COVID-19 Resources for Lawyers
Featured Guest
Jonathan Greenblatt

A retired Shearman & Sterling litigator, Jonathan Greenblatt is a co-founder and chairman of Legal Innovators. He and co-founder...

Your Host
Adriana Linares

Adriana Linares is a law practice consultant and legal technology coach. After several years at two of Florida’s largest...

Episode Notes

Even in law school with a career track in mind, promising lawyers don’t really know where they’ll land. Legal Innovators Chairman Jonathan Greenblatt talks with host Adriana Linares about modern career paths and their inevitable shifts because of challenges and unexpected opportunities.

Greenblatt points out what he believes are fundamental flaws in BigLaw hiring and training junior talent and how his startup is creating alternatives for firms and corporate law departments while ensuring young lawyers from diverse backgrounds get on-the-job training.

He and Linares talk through four good habits for developing a successful career: Go where opportunity takes you, network, develop mentors, and make yourself indispensable.

Jonathan Greenblatt is a co-founder and chairman of Legal Innovators.

Special thanks to our sponsors, ClioLawclerkROSS, and Alert Communications.


New Solo

Why a Career Path Isn’t a Straight Line





Intro: So you’re an attorney and you’ve decided to go out on your own. Now what? You need a plan and you’re not alone. Join expert host, Adriana Linares and her distinguished guests on New Solo. Tune in to the lively conversation as they share insights and information about how to successfully run your law firm here on Legal Talk Network.


Adriana Linares: All right! It’s time for another episode of New Solo on Legal Talk Network. I’m your host, Adriana Linares. I’m a legal technology trainer and consultant. I help lawyers and law firms use technology better. My guest today is Jonathan Greenblatt from Legal Innovators but before we get started with him, I’m going to read off a couple of messages from some sponsors.


Thanks for our sponsor ROSS Intelligence, the legal research platform that leverages AI to get to the heart of legal issues fast. Go to for a 14-day free trial.


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Of course, I want to make sure and thank Clio and check out Clio’s Daily Matters podcast featuring valuable perspective on legal in the COVID-19 era. Listen to Daily Matters at or subscribe wherever you get your podcasts.


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Adriana Linares: All right. Hi, Jonathan!


Jonathan Greenblatt: Hello! How are you this morning?


Adriana Linares: Can I call you John?


Jonathan Greenblatt: That would be fantastic. I would love it.


Adriana Linares: John, you had a company called Legal Innovators in the DC area. You come from a big firm background. Tell me a little bit about your experience and what led you to start Legal Innovators and what you all do at Legal Innovators.


Jonathan Greenblatt: I was at Sherman & Sterling for 40 years. Basically, I was a summer associate and then stayed there my whole career which is a relatively rare thing to do in today’s environment. It wasn’t so unusual then, which actually leads into some of the topics I think we’ll discuss because the whole nature of a career path has changed over the years.


I basically have worked in a plexiglass factory, was a Senate intern and worked at Sherman & Sterling. Those are my three big pictures in my life.


Adriana Linares: It’s not a long resume.


Jonathan Greenblatt: No and I was a litigation and international arbitration partner there, which also bears into some of the observations that I made. I was on the policy committee of the firm for a four-year term and I co-manage the DC office towards the end of my career at the firm. I also co-founded the firm’s diversity committee in 1990 in another wave of awareness about diverse issues 30 years ago. Over the course of my career, I came to observe two systemic/structural problems that I saw with the way big law was operating. One was despite some meaningful efforts made by law firms; we have not made the strides in diversity that our profession needs to make and should make.


And second was, we’ve managed to get ourselves into an insane arms race over the salaries that we pay for young legal talent and that has caused all sorts of repercussions. And we meet that someone will decide in the market that they want to break away from everyone else, the rest of the legal market will gnash their teeth and decide whether they want to meet it knowing it’s not particularly good for them and then they will. And that’s really created a have versus have not environment for law students graduating from law school which is only going to get worse in my view post COVID.


Adriana Linares: I mean it couldn’t be worse right now than it’s ever been. This has to be the bottom of the valley for being a new graduate or someone who’s been thinking about starting a law practice unless you’ve decided to carve a niche in the new COVID law.


Jonathan Greenblatt: Yeah. Hopefully that’s not a long-term professional pass —


Adriana Linares: God, I know. I’m wondering I should have checked to see if anybody has bought yet. I’m sure there’s that and a million variations of it.


Jonathan Greenblatt: But you know from being in big law that law firms are very, very cautious, really smart people, very cautious don’t make changes quickly, don’t take a lot of risk, very much believe that their brand is critical to them and talent and quality is critical. That causes them to take very little risk.




But if COVID doesn’t cause some disruption in the way that law firms recruit, retain, develop talent including on the diverse side, then nothing’s going to because it’s an open field for innovation right now. In fact, I think the market will demand it and it’ll be a question as to whether firms can get on the right side of that, I think. So we looked at that at Legal Innova– well, when I was retiring from Sherman, I said, “Look, that was a fantastic experience and I loved the firm and had great relationships with the firm and learned a ton but was that the only thing I wanted on my gravestone?”


Adriana Linares: On your very short resume that you could tweet.


Jonathan Greenblatt: Yeah, exactly. So we saw two structural/systemic issues that we thought maybe we could help address. One was could we rationalize the price point for young legal talent, which we think would open up opportunity to some people who are being left out maintaining quality because we understand completely the need for big law corporate legal departments at a high level to feel confident that they’re hiring quality people. And could we also at the same time, make an inroad on the diversity side by identifying people who got missed in the hiring process and I’ll come back and talk about what I think some of the flaws with the hiring process are but got missed in the hiring process who, through our program, which operates on a quasi-apprenticeship basis with a law firm or with a legal department would give people an opportunity to prove themselves over time before the law firm or the legal department in a corporation would hire them permanently.


So we hire them, we train, we place and then after a period of exposure to them on real matters doing traditional junior associate work not what we think of as contract attorney work, the idea is they would get placed in that place and have a career path that they didn’t otherwise have.


This is an outgrowth of, to some extent, the all or nothing way that law school works right now and this isn’t the way it was when I started but it is the way it is now. You either get hired into a summer program after one year of law school, which means you’ve got your performance in two semesters of school on the basis that performance law firms make their interview decisions and then on the basis of those interview decisions, they hire you into their summer program if they are inclined. Once you accept that offer, you effectively have an offer to come back two years later for permanent employment because the summer program has stopped being a screen in any way.


I jokingly say a summer associate would have to kill a very high-earning partner in the firm not to get an offer. They could kill me at the end of my career and that would be no problem, the firm would thank them and they probably would get a bonus. But other than that, they’re coming back. So law firms are making a decision two years before they know their needs and two years before they’ve really had an opportunity to see the person in action.


Adriana Linares: Tell me what other profession this happens in.


Jonathan Greenblatt: None that I know.


Adriana Linares: None.


Jonathan Greenblatt: No profession that does that. If COVID proves anything yet again after 9/11 and 2008-2009, we are in volatile markets that go very much up and down and yet we’re fixing the size and identity of our incoming class two years before they start. That doesn’t make a lot of business sense in my view for law firms but it also doesn’t make a lot of — it actually leaves out a lot of people who didn’t happen to, for whatever reason, catch the eye of these law firms after their first year.


So, you either get overpaid because firms are now up to approximately $200,000 a year for incoming first-year associates in big law or you really struggle to get paid at all as a law student, all on the basis of essentially what happened in your first year of law school and it was my supposition that there were a lot of strong law students and particularly those who come from backgrounds that may not have provided them with the equipment to shine in their first year of law school or have the context to do as well as they might otherwise have done their first year of law school, but have a lot of intelligence, a lot of native skill, those people get missed and no one ever goes back in and looks again. In part because we’re oversubscribed with people we don’t really need through the summer program from the perspective of big law.




So we said, “Can we tackle that problem?”


Adriana Linares: It’s funny when you say that we’re oversubscribed to the people we need and you’re probably thinking just about interns and summer clerks and associates. In my experience, you could have just stopped it. They’re over-subscribed with people they don’t need. To me, big firms — so what I have said several times when someone says, “Oh, these big law firms are doing all these layoffs.” I’m like this is an opportunity for big law firms to cut out the cancer as they call it, as we always called it in big law which was maybe and I don’t mean that in a toxic or negative way for employees but you don’t always need these days a one-to-one secretary and lawyer environment, you don’t need a mail clerk, you don’t need somebody that does filing if you’re an efficient and modern law firm and a lot of times in a sad but nice way, law firms are very, very loyal to staff, lawyers are and they’ll keep someone around that has maybe an attorney started with an assistant when that attorney was a baby lawyer, that assistant basically groomed them and now they’re not tech savvy, they’re not efficient, they’re great with clients on the phone, but that’s why we keep them and continue to give them a raise.


So it’s times like this where yes, there’s legitimate job cuts that are made but there’s also an opportunity that I know a lot of big law firms take and maybe small ones too.


Jonathan Greenblatt: For young lawyers, I think it’s even deeper than that. I think that what we haven’t come to grips with as big law is what is the functionality that you can actually charge the rates we want to charge for young legal talent. As clients are pushing back and that’s because the arms race has caused us to — because we’re so overpaying for unproven talent across the board, I’m not saying all people, I’m saying we’ve actually commoditized the price at a non-commodity rate, which doesn’t make a lot of sense.


I’m not sure there’s a market that I can think of that does that but that’s what we’ve done and as a result, that causes law firms to have to charge $500, $600, $700 an hour for junior talent which clients are choking on and they’re pushing back. And I think law firms are going to have to identify different functions that junior attorneys do and price accordingly, which means they’re not going to be able to afford the high price legal talent at that entry level. Doesn’t mean they can’t get there at a very high salary rate once they get experience and once clients are reaching for them, but we know the market is telling us it doesn’t want to pay that much and we keep forcing it on the client base.


The consequence for law schools is that law firms are cutting back on the size of their summer programs to some extent, not all, some are some are expanding them, there are a few. But by and large, law firms are grappling with what to put junior associates on. In my view, the profession hasn’t done two things. It hasn’t really right-sized to accommodate a world in which we can’t put junior associates on high leverage-type things that we used to. Document reviews has been taken away from us, that’s in contract attorney hands, corporate due diligence taken away from us, the repetitive kinds of work that some lawyers are able to do, loan agreements, et cetera, that’ll end up being covered by AI.


So the question will be, well, what will young attorneys add value on and should there be another path which is our view that there should be another path in at a lower price point where people get to demonstrate their skillset in real time where the law firm or the legal department can actually see them in action and then make the more permanent hiring decision once they’ve seen them and they know what their skillset is but also once they got experience.


And so our objective is to place people pursuant to a contract with a law firm or a legal department or anyone who wants to utilize talent, let the people demonstrate their skills over the course of a year or two and then our hope is they’ll fly away from us and they’ll actually land either at the place that they will call it apprentice if you want to call it that or whatever you want to call it, something like the English trainee system but a bit of a hybrid between that and what we do here. And then you’ll make the hiring decision. It’ll be a more intelligent hiring decision I would propose and it also allows people to launch their career with I think you can take a risk on more people if you bring the price point down and you’re not committed to them because it’s so hard.


As you said, it’s hard for law firms for lots of times for very noble reasons, but it’s very hard for law firms to part with people.




Adriana Linares: It is.


Jonathan Greenblatt: And it’s extremely expensive to carry people that you’re not keeping busy and it creates terrible morale issues when someone is essentially sidelined because nobody wants to work with them but they continue to be there for another year or two.


Adriana Linares: Well, let’s take a quick break, listen to some messages from some sponsors and then I want to come back and talk about this idea of getting that experience and going down that path and using that as a way for like you said, either landing where you want or in the case of a lot of listeners for this podcast, going out on their own and starting their own firm and using this opportunity or these types of opportunities as a way to get that experience so that when you do hang your own shingle, you’ve got a little more experience not just coming straight out of law school. We’ll be right back.




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Adriana Linares: All right. I’m back, I’m talking to Jonathan Greenblatt from Legal Innovators and we were just sort of talking about the role his company plays in helping law firms match sort of is that a good way to put it John, match new and young lawyers with the appropriate law firms and talents and pace schedules that they’re after? But I’m really interested in hearing you tell me either that this has happened or this is a good opportunity for a new lawyer, a young lawyer to go through the program to become part of Legal Innovators, get that experience at a big law firm. If their long-term goal is to be a solo practitioner or move to a small firm environment, I know that you deal mostly with big law, most of our listeners are solo small, maybe it’s an attorney who’s thinking about leaving a big firm. I have a lot of what I call big law refugees that leave and then go out. So have you seen that happen or is that something that you think would work in programs like this?


Jonathan Greenblatt: Yeah. I mean look, there are people who want to have nothing to do with big law or big law just doesn’t come in contact with and that doesn’t mean you can’t launch your career in many ways but I think and I didn’t understand this for example in a parallel situation which was the importance of clerking. When I came out of law school, I was tired of working in quasi academic type environments and wasn’t really interested in being a law clerk. Now, I understand that’s one of those badges that you use on your resume. So my resume would have been slightly less boring if I had said “and clerk for.”


Adriana Linares: Four items.


Jonathan Greenblatt: There would have been four items on mine. But it’s a network and we’ll talk about the importance of networking in a minute. It’s a network.


Adriana Linares: Yeah. I always like to remind people they hear that all the time but some people still are stubborn to really appreciate the value of networking. So yeah, let’s talk about that too.


Jonathan Greenblatt: Yeah, I will. If you can get into a big law firm through whatever exposure you can get and attach that to your CV and take the practical experience that comes with it as well, that’s forever there. You’re always an alum of that place. So in some ways, that firm may feel some allegiance to you even 20 years down the road through your own network at that firm but also, it’s a badge of credibility that other people look at and if you’ve got a boutique law firm that you’ve started on your own or you’re going to be picked as local counsel in a particular area and big firms are going to team up with you, it’s great to have that. It may not really a measure of credibility but it sends that signal.


Adriana Linares: No, I think that’s a really good point to make and it’s the type of thing where these days, feel like for the next couple years, new lawyers, new graduates are going to have to be creative, more creative than ever and it’s something I say all the time we lack a lot of creativity in legal but these are those times where looking at opportunities like this as a way to get your feet wet, get that experience, get that line item on your CV, on your bio, on your resume is critical. There aren’t a lot of programs like yours. There aren’t a lot of companies like yours, so if we’ve got listeners that we’ve piqued their interest and hadn’t thought about this, what would be two or three tips you’d give them in looking for programs like Legal Innovators or just looking at Legal Innovators?




Jonathan Greenblatt: Well, I think the starting point is some law schools aren’t great at this but if your place — I think you need to encourage your placement offices at the law schools to start thinking outside the box. They tend to know the law firms that they have a relationship with that come year after year to interview and I think it’s incumbent on the law schools themselves to adopt some of that creativity and help the law students and actually our program has gained quite a bit of traction with a lot of law schools. I mean, they have a self-interest in having people placed. It helps their US news and world report rankings so they want to do it. They also want to help their law students but I think some people have been in that office or those offices are very, you know, they’ve been there for a long time and they have their relationships and I think pushing them to expand their knowledge base as to what’s out there. We’re not the only alternative legal service provider out there that’s a growing segment of the market, tends not to focus on juniors. We’re focusing on juniors because we think that’s an area that has been neglected and if we can launch people in their careers even if they don’t land at the place that they apprentice, the idea is they’ll be more experienced than they are now.


Whether they start their own law firm, whether they use it to find a job, they’re in better shape than they were coming out of law school without a job and I think that young people are great at using the web and all sorts of ways of communicating through social media that the word gets out a lot faster that things exist, so some of it is incumbent on you yourself as a young lawyer to do and some of it is getting your law schools and the various affinity groups that you’re connected with like for example, BLSA. Because a lot of where we want to have ideally 50 of our lawyers be from underrepresented minorities.


Adriana Linares: What is BLSA?


Jonathan Greenblatt: BLSA is the black law student association at most law schools. So having those organizations become knowledgeable and if you’re not affiliated with BLSA, you may be affiliated with something else. But instead of relying solely on the placement office, there are these groups that you connect with often as a law student that can start to also pursue these leads and find ways for the people that are their members to open up opportunities because we’re going to have to be entrepreneurial.


Lawyers by nature are generally conservative. I don’t mean politically conservative, but conservative risk takers. It’s a whole different question as to whether the pay structure even at the partner level is designed to match the lack of risk that lawyers take, which investment bankers will tell you they find ridiculous that lawyers want to be paid as if they’re taking risk when they don’t take risk. But that’s a different conversation. At a young person’s level, it’s hard to be entrepreneurial when your nature is to be very conservative and not take a lot of risk.


But I’ve talked to enough people who have told me over the course of their careers that they were glad they took a risk on something because they did much better by pursuing something on their own rather than getting locked into a structure where they were dependent on other people’s evaluations of them all the time.


Now, that’s easy to say and hard to do but it’s a mindset I think we have to adopt.


Adriana Linares: Well, let’s take a last break we’ll be right back and wrap up our great conversation.




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Adriana Linares: All right, we’re back. I’m talking to Jonathan Greenblatt from Legal Innovators and I wanted to ask you, Jonathan, in this last segment as we talk about encouraging maybe young lawyers even if you’ve tried to go out on your own and maybe you’re struggling a little bit, you don’t have enough experience, maybe take an opportunity to go to a big firm for a year or two and gain that experience.




So my question for you would be let’s say we’ve got a listener or a couple or several that hear this and they think, “Huh, that’s not a bad idea. I’ll go in-house for a couple years.” To me, what I want to do is think of three or four tips or suggestions of how to make the most of that time so that if you do decide to move or stay or in my mind’s eye go out on your own and have your own law practice, what are the things I would want a young lawyer to really create good habits doing at big law and the first thing that is just obvious to me, which is the hardest thing if you’re not trained from the beginning is really good time keeping?


I deal with mostly solos, a lot of small firms and really a ton of lawyers who are not in the habit of tracking their time really well, which inevitably turns into the inability to bill at the level that they should be billing. So my first tip would be become a maniac about making a habit of tracking time, which at a big firm, they make that habit to create really easy because they push, they remind, they prod, they have tools. So that’s one thing I would definitely encourage. From your perspective watching these young lawyers go through clerkships, apprenticeships, maybe their first year as an associate at a big firm, what are some other good habits that they can develop and use as an opportunity to have for years later that people like me don’t have to try and break?


Jonathan Greenblatt: I have four. Follow leads, by that I mean go where the opportunity takes you and be open-minded about it and I’ll come back to it. Network, build a network-network even at a young age. It’s not just for partners at big law firms. Develop mentors and most people actually are honored to be mentoring someone who they who they click with but it’s on both parties to develop that relationship. You can’t just wait. The mentee has to also be proactive about it. And then the fourth thing is make yourself indispensable. If people can’t live without you, then they’re going to keep you and if you don’t want to stay, then they’re going to want to be sure that you land someplace that they’re comfortable you’re going to be potentially useful to them in the future.


Adriana Linares: That’s a great tip, exactly.


Jonathan Greenblatt: So, follow leads. You don’t take a straight path to your ultimate career. I can’t tell you a number of people who come to a big firm or not start in an area and they didn’t think they were going to become an aeronautics expert but you know what? They get a job by virtue of working on a deal for an aeronautics company. They end up going in-house and the next thing you know, they’re the associate general counsel in charge of securities for a big aerospace company.


They would not have predicted that coming out of — almost none of us are doing what we predicted we would do coming out of law school. I thought I was going to be arguing constitutional cases and the courts of appeals and I also thought I’d never have to deal with a number and I cross-examine damage experts all the time.


Adriana Linares: I was told there would be no math.


Jonathan Greenblatt: Yeah, exactly. I did everything possible to avoid that. I found that I’m not bad at it. Then network, build your network. I mean, that is senior people, peers, they’re people you stay in touch with your whole life and people want to help people they know. So there’s being the best at something and then there’s being known to someone and both of those things count. So develop your network at a young part of your career.


Adriana Linares: And let me jump in and give a couple more points there and that is you mentioned earlier really increasing diversity and using that as an asset. Well, there are a ton like you mentioned BLSA. In Miami, I can think of the Cuban-American Bar Association, the Black Bar Association, the Caribbean Bar Association. In San Diego, I can think of La Raza, the Latin-American Bar Association there. They welcome young lawyers and law school students and as a matter of fact, I’ll tell you real quick, the San Diego County Bar that I worked part-time for to help their members with technology had a virtual bench bar conference and I think there was one or two three Ls that showed up and everyone was thrilled and I think a lot of thrills don’t get involved at that level. Why would I go to a bench bar conference? But the judges were thrilled that there were law students there and it was a big deal and they were very welcoming and that’s the type you want to be seen. You want to shine from the very beginning.


So just throwing yourselves into those networking opportunities, those connecting opportunities especially now when you almost don’t have to leave your house and you can have that kind of welcome, it’s critical. So, I really encourage lawyers now it might seem like networking is harder than ever and keeping that community going but bar associations like San Diego are working really hard, harder than ever and we’ve got more engagement than ever now during this time. So, I just want to remind everybody this is not the time to slow down.




Jonathan Greenblatt: It took getting old myself to appreciate that when you’re old, you actually like — it’s kind of flattering to be asked to for assistance but when you’re young, you think it’s an intrusion and it’s really not. Not if it’s done correctly and not if it’s not overwhelming but there’s a way to do it and so, I would say develop these mentors and listen to what they have to say. You don’t have to follow their advice but listen to what they have to say. Factor it in and then make yourself indispensable. That just means on anything you do whether you’re interested in it or not, whether it’s grunt work or not, do it at a high level so that whoever is evaluating you thinks this person is always going to make me look better and help me in a way.


And most of us are humble enough to know what we’re not good at and that we need help in certain areas and when you have somebody who can fill that gap for you and makes themselves indispensable, you want to promote them and you certainly don’t want to lose them.


Adriana Linares: I love that. Well, it’s been so nice chatting with you, Jonathan. I very much appreciate your time. Before I let you go, tell our listeners where they can find friend, follow you or learn more about Legal Innovators.


Jonathan Greenblatt: Well, you can reach me at [email protected]. I’m on LinkedIn. I have no idea how to use Twitter or Facebook yet but the company Legal Innovators is on all of those things. Thankfully, we have people — that’s another example of where you have to rely on people who can fill in the gaps and we have them and my business partner Bryan Parker is very active on that as is our director of operations Meghan Smith.


Adriana Linares: Great! Well, thanks everyone for listening to another episode of New Solo on Legal Talk Network. If you like what you’ve heard today, please make sure to subscribe, share New Solo with your friends and colleagues, give us a nice rating on iTunes, I’d really appreciate that. We’ll see you next time and remember, you’re not alone, you’re a new solo.




Outro: Thanks for listening to New Solo with host Adriana Linares. Tune in again to learn more about how to successfully run your new practice solo here on Legal Talk Network.


The views expressed by the participants of this program are their own and do not represent the views of, nor are they endorsed by Legal Talk Network, its officers, directors, employees, agents, representatives, shareholders, and subsidiaries. None of the content should be considered legal advice. As always, consult a lawyer.



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Episode Details
Published: November 5, 2020
Podcast: New Solo
Category: Best Legal Practices
New Solo
New Solo

New Solo covers a diverse range of topics including transitioning from law firm to solo practice, law practice management, and more.

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