Becoming a lawyer in a litigation boutique – the view from Holwell Shuster & Goldberg

Can you give a brief description of the work that Holwell Shuster & Goldberg focuses on?

Michael S. Shuster: At HSG, the litigation group is the entire firm. Since our founding in 2012, we have grown to about 60 lawyers, focusing on complex, high-stakes cases. We represent Visa in the largest-ever multi-district antitrust litigation, Chubb in litigation across the country regarding insurance coverage for opioid lawsuits, and are leading COVID-19-related litigation. We have represented PetSmart in an $8 billion dispute over corporate debtors’ rights, MacAndrews & Forbes in a substantial trial against News Corp, and Linda Macklowe in a historic marital dispute. We are also very proud of our robust associate-driven pro bono practice. 

Brian Goldman: The firm handles a broad spectrum of cases and disputes at all phases of a case.  Since starting here about two-and-a-half years ago, I have worked on an antitrust case, several multi-forum commercial disputes, a quirky separation-of-powers case progressing through state court, securities-related matters, and a number of appeals.  I’ve also been fortunate to have been part of two trial teams (one, an SDNY jury trial and the other, an international arbitration hearing), and have three trials scheduled to take place in 2022.   The firm is a group of litigators, and the firm’s attitude is basically that we can handle nearly any dispute from the pleadings to trial, and through appeal.

What do associates do?

BG: A lot. That is one of the reasons why I joined HSG, and it's proven to be true.  Associates, right from the jump, are expected to contribute substantively to cases—whether that’s drafting dispositive motions or appellate briefs, or liaising with the client (all of which I did in my first few weeks here).  Like traditional BigLaw firms, associates are expected to be intimately familiar with the facts and documents central to a case, and to know key deadlines.  But associates are also involved with bigger-picture strategic thinking and are actively encouraged to speak up in meetings.  The bottom line is that associates at HSG really get to see the entire case—from high-level strategy and client contact down to discovery—and the responsibility given to associates tracks that broad vista.  One of my most memorable experiences at the firm was taking a major witness at a trial, where the opposing counsel across from me was the senior partner on the case at a major international law firm.  It was just awesome.

Alison Miller: Associates participate in all aspects of a case, it’s truly a soup to nuts experience.  I typically have at least one major writing project on my desk at any given time—be it drafting a brief, complaint or discovery letter.  Beyond that, my day-to-day varies greatly depending on my caseload.  This past year I’ve been fortunate to serve on two fast-paced trial teams.  On these matters, I’ve been responsible for strategizing how to get our key evidence in at trial, second-chairing cross-examinations, preparing witnesses to testify, and negotiating evidentiary and logistical issues with the other side.   

Lauren Cole: Associates at HSG do everything.  HSG is a place where associates are given an abundance of learning opportunities to really develop their skills as litigators.  It is a place where the views and perspectives of the associates arevalued and taken into account as each team develops its strategy for litigating the case.  Associates write briefs and deposition outlines, but more than that, they are given opportunities to take and defend depositions, to communicate with opposing counsel, to talk to the client, etc.  Associates have the opportunity at HSG to be front-facing on high stakes and important litigation matters. 

MS: In our non-hierarchical structure, associates play an outsized role: meeting with clients, determining strategy, taking witnesses in trials, making arguments to judges, and even helping to set the direction of the firm itself. We staff matters leanly, and our partners don’t have the luxury or the desire to keep associates in the shadows. Quite the contrary. When HSG was appointed to the steering committee in multibillion-dollar litigation, we placed a mid-level associate in a position to become the de facto leader of the committee, which she did with exceptional results. She’s now a partner and member of our management committee. Our partners frequently “second-chair” lawyers at their first deposition, hearing, or trial as part of our commitment to developing talent. Associates play a lead role in our pro bono efforts, pressing cases and causes they (and we) are passionate about. 

What do partners do?

BG: At least from my perspective as an associate, the partner provides the primary point of client contact, and maps out the big-picture strategy – often after substantial back-and-forth with the whole team.  The partners and associates then work together to implement that strategy.  But beyond case management, the partners at HSG are actively involved with associate mentorship.  For myself, this has manifested in two forms of mentorship.  I’ve had partners provide substantive and technical feedback on my writing, which is enormously useful as a young lawyer.  The other form of mentorship that the partnership engages in is the more personal—asking whether I’m satisfied with what I’m working on, making sure I’m busy (but not hair-on-fire busy), and simply asking whether everything is alright.  The culture at HSG very much emphasizes inclusiveness, tightness, and collegiality among its lawyers, and that culture flows from the partnership on downwards. 

“The other form of mentorship the partnership engages in is the more personal… making sure I’m busy (but not hair-on-fire busy) and simply asking whether everything is alright.”

MS: Lean staffing goes both ways. Just like no job is too big for an associate, no job is too small for a partner. We are in the trenches on our cases, even while we are supervising them. Whether as part of our client work or through our structured and unstructured mentorship activities, we spend time working with associates to develop the skills and confidence necessary to succeed. 

AM: Partners serve as the client’s main point of contact and work closely with their teams to shape strategy and finalize work product.  Partners also serve as mentors.  When new matters come in the door, they take care to staff associates with an eye toward career development.

What makes for a successful litigation lawyer?

BG: Speaking from the perspective of a young lawyer, I think two skills stand out.  First, it’s important to have a mastery of the fundamentals of the case—the facts, the arguments, the weaknesses of your positions, and what’s likely to come down the pike in the litigation.  The second skill is learning to how to craft, synthesize, and then articulate your views.  I think many firms focus associate training on the former, but at HSG there is an emphasis on the latter as well.  It is routine here for associates to take or defend depositions, examine witnesses at hearings, present oral argument, pitch clients, etc.

AM: The word “tenacity” comes to mind.  Each case presents its thorny legal issues and delicate strategic considerations.  The most successful lawyers relish the challenge to navigate these roadblocks with curiosity, creativity and persistence.  There’s also no substitute for genuinely enjoying the art of lawyering and having a hunger to hone one’s craft.   

Lauren Cole: Creativity.  I have seen a creative lawyer turn a case from a likely loser into a winner.  You don’t have to litigate a case in a formulaic way.  If you are willing to put in some thought on how to do things differently, you can achieve different and better results for the client.  

MS: There is no single answer to this question. Being a litigator is, in some respects, more art than science—there are a lot of ways to do it well. That said, certain skills help: the ability to write clearly, think critically, present oneself confidently, anticipate counterarguments, and connect with people. It doesn’t hurt to have a little showmanship, either. Most important of all is the moral grounding and commitment to do the right thing, which was reinforced to me early on by my own mentors, including Judge Holwell. 

“Being a litigator is, in some respects, more art than science – there are a lot of ways to do it well.”

What are the positives of being at a litigation boutique?

BG: There really seem to me to be a lot of positives.  First, there is skill development, which results from substantive involvement in cases.  I interviewed an associate candidate recently whose writing sample was an internal research memo circulated to partners.  I had not seen one of these before; I later learned from a partner here that at HSG we generally don’t write research memos—you just do the research and then start writing the brief.  And so you develop skills quickly in a litigation boutique because you’re simply doing the work. 

The second positive is a strong culture.  Obviously, this differs boutique to boutique, but because boutiques are smaller than their BigLaw counterparts, culture actually exists—and matters.  We take great pride in our culture at HSG.  You celebrate wins and grumble about setbacks with the same group of people, day in and day out, and that creates a closeness that is hard to match in a bigger firm.      

MS: Litigation boutiques obviously differ from one another in culture, size, and in other ways. At HSG, we appreciate that our status as a boutique allows everyone to have a good overall sense of what the firm is doing and where it’s going, andto maintain an atmosphere of informality and friendliness. We are small enough that everyone knows one another, yet large enough that we can handle any case no matter the size or complexity. Partners work closely with all of our associates, and are able to provide day-to-day mentoring, making sure our associates are getting the training and work experience they came to HSG to receive. 

AM: Working at a litigation boutique enables young lawyers to roll up their sleeves and gain early experience from the get-go.  We get to know our colleagues very well and work with each other on multiple matters; you are never just a face in the crowd.   

LC: Being at a litigation boutique means that the hierarchical structure that applies at most big firms falls away.  This is great for associates because it means that you get to do higher level work as an associate and at an earlier stage in your career.  As a more junior associate, you operate in much the same way as a mid-level to more senior associate.  You also have much more contact with the partners and more opportunities to learn from them, as well as their ear to talk through various issues on each matter.  

What challenges are your lawyers facing at the moment within the current climate?

LC: One challenge is that the firm is quite busy at the moment, as is the legal market in general.  Unlike a big firm, a litigation boutique is less able to absorb additional work as the workforce is more finite.  But this can also be a boon for a more junior lawyer because it means there are more opportunities to go around. 

MS: Lawyers today are dealing with more uncertainty about the future of legal practice than we have at any point in recent years. The pandemic has made courts and law firms rethink basic questions. One is the role of the office—although thankfully, as a boutique with strong interpersonal ties, HSG enjoys some protection from the potential downside of work-from-home arrangements. Another question is whether “virtual” courtroom proceedings are here to stay. We successfully staged one of the first large civil trials to take place in New York during the pandemic, and hope that something resembling “normal” courtroom practice can return.  

AM: Law practice tends to be countercyclical in the sense that moments of turbulence are good for business.  The biggest challenge right now is that we are very busy!  

What are the trends and big stories in the litigation market?

MS: Here too, COVID-19 remains a significant story. HSG is at the forefront of a wave of pandemic-related litigation that we can expect to continue, if not grow, for years. Beyond the legal disputes, however, are the mental health impacts of the pandemic, including lawyer burnout and feelings of alienation, that we formed HSG in part to avoid. We think it’s more important than ever that law firms remain committed to maintaining supportive, inclusive, and welcoming environments. 

AM: There is a remarkable “race to the top” in associate compensation among the New York firms at the moment.  I began my career when we were still turning the corner on the financial crisis and firm jobs were hard to come by.  We seem to have come through on the other side and firms are eager to retain talent and keep up with the Joneses.  It’s not a bad time to be a law firm associate. 

“It’s more important than ever that law firms remain committed to maintaining inclusive and welcoming environments.”

What makes Holwell Shuster & Goldberg stand out as a place to practice litigation?

BG: Three things:  culture, responsibility, and breadth of practice.  The culture here is really thick—folks simply care about one another, and while we have high expectations of ourselves and our work, the partners treat associates and staff like people.  Unfortunately, the same is not true in many BigLaw firms.  Then there is responsibility.  At HSG, as an associate, you often take the lead on drafting pleadings, motions, and briefs.  That means a lot is expected of you, which can be both terrifying and exhilarating—but that’s what makes the practice of law fun.            

AM: As I like to tell anyone who asks, I believe HSG is the best place to practice law in New York.  We litigate at the highest levels opposite the most elite firms.  Our caseload is varied and generalized in subject matter and stage of litigation—from the initiation of an action all the way up to the Supreme Court.  The firm encourages associates to carve out their own career paths, such as through taking on pro bono matters, engaging in business development, or leading CLEs.  My colleagues are the best and the brightest.  Above all else, we value our tight-knit and non-hierarchical culture.  I appreciate the strong degree of support both personal and professional I receive on a daily basis. 

LC: There is a strong dedication among the partnership to associate development.  They want the associates to become better litigators and to have opportunities to learn and grow.  They also want to make sure that the associates are happy.  It is big enough to not feel like too small of a place, but small enough that the partners can really invest in the growth of each and every associate at the firm. 

MS: We think we have an extraordinary combination of highly talented and caring lawyers and staff who came to HSG because they were attracted by our culture, clients, and caseload. A decade after we started with just four lawyers, we’re well-established as a brand name in the New York and national market, but still young enough that everyone here plays a meaningful role in building the firm. In short: we have a great foundation, but lawyers who join us now are still getting in at the start of something. There’s an excitement to building something from the ground up, which is still very much in the air here. It contributes to the friendly culture we’ve built and work hard to maintain. 

What advice do you have for students looking to work within a litigation boutique?

BG:  During my clerkship, when I was deciding whether to join HSG or join a larger, more traditional BigLaw firm, one of the hiring partners here noted how, contrary to conventional wisdom, it’s actually riskier to simply join a BigLaw firm—where the training can be hit or miss, and partnership prospects are often slim—than joining a boutique.  That seemed kind of backwards to me at the time, but I really think it has turned out to be true.  If someone were to tell you that you could take on (much) more substantive responsibility, be involved on case strategy, and work with a close-knit group of lawyers who care about one another—all while being paid the same as a BigLaw firm—I think the decision would be obvious:  go to the boutique.  People complicate that choice when they lean more heavily on considerations, such as a firm’s name or ranking, which, while important, don’t by themselves develop any skills.  So my first piece of advice when choosing a firm is to put proper weight on things that actually matter.

If you’ve made the decision to join a boutique, one thing that often gets overlooked—beyond law school, or grades, or clerkship—is connection with the people.  Like I said, HSG has a special culture, and the lawyers here are protective of that.  The more you can learn about a boutique, whether it’s HSG or otherwise, the better you’ll be able to present yourself in a way that suggests you’ll fit seamlessly into the culture.  Don’t be afraid to email a lawyer at the firm before your interview, even if you only have a tangential connection to him or her.

AM: Litigation boutiques are for self-starters.  Take a wide array of courses to find out what interests you and be prepared to hit the ground running.  Don’t hesitate to reach out to connections or even lawyers whose firm bios grab you.  The only way to get to know a firm is to get to know its people. 

LC: Students should talk to as many lawyers as possible at each firm.  Boutiques are often small enough that it is conceivable you could speak with everyone or almost everyone at a firm.  Students should try to really get a sense of each firm and the types of personalities and culture at each firm. 

MS: I don’t think students need to prepare much differently for a litigation boutique than for a larger firm, clerkship, or government position. I would say, though, that they should come prepared to roll up their sleeves and contribute. Many litigation boutiques, like HSG, have “flat” teams where younger lawyers will get a lot of exposure to partners, clients, and lawyers at other firms. That presents wonderful opportunities for growth and learning. There’s not a lot of “waiting your turn” at HSG—at least that’s the hope. As much as possible, junior lawyers should be prepared, and eager, to take depositions, argue motions, and communicate directly with clients.