Khurram’s Quorum – Ep 035: Hilary Gerzhoy on why ethics failures start with fear, not greed

Khurram’s Quorum – Ep 035: Hilary Gerzhoy on why ethics failures start with fear, not greed

Hilary Gerzhoy advises lawyers, law firms, and GCs on the messiest, most human decisions in legal practice—and she's convinced that most ethics violations don't start with greed. They start with fear.

As a partner at HWG who specializes in legal ethics and malpractice, Hilary sees patterns most lawyers never notice: the junior partner who takes firm templates because they're terrified they can't succeed without them, the equity partner who solicits clients early because they fear losing portability, the associate who stops billing time before giving notice because they feel the firm treated them unjustly. In this conversation, Hilary breaks down why 90% of clients fall into two buckets (they're either coming with you or they're not—and timing rarely matters), why confidence is the underrated trait of successful rainmakers, and how her middle school debate training prepared her to think on her feet in high-stakes ethics conversations.

We discuss the Rules of Professional Conduct that lawyers misunderstand most (client confidentiality is much broader than attorney-client privilege), why trust accounting violations lead to presumptive six-month suspensions even when no client loses money, and how Hillary's work is fundamentally about helping lawyers navigate the emotions—fear, perceived injustice, attention scarcity—that drive risky decisions.

Keep reading below for the full link to the episode and the full transcript of our conversation.

Top Insights

Below are the highlights of our conversation:

• Fear, Not Greed, Drives Most Ethics Violations: Hilary rarely sees lawyers intentionally stealing from clients or acting maliciously. Instead, most violations stem from fear—fear of losing business, fear of not being equipped to succeed at a new firm, fear that clients won't follow. That fear leads junior partners to take proprietary documents, equity partners to solicit clients before giving notice, and associates to stop billing time because they feel the firm owes them something.
• The 90% Rule for Client Portability: Most clients fall into two buckets: they identify you as their lawyer (and will follow you anywhere) or they're loyal to the firm (and won't leave no matter what you do). Hilary estimates this covers 90% of books—meaning the timing of when you talk to clients rarely moves the needle, and the anxiety-provoking risk of early solicitation usually isn't worth the minimal upside.
• Client Confidentiality ≠ Attorney-Client Privilege: Rule 1.6 (client confidentiality) is much broader than privilege—it covers any information learned during representation that the client doesn't want disclosed, even if it's public or just the fact that you represent them. Hilary sees lawyers violate this constantly because they conflate the two concepts and don't realize how wide the net actually is.
• Confidence (or Projecting It) Separates Rainmakers: The most successful lawyers Hilary works with exude calm, self-assured energy—a "I've got this" vibe that makes clients feel protected. Many are deeply insecure underneath, but they project confidence because clients need to believe their lawyer will anticipate problems and handle anything that comes up.

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Full Transcript

Khurram Naik: This is Forum with Khurram's Quorum. My guest today is Hilary Gerzhoy. Hilary is a partner at HWG and she focuses on legal ethics and malpractice issues. Hilary is a frequent speaker on legal ethics, and so that's how I learned about her practice. I find she has such a thoughtful approach to advising on the intersection of the business of law and the ethical duties of lawyers. It’s also a fascinating niche to occupy, so I was really curious about how she came to this niche as well. So, a lot to explore here. Here's Hilary.

Khurram Naik: Hilary, I'm so excited to have you on. Since the first time I saw you speak, you're a dynamite speaker, and so… I didn't think probably the very first time that I’d have you on the podcast, but the second time I saw you speak, I definitely thought about it. So, excited to have you on. We've been having some conversations about your background, and so one part that is really interesting in your journey: you always knew you wanted to be a lawyer from as soon as you learned about what a lawyer is. You said, "That's me, that's what I want." And but interestingly, your first job after college was in sales at Google. And so I’ll be interested in hearing about that experience and then how it tied into now your work as a partner—and as a partner, you have business development to do. And so I’d be curious to hear about what that first foray into sales was like for you, and then the maybe somewhat surprising return to sales in your career now.

Hilary Gerzhoy: Yeah, for sure. Well, thank you for having me on. I, so as you said, I always knew that I wanted to be a lawyer. I went to U Chicago undergrad, which I absolutely loved, and met my husband there, and some of my best friends are from U Chicago. And I… but it was an intense academic experience, and I knew that I wanted to go to law school, but I wanted to take a year between undergrad and law school so that I could rest a little bit. And so I had been applying to paralegal positions in DC. That's what I thought would be interesting for me. And Google came to campus and they were interviewing, and I got an email saying, "Do you want to interview?" And so it seemed like it was worthwhile to go and interview. And so what they were hiring for were college—recent college grads—to go and sell AdWords, which at the time were on the left-hand side of your screen is where you had the list of all your AdWords ads. And so I took the job because it seemed like, "If I'm going to do something for a year, this is a really cool thing to do. Google's a super cool company. This is a unique opportunity to do it. Maybe I want to stay for more than a year, maybe I want to stay for a few years. Living in California is awesome." So I went and being at Google was pretty amazing because being at Google—and this was in 2010—so being at Google in 2010, Larry and Sergey still gave their talks to all the Google employees. And so every Friday, like, you could go and just sit and watch Larry and Sergey talk about what they were doing and what the company was up to. And but I realized very quickly that I was really not good at this job. The job was to… I was working for financial in the financial services vertical, and my job was to call potential leads and try to sell them ad space. And I… I wasn't good at it in multiple ways. I was… I found it really hard to get motivated to do it because I didn't find it to be all that interesting. And I think that was sort of the biggest factor. But I also just felt really uncomfortable selling things—like selling something to somebody. It didn't… it just didn't sort of speak to any natural strength that I had. And I just didn't… didn't do a good job and realized I like really, really dislike being in sales. Which sort of goes to your point sort of initially, which is things have… there is a sales element to business development. It feels very, very different to me though, because selling ad space, for example, or selling a product versus selling your expertise: I feel very confident in my expertise. I did not have that and so it all feels very genuine because I'm just talking about what I like to do and what I do and what I think is interesting and what value that I truly believe I can add. Which I think is like what the best sales people do in other ways, right? Like they do it in… they don't just do it about selling, you know, "hire me to do something." So it doesn't feel that way. And but I… it’s interesting that you that you phrased it that way and that you sort of said it that way because it makes sense. You were… I mean, business development is sales in some way. I just never sort of thought about it like that.

Khurram Naik: And today, are there any principles you learned in business development… I imagine they had a fairly structured process or set of principles you used. Do you find yourself drawing on any of those? Was any of the things you learned in Google in that way beneficial to you today?

Hilary Gerzhoy: Yeah, well, I think like being systematic about how you're doing things. So thinking about: where do you get… where do you get your business from? Where and where do you get repeat business from? What are some of the maybe unexpected places that you get business? And really mapping that out and thinking about how to be targeted in that. Like that is… that’s what the job really was. And so I think that's a nice lens through which to think about business development now is really trying to be targeted in the way that I approach it because doing sort of what's effective. But also the things that are effective can surprise you, right? And the avenues that you think maybe wouldn't be worthwhile are incredibly worthwhile, and some of the avenues that you thought would be really worthwhile are not worthwhile. And trying to be objective about that. Because I think a lot of times lawyers… well, you gravitate towards what I think you enjoy doing and what comes naturally. I think those two things often are the same thing, but sometimes they can be different things. But you sort of want to do the thing that comes naturally, the thing that you enjoy doing or speak to the audience that is motivating to you in that way, for example. But some things don't lead to business and other things do. And and I think like where when it comes to what I do, there's a bunch of different pieces to this. There's developing sort of industry expertise, which is just useful in general. And so that's more marketing, right? But having the… so doing things like writing articles, which I love to do and I write a lot of. But do they lead directly to business? Not really. It’s much more indirect, right? It’s not… there have been a couple cases I've gotten that people have said, "I read… I read your stuff. I have an ethics issue." But if I did sort of pure time of writing articles to business leads, that's not the way to spend most of my time, but I really like to do it, so I continue to do it. But I think that's one of the takeaways that I had is being… having a systematic approach to it all.

Khurram Naik: Can you say some more about like what is systematic about your approach now? Is it scheduled? Is it… you are thinking about, you know, "Hey, I like writing, I like giving speeches, let me make sure I'm doing one of each a month." Like tell me what are the ways in which you are systematic.

Hilary Gerzhoy: So I've found that speaking is much, much more effective. And so I still write, but I write a lot less than I used to. And I've found that a lot of one-on-one conversations are really… can be very useful and and good as a way to develop business and and keep that going. And so being targeted in communications with people—like having sort of the people that I speak to regularly and staying in touch with them, that's another piece of it. But if I could sort of purely do just like what I think is interesting and fun to do, I probably would have more of the writing in terms of the ratio of what I do. But now it’s more of the speaking, more of the one-on-one meetings with people, lunches, coffees, that kind of thing.

Khurram Naik: To what extent are you repurposing the content of the things that you're writing for presentations, etc.?

Hilary Gerzhoy: Not really that much, which is I think a potential to do. I'm trying to do it more. What I have done with speaking is I've been… where I'm asked to speak about things. I haven't done a lot of like pitching, "Can I speak at this thing?" And so then I speak to whatever that audience wants. So there… it runs the gamut from, you know, law firms around the country to companies, industry associations—like just, you know, all over the place. And like what they… what they care about with respect to ethics and what they need to know. So a lot of times it’s things like, you know, "What are my malpractice risks as a law firm? How can I avoid them?" "How do I use AI effectively in my practice? What's available? What are the ethical potential… what are the potential ethics traps there?" "How do I navigate outside counsel guidelines?" So a lot of it is sort of answering those questions, whereas the stuff that I write about is all current events. So if something has happened in the news that implicates an ethics issue, and then I write about that because I think it’s interesting. And so a lot of that stuff is sort of not great for then turning into a talk because the audience… it could be interesting for the audience, but when people want to listen to me talk, it’s usually because they want something very practical, which is: "How do I do this thing consistent with the rules? What is my risk? How do I mitigate risk?" versus when I write it’s about sort of, "Here's this thing that's happened in the news and and why is it relevant? Why should we care about it? What does it mean for lawyers more broadly?"

Khurram Naik: And I think that's where, in watching you speak, that's where you really shine is in the being able to address questions off-the-cuff. And you know, there's any number of fact patterns that seem… that are familiar. Sometimes there's some edge cases like, "Hey, I'm not really familiar with it, but here's how I think about it." And so I think you do definitely have a good instinct for a concise, thoughtful take on how to mitigate the practicalities of what someone might be dealing with. I've observed you in the context of talking about ethical issues for partners in law firms and lateral moves. And so yeah, I think that is definitely a competitive advantage you have—is to be able to translate: here are the rules, and then here's the sources of ambiguity, and then what are some takeaways that you have. How did you hone that?

Hilary Gerzhoy: I've always loved speaking. I've always loved debate. I always loved debate. I was in starting in fifth grade, I was in the middle school debate club and and I never stopped. I didn't do any sports in high school because I just did debate as a sport, which I think is a sport, but you know, most people would beg to differ. And then in college, I actually coached middle school debate in Chicago to to kids who lived in on the south side. And I think it's a powerful skill. I think being able to speak in front of a group of people is… is very can be very useful and very powerful, and I enjoy doing it. And I think part of what I liked about debate is I liked the thinking on my feet piece of it. Like the most fun was the fact that you constantly had to adapt. It wasn't just sort of giving a speech, it was you have to anticipate what your opponent is going to say and respond to it in real time. And then that sort of within being a litigator, that happens in in all kinds of contexts where you have in real time to be able to articulate a response. And I found that that just was something that came more naturally to me. That wasn't as… there are things that… that was one of the categories that I felt came more naturally. And then when it comes, I think, to doing it in the context of of my job and what I do, because what I do all day every day is help lawyers, law firms, companies navigate the ethics rules and all things that go along with that, I have seen so many permutations of these problems. So, you know, as relevant to the the talks that you've heard me give about partner recruiting and and how it impacts firms, how it impacts the partners. I've seen this so many times that I've seen where where things fall apart or how you can mitigate risk or how you should think about it. And I think part of… and that's I think just incredibly useful to responding to folks' questions about how to do it—is like I've seen it and so this is what I think works and this is what I think doesn't work. I also think an important piece of this is what I'm doing with with my clients is giving them a roadmap and giving them a series of options. So here is what the framework that you need to think about and here are the potential risks and here's the ways to mitigate the risk. But here's the way to also think about what that risk is and the risk that you're willing to take. So there's different… people's risk profile is can be dramatically different. So I have clients who are willing to take much, much bigger risks and clients who are willing to take no risk at all, right? And so I think also being able to adapt to what your audience is interested in and giving them sort of the range of options so that they can make an informed decision about what they're going to do.

Khurram Naik: How do… do you think that clients tend to know what their risk profile is? Do you think risk-averse… I feel like risk-averse people tend to know they're risk-averse. Do you think people who think they're risk-seeking… it seems to me people who are risk… think they're risk-seeking are often mistaken about that, or can be mistaken about that, more than risk-averse people are mistaken about being risk-averse.

Hilary Gerzhoy: I think that's definitely true. So risk-averse people know they're risk-averse, right? And they will come to you and they will say, "I'm risk-averse, I don't want to do anything that's even close to being risky. Could get me in trouble, could get, you know, my current firm angry at me, I could get an angry email from the GC… like I don't want to do anything like that." People who have risk tolerance, I have almost never seen acknowledge that they have a greater risk tolerance. They don't… I don't think that lawyers ever want to ever really see themselves as as risk-takers. We follow the law, we're rule-followers, right? And we help other people follow… we make creative arguments about what the law is, but like our profession is rule-based. And so I think when I see that, it’s always… it’s interesting to me when people have taken huge risks and I'm like, "I just want to make sure that you know that what you did was a huge risk." Because a lot of times folks come to me after they've done things, right? So there's actually a… it’s not just "How… what do I do in anticipation of this decision that's going to implicate a bunch of ethics issues?" It's "I've done something already, I'm afraid of what the ramifications are. What are the ramifications? How do I get out of it? How do I navigate?" All of that. And so much… I’d say, you know, 95% of the time, people will come to me and say that they've done something, and I will be shocked at the way that they perceive what to me is an enormous risk. And sometimes it’s… it’s usually one of two things. It’s usually one, they don't know—like they don't actually… they weren't thinking in real time that this was such a big risk. They were… because they don't know the rules as well, they weren't sort of thinking about what the implications of the rules would be. So I think that's… that’s a decent category is like "I made a mistake, like I took a risk without really knowing it was a risk." And then I think the other category is "I took a risk but because my reason for doing it was so good, it doesn't really count as like me being a risk-taker," right? It's that the motivating reason was so… so top of mind for me that like I could sort of… I don't even see the choices that way anymore, right? It's like a no… "I have to do this." Right? There's a lot of people who I speak to who feel like they have to do things. And the truth is you don't, right? You have lots of choices about how to… how to do things, but they sort of have framed it such that when they have taken a risk, it was a necessity.

Khurram Naik: You know, this… this came… this came up for me recently because I, you know, I practice law, and so yes, you you're trained in following rules. And so now I'm a business owner, and so in many ways there's context switch you have to do where you feel like comfortable with using things like, "Hey, this I'm getting 80% of the returns for 20% of the effort in this way." And so yes, I could run down every single detail, every single comma, but it’s just… it’s just not a good spend on investment. So there's some things that I feel very comfortable making that switch where, you know, that was parts of the parts of the practice that chafed for me was that that what felt like an excessive attention to detail that just didn't really move the needle, right? So I feel very comfortable there. It’s interesting because, so I ran into… not a terribly obscure… a common tax issue that, you know, upon a read of a of an ordinance seemed to create some ambiguity. And so I talked to a tax lawyer about it recently who agreed, "Yes, there is ambiguity, and here's how to…" You know, and this lawyer just happened to have just run into this issue for an another similarly situated recruitment agency. And so it was very top of mind and she was able to speak to this in great detail. And it was interesting because like, I was in a position to make a risk assessment of whether I was comfortable with taking a risk here. And so part of it, some of the training you have to undo as a lawyer in this context—and I'd be curious to what extent you feel that equity partners have to go this analysis too where they're both a lawyer and then also a business owner—where you have to say to yourself, "Okay, yes, I could take a risk here." What I'm finding is that actually the analysis of a risk and taking a low-risk option can actually… on one hand I'm trying to train myself to say it’s okay to take risks, but actually another constant I'm finding is actually it's totally fine to take low-risk options because in any number of scenarios the low-risk option in this case—that’s my conclusion—the low-risk option here will involve the certainty of some small, relatively small payment and I'm okay with doing that because I don't have to think about that. What's most important to me and what's most scarce is my attention, and so I don't want to distract at all from my focus. But what… an instinct that I do have to unlearn is sometimes proving a point, like "Well, I'm a litigator, I know how to take a dispute." So that's the instinct to unwind in any number of cases. But it's interesting because I'm starting to discover very, very recently is that sometimes the low-risk option is just the best option because yes, you can prove a point and and make some new law maybe or something like that if you want to take that risk, but it's a distraction. So unless it's core to your business, core to your practice, you know, you don't have to do that. So I don't know if you… if that's some of what you've seen or advice that you've you've given that that's on point.

Hilary’s thesis that fear drives professional missteps is something Joe Ahmad has observed from the trial side — he told me that fear of loss prevents young lawyers from trying cases and being authentic.

Hilary Gerzhoy: I've definitely seen it, and it makes me think of two two primary instances where this comes up. The first is the equity partner category which you which you mentioned. And then the second—and I can talk about both of them—and the second category is focus—just putting people's attention back on like that what you said: you don't have to think about this anymore. If you take the riskier option, it’s going to be in the back of your mind constantly, right? You're going to wake up, you're going to be nervous about it, you're going to think, "Oh no, like what if, you know, somebody figures out that I did this thing I wasn't supposed to do?" And so for people that I talk to who are tempted to take the risk—because the temptation to take the risk is is usually from what I've seen born of two things. One, a fear that you're not going to keep business or continue to make money, or fear that you won't be equipped to continue to do your work. So like some people feel tempted to take proprietary documents with them when they go from one job to another job, right? Because they're afraid, "Oh, I've been trained up in in this, I know these templates, I know how this all operates and the reason I'm really good at my job is because I have all of this. I have all this material." Well, it’s firm proprietary material, it’s not your material, but there's a huge temptation to take it. Why is that temptation? Usually what I see is the temptation is not because people are being greedy or thinking "It's mine," it’s a combination of two things. It’s feeling like "I worked a lot on it," right? There's a piece of it, but a lot of it is fear-based. Like, "If I get to this other job and I don't have all the things I had at this other firm, I'm… I can't be successful." And that but you have to weigh that fear against the "Do you really want to be waking up in the middle of the night worried that the firm is going to know that you took documents that you're not allowed to take?" Like this… do you want that to hang over your head? Because it will continue to hang over your head. And a lot of folks are like, "You know what? That makes sense. Like it’s not worth it." And the other piece that I always say to people, and I'm sure you have a lot of experience with this, is if you're getting recruited to go to another great job, great firm, it’s not because you had templates at your old law firm. It’s because you're a really good lawyer. And what makes you a really good lawyer is yes, you had access to these resources, but it's all the skills that you've developed. And so like don't sell yourself short in thinking that you need all of these things to do to do your job and to be effective at your job. With respect to the equity… and that tends to be a much more junior person thing, right? So like a junior partner, somebody who's counsel, who's sort of just getting started and feels very unsteady in their position at a firm because they don't have a big book of business. And your power in Big Law is the size of the book of business that you have. It's your power and it's your autonomy. And if you don't have that, you're on shakier ground. And so that you see that happen much, much more frequently in the context of folks who are more junior. In the equity partner camp, it’s the risk-taking that comes up is talking to clients before you told the firm that you're going to leave, for example, right? Which is a breach of your fiduciary duty and you can't do it. And the reason that people do it is because they're afraid that the clients are not going to come with them. And that can come in a bunch of different ways. Like they're afraid, like "Maybe this client hates the law firm I'm potentially going to, and I have no way of knowing that they hate that law firm unless I test the waters and say, 'How do you feel about that law firm?'" "What about if… if I don't sort of set it up in motion, somebody else is going to swoop in? As soon as I give my notice, they're going to swoop in and take take that client from me." "I need to give assurances to the new firm that I'm bringing this client. How can I possibly bring… give… give them assurances?" Right? The target firms put a lot of pressure on candidates to make commitments about how much money they're going to bring in, honestly from the jump. And so how can… for a lot of people they're like, "Well, how can I truthfully say I have X as my book of business if I haven't talked to these clients and these clients haven't actually told me that this is portable work, that they're coming with me, right? So I… do I have to… I lie on my lateral partner questionnaire? Because I don't know. I'm sort of guessing. Like, what am I supposed to do there?" And so a lot of it is like they take a risk because it feels like it’s a necessity, right? Like "I can't answer these questions and make a move unless I have violated my ethical and fiduciary obligations." What I have seen and what I tell people is that I think 90% of clients fall into one of two buckets. They are either… they identify the lawyer as their lawyer, and it… that lawyer can go basically anywhere and they will come with the lawyer. Or they view they have loyalty to the firm. And and it doesn't… and they work with the lawyer and they think the lawyer's great, but the loyalty is really to the firm. I think most clients fall into the first category, but I think 90% of all clients are like easily bucketed into one or the other. And so and it's really that 10% in the middle where maybe if you talk to them first, maybe when the order in which you speak to them, maybe that matters. But 90% of your book is either like with you or not with you and it has nothing to do with the timing of when you say it, right? And if somebody from your existing firm talks to the client first, it’s not going to matter. And that's what I've seen over and over again. And so for people who sort of try to to take these risks and solicit the clients when they're not allowed to solicit the clients, there's not a lot of upside and there's a huge amount of downside risk. And I've represented lawyers in like arbitrations that ultimately result where firms will sue lawyers for leaving, for doing things like violating their solicitation… violating anti-solicitation provisions and it is… it's ugly, it is… it’s not a pleasant thing that anyone lawyer… any lawyer wants to be in because it’s literally your former colleagues coming up against you and like as witnesses, right? And like testifying against you like somebody that worked down the hall from you for 15 years. Your professional reputation is impugned. It stays with you. It… it takes an emotional… it’s not just money, it’s an emotional tax to do it. So and that's if… if the whole thing ends up in litigation. But like there's lots of stages before then that are incredibly anxiety-provoking. And so is it… is it ultimately worth it? I don't think it is when it’s not going to move the… it doesn't move the needle in my… in what I've seen.

Khurram Naik: For that 90% bucket, do you feel like lawyers tend to have… this is kind of similar to the question of like, "Do you know your own risk profile?" Do you think lawyers tend to know gut-level like, "Hey, like is a client really going to go with you?" My guess is most lawyers know, but like what do you think?

Hilary Gerzhoy: I think most lawyers know. I think most lawyers know. I think most lawyers when they talk to me can say like, "I can tell you that 90% right now." And then there's this 10% and I'm not really sure exactly what to do. And the question is, how important is that 10%? Right? Is it 10% of your total book of business? Or is it 10% of your clients, but they're the most important clients? And but I think a lot of it is lawyer… there are a wide range of personalities at play, but there… I speak to a lot of folks who are like, "I don't want to say that this is going to happen with certainty and that my compensation is tied to an expectation I am going to do X, Y, and Z unless I feel really confident that I can do X, Y, and Z. And because I am a risk-averse lawyer and because I have to, you know, dot my I’s and cross my T’s about everything, I can't be sure unless I… unless the client tells me, right?" And so "I want to be… feel confident that I'm giving a truthful answer and that my…" and then that I'm not setting expectations in a way that is not realistic. Both because I think people feel uncomfortable—like if, you know, if your target is to bring in a certain amount of money and you clearly can't do it, that's an awkward position to be in—but also to go down in compensation psychologically is very hard for people. So like you go in with this very like competitive compensation package and then the next year you make a lot less. And I think people just do a lot better with small incremental gains versus a big jump and then back down even though back down is still better than what you had before. It's hard for folks. I think that's what… when we talked a little bit about remote work, I think it comes up in remote work. Like taking away a benefit is a lot harder than if people just sort of like gradually got… okay, you can work from… If you told lawyers five years ago, "You could all work from home one day a week," people would be like, "That's amazing," right? Like that was a huge appeal of working for the government was that you could earn days to work at home. And I… we would talk about in private practice all the time that we were like, "Oh my God, government lawyers can work… like earn a day to work from home. That's so amazing." But then people get used to what they have and they get used to what they have really, really quickly. Like almost instantaneously is how fast it is. So then you cut compensation, you cut benefits, even if they're better off than they ever had been before, it hurts and people… and I think a lot of people want to avoid that.

Khurram Naik: I feel like we're really… this is such an interesting delve into psychology, professional psychology because like you just touched on this like loss aversion kind of principle. And I was about to ask you about… I think two things you've already identified as emotions or or emotional beliefs that are recurring are fear—so identified fear as a big one for the lawyer who's going to try to take the firm templates or whatever that they worked on. And then you also identified attention—you know, something I was talking about, something you're talking about is the importance of "Hey, like do you really want this as a distraction?" So I feel like we're starting to identify some of the fundamental underlying emotions or beliefs that are really govern… there's so many different kinds of ways you can challenge ethical rules or run afoul of a contractual provision. Do you think in terms of this this kind of this ontology of of of emotions? Like are there other fundamental emotions that you think of that that recur in the same way that we've already identified a few of?

Hilary’s description of BigLaw as a “greedy profession” — trading a huge portion of your life for high compensation — made me think of Patti Burris, who found a way through it. Billing over 2,400 hours, Patti maintained a 7:2:3:1 wellness ratio that protected her non-negotiables.

Hilary Gerzhoy: Absolutely. And I think so much of my job deals with people's emotions. Like it's a huge part of of conversations that I have. A disproportionate… like if I sort of think about other people's practice and their legal practice, I would imagine I have a really disproportionate number of conversations about how people feel about things. And I think that's honestly one way in which I have an advantage—is I think I'm good at talking to people about how they feel, and I think I can understand how people feel and I… can… what I have been told is that I that people feel comfortable talking to me about things that they don't necessarily feel comfortable talking to other people about. And getting to sort of the core of what's motivating you can be hugely helpful in thinking about the problem, right? Because the problem is framed by what you care about and what is… what your drivers are. I think another big driver, so I think fear is a big one. I think, you know, how you spend your time and energy. I think a sense of equity and justice is huge. And I think that is… so when people do things like, for example, you know, solicit clients when they can't solicit clients, or when they… they know they're making a lateral move and they stop billing their existing work—like they stop invoicing clients, they stop recording their billable time. That's a breach of your fiduciary duty, right? You're an employee for a law firm. You can't just stop billing the time that you spend. But they feel like they've been mistreated. And they feel like there has not been equity because other people have gotten paid more than they have and they deserve to get paid more, or other people have been treated better, gotten practice group chair, gotten whatever sort of highlight from the firm and they haven't and that was unfair and unjust and therefore they want to get some sort of revenge to feel like there's there's more equal footing, right? Like "I've been treated unfairly, therefore I can treat you unfairly." And I think that's a big motivator for for just human beings in general, right? Like it's even even if you don't care so much about the thing, the fact that you've been not treated equally irks people at a fundamental level. And you'd be surprised like how how small those things can be. Like to an outsider, they can be like, "Really? Like that? You're so upset about that?" But it's because like people have a visceral reaction to being treated to perceiving themselves to be treated unjustly. And part of like compensation structures—but it becomes so hard in that context because most law firm compensation structures are pretty black box. And so you don't really know, and I think a big reason that they are black boxes is because when they are more open systems, it lets everyone say like, "Wait, but my hours were this, my receivables were this, my, you know, all how is she getting more than I am?" And when it’s black box, you sort of take that piece away. But then what you introduce is sort of this sense of suspicion among everyone. Like this is what I I talk to lawyers about this all the time—is always feeling just a little unsure and a little bit like you have you got the raw end of the deal. Basically every lawyer I talk to like thinks that that's prop… something like that might be at play. In part because like the way that that the private practice of law operates is: Have you ever heard of the idea of a greedy profession? I think there was like a New York Times article about this a few years ago, and it listed a few greedy professions. The law was one, being a consultant was one—like a management consultant, you know, you like work for Bain or BCG and you travel five days a week—professions where there's people who you get people who have specialized skills. It usually takes a a lot of expensive education to get them to a position where they can participate in a greedy profession. It is highly… it is really well compensated, but it takes from you. It it demands from you. It is the profession is greedy in what it demands of the people who work for it. So you get to have this fancy job where you're doing really intellectual… intellectually stimulating work and you're making a ton of money. But in return, you're going to give us a huge portion of your life.

Khurram Naik: And I'll add to what you're saying is, in contrast to let's say you were a real estate agent and you sold a thousand homes in a year, there's much more ambiguity about the nature of your work product.

Hilary Gerzhoy: Absolutely. Yeah. I think that's absolutely right. Like you can do because in those professions too, you can do… it’s a little bit more "choose your own adventure" than it is in something like consult… management consulting. You know, there's a very specific path. This is what you're supposed to… and and the law is that way in a way that like very few other like very few professions are, right? Like you start in as an associate, you work as an associate for X number of years. Then at most firms you become counsel. Then if you become counsel you can become a non-equity partner. Then after non-equity partner, you become an equity partner. But even if you go before that, right? You start you do really well in college, then you go to a competitive law school, then you try to get a clerkship, right? Like there's this path that is laid out that is the the front getting in the front door, right? And that doesn't mean that people don't get in on the side doors and there's other ways to achieve that. But there is this sort of like "Here's how you do it to end up at the place that a lot of people want to end up." But there are sacrifices that are involved in that, right? Which is really that you're giving up a huge amount of your time. And so I think all of the… the reason I bring this up is because I think all lawyers—not all lawyers—I think a lot of lawyers who work in Big Law feel like they've given too much and that they sacrifice too much. And that and so and because of that, that money becomes such a huge piece of the puzzle for them—it’s an outsized piece of the puzzle because they feel like they've given the firm more than they should have. And I think that's part of the nature of of Big Law is that's the way it operates. And I mean, it’s not for no reason at all, right? It’s you have clients that are incredibly demanding, right? And the market is incre- is super competitive, right? Everybody's competing for a finite amount of work at a really high level, right? And so you have to be availability becomes incredibly important because if you are not available in that way, the client can find another law firm that is, right? And so why is it taking from you in that way? A lot of it is just the practical nature of who the clients are. This is client services, right? Client services are demanding. I think that's a piece of it. And then I think the other piece of it is, you know, mandatory billables, right? We have to you have to bill X amount. That's where I think where people get more frustrated and have sort of more bad reactions versus I think folks know like clients can be demanding, right? And I if I have to be available on my vacation, I have to be available on my my vacation. But it's where it feels arbitrary. So like the senior partner is insisting that I be available, but nothing's actually happening right now. That's when people start to to be motivated by to do things that maybe they otherwise wouldn't do.

Khurram Naik: There's there's a lot of interesting things you just talked about and there's a few jumping-off points. One jumping-off point is when you're initially, so you mentioned that you have really resonated with the emotional core of this and and helping people express and communicate and identify those emotional underpinnings and then using that to guide action. So one question I have is, was that part of the role apparent to you earlier on, or were you drawn to the work for some other reason?

Hilary Gerzhoy: It was not apparent to me before I started doing the work. I started… I had just done general general litigation, right? Doing and I did sort of probably half appellate stuff, half half district court work. And then some white-collar stuff, but mostly in the commercial space. And then I came to the firm I'm at now, and I started working with Tom Mason who had founded our practice group. And his his pitch was just "You like litigation, this is litigation for lawyers." And I did not appreciate initially how much it involved sort of thinking about the human being and not just the lawyer behind all of it. And and it also became much more apparent to me the more senior I got because now I have my own clients, right? And so when it… when you're working with somebody else's clients, there's always sort of there's a level in between, right? I'm doing the… I'm drafting the memos, I'm drafting the briefs, I am sometimes getting relayed what the client cares about and what the client wants, but I'm not the one having those phone calls as a junior person. But now, it's they're my clients, right? And so I'm talking to them and so I I sort of see it in a very different way. So it was not something that was obvious to me at the beginning, but it is definitely something that makes me love doing what I do because I find it very motivating and satisfying to try to help people figure out like "What's the right thing for you to do? What's going to make you feel like you came to the right answer?" And how do I solve your problem? That's the other piece is like litigation… this is one of the reasons I like the ethics work so much is litigation is adversarial. And so and that's draining for me, right? Like there's some people who just like the fight. I like the things that the the things that you do to be a litigator, like research, writing, oral advocacy. I hate the fight. So like the thing about debate that I loved was I liked thinking on my feet. I liked that that like it pushed me to be creative, but it’s not that I liked like "I'm going to fight someone." That is just I don't have that. That's not enjoyable to me. And with the ethics work, some of it is litigation, right? Like sometimes we've got to fight. We're we're, you know, in a disciplinary proceeding, it’s a malpractice suit—like that's what we got to do. But a big chunk of it is: I can solve the problem. And we can come up with a solution, and there's like so little in the world of litigation that actually falls within the "Let me come up with a solution" category that there's something really nice about that.

Khurram Naik: It also seems to me that what you're helping people do is make decisions that are, I think, at their core everyone… most people have an ethical compass, and sometimes it gets compromised and then but then I think people regret that and you can they can go pretty far down that route but then and just of just consistently makes decisions in life that compromise some ethical value they have. But I think at their core people want to help be guided to ethical action. And so I imagine it’s a gratifying part of your process. What what's the principle you use? So let's say somebody communicated to you, "Hey, I'm operating out of fear," "Hey, I'm operating out of out of feeling unjust." Like, how do you then say, "Hey, I get you're feeling those things. How do you use those as like, now I understand that's your framing, how do you get them back on making decisions that are consistent with their ethical compass and so they have autonomy, agency to that… that is the motivation, not like the fear of the rule and getting, you know, the stick" or whatever?

Hilary Gerzhoy: Yeah, I think it’s it’s understanding what the… what the risk is of doing the wrong thing, not in terms of the stick of getting disciplined, but that you are taking on this risk and you don't need to be, right? And I think it’s like so people understanding that the fear is they feel fear that is not proportional to what the actual danger is. And that and and I think that can be relieving for people to sort of understand to put everything into context. And I think the other thing is for people to know that every… that other people feel that way too. Because I talk to lawyers all day, and I talk to lawyers who are similarly situated to one another—and and that means like I've talked to lawyers of all, like solo practitioners to working in Am Law 5 firms to government lawyers, public interest lawyers—like but I've talked to enough of them that I can say to people like, "I know you feel this way. You… this is not unusual, right? A lot of other people in your position feel this way." And I think that is hugely satisfying to people because that's just like human nature, right? When you feel like you're not alone. One of the… I had an interesting call with a client the other day where because I've just seen how this works and I see how the market operates, I… true… he’s at his current firm thinking about moving, thinking about all the things that are associated with that. And what I said, like he explained his compensation to me. And I said like, "You… your ratio of hours toward hours versus what you take home, your origination, your hours, what you take home is a better deal than I've ever seen anybody get." And that like just fundamentally changed the way he thought about his current job. And nothing else changed, right? Nothing else… he worked with the same people, same clients, same type of work, same hours, all that. But knowing that it was a good deal in comparison to others was satisfying to him and made him feel a lot better. And I think the other piece of that is knowing that like other people feel that they've been treated unjustly in this circumstance or that I honestly think that nobody ever feels like it’s completely fair how compensation happens, for example. That is also I think very helpful for folks.

Khurram Naik: You know, you spend a lot of time thinking about ethical rules and I imagine a lot of that: what percentage of the ethical rules that you're thinking about are like the Rules of Professional Conduct?

Hilary Gerzhoy: Oh no, so that's it. That's what I'm thinking is the Rules of Professional Conduct. So that's the ethical restrictions—like it's rare… it’s that the lens through which I'm seeing things. So like when I get hired, it’s because lawyers have questions about what they can do, they've been accused of doing something under the ethics rules that is improper. When with any malpractice suit, ethics stuff comes into play because the the central argument in a malpractice suit is that you fell below the standard of care, which is you didn't zealously and diligently represent me, which is implicates all the ethics rules. Um, so it's always thinking… it’s either litigating with respect to the ethics rules or giving advice with respect to the ethics rules or defending somebody who's in a disciplinary proceeding, for example, which is purely about the ethics rules. There's no monetary sanctions, for example, in a disciplinary proceeding versus a malpractice suit is obviously done for monetary damages.

Khurram Naik: You know, I haven't given a death of thought to the Rules of Professional Conduct since, you know, taking the MPRE, and I imagine that's true for any number of lawyers. You, especially if you're at a bigger firm—like, "Hey, we kind of have like largely guidelines for how to progress here and how we do our work and there's guard rails." And so just there's plenty of ways to not be thinking about those issues. Of course, I think there's plenty of ways to run afoul of them in ways you don't realize—like "Hey, I'll just download this material from, you know, from the firm and, you know, what's the difference?" But so are there… is I'm curious how you think about this. Do you feel that there are… um… I can imagine someone, let's say a trial lawyer, might have an opinion that "Hey, there's underrated rules of evidence" or "underrated hearsay exceptions" or something like that that, you know, if you're just thinking about them all the time like "Here's… here's something in your repertoire that you may not really appreciate." Do you feel there are underrated or underappreciated Rules of Professional Conduct that affect lawyers more than they realize?

Hilary chose speaking over writing as her primary business development channel — and so did Jaimie Nawaday, who built Disrupting Drinking as a speaking venture rather than writing a book. Both found that talks are faster to iterate on and create deeper audience connection.

Hilary Gerzhoy: Yeah, I think there's there's different ways to think about that question. One is like: Where do people run into trouble? And if it was top of mind, they wouldn't run into trouble. I think that's one avenue. And then I think another avenue is: What do the Rules of Professional Conduct say about X such that I could do X more and then be better at my job, right? So not that the risk is that I don't do it and I get in trouble, but I could do it more. With respect to like where people get into trouble, the… so where people get into trouble in the disciplinary process is extremely different from where people get into trouble in the malpractice world. Um, so disciplinary proceedings are about… anybody can file a bar complaint, and disciplinary counsel can can institute an investigation on its own based on anything, right? Like they can read an article in the New York Times that talks about a lawyer doing something that seems shady and they institute an investigation. They've subpoena power. It much… it really mirrors the sort of criminal justice system a lot more than it does civil litigation. I mean, like there's a lot of due process, all of that. But what do lawyers get in trouble for? I mean, disproportionately small firms and solos get in trouble. Why? Because client money is a big concern, right? It’s a big concern of the bar of disciplinary counsel for good reason, right? We don't want lawyers stealing client money. But the trust accounting rules—the rules that govern like how you deal with client money—no lawyer at any big firm has any idea, right? Like they don't… do they even know what an IOLTA account is? Like why would you because you're not touching client money. You maybe are the one sending out an invoice, but that's it. Um, and so you sort of have the the freedom to not care about it because there's a whole infrastructure that does care about it and that is tasked with doing it as a full-time. But if you're solo or a small firm, you're absolutely dealing with client money and there are so many opportunities to make mistakes in this process. So I'm not talking about the client who like intentionally steals from there… the lawyer who intentionally steals from their client. I basically never see that is the truth. It’s the lawyer who made a mistake in the process. Either… so in in DC, for example, the rule—it’s 1.15—is incredibly draconian. If you commingle any client money with your money—with the firm operating account money—even if the client doesn't lose a dollar, it’s a presumptive six-month suspension. And that's huge, right? Like what does a presumptive six-month suspension do? So you made… you truly made a good faith mistake, right? You used the wrong checkbook and we are presuming six… six-month suspension. So that's one aspect—like if I ever… when I talk to small firms and solos about what to do, I always say like, "Make sure that that is as perfect as possibly can be because that's something that you're going to run into trouble with." In terms of an under… where people where lawyers I find don't don't appreciate what the rules say, it comes client confidentiality. So Rule 1.6 is what governs client confidentiality and it is much, much broader than attorney-client privilege. So lawyers all know attorney-client privilege. They all think about attorney-client privilege and they think about work product privilege, right? Um, but client confidentiality is any information that's learned in the course of the representation that a client doesn't want you telling people. And it could be… and it doesn't have to be learned from the client, right? It’s in the course of the representation. It could be public information. It could be the fact that you even represent the client. So like if somebody could go on Pacer and see that you represent a client, if the client doesn't want the world knowing, that's client confidential. And so a lot of… of sort of ethical issues that happen is because lawyers have revealed information without appreciating that confidentiality is much broader than attorney-client privileged information. Um, with respect to like sort of tools in one's toolkit that can be used more, because that was your question about sort of like, you know, evidence: I think so 1.4 is your communication obligation. You basically have an obligation to keep clients reasonably informed about matters. The key one that everyone always thinks about is like if there's a plea… if there's a plea offer, you got to tell the client there's a plea offer, right? Or like if you're in some kind of negotiation and there's a counter-offer, you got to tell the client, right? You can't just say no without talking to the client. But I think so many problems could be avoided for lawyers if they embraced that obligation more um consistently with what it actually says, which which is keeping clients reasonably informed. When clients get angry, a lot of times they get angry because they don't know what's happening and they don't know what's happening in real time. And so simply just like giving them a little bit of information as things go on can actually avoid a whole host of problems down the road. So like a two-sentence email can avoid a lot of issues. And if that’s sort of regularly part of your practice is keeping clients updated and informed. The other thing is when you make a mistake, and that's the hardest. And that's the hardest, I think for particularly for lawyers in Big Law with all the credentials and all the fancy things. Every person makes mistakes. We are all fallible. We make mistakes every day. But it becomes… when the stakes are really high because there's a lot of money on the line, because you are making a lot of money, because um getting to that position took… took a lot of money, right? You had to spend a lot of money to get educated to get there. Making a mistake and the human desire to make it go away is very, very powerful. To not tell other people that you've made a mistake, to figure out if you can fix it before anyone finds out. That piece, and like creating a work atmosphere where people feel comfortable to say they've made a mistake, another area where you can avoid a ton of problems. Because you haven't… if you make a mistake and it’s critical to the matter in some way, even if you fix it, you still have to tell the client about it. And clients can be… some clients can be unforgiving, but a lot of clients are… you know, can understand that people make mistakes. But I think that's a really hard one, and I've seen it be harder sort of the the fancier you you are and the more you have the all the fancy things, the harder it is for folks to say, "I made a mistake."

Khurram Naik: Are there any instances of with… with both of these rules with respect to any of them, where you feel that people are unnecessarily taking obligations that don't actually exist, where people are making it harder for themselves?

Hilary Gerzhoy: Oh, well so that's the sort of the opposite of the rule the 1.4 issue is some lawyers feel like they have to tell their clients every… they have to be responsive all the time. That's… that’s a way in which I think the practice of law becomes super greedy. If and lawyers—and it will be as greedy as lawyers let it be—because particularly there are clients out there that do not respect the time of their lawyers, right? They think, "I'm paying you a lot of money and therefore you are perpetually available to me at any given time." Nothing actually requires you to do that, right? And so nothing requires you to be… being responsive to a client does not mean being available all the time. And I think setting boundaries a lot of the time is respected and you can… I think lawyers have more freedom to set more boundaries with their clients than they often think they do. Which again, I think is a lot of the fear motivator, because they're afraid, "Well, if I'm not responsive all the time, there's somebody, you know, there's another law firm down the street, they'll be responsive at… at all hours." Um, but if you're good at what you do, like having confidence in that and saying like, "I'm not… you know, I see that you emailed me on a Saturday. I'm going to email you back on Monday morning," unless it’s truly urgent. And the category of things in the law that are truly urgent is very small. And like recognizing that it’s actually very small. I think it’s much easier said than done in general, but it’s also much easier for those who have the direct client relationship. Where it becomes really hard is if you don't have the direct client relationship and you're working for other lawyers, then like what your boss says is what your you… your boss is really the client that you're thinking about is the person that you work for at the firm. And if they have unrealistic expectations and demands, setting boundaries can be really hard. But you see the next… you know, the next generation is doing that a lot more. Um, but I I wonder what the… you hear I hear all the time from senior lawyers that they're frustrated with that generation because for them, like you had to be available all the time. That was just the nature of working in Big Law—like that's what you signed up for. How come they don't get it? And how come they don't want to do that? And I think they just have they're different values and they're different priorities that are placed on things. But that is one area in which I feel like lawyers feel they have to be responsive to to a degree that nothing requires them to be, and that they probably could set more guard rails and be happier as a result.

Khurram Naik: Yeah, I love that. What… what Rule of Professional Conduct would you change?

Hilary Gerzhoy: Oh, the one… the trust accounting rules, for sure. So I'm uh the Vice Chair of the DC Rules Committee, so that's the committee that proposes changes to the Rules of Professional Conduct that then go to the DC Court of Appeals. Um, and that was a proposal and there's been a lot of pushback um on it. But I think it’s incredibly important because I think you do not want to have penalties… the penalty has to fit what the crime is and the severity of the crime, right? And when somebody makes a mistake and nobody's hurt, having a presumptive six-month suspension, that can destroy somebody's career. Like if you're a litigator, every time you pro hac into every into any court, you have to say if you've been disciplined before. And there are lots of courts out there that will not let people pro hac in if they've ever been subject to discipline. It it is public—it’s public record—like at the the Washington Lawyer magazine and every every jurisdiction has their magazine, it has a list of everybody who's gotten disciplined. Um, it’s out there, right? It’s a… has huge career ramifications. And if it was really a a mistake that was not because you were being reckless, but was just because you're a human being who made a mistake and nobody was hurt, I do not think it is appropriate that we have a presumptive six-month suspension.

Khurram Naik: What's rule number two? Rule number two that you'd change.

Hilary Gerzhoy: Well, I don't know that I'd change it, it’s just it’s a really hard one to navigate, which is 8.3—which is your obligation to report when other people do things that violate the rules. That's a really, really tough one for people. Um, and I don't know what the answer is. And I think that the rules have… I think where we have landed is is sort of the best you can get, but it’s not very satisfying because it’s when somebody has done something that calls into question their fitness to practice law. What does that mean? That means very different things to different people, right? So like I was… so I teach legal ethics to professional responsibility at Georgetown. Um, and yes, my class was yesterday or two days ago. Um, and we were talking about reporting obligations and and somebody said, "Well, if you know that a lawyer is like consistently unfaithful, right? And cheating on his wife and cheating on his wife with tons of different people. Like doesn't that mean he's like not a trustworthy guy? Shouldn't I report him?" Right? And I mean, that's a hard question, right? I think the answer is no, that doesn't trigger a reporting obligation, but I could see why you might think that. Um, or, you know, somebody has a drinking problem, for example. Do I report somebody who has a drinking problem? What are the ramifications of reporting somebody who has a drinking problem? Um, the thing about 8.3 too is the reason that it’s sort of it’s hard to navigate—it’s also really, really hard to discipline people as a result for violating it. So it becomes a little bit toothless because you see basically no prosecutions for like, "Oh, you knew that he was forging documents and you didn't report him to the bar." That fact pattern comes up basically never. So that's a hard one for for people to figure out—like "When do I actually have to do this?" is… can become a very tricky question.

Khurram Naik: I'm curious in… you know, you see successful partners and you you see an interesting cross-section of their circumstances and and get really gritty into finances and that kind of stuff, and so you see patterns and commonalities. I'm curious apart from working hard and being great with relationships and thinking in terms of business, apart from those qualities that somebody could possess in in in as a as a rainmaker, what are commonalities you've observed among various successful lawyers that… and let me qualify as say um not just ones who are successful monetarily, but ones you think big picture are good lawyers, good ethical compass, you know, just overall like good people like who are very successful. Like what are commonalities that you're seeing among those people?

Hilary Gerzhoy: Note, I would I think of two categories that go to each each of those things, because I think that there they're two different answers. I think for somebody who's successful in being a rainmaker and successful at what they do and has a big book of business and is well-regarded, one quality other than the qualities that you mentioned, I think is confidence. And or at least projecting confidence. Um, because you meet a lot of people who actually are are deeply insecure, but they project confidence. Because the thing is that clients are hiring… they want to feel like they've hired somebody who's going to protect them, right? In whatever way that is, right? If you're in a transaction, if you're a personal injury lawyer, if you are um doing, you know, a private equity deal, right? You just clients want to feel like their lawyer knows what's… knows what's happening, knows what's going on, is going to see problems before they happen and is going to protect them. And so if you give off that just energy in life, that I've seen that as a very, very consistent thing with the people that I talk to who have very successful law practices is they sort of give off this air of confidence, confidence, like self-assuredness and calm. Like a calm energy about… because it’s sort of like a "I got this" vibe, right? I think that's one piece. Now with respect to like what sort of sets people up for being ethical um and being sort of compliant with the rules and staying on the right side of things, um I think thinking about the client is the most important thing. The lawyers who think about the client first because, as I said, like we're a client services profession and I think sometimes lawyers don't think about that in quite the way that that is contemplated by the Rules of Professional Conduct, which is all of this is designed to have the public have faith that lawyers are held to a certain standard. And so when a lawyer says something or does something that we can have trust in them, right? Like that a lawyer's not going to get in front of a court and lie. That a lawyer when they're when you're interacting and negotiating with a lawyer, that they're going to be truthful in those negotiations. It's sort of the… there's lots of jokes about lawyers being liars, but the way that the profession actually looks at it is because you occupy a position of power and therefore there are certain restrictions that are put on you and certain expectations. And I think the lawyers who think about their role as being an advocate for their client first don't fall into so many of these traps. Because if you're focused on what's in the client's best interest, you're not going to… you're not going to make a mistake that's going to be a mistake that amounts to a violation of the rules. You might make a mistake because we make mistakes as human beings and you might get sued for malpractice, uh but lots of folks can get sued for malpractice when they didn't commit malpractice. Uh, but you're going to stay on the right side of things if that's the perspective that you occupy.

Khurram Naik: That's interesting. I wonder how you'd also consider scenarios where there's any clients who don't have full appreciation for ethical conduct or um and then also aren't repeat players in court or or otherwise in the practice of law, where there's scenarios where lawyers have to challenge their clients or or or decline representation as as necessary, where clients are expecting… saying, "Hey, like this is fine," then they expect and the lawyer's saying, "Hey, like I know that that's a departure from what's right." So I don't know how often you run to observe that as a pattern. Because I totally understand what you're saying with like having a client-centric focus and that is a good North Star for saying, "Hey, am I doing the right thing here? Am I just looking out for myself or looking out for the client?" It seems to me there's sometimes situations where the inverse is is the most ethical path and and so that's also a tool mindset that lawyers have to keep in mind too is their reputation, the firm's reputation, and and the profession's reputation. And so um I wonder about that.

Hilary’s discussion of government lawyers facing ethical dilemmas in the current political moment connects to my conversation with Judge Vince Chhabria about public service as the north star of a legal career.

Hilary Gerzhoy: Absolutely. Yeah, I think I mean it’s absolutely true. Um, and I think it can come up in all kinds of contexts. But one way that I'm seeing it happen now is politically. And lawyers who are involved in in politics um and with this administration and being pressured to do things that they know are unethical. So I I have a lot of clients that are government lawyers, uh recent recently departed government lawyers, currently government lawyers that that may or may not be government lawyers for very long, and a big chunk of of the conversations that I'm having are: First of all, the general counsels from my agency have been fired, there's no general counsel to to talk to, so I need to hire an outside ethics lawyer. And I am being asked to do something that I don't think is right. What do I do? And the answer is for every client representation: if you are being asked to do something that violates your ethical obligations, the answer is withdrawal. You have to withdraw from the representation. Now, first you try to persuade your client to not do that thing, right? And but if your client insists on a course of action that requires that you violate your ethical obligations, you have to withdraw from the representation. And I think that is easier in certain circumstances and harder in others. Um, but I would imagine that there are plenty of lawyers right now who are working in the administration who feel deeply conflicted. And I think there's probably plenty that don't feel conflicted at all. Um, there are plenty that were there and just, you know, immediately, you know, resigned. But I think that there are lawyers who feel deeply conflicted about what to do, um who their client is too, right? When it’s the government, that's also like the government when you when you work for the government, the client is not the president. The client is the head of the agency is the agency that you work for, right? Like the Justice Department. Uh, so what is in the best interest of the Justice Department? Um, but I think that that is sort of a has come to the forefront because of where we are in history, um in a way that it sort of never… I don't think it has before.

Khurram Naik: Hmm. Can you give us a breakdown… I we haven't talked about the big picture breakdown of your practice to help people understand the context of of the mixture work that you have.

Hilary Gerzhoy: Yeah. So I do um a big chunk of my practice is serving as outside general counsel, um which means that I get hired by firms of all sizes—from solo firms, small firms that don't have a dedicated general counsel to basically be that person for them. Um, or get hired by big law firms that have just sort of a dicey weird ethics question that needs somebody to do a deep dive. A lot of times that goes to things that deal with conflicts of interest because those are… that can be really hard to to navigate, um and they can get particularly when there's lots of um lots of clients with competing interests with where there's overlap, there's subsidiaries, affiliates, there's outside counsel guidelines, there's lots of things to navigate sort of what the answer is there. Um, so I do a lot of outside general counsel work that deals with with that and also with just managing clients—like "Looks like there's going to be a fee dispute. What do we do here?" And then I do the litigation aspect of it, which I think of in two categories, which is the malpractice litigation and then also litigation with respect to the disciplinary conduct. So representing lawyers and firms that have been accused of violation of the Rules of Professional Conduct in that whole process, which results in… it’s an investigation and then if it if you ultimately don't get it dismissed or have negotiated discipline, which is sort of like a plea deal, um then it goes to a trial and then it can and then it goes to an appeal. And so litigating that those cases. Um, so that's like the combination. And then within the sort of general counsel stuff, a lot of it is just like one-off ethics things that lawyers are dealing with. So like the context in which we met, which is lawyers who are making lateral moves, there's just a lot of ethics issues that come up in that. And so some people wanting guidance about "How do I… how do I do this? What tell me what I don't know what I don't know." Um, "I took professional responsibility 30 years ago" or even "I didn't ever take professional responsibility because 30 years ago we didn't even do that." Um, "and I basically remember none of it other than 'don't steal from your clients.' So like tell me here what I need to be thinking about."

Khurram Naik: So in your capacity, you see lots of things that work and lots of things that don't work, and I wonder if you think of your work the same way that I do. So, you know, something that I've come to appreciate in my role as a in a recruiting agency is we see recruiting practice in lots of firms. We see how lawyers think in terms of making moves in lots of instances. And so that that helps inform us in a couple tangible ways. So it comes to things like agreements. So things like a recruiting agreement, there's terms in there that I've come to have an appreciation for, there's market terms that you can kind of understand like "Hey, across firms there's maybe variations in some ways on some of these terms, but there's a a abstraction away across these firms of the market terms." And so part of what I do is guide firms on "Hey, what is market terms? You may not appreciate what are market terms. Even really large law firms may not have an appreciation for market terms." But more fundamentally, I think what's really helpful in my capacity explain why these are market terms. What is it that is beneficial to the firm for using market terms? And um and that what benefits a firm is not zero-sum to what benefits the recruiter, not zero-sum to what benefits the candidate. What do you mean by market terms? Uh, terms of say like how much recruiters are compensated, the structure of their compensation, payment terms, things like guarantees for how long, you know, that a lawyer is going to be at a firm. There's those I think are the three most important terms you might find in a recruiting agreement. And that would be the recruiting agreement between the law—like a law firm who's hiring you to be their dedicated recruiter to place a place a certain like "We need somebody for this role, go find them." Yes, that's right. Yep. Okay. And so my question was again… I'm curious so I'm making the observation that what what I am finding is that's the key part of what I think is a lot of the value that I bring is to explain: A, here are market processes, so apart from this tangible recruiting agreement, generally processes for firms have a goal: bring in the best talent. Okay, here's what I’ve observed are the best processes to do that, and some of it is reducible to the mechanics of the terms in an agreement and showing, "Hey, here's why there's there's standard process across firms and here's the benefit to you to comporting to these market terms." And the benefit to you is not zero-sum to the benefit to the recruiter to the lawyer. Okay. I'm curious if you see an analog in your work where you're able to observe patterns across law firms in in and how they structure things like partnership agreements or in terms of how equity partnership is structured—is it lockstep, modified lockstep, etc.? And I'm curious if you have takes on "Hey, like what are fair market terms in partnership groups, what are fair market terms in in law firms that is most effective for for structuring partnerships?"

Hilary Gerzhoy: Yeah, well, so I I think it’s a great question and I think it runs the gamut. I think the what has changed dramatically in just the last like five to eight years is this new class of non-equity partners. Because what it was for so long is partnership was partnership, as in you owned part of the law firm. And so that came with a lot of huge benefits, which is like we all when the firm is doing really well, we all do really well. There's like general buy-in to the success of the firm. Um, and it makes it makes people feel like they're part of a collective and that they have pride in the institution, right? And that like a win for someone else is a win for them too. It’s not a zero-sum game. It’s a we all sort of share in the upside. And then I think now that almost every firm, right? I don't think there's that many Am Law 100 firms left that don't have a non-equity tier. I think that has really changed the way that people who join the partnership sort of feel. It… you become a partner, you're sort of a partner in name only because you don't actually own… you don't actually have, you know, you don't get a benefit from the upside that's a direct benefit of having equity in the firm. Um, and in a lot of ways it it feels to folks kind of like a trap because you are now the only… the only path to becoming an equity partner is to generate a book. But to be sort of viewed as in good standing at the firm, you have to continue to bill at a certain level that makes it really, really hard to generate a book unless you want to like never sleep, right? Like doing business development takes a lot of time and it’s not as though like you just get this whole chunk of time that everyone's like, "Okay, great, you're fine, you're doing business development," right? You're at a at a hugely profitable company, right? If we think about law firms as companies, you're at a hugely profitable company that expects that everybody's contributing. And so the way out for a lot of people becomes… like the way to like the thing that gives you more freedom, which is being an equity partner, feels kind of impossible in a way that it didn't before, right? Like it would be you did your seven or eight years, you did superlative work, now you share in the equity. And and that means that you feel differently about… you don't feel this rush to generate your own business. And if you do, great, but there's plenty of folks out there that don't that are also equity partners and also feel valued. So I think that's a big change that has made it harder for people who are sort of coming through the ranks to feel valued. The other piece to like what I see where there's more harmony among the partnership is more transparency. More transparency about how compensation works. And every and firms do it all they all do it differently in terms of how things are um how factors are weighed in terms of how you get equity. But I think everyone understanding what the process is and having a process, right? Not and making it so that there is transparency not just about what the outcome is, but what the inputs are. Because then people feel like they can change their priorities, right? And so I think one way in which people feel unfairly treated is: it’s a black box compensation structure, the firm says that they care a lot about time that you spend devoted to the firm, devoted to mentoring associates, serving on committees, but nobody ever feels like that’s tied into their compensation. They feel like they're supposed to do it and it's valuable, but it’s not tied to their compensation. And "I think the Jimmy down the hall, he I know he doesn't do any of it and I know he makes more money than me." That so like knowing what truly what the inputs are and the firm articulating what those inputs are and then having transparency around it, I think that's a big driver. Um, I think not having billable hour requirements fundamentally changes a law firm in ways that I ultimately think are so much better for clients too. Because when you have an arbitrary requirement, it makes people feel it it incentivizes people to do things that we do not want to incentivize lawyers to do. Which is to to maybe one lie, right? Say they're they're spending time doing something that they're not, or more often just being inefficient, right? And take because I have to get to this number and if I have to get to this number like "All right, I’ll read that deposition transcript again." That's not in the client's best interest. And so it should be that you do the work that’s needed to get the result for the client and do the A+ product, right? But like once you get there, stop. And when you have the billable requirements, it makes people feel like that's not possible. Because you're always sort of afraid for like what next week looks like. "Well, maybe everything drops off next week, so I got to like keep it up," right? Or in any given moment, like "I've been slow for this week, what does that mean for the future?" And that like creates a sense of panic and urgency that is makes people feel terrible, one, and ultimately I don't think is good for for for lawyers generally. So I think firms I've seen where there really is no requirement um and they but your compensation is tied to your contribution to the firm in a way that that's articulated to you. So your contribution for some firms is just purely what you originate, right? And that can actually make people feel quite happy because they know if I if I bring in X, I will make Y, period end of story, right? That can actually just be very satisfying to people. Or there's other factors, but I know what those other factors are and they feel in my control to some extent. Versus a billable hour requirement for a lot of people does not feel like it's in their control if they're not generating their own work.

Khurram Naik: And then in terms of the structure of equity partnership—in terms of things like lockstep or all the variations there are—do you have any point of view on one um one format that is more conducive to success holistically of the law firm?

Hilary Gerzhoy: I think lockstep works really well when everyone feels like they're they're sort of bought in, right? Like the when when lockstep doesn't work is when you feel like other people you're working harder than everyone else, right? Uh, and you're sort of pulling and you're not making a differential salary to compensate you for that fact. But when it is lockstep and everyone is a hard worker and you feel like your peers and those like in lockstep with you are pulling their weight, I think it works incredibly well because what it does is it basically gives people more runway to actually develop their practice in a way that’s like more long-term successful for them, right? So like you know you're going to this is what the compensation is going to be for these years and then you can decide how you want to spend your time um in terms of how you want to develop business, what expertise you want, uh what relationships with particular clients are going to be really important for you to be take take the lead on—that kind of thing. So I think it works it works really well until it doesn't work, until somebody feels like they they got the raw end of the deal. Um, but a lot of firms are getting rid of lock… I mean, there's very few firms left now that are really doing true lockstep equity. Lockstep for I mean it’s for associates it’s the market is the market, right? And it’s there's some deviation but not very much. And there's actually like incredible transparency about that in the way that in like a lot of professions there's not. Like you can literally look up: "What does a 7th year associate make at an Am Law 100 firm?" And like you will find out. Like I can't I couldn't look up like "Random Fortune 500 company, what does like somebody who's worked there for seven years make?" There there could be like an enormous range, right? But so there's something very strange about going from a place a structure where there's complete transparency and everyone makes the exact same amount of money other than bonuses, which are as a as a percentage a pretty small percentage of your sort of ultimate compensation in terms of differences um to a system where you have no idea what anybody else is making. Um, and and often what like the basis is for what you're making. Because a lot of times with firms too, the bonuses it like if you hit the hours target, then you get the full bonus. And the full bonus is X. But even with the partner like with the equity partner situation, it’s not unless it’s really a you get a percentage of what you bring in, then you sort of have no idea what I worked this amount of hours, this is how much I billed, and like I don't know what the compensation committee's going to tell me I made. That's where most people live, and I think it's not super pleasant. But there are things with… but there are reasons why firms do not want transparency um because it gives them a lot more power to make decisions.

Khurram Naik: And you mentioned, you know, I've seen you previously speak about partnership agreements and some of the somewhat punitive terms that can be in there that don't really come up until they come up, kind of like what you're just saying. And do you think upstream there's any issues? I mean, like what does it speak to something else about the firm—the firms that have these kinds of terms? You know, it’s probably not these these firms that have these other high-quality aspects of of harmony among partners uh even if there's differences in in terms of work product and compensation. Can you speak to the impact of a fair partnership agreement and what are some of the terms you think should be in a fair partnership agreement?

Hilary Gerzhoy: So the vast majority of partners I think don't know what their partnership agreements say. Because when you are offered to join the partnership, the answer is yes. And it’s sort of "Whatever you want me to sign, I'm going to sign it." And partnership agreements can be hundreds of pages long. Um, so I don't think that they impact the culture in anybody's lived experience at the firm until they want to leave. And I don't and in basically any way at all. So like a a really unfairly drafted partnership agreement that has a lot of punitive terms I don't think impacts somebody's day-to-day existence basically at all until the moment that they leave. And so if they never leave, they spend their, you know, entire career at a firm that the firm has a bunch of provisions in a partnership agreement that that would if they knew about them would would be unfair, they have they don't have any ramifications on their existence. The firms that have and like what are the punitive things that we're talking about? One of them the one of the most punitive that I've seen is that your capital contribution can be used to count against your accounts receivable. So if clients haven't paid, that the amount that they have not paid can be deducted from your capital contribution. Capital contributions are supposed to be money that you give the firm for a period of time up until the time that you leave so that the firm can stay afloat and there's not cash flow issues, right? And almost every partnership agreement has a payback period, just because partnerships don't want to be in a position that say 50 lawyers leave and then all of a sudden they can't pay their lease or they can't pay their staff. Um, but there's a payback period, right? But the idea is that you get your capital contribution back. It’s not money that you are giving it’s not a donation. Um, but with firms—and I've seen this, and it’s not super common, but I've seen it a few times—where "If your clients don't pay, we're going to deduct it from your capital contribution." I think that because… and the reason it’s so unfair is because as any practicing lawyer knows, you do not have control over whether or not your client pays. There are some clients that just do not pay. Um, and what's your recourse? Your recourse is to initia- to sue them um to try to collect fees. What's the consequence of that? You will get sued for malpractice. Basically every time I've see- so many of the malpractice cases I see are because you tried to collect on unpaid fees. Because what does a client… a client who’s not going to pay you in the first instance, that's obviously not a client who's being fully, you know, fair. Pro- honest about things. Fair, right? Like you've performed a service, you need to get paid. And if somebody thinks, "Ah, they performed a service but I'm not going to pay them," they may might also be disproportionately the type of person that says, "Well, I'm going to then sue you so that you go away." Um, and so all of that is to say that we have very little control as lawyers over whether or not our clients pay, uh and very little power over what to do if they don't. So that's a that's a harsh measure. But I think the answer to your question is that for in most circumstances, I don't think it really impacts people's day-to-day existence if they have if there are provisions in their partnership agreement that are that are pretty unfair.

Khurram Naik: Well, I know that we're right up on time here and, you know, there's just so much more about, you know, your backstory that we didn't even touch. Um, so we might have we might have to do a round two here. But I think you've, as always, had lots of food for thought for lawyers and um yeah, it’s just super interesting to hear about your practice because as you say, I think you know the having an ethics practice you were talking about the emotional core like "I think I think about things in a job that probably other lawyers or litigators don't." And so yeah, I think you're right about that. So a lot more to mine in that, hopefully in another conversation.

Hilary Gerzhoy: Yeah, great! Well, thank you so much for having me on. This was great.

Khurram Naik: Thanks, Hilary.