Josh Seidenfeld | How to Scale a Law Practice Without Sacrificing Client Service

Josh Seidenfeld is a partner at DLA Piper, where he co-leads the Emerging Growth and Venture Capital practice and chairs the Northern California Corporate and Securities practice. Based in Palo Alto, he advises high-growth companies in life sciences, digital health, and technology through every stage of the corporate lifecycle, from formation and venture capital financings to IPOs and M&A. With more than 15 years of experience, Josh has led hundreds of venture financings and advised companies ranging from early-stage startups to multibillion-dollar public corporations. Before joining DLA Piper, he served as Global Chair of the Digital Health Group at his previous firm and worked on the business side of the venture-backed health technology company Practice Fusion as Director of Business Development and Corporate Counsel. He was named the 2025 Venture Capital Attorney of the Year by LMG Life Sciences and holds a JD/MBA from Santa Clara University and a bachelor’s degree from the University of California, Riverside.

 

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WHAT’S COVERED IN THIS EPISODE ABOUT SCALING A LAW PRACTICE

Growing a law practice means relying on other attorneys to take greater responsibility for client relationships and the work that supports them. For partners who have developed their own approach to serving clients, that can be difficult. When associates don’t handle situations the way a partner would, frustration can lead to more oversight and less delegation, leaving the partner responsible for work the team should be able to manage.

Josh Seidenfeld has approached that challenge by setting clear expectations for client communication and investing time in developing his associates. He focuses on giving them a framework for thinking through unfamiliar situations rather than trying to teach them how to handle every possible problem. Through regular training, individual conversations, and opportunities to take responsibility for client relationships, he helps associates develop the judgment and confidence to make decisions and work more independently.

In this episode of The Lawyer’s Edge podcast, Elise Holtzman talks with Josh Seidenfeld of DLA Piper about the connection between client trust and practice growth, helping associates take greater initiative, reducing unnecessary pressure through proactive communication, and the challenges of growing faster than expected. Josh also shares how his experience on the business side shaped his approach to legal advice and what he learned when his practice grew beyond the team he had originally planned for.

2:48 – How Josh’s business experience and athletic background shaped his approach to practicing law

4:52 – Why lawyers need to think like business owners

7:48 – What Josh does differently in managing client relationships

9:42 – Using proactive communication and deal calendars to manage client expectations

12:30 – Training a team to deliver a consistent approach to client service

14:09 – Teaching associates how to think through unfamiliar situations

17:40 – Why investing in associates is worthwhile even when they leave

19:56 – How Josh structures individual mentoring and team training

22:29 – Creating an environment where associates can receive honest feedback

25:47 – Finding time to develop lawyers while managing a demanding practice

28:29 – Setting clear standards for client responsiveness

32:24 – Giving associates more ownership of client relationships

33:45 – What Josh learned from growing his team to more than 25 people

36:41 – Helping associates overcome the fear of making mistakes and take initiative

MENTIONED IN HOW TO SCALE A LAW PRACTICE WITHOUT SACRIFICING CLIENT SERVICE

DLA Piper | LinkedIn

Josh Seidenfeld | LinkedIn

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This episode is brought to you by the coaching team at The Lawyer’s Edge, a training and coaching firm that has been focused exclusively on lawyers and law firms since 2008. Each member of the team is a trained, certified, and experienced professional coach—and either a former practicing attorney or a former law firm marketing and business development professional.

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Elise Holtzman: Hi everyone, It’s Elise Holtzman here, a former practicing lawyer and the host of The Lawyer's Edge podcast. Welcome back for another episode.

Many excellent lawyers assume that everyone else practices pretty much the same way they do. Today's guest believed that for years, until working closely with other partners showed him how differently he approaches clients, communication, and the work itself. When he stepped into a bigger leadership role recently, his challenge became turning that approach into something a whole team could deliver, and his practice grew faster than he had planned. Today he's going to share with us how he thinks about client service, what it took to build the team, and what he's learned about scaling a practice beyond one person.

Before we dive in, today's episode is brought to you by the coaching team at the Lawyer's Edge, a training and coaching firm which has been focused exclusively on lawyers and law firms since 2008. Each member of the Lawyer's Edge coaching team is a trained certified and experienced professional coach, and either a former practicing attorney or a former law firm marketing and business development professional. Whatever your professional objectives, our coaches can help you achieve your goals more quickly, more easily, and with significantly less stress. To get connected with your coach, just email the team at hello@thelawyersedge.com.

I'm delighted to welcome my guest today Josh Seidenfeld. Josh is a partner at global law firm DLA Piper, where he co-leads the emerging growth and venture capital practice, and chairs the Northern California corporate and securities practice. Based in Palo Alto, he guides high-growth companies in life sciences, digital health, and technology through every stage of the corporate life cycle. From formation and venture rounds to IPOs and M&A. Josh has more than 15 years of experience and has led hundreds of venture financing, advising everyone from garage stage startups to multi-billion dollar public companies. Before joining DLA Piper he served as global chair of the digital health group at his previous firm. His legal work is shaped by time on the business side as Director of Business Development and corporate council for the venture-backed health tech company Practice Fusion. He's also started companies of his own, and he's a former athlete. He was named the 2025 Venture Capital Attorney of the Year by LMG Life Sciences, holds a JD MBA from Santa Clara University, and has a BS from the University of California Riverside. My goodness Josh, welcome to the Lawyer's Edge.

Josh Seidenfeld: Oh, thank you for having me. I’m excited to be here.

Elise Holtzman: I'm excited to talk to you, especially about this topic of growing and scaling a business and doing it in a way that continues to deliver real value to your clients. Before you built a law practice, as I mentioned, you worked on the business side of a venture-backed health tech company, started companies of your own and you competed as an athlete. What do you think those experiences did to shape the kind of lawyer and leader that you are today?

Josh Seidenfeld: They were tremendously valuable. And they’re some of the characteristics I look for when I try to recruit people to the firm. When I look for talent I usually think, when you're in a corporate legal practice it's not the kind of thing that you learn in law school. And so you have to have certain features that ultimately go beyond your ability to comprehend things quickly or have the right level of intellect. Which, you know, presumably law schools teach people that. It really boils down to like, do you have grit? Do you have determination? Are you willing to do things other people may not be willing to do?

Because when you start in a corporate practice, you do a lot of work that may not be particularly glamorous. And even with the advent of AI, you're still not doing things that are particularly glamorous. And I found that those were characteristics, or qualities I developed through some of the experience that I’ve had in my own career. I think a lot of those, kind of, help me push through otherwise really challenging moments that, you know, one might have looked at and said “Okay do I still want to do this or not?” But instead you know, get to places that you realize what an amazing career this is and what a great opportunity it is. And I think those are, those are some of the drivers behind it.

And then the example I use, to the question you're asking, is that when you play sports you miss more shots than you make. I mean you look at baseball as an example, which is not, not my sport. If you're a 300 hitter, you're a good hitter. If you're a 400 hitter, you're a generational hitter. That means 4 of 10. I mean that's a failure in every other category of the world, but that's the best in the world ever. And so in sports you learn the idea that you're going to fail, and the question is not that you fail. It's, do you have the ability to get back up and do it again, and try to be successful, and learn from your mistakes? And I think that is a hallmark feature of a successful corporate lawyer, it’s the same thing with being an entrepreneur. You're making decisions with imperfect information, so you learn how to develop judgment. And that's what people pay lawyers to do. At the end of the day they want folks with, with judgment. That get the right answer. And no one ever puts it that way, but I think that's the scorecard that we all play by.

Elise Holtzman: What about the idea of thinking like a business person? Whether you're in a corporate practice or not, but just as a lawyer and a private practice law firm? Because in addition to doing all those things I mentioned,\ you have an MBA. And you know, while we know some lawyers have MBA’s and most don't. And I think as a result, they think very differently about the business of law.

Josh Seidenfeld: Yeah it's, it's, it’s funny. Everyone I know that's ever got an MBA will come away with the same answer I'll give you here, which is I don't know that the MBA itself is what drives a different behavior. I think it's the desire that you wanted to get the MBA to begin with, that has you in the mindset that solves these issues. So the good news is, if you don't have an MBA do I think you need to go back and get one? Do I think it'll change the course of your practice? I don't. Does it help that you learn how to read financial statements? It does. But you can pick that up off a video on the internet or through other forms of training.

What starts to matter the most is, do you start to think about being in the shoes of someone who has to execute? And a lot of lawyers and you watch this in the way that they process transactions, they process matters. They're so focused on the area that they know, that it's almost like you have blinders to the rest of the world. And you know we, we tend to, which is one of the beauty’s of the job, we get to work with these profound executives. And a lot of times the other people running companies; chairs, or boards, or CEOs. And they are not just thinking about legal input. That is one input that they have. They're thinking legal, they're thinking finance, they’re thinking operations. They’re thinking the relationships with these people. And are they the ones that should spill blood, they ask for others to help them do that.

And so sometimes you have to understand, if I put myself in the shoes of the operator, what are they really going to care about and what matters to them the most? Is it the indemnity provision? Is it the amount of liability in this? Or is it the fact that this might be on the news or whatever else it may be? And if you start really thinking about the other components, and I think this is where that kind of mindset starts to be very valuable, you, you change the way that you render your advice. It’s going to happen, it'll change the way that you think about the process of what you do. And the more you do that, I think the more clients realize they identify with you because you are like-minded. And that that engenders a certain kind of relationship with them. And that's, that's where the job gets really fun. Like when you get to that place where a client intrinsically trusts the decisions that you're making with them, it's fun for you too ‘cause you realize like “Okay I actually have a real role in this company’s success. Maybe a minor role. It may not actually have that, that much meaning in the big picture of everything, but it does, it does matter.” And it matters in certain levels more than others. And that's the part that I get, I get a lot of joy in when you get a chance to play at that level with the clients that you work with.

Elise Holtzman: You said that for a long time, you just assumed you were doing the same, normal job everybody else was doing. And so you've already started describing how people practice law differently. But what you told me when we talked before our recording, is that you worked alongside other partners and you saw that the way you approach clients is different. So what did you start to notice that was different about the way you did things?

Josh Seidenfeld: The biggest thing for me, is I, I noticed that the way that I was processing information and the way that I would communicate back to clients has generally been different than, that I found a lot of like my colleagues or counterparts. And I, and I think a lot of that just goes back to the comment that we were just talking about. Which is, are you really thinking about from the shoes of the entrepreneur or founder, what their biggest objectives are? What their fears are? You know, what the risk factors are? In order to get to the right answer for them. And so like, and some of it just came from the idea of like “How do I become an independent operator as an associate?”

So it was like the idea of like “How do I get out from underneath working for a partner?” ‘Cause then the reality is, partners are really hard clients. And they know exactly what you're doing, they know exactly how long things are supposed to take. And you know they know when you're prioritizing your work or not. Whether they're watching over your shoulder, one way or the other. And so the idea of like, someone coming and telling me I need to finish something four days before it's really due, never was that appealing to me. And so what I started realizing was “Great, if I can manage the client relationship, and I can give them insight into when things are going to be done. And then I execute on what I promise I will do, the client is going to be happy because I've calmed them down. I've given them a north star that we're going to follow and drive a transaction.”

And so I started to realize this probably somewhere in my, I want to say my third or fourth year of practice, where I used to challenge myself to say “Okay my job is if a partner delivers a term sheet on a deal.” Which I would have no insight to, knowing it was happening. I'm just, wake up Monday morning there's a term sheet on my desk. My goal is to say “Okay how little can I speak to the partner in order to get this deal done? How little input do I really need from them in order to get the deal closed?” And that always became a function of; did the client follow up? ‘Cause if they follow it up, they were going to the partner. And usually that meant, okay now all of a sudden like the, the intensity would pick up, or the pace would change, or the advice would be different than what I would want to render.

And so I started doing things where all of a sudden, I would get a term sheet and I would set up a call with the client immediately. And I would walk them through “Here's what the next 30 days are like, and here's what you need to do, what I need to do.” And then I realized the phone call wasn't enough, so I started creating visual cues for the same thing thinking that different people learn different ways, and some people are visual learners, some people are auditory learners so I'll do both together. So I would have a phone call, I would create a deal calendar, and a lot of these things I would borrow from other practice areas and other people's success. So if you ever watch a capital markets lawyer or an M&A lawyer, they create a very big checklist, you know TNR, and they have a calendar, and they show you what's going to happen when, and when the holidays are. And I said “Okay why can't I do that venture financing?” And you can. Like, the simple thing is it's just a shorter calendar. It's one month instead of six. So fine. And I started building out tools like that.

And this the same would be true closing a financing. ‘Cause all the sudden, you get an astute CFO that would start, you know, basically trying to issue spot in the deal. And say, would ask a million questions, and you'd find yourself scrambling to get the right answer. I said “Okay great. If I can get in front of that, and I can manage this process better for them, then I can basically take all the concern away from my clients. ‘Cause they know they're working with someone that knows exactly what they're doing. And will lead them to the outcome that they want.” And over time just doing more, and more, and more of the same things you gain more confidence in the approach that you have. And so nowadays, you know I, the way I try to raise it for people in, in my own work is. I'll get on the phone with the client and say “Your job is to deliver investors and a term sheet, then my job is to basically lead your deal to closure.” You, you start as the leader, I’ll finish as the leader and that's how we team up and get a deal done. And there’s something that is very confidence-instilling from a client when you’re able to do that. And I’ve realized as I worked with other people, a lot of these, kind of, process points are things that other people aren’t focused on. They’re immediately focused into the, what are the terms I have to draft? And what are the documents that we prepare? And they start going through a serial process, when you don't have to do a serial process. And you create pressure in the system. Or they, they want to deliver documents in a way, but they don't want to deliver something or tell the client where they're going, ‘cause they want to do it all at once. In the meantime, like, now the client’s waiting a couple extra days, and so you build pressure to the system inadvertently ‘cause you're not thinking about the human element of the work.

And I think that's the piece that if, if I could give one friendly piece of advice to all of us lawyers, it's you know, don't forget how important the human element is. Like your colleagues, you know your associates, your paralegals, your clients. Like that is really what, what drives everything that we do, it's the people. And so if you, if you can be good in that category, like everything else will fall into place. ‘Cause I. It's, it's never the case that people aren't an expert in their subject matter, that's usually always taken for granted that you are ‘cause you get the training for it. And you're, you know, smart, hard working people generally in the profession.

Elise Holtzman: Let's talk about how you take that, you have a philosophy, you have a way of doing things, you have a way that you serve clients. How do you take that and train a team to do that sort of thing? For you, for example, you've talked about productizing the way you practice, so a whole team can deliver it. And I think a lot of lawyers struggle with that. It's like “Well I know the way I do it. And I don't understand why people won't and don't do it my way. And if they don't do it my way, then I get annoyed and they're not very good at what they do, and I don't feel confident putting them in front of clients. So now I'm back to trying to do everything myself.” Right? So what does that look like for you?

Josh Seidenfeld: I have 100% been in the bucket that you just mentioned. I can recall lots of moments on like a Saturday, reviewing documents and, and talking aloud to myself about levels of frustration. And then realizing when you take a step back from your own circumstances and the way that you're viewing the world, and you think about the people that are participating with you on the transaction like your team. What I realized is, everyone is trying their best. They are actually trying very hard to be good. It's very rare, and that's one of the things that I think people take for granted in the legal practice that I don't think exist in ordinary companies. I can assure you of that just, just being in some of them when you work in a regular company, not everyone there is playing to win. There are some people there that are playing to punch the clock and get out, because that's their job.

I think when people go into legal practice, I think people do play to win. Like they want to be successful, there’s a lot of type A’s in this business. And so generally, you find that people are trying their best. They just might not have the right framework to be thinking about how they could do things in a better way.

And so then the question is, are you willing to take the extra time? Which yes it does cost you in the front end. But if you make that investment in people, and you are able to give them a framework of how to think about things, so that you start to think in a similar manner when you're dealing with circumstances. So what are the examples that you can give them? What are the scenarios you can play through with them so they start thinking the right way about how to handle a situation? ‘Cause you can't teach people every minutia of everything you've ever going to do. But what you can do, is you can give them the way to take a thought process of “Okay, how am I going to solve a problem that I don't know? What's the framework I'm going to use to address something that I've never, never seen before and never done?”

I think in my practice, it, maybe it's easier than it is for others. At least I'll keep telling people that. Because there are lots of examples that you can point out to, and when you start doing that with people what ends up happening is, they get better. And they get better at an exponential rate. And so then, then all of a sudden, within one year you can watch someone that may have known nothing about the practice be a professional operator. And then in two years you can watch them start to execute somewhat independently. And by year 3 or 4 somewhere in that zone, maybe year 5, you watch these people flourish. And I can tell you from, from my own career, like, that is the part that I get the most joy out of.

I, I look back and it’s like, yes I've worked on a lot of really great transactions. I'm very fortunate. I'm not, knock on wood. And I'm you know, I'm, I'm lucky that way. I don't look back even on like, this part of my career and say “You know what I'm most proud of? I’m most proud of this billion dollar financing I did, or this 3-day transaction I did.” I look back and it's like, the email from the associate who said “Thank you for doing this.” or “I have confidence in what I'm doing now, where I'm a partner.” You know? “That I worked with you.” You know? Those are the things that you actually look back on, that are really rewarding. And it's, it's no different than like, maybe you're familial relationship. It's just your work family. And so the question there is, you know, can you make that investment? And I know a lot of people worry “Well, if I invest in somebody and they leave the firm it's wasted effort.” And I don't think that's true either.

You know the, the reality is that the world is so small, that a lot of the people that you, you touch and you know and have an impact in your life as well it comes back in spades. You know like, they, they, maybe they're a client in the future, maybe they're just a referral source for you, maybe they just say good things about you in the market, or maybe you just made their life better. And you know we're only going to, you're only going to be a lawyer for so long in your life, like you're going to be a human for a lot longer. Until like, what do you really want out of this? Like what are you really trying to achieve out of the job?

And if you, if you can step back and think about that, like its impacts. Like that's what we get to do, we get to make a real impact. And so, so we should all do that. Like we should all take the extra 5 minutes and make everyone's life a little bit easier, ‘cause at the end it does make your life better as well. And it creates scale. And once you can create scale, you can serve many more clients. Or you can move at a faster pace than you've ever imagined. It doesn't mean that it, it's always perfect. Like, like I can, I can tell you, I get, I still get frustrated every once in a while of course. But, but you do get a higher level of reward that way. And that's like a very enriching part about the job.

Elise Holtzman: One of the things that we know about lawyers is they do tend to show up in certain ways. Very linear, very concrete. I think in some ways you fall into that category of lawyers that are a little bit more strategic, maybe thinking outside the box a little bit. And some of what makes the former group so successful is just that. They're very reliable, they're responsible, they’re productive, they get things done, they check off the boxes, they make it happen. What I hear you talking about is a bigger picture vision, right? Sort of pulling yourself up, looking down, having that 30,000 ft view of “How do I grow a team?” And the philosophy that you're living by, you know? One of the things that, like you, I hear people say things like “Well yeah Elise, you're talking about investing in our people. But some of those people are going to leave.” On top of all of the great reasons that you shared for not taking that attitude is, what I think of as what's the alternative, right?

Are you going to just decide “You know what? These people might leave me, they might abandon me, they might not appreciate me, and I might not be able to see the fruits of my labor. So I'm not going to do any of it at all.” Or are you going to say “You know what? I want to grow something here, and I want it, so I'm going to invest in people, and I'm, on the whole it's going to work out well for me.” So, you know one of the things I'm curious about is when you talk about investing in people, and talking about teaching them kind of a thought process, and a global methodology and philosophy for how to do things, and then they start figuring out how to do it themselves, are you talking about one-on-one investment and relationships? Are you talking about sitting a team in the room and saying “Hey this is kind of the Sidenfeld way of doing things, or the DLA Piper way of doing things?” What does that tend to look like for you? And for those of us who are more concrete thinkers?

Josh Seidenfeld: I'll go back to one other point that you made and I'll, I'll put a challenge out there. There's no other aspect of your life that people take that kind of mindset that “I'm just going to keep doing it myself.” Like, if one relationship, if you. If you've ever tried to date someone and that didn't work out well, you don't stop dating people you know? If you’ve ever got into a fight with one of your kids because you disagree with them, you don't stop loving your kids. You don't stop playing basketball ‘cause you missed a shot. Like, all these things you go back to the well, and you keep doing it over, and over, and over again until you get better.

And there’s no difference with management and development of talent. You keep going back to the well. And you find ways to make it fit for you and your personality. Now to your direct question, I do all of those things. So I tell people before they join the firm, I try to be very, very clear with you know what, what the expectations are. Which is we're trying to build something that's generational. And so like, I'm not looking for someone that's coming here to punch the clock. I want someone here that wants to invest in their career, I want someone that wants to be successful. I want someone that cares about, when their names on paper. And, and I always tell people the phrase is you know “Are you going to spend the extra five minutes on Friday? If it's 5:00 on Friday you stay until 5:05? Or 4:55? If you’re 4:55, you're not going to love it. If you're 5:05, you're going to love it.” And, ‘cause you're going to get the investment back.

And what does that investment look like? So for all of my associates, and the folks I work with I do a handful of things that are group orientated. I do a lot of things that are one-on-one, and then I also offer kind of an open door policy as well. Because it's hard for me to know what's on people's minds or what their concerns are. I can only guess just by getting to know them a little better, and getting to know their personality. So you know, one of my junior attorneys that joined from another firm this year, you know, we now are doing, every two weeks we do a check in call. And, and his concerns are more around making sure he's learning to practice the right way, because in his prior firm he didn't have a mentor that invested in him. And so he feels like he's behind in his, his development as a technical lawyer. And so he just wants to get candid advice. And so I'm like “Great. These are all the things that are just you and me. And I'm going to be honest with you and tell you where you need to focus. So that you know, you're gaining the respect of your teammates.”

And they start thinking about things from the 4th year’s perspective, and the seniors perspective. So that you can operate on a team and play the team game the way it's supposed to be played. Which is helpful ‘cause we could just have that kind of direct relationship. That's really it's, it's great to do it. I mean we did one the other night like, it was a late call ‘cause I had a client dinner to go to, so we, we did like a 7:30 p.m. call. But the beauty of that was neither one of us had anything we had to do with, for anybody else. So we could just have a relaxed conversation and really talk about, you know, ways that we can improve together, and ways we can communicate better together. ‘Cause it's not a one-way street.

And then the other couple things that we do, like I do a Tuesday training session every Tuesday. It's 30 minutes. I do one every Friday as well. Tuesday is substantive, so we'll go through an actual thing. Which is like, let's talk about how to do this kind of transaction. Let's talk about the implications of this kind of transaction. So everybody can learn the, the way a deal is supposed to be done, at least according to the playbook that we tried to follow. And then it's an open book like people can comment on that, or they can ask questions. So we're all learning together. ‘Cause that one-to-many can be helpful in that setting. But not, not everything is successful in the one-to-many’s, then you still have one-on-ones of course. ‘Cause you want to talk about something that someone did specifically, so I'll do that too.

And then I do other little things. Like every deal we close, we have a 15 minute conversation after we close the deal. Which is; what did we do well? What can we do better? And it's not intended to be like some rah-ha or anything like that, it's a very quick “Here's what you all did great, here’re the things that we can improve on.” And every deal we can do something better, ‘cause we're always striving to be better. Because if you, if you don't strive to be better, you're going to get worse. It's like, it's really, it's really binary in my mind.

Elise Holtzman: I just want to pause here and highlight a few things. So, I'm hearing a few things that I think are really important to point out. One is it sounds to me, and you can correct me if I'm wrong, but it sounds to me like your associate is willing to share all of these things with you because he knows that you are quote unquote critiquing him or giving him constructive feedback to help him grow. I think that many people, especially because lawyers are so busy billing hours. We give feedback when we see something to criticize. Because we want it to go right.

And I think that sometimes people shy away from that. They get nervous about the feedback because they don't necessarily believe that the person has their best interest in mind. You're doing it in a way where you're saying “Hey I'm going to be honest with you, and the purpose of this is to help you grow. And I'm not going to think of less of you because maybe, you didn't get it right the first time. Or because you have a quote unquote a stupid question.” So I think that the mindset that people show up with, when they're training their people is so important

Josh Seidenfeld: Oh I, I agree completely and I’m, I’m as guilty of that as anybody. It’s like, you know, we're all learning. And so you know, you learn how to be a better manager too. And it's the same thing like, if you, if you actually go get an MBA, and they talk to you about how to get feedback. They will tell you like, separate positive and negative feedback. Like do it in a neutral session, like don't do it in your own office. And just all these different tricks of the trade that people talk about.

And you can use those as like, frameworks to get the answer. But they're all designed to come to the same conclusion. Which is; how do I get people comfortable so we can actually have an honest conversation and we can grow together? And so I tell folks when I'm giving them feedback “I'm only giving this feedback to you, this isn't like something I'm putting in a review. No one else is on this phone call.” And the whole point of it is like “I want you to be honest with me too. Like what are you worried about? What are you struggling with?” And I don't. I ask, I ask everyone to do the same thing I do, which is once a year, when you get done with the year and we have that like, that final slowdown before the year is over. You know, whenever that break that you take is. Sit down and ask yourself, like “Am I happy with what I'm doing? And do I want to opt in to the next year?”

And if there's something that is bothering me, or something I'm worried about, like what's the best way for me to address it? And it's not going to be on your own, like no one's going to get there on their own. Like you have to have a team of people around you to get there. The same is true for me, like I can't be successful if my team's not successful. And so like it's, it's important that I'm there for them the same way they’re there for me. ‘Cause sometimes a client calls you and says “I need you to do this overnight.” And so we're stuck staying up super late getting a deal done.

That’s a big ask to put on someone's life. If they have children or they have a spouse or whatever it is, you're asking them to invest in off hours to get a project done that no one else understands why it's meaningful. But for, for everyone in the profession, we all get it. And so, if I'm going to ask that of people and I have to be there for them too. And then you create a relationship with people. And if you have that, that little extra where someone might say to you “I don't know if I'm developing this fast enough. Or I want to do this kind of deal, ‘cause I haven't gotten exposure to it, or having trouble getting Junior help.” Any of the myriad of things people would ask you about. It gives you the ability to help solve that problem. Versus like, what I think tends to happen, which is one day someone comes into your office and says “I'm leaving.”

And you’re like “Wait a minute. I've been investing, I thought everything was great? I didn't know any better.” And I don't want that. I want people to stay here as long as they possibly want. I want to help people get as far as they can in their career. And the reality is like, selfishly it means like my career goes better if that's the case. So like, why would I not do that?

Elise Holtzman: I can hear some lawyers saying “Sure Josh, that sounds great. But you don't understand how busy I am.” Right? “I don't have time. Like, these lawyers are going to have, these young lawyers, they just don't get it. They need to figure, we figured it out ourselves. They need to figure out a lot of this themselves. I can't be, you know, spending all my time managing people on practicing law here.” What do you say to that?

Josh Seidenfeld: The two things I say to that are. You know, one. Just because you were hazed doesn't mean you need to haze the next group of people. Like that is like, definitively true. Like our job is to make the world a better place than it was, than we got in to begin with. And like, let's all like, chip in and do that. And you know, 5 minutes is 5 minutes. 15 minutes, is 15 minutes. You can find those windows.

You know, looking in fairness like, I've had years I billed 3,000 hours. It doesn't mean I spend less time with, with the team I work with. ‘Cause I'll find those extra minutes. ‘Cause like the minute I lose someone that I've spent two or three years working with, or training, I'm going to be set back. And. And the reality is like, that's not a good answer. And so I'd rather find ways to make sure we don't get to that place. Or at least, to the best of my ability.

Does that mean that I’m expecting everyone's going to make partner in a law firm? Of course not. Like it's a, it's a very particular role. But does it mean that I might help someone become a GC one day? Sure. I've done that with lots of people in my career. And then I look back, and you know we, I still have relationships with them. And again I. I just go back to like, that's the part that's, it's very rewarding.

And so it doesn't require this overarching investment. It's, it's all the same things of like, are you developing habits in your life? And what are the habits that you choose to develop? And even 5 minutes, even just the, I walk by someone's office, give ‘em a fist bump and say “Let's have a good day.” I think that is more meaningful than skipping that step. And that's 30 seconds. So like if you put that 30 seconds to use once a week, over the course of a year for 10 people? That is a profound impact across a lot of different people, that someone cares about me, is thinking about me. And if it means a team talks together too, and they are more collaborative ‘cause they all feel like they're one unit. Then again, you're the same thing. Like you get, you get like, that, that mindset that says we can do anything together.

And if you go back and look in sports, which is the background I have. So I always turn to things I know. Look at, look at any winning team. You know, all the winning teams that are out there, they find a way to gel. They find a way to trust each other, and know that people are going to do their responsibilities when they're supposed to. That doesn't just happen because they show up and do a deal together, it happens because they spend time outside of that required moment of practice to get to that same outcome.

Elise Holtzman: While you are very much focused on nurturing your team, and growing this team, which of course helps you retain your best people and serve the client really well. You are very particular about client service. And how these lawyers are expected to show up for clients. So one of the things you mentioned to me is that you have a responsiveness standard with your clients, almost like a service level kind of agreement, an SLA. Where people are told you know “You have to get back to your client in a certain amount of time.” What does that standard look like day-to-day? How does that happen in a law firm? Because I think that, most people it's like “We've got to get back to them immediately, if we don't it's the end of the world. But then these other things can drag out as long as they know what we're doing.” Like, what does that look like for you?

Josh Seidenfeld: In some cases there's a little flexibility there, but in, in most cases there are things that we have to be able to meet and honor our word. And it goes towards creating the right level of credibility. And, and it also requires the people kind of buy in to the, the mindset of what you're solving for. And so, what I mean by that is like. I'll give you, I'll give you one example of it. Where there’re lawyers I’ve worked with in the past, and it's, it's a very typical lawyer trait that says “You send me a document. Before I can give you comments, I need to set up a phone call. I’m not going to do anything until I’ve set up a phone call.” And through the morass of scheduling, maybe that phone call happens 48 hours later. And then once it does, then you're expected to turn in the document. You might need a day or two, because of the other work that you have.

So now you’ve taken a week to deliver a project that the client wanted back in a day or two. And so that client is going to give you a lot of pressure on getting that document delivered. So if you are a senior partner, you're now going to put a lot of pressure on your associates. That creates a lot of stress in the system. And it's stress because you put a process together that you wanted perfect input to be able to deliver a result. But ultimately what it ended up doing was causing a lot of pressure on people. And that might accelerate people's exit of a firm. Or dissatisfaction with the profession.

So instead my, my view on that is. I can imagine, I probably know what you want to do with most of these things. Maybe 20% is what I really need input on. So why am I going to wait to get that 80% done? Let's get the 80% done. And even if it means I need to eat some of the cost of that, because maybe we deviated 5 or 10% in the wrong direction, that means my team gets an extra day or two to do the work. So we can still get the deliverable out on Thursday instead of Friday. I can still have the client phone call. But I got the associate started a couple of days early. And all it meant was I have a little bit of cost to eat. I would rather do that because I'm going to create a less stressful environment on that answer, than I am by putting everything into the last minute. And then you know, putting people through the blender.

And so with clients, what I try to tell them, because there is this you know process of developing trust. And also the rapport in process with the client. I will, I'm very explicit “You will hear from us, same day, like every time you ever, you send us an email. You’ll hear from us the same day." Does that mean you will, we will deliver final documents the same day, of course not. Like, that's not possible to do, but we will tell you when we will. And we'll tell you what roughly we think it will cost. Because that's the level of transparency that you want. And as an operator, the worst thing in the world is no time and no budget. ‘cause you can't plan for that accordingly. Like negotiation or surprise that you're dealing with.

And so when people start to realize “Oh by doing it this way, I'm actually buying myself time because my clients think I have credibility with them.” We tell them it's Wednesday, it's going to be Wednesday so they don't ping me on Tuesday and Monday, for Monday or Tuesday. ‘Cause we all agreed Wednesday. That is such a better answer and even in the client's mind it's like “Cool I know it's coming Wednesday.” And if you do that two or three times, they actually believe you're really going to do it Wednesday

Elise Holtzman: It's an interesting take. Because I think, you know, and, and at first blush it could sound so unreasonable. Like “What do you mean we have to get back to clients exactly the same day. That sounds completely crazy.” It can happen sometimes. We try to make it happen. But we can't guarantee it’s going to happen all the time. And yet when you describe it the way you have, and you create these trusting relationships with clients over time. Then no, they're not breathing down your neck every second because they know that you're going to. They know you're on it. Which is what they want to know.

Josh Seidenfeld: Right. And it also the chance to go to them every once in a while and say “This isn't going to happen for these reasons. Like we need more time to get something done.” ‘Cause you build real trust.

Elise Holtzman: Yeah, you have the credibility.

Josh Seidenfeld: Right. And, and also to me like, has these other ancillary benefits. It’s like, it lets your associates also form relationships with clients themselves. And so if you want to build a team, and you want to scale. That means in some cases you have to get out of the middle. You have to, you have to be out of the starring role, and you have to take the supporting role. So you create the assist. And so if it means that my second year attorney can respond back to a client and says “Yes we got your request for x. We're going to work on it now.” And then they send me an email saying “Here's what I think we need to do and I'm going to start in this order, does this make sense to you? And here’s when I think I can get it to you.” Like “Great.” Now this person has done something that everyone always begs associates to do. They’ve taken leadership and taken initiative. They told me the order they think they're going to do it, they told me when they think they can get it done. Or, I had this email actually right before this call. An associate said “I am so busy, I don't think I can do this project. Do you think it would be possible if we get another first year to join in on doing it instead of me.” And the answer is like, that's the beauty of working in a big law firm is that, to a certain extent we are all interchangeable. We all know what to do. And so yes, could you sub someone in for a discreet project? Of course you can. And so like, it goes to the same, the same fact pattern of; let's build cohesiveness and if you pitch in here, maybe they pitch in for you later. And the client still gets the same result. To get the work product, and they get responsiveness.

Elise Holtzman: We talked about how quickly your team has grown. So you've grown to more than 25 people, just this year. And my understanding is that you said you've kind of underestimated what you were going to need, and what the team was going to need to support that growth. So what does that look like? And what would you tell a practice group leader who wants to grow quickly or is about to grow quickly? So that perhaps they don’t have the same level of stress that maybe you’ve had doing it.

Josh Seidenfeld: Yeah, and it’s. It’s hard to forecast a business. And I think what I would tell people is, I mean it at all levels, like you have to start with like your first principles. Which is like, have confidence in yourself, have confidence in the fact that like, people are here to work with you. You know, it is amazing to have you know like, the like, the firm I work for is incredible. Like the it's, it's such like, a talented group of people that exist at DLA. It's like, it's, it's very, very impressive to me.

That being said, like, clients don't hire a law firm, they hire a lawyer. And you know. And that's the one thing I think everyone always forgets is that, someone at some point in time chose to work with you, and you chose to work with them. And so when you form a relationship, if for whatever reason like, like I did. And I moved, moved law firms. Most of those clients are going to want to go with you, because they still want to work with you. And I think you know, I went through this process of “Is that really going to be a true statement or not.” I've never moved firms before, you know? I don't know if everyone's going to work with me.

So I underestimated what that would look like. And I underestimated you know, therefore like the, the scale of a team I would be needing, that I would need in order to serve everyone the way that I want to. I mean so that's one of the things I would tell folks which is like, don't underestimate your success. Be confident. Bet on yourself. Because you're, you're the only person that should do that. Like day in and day out. Like if, if you're not going to bet on yourself, no one else is.

And if you think that you're going to be successful, then you can plan for success. Versus like, what we are trained to do. Which is like always worry about mitigating risk. And then thinking therefore okay I need to be more conservative in my approach. Which doesn't necessarily lead to the result that you want. And so, you know like. So that the, that's the one thing I would try to try to harp on. And I, I, I certainly made that mistake myself in this instance. But you know ultimately it's like a, it's a good, it's a good learning point. And it was just a good, good thing to emphasize about making sure that you really do, you know, look in the mirror and say “Okay I, I know I can do this.”

Elise Holtzman: Josh, as we wrap up our time together today, I'm going to ask you the same question that I ask all of my guests at the end of the show. There's a phenomenon called The Curse of Knowledge, where experts sometimes forget that what is so obvious and natural to them is not at all obvious to others. From where you sit today, with everything that you've learned and done, especially over the last year. As you've moved firms and built this practice. When it comes to growing a practice beyond just you, beyond what one lawyer can personally deliver. What's a principle or piece of advice that may seem obvious to you at this point that you think is really important for other people to hear?

Josh Seidenfeld: Maybe the two things for me would be, don't forget to put yourself in the shoes of the person that you're speaking to. And you know, make sure you understand that everyone usually has the best intentions in mind. You know, they are coming in with the intention of being successful and trying to do right. And so therefore, they're worried about making mistakes. And so the more you can free people up from the fear of making mistakes, and instead like you know, make sure that you reward them for making decisions. Even if they're not the right decision, and support their ability to do so. The faster the growth curve will go up for everyone, the more confidence they will have, and therefore the more success you and your team will have together.

And that's probably the biggest thing for me is to really flip it on its head. Which is like don't be worried about people making a mistake. Be worried that people aren't going to make a decision, which is going to be wrong to begin with. And so really try to emphasize like, that, that is a value driver for the team and for yourself. ‘Cause that’s how we’ve all learned. We all learn by going into something that we haven’t done before and figuring it out. And if you can teach people how to do that, and you can give them a framework of how to do that. Like, you open up like a whole, another range of practice and experience that doesn't exist when you're doing the one-to-one that you were talking about before.

Elise Holtzman: I love that because I think it's, it's so hard for many, many lawyers to do. We’re so trained, as you said, to avoid the risk. And to make everything perfect, even though we know that there’s no such thing as perfection, we’re still driving for it. And to open it up that way, to let other people find their own way to succeed, is a great thing to remember. Not necessarily as easy to execute on. But certainly something to strive for.

Josh Seidenfeld: That is a fair point.

Elise Holtzman: So thank you for that. Yeah, thank you so much for being here Josh. It was such a great conversation.

Josh Seidenfeld: Of course. Thank you for having me for this.

Elise Holtzman: I'm going to thank our listeners for tuning in as well. If you've enjoyed today's show, please subscribe, rate and review us at Apple podcasts, Spotify, or your favorite podcast app. In the meantime, be bold, take action and make things happen. We'll see you next time.

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