things, and nobody knows what they need. Nobody knows what this job really is. And so they become very paralyzed. That's why I think having recruiters in this space like yourselves is really useful. I'm sure that happens to you too, where you get just an influx. What do you look for? Like, how do you go through that pile and find the nuggets, the first piece of that.

As you know, Mary is just really listening to the client in terms of the leveling, you know, really aligning with them. And we spend a lot of time with our clients up front. It's a fast work, but it's. Let's align on what this hire is. Let's look at some profiles and calibrate right up off the bat. And, you know, frankly, you can go through a pile of these resumes pretty quickly, like, yes, no. But then as a search professional, I just. There's this creative piece where you have to talk to the people in between, because a lot of times those people that have done, you know, something different or touched upon legal op, whatever it is, are the gems, right? They might have that leadership style. They might just happen to be the person that really has chemistry with this gc. You just never know. So you really have to vet and cover, cover the pile well. But you can do it pretty quickly. And you have to, you know, you're matching what the client is saying, but at the same time thinking creatively in terms of what they're saying as well. The nuances, you know, you just never know.

Are there ways to make your resume stand out? And I will say, having hired a bunch of people this year, I have seen some of the AI resumes where it's almost like word for word, what I put in my job description. And those are my words, so I recognize them. And it's like, like, why would you have come up with the same kind of text and diction? So those are flags for me. And even if I like the person, when I interview them, it's always in my back of my head. I feel like you're trying to pull a fast one on me by putting some of this into the resume. There's also, I'm seeing on the one hand, like, the traditional dancery font type, classic resumes, and then there's these, like, colorful things that have photos and not necessarily your experience, but more color as to, you know, soft skills and all these other things. What do you think is the right direction and does it matter?

Personally, I like a very simple professional resume. I do.

Me too.

There's all these tools now that people can upload the job description, upload their resume, and they can see, they can either have it tweaked so it meets the jd, or they can see how likely they are to be a fit for the role, which is great. AI is being incredibly helpful in a lot of ways. But the standard professional resume is where you show, you know, first of all your soft skills, some kind of summary at the top. I do like a summary at the top because I think you can put your soft skills in there. But I also think if you're going to put, I worked at, like, where did you fit in? How big was the company, what growth did you see, what value add did you have? And just doing it very simply. I'm not into the pictures. I don't like a lot of color, you know, So I just think simple, straightforward, but really good writing. You know, if you think about a resume, it'll get you in the door if it's well written and it's simple. But it could also just prevent you. If it's bad or there's a typo, it doesn't have to be that great, but it, it can keep you out of the door too.

Totally.

Just like, people look at it and I'm like, why would someone do this? It's so dense. There's so many words on it. You know, people don't want to read, obviously the way of the world, they want to read bullets. Now people who've been practicing law or the laws for a long time, they might share a resume that has just huge paragraphs on it. So I'm. All of the simpler is better.

Yeah, I am too. What about LinkedIn profiles? So there are, there are some companies that I'm aware of that they don't even look at your resume. They just circulate your LinkedIn profile to your interviewers. And so does that need to read? I usually tell people to make it read like your resume. What are your thoughts?

It should read like your resume. And it is interesting because I, you know, I remember early on this might have been 10 years ago, a CEO saying, this person doesn't have a LinkedIn profile.

I'm not going to.

If he doesn't have LinkedIn profile, I'm not going to interview him. I was like, wow. But your LinkedIn profile should mirror your resume. And a lot of companies, even if you're doing that, sync with your client and you've got it all beautifully prepared with the resume and everything, that they're just pulling up your LinkedIn to look.

Exactly.

They're all just pulling it up. So you have to have that really buttoned up.

Yeah.

And people will look at, oh my God, look how many followers someone has. Yes. That impresses some people. I don't know that's necessarily indicative of how someone, how good someone is at their job.

But it does help me back channel where I'm like, oh, they know someone I know from this past life, I'm going to go find out about them. So it's always a helpful tool. Yeah, yeah. The other advice I often give people who are searching for roles is that, you know, they tell me these job descriptions, they say you need 10 years. They say you need a JD. They say, you know, it's only a manager title. I want to be a director. And I've often said, look, the person who's looking for the role doesn't even know what they want. And, and they're really looking for that chemistry fit, like you said. And that person who just is going to be able to jump right in and mesh with them well and mesh with the team and get stuff done. And so I've always tried to encourage them to try to get the interview anyway. And then a lot of times they get impressed and they elevate the role. They change the title, they change the comp or they change the scope based on what you're saying that you're able to bring to the table because you're there to educate them as well.

Yeah, I would agree with that. I think the job descriptions, sometimes it says whatever title they do, elevate it, sometimes they'll bring it down. I would say in over 35 years of legal recruiting, I would say the title and call, things get changed a lot due to whatever goes on through the process getting calibrated. And so I would always encourage, you know, people too. I had a lawyer say to me, he had an interview, it was a junior law, it was a super hot, fast growing company. I don't know, I'm like, interview, just go meet them.

Yeah, exactly.

Just do it and impress them. If nothing else, the more people that you talk to, the more you learn from, you learn about how they're doing. You make connections, you build a network, you build a brand.

Yeah.

So I think that these job descriptions are just, they're doing their best. Right. They're putting it all out there. You just never know. It's really hard for candidates because you're oftentimes in this black hole. You don't know why people don't get back to you you think you're right. Really can't take it personally. Everyone's just really trying to do their best, but like you said, sometimes they just really don't know.

Yeah, yeah. For both, for both the Google and Goodwin roles, I worked with an external recruiter who called me, and for both of those, I was kind of like, yeah, thanks, not really interested. And they encouraged me, just go meet them and see what they have to say. And in both cases, absolutely fell in love with the people and ended up taking the role. So, yeah, you should go and find out more in person.

You know, on the flip side, you don't want to waste people's time.

Yeah.

Then what happens? But a lot of times is people think, oh, they'll, you know, you vet. You say, okay, this is what the role is. You share that as a legal search professional, you read through the process, you're saying, okay, it's going to look like this, it's going to look like this. If you get to the 11th hour and someone says, you know what? I want this title, I want to manage this, they start putting pressures on the process. It really can then turn the other way where people will pull offers, not make offers, because of what we've shown these true colors through that. So it's a very fine balance of how you behave in terms of that. But you got to take the meeting. You got to start having the conversations.

Let's talk about that a little, because that has happened where a candidate says, yeah, I'm totally fine with X compensation. And then when they knew that we fell in love with them, they're like, no, it's going to be 50% more than that. And we're like, you know, that's really icky that you're doing that. But there's also folks that really fixate on title and compensation. I always think that's a little bit of a red flag. You've assessed so many people. How does that usually work and what it does. You know what?

I love a candidate that is so interested in what someone's doing, like what the company, the people and the passion comes through in the conversations. And then we're talking about calm and they're saying, I really want enough. A little bit more. I want a little bit more. And I'm saying, they can't. Let me tell you, they can't. Or they might be. There might be some room. But I think that what really impresses me is, wow, this would be a step up for me. I love the people. I love what I could do. There I'm connecting with this and that. They're already thinking about how they plan the function. Then they're. The title thing, Mary has become so much in the last 10 years, people have been so hung up on title. You know, I was at Google in 2001 for two years building their legal team. No one cared what the title was. They all came in as counsel and no one argued.

Yeah.

And a lot of times it's over indexing and title, but it's just. It's a little too much because these jobs can be so wonderful and they just don't give big titles for whatever reason. On the flip side, I feel for candidates because they've been burned, where they're like, I want a Head of Legal Ops title. I want this because I didn't have it before. And it's a pain point for them, just like it's a pain point to the company. So you have to respect that. Yeah, but it is. It's become. I don't know if you've seen it. The titles have become just forefront for a lot of people.

And then does it hinder or help you in the next role, too? So let's say you're going up for an external director role and you're a manager. And so there's a few steps between as a manager, you were operating as, you know, but they didn't give you the title, and then vice versa. If you're a senior director at a small company, are they thinking, ooh, I can't hire that person because it would be a step down. So the title's get in the way sometimes as well.

Yeah, I think the titles do get in the way sometimes. On the hiring side. If you have. If you're head of Legal Ops and you're going to come in and be number two.

Exactly.

Because it's a bigger place and they're thinking, is this person the right level of work? I have to explain that a lot of people are saying, but I can do it. But you have to think about, on the hiring side, is it going to be the right level for you? Is the candidate going to be happy? So that does happen a lot on that side. But I do think that there's a lot of times where someone may have a big title and they go into a place and they don't care. Not they don't care. They take a lower title and the job could be a lot bigger than what they had and the upside can be a lot greater. So it doesn't always follow this sequence, but people have Been in larger companies and they've seen the lockstep where, yeah, legal profession comes out of that. Associate, senior associate partner, it becomes out of that. So people have that mindset and they can't get around it, but it can really work in your favor. And it's, you know, there's a lot of people that are GCs that go back then become head of legal ops, you know, and they love it. So there are a lot of things involved in these decisions about titles, I think.

Okay. And then what about compensation? Then taking a step back for a bigger role, a more interesting role, broadening your scope, leaving a certain industry. Like, how do we think about that?

I think it's that, you know, I'm in the. I would say that I'm in the profession of pay cuts because we do in house legal recruiting and historically moving people from a law firm environment that we used to do a lot more of that in house to in house or if we're moving in house to startup company. It's these conversations around calling. And I think that there's been some people who've taken risks. There's a lot of people who've taken risks, gone to startups, gone to companies, and they've taken less money and it's paid out really well for them, either financially or these candidates need to really think, Mary, like, what platform is going to get me to my end goal? You know, so if you step off a big company and you were at Google and you know, and you saw people do it, they step off the mothership and they go somewhere else, their scope is larger, they're closer to the top, they're doing more sophisticated work. Yeah. More impact rewarding.

Yeah. The tooling.

And you know, it's hard to make less money. No one wants to make less money. So it's a big decision. And especially right now with families and the cost of things, it's very tough.

It is tough. You also see the difference between people who see a job versus a career. I don't know, more and more I'm feeling like that's a distinction. It's a conversation I've had in so many different areas recently where there's people who are like, I just want the job and I want the title and I want the money and I just want to go in and out and have my life. And then there's others who are like, I'm thinking about this long term and where I can go next and I have an end goal in sight or just thinking about following their curiosity and their need to learn and expand.

Yeah. I think that goes to being like what I was saying about the people that are passionate or connected to what the role is in this way where they're connected. It's more about. They're connected because it's a part of their career and it's not just a job. They're, you know, they're just. There's no way to describe it. It's just there's so many people that are passionate about legal ops. It's crazy. And they'll. They talk about it like they've done, and they're so proud of it and they feel it, and that's great to feel that way. You know, whether it's me or a company interviewing them, you know, there are. There's always going to be those people that are just doing a job. It's not really their passion for the money, and they're stuck in that. Yeah.

It's so true. And it's been another wonderful hour with you. There's so much happening in this segment. There's so many people that want to hire for. There's so many people that want to transition into these roles and to elevate themselves in these roles. Any final words of wisdom or thoughts for the future?

Well, I just really think if you believe that you can do it, I would really mirror the market and look at what's going on in the market with AI, with legal tech or the legal ops. Learn as much as you can, realize what you know and what you don't know, and start chipping away, setting goals for yourself and really getting there and where, you know what move is going to get me to the next step and really think about creating a brand and a career step by step.

Such a pleasure. Great advice.

Thanks so much, Mary.

Yeah. Thanks for being here.

Yeah. Great to see you again, everyone.

Thanks for listening. We'll see you next time.