Becoming a commercial litigator – by Cleary Gottlieb

Commercial Litigation

We've asked Cleary’s litigators to tell you about the thrill of the wins; why mastering the art of storytelling is crucial; and how a high degree of empathy can make all the difference.

Chambers Associate: How would you define litigation?

Jonathan Kolodner, partner: At Cleary Gottlieb, we define our litigation group broadly to cover a range of different practice areas, including civil litigation, arbitration, and white-collar criminal defense and enforcement. We are also a global disputes practice, meaning that we often work on matters across our 16 offices and handle litigation and investigations that involve multiple jurisdictions. And, of course, we have a significant pro bono litigation practice as well.

Thomas Kessler, associate: I think litigation is the height of strategic lawyering. In most situations, whether in our securities cases, bankruptcy litigation, arbitration, or regulatory or internal investigations, we are working to determine facts that have already happened and figuring out how to utilize them as we work to achieve our clients’ desired outcome.

We also work with our transactional colleagues on corporate deals and, in that respect, we get to help structure transactions in order to minimize or eliminate the risk of litigation (or at least make sure that, if litigation does occur, our clients are in the best position to respond).

Lindsay McKenzie, associate: As a practicing attorney, I try to challenge myself to think about litigation in the larger context of a problem that a client has; often, one of many problems. Understanding that context is key to thinking strategically about litigation strategy and what approach best meets the client’s needs.

Vanessa Richardson, associate: Litigation also includes strategic thinking before any proceedings begin to help parties anticipate potential risk, understand their options, and build a stronger case.

CA: What do the partners do?

JK: Litigation partners obviously have a range of responsibilities. Partners are responsible for advising clients and supervising litigation matters. Partners are also responsible for managing the practice generally, as well as marketing and business development. And critically, partners are responsible for training and mentoring associates, who are the future of the firm.

“Junior associates are the engines of any litigation.”

Partners are also very involved in making sure that the client and firm put their best foot forward during high-stakes events, like court appearances and high-profile presentations or conference calls.

CA: What do the senior associates do?

TK: Senior associates are largely responsible for the workflow of a case. They work with the partners on strategic planning and often have significant client interaction, sometimes serving as a primary contact for particular issues or work streams. Senior associates also typically review drafts of work product (i.e. briefs, arbitral submissions, whitepapers, etc.) written by junior associates before they are circulated to partners and are actively encouraged to ensure that the more junior members of the team receive both substantive experience and direct contact with partners and clients.

LM: Senior associates manage the matters on a day-to-day basis, with an eye toward bridging the gap between the work product and activity happening at the junior associate level, and channeling the big-picture perspectives that a partner or client is more likely to be attuned to. Senior associates make important decisions on their matters all the time based on these considerations.

CA: What do the junior associates do?

TK: Junior associates are the engines of any litigation. They often take the lead on research and, when timing and caseload permit, funnel that work into drafted work product. A junior associate may also have the opportunity to try their hand at more senior-level work, including taking or second-seating a deposition, or being the primary associate to prepare for a hearing. When I was a first-year associate, I took the lead on several motions/briefs, including an oral argument, and was even able to take my first deposition.

LM: Junior associates are frequently the ones taking the first shot at drafting work product, whether it is important correspondence with clients, regulators, or opposing counsel, or research memos for the partners, clients, or others. Each matter is an opportunity to show enthusiasm and a willingness to learn and improve.

CA: What kind of work is involved in the day-to-day?

JK: Our daily work varies tremendously; that is one of the exciting parts of our practice. On some days, I will be actively engaged in an investigation, often across multiple jurisdictions, conducting interviews, reviewing key documents, or discussing strategy with the client or the global Cleary team. On other occasions, I will be having discussions with, or making presentations to, regulators and authorities. I also spend time meeting with clients, discussing their needs and concerns and providing guidance (as best I can) to help them.

“Winning is obviously a high – it feels pretty great when a judge grants your motion!”

For civil litigation matters, research and analysis are key and frequent components of our work, so we spend time exploring, revising, sharpening arguments in our cases, and infusing our strategic decisions with legal authority. There is similar work done in our white-collar enforcement matters, a practice that is part of the broader litigation group but involves matters that are quite different procedurally. In those matters, we also spend a lot of time investigating the facts of the case by reviewing key evidence, interviewing witnesses, and developing a broader understanding of the context in which the alleged conduct occurred.

CA: What are the highs and lows?

JK: It is always exciting to achieve a good result for a client in an investigation or a dispute, such as a civil litigation. But I also find it satisfying to help a client solve a difficult legal problem, to provide the answer to a question that a client has asked, and to help a client prepare for problems in advance, by giving them the benefit of our experience.

As you can imagine, as a litigator in the arena (to paraphrase Teddy Roosevelt), there are sometimes lows (and losses) as well.

“I was lucky enough to join the case when Cleary first got the call...”

Winning is obviously a high – it feels pretty great when a judge grants your motion! But it is also a high when you find a very helpful document, get someone to make a great admission in a deposition, or put the finishing touches on a strong brief. Our cases are challenging and exciting, and it is thrilling to read about your work in the paper.

Lows come when it feels like there is just too much to prepare and not enough time. The only way to get through those times is to have a laugh with your team and take it step by step.

TK: There is nothing like a jury announcing a verdict in your favor in a case you have been a part of since its inception. Securing an advantageous settlement might not feel like the classic win, but it is often the best outcome for a client and a well-earned source of pride for the legal team. Beyond the outcome of a case, it’s always great to hear from a client that a brief or presentation, which necessarily represents many hours of hard work by the team, was persuasive and well done.

CA: Describe your latest case: what was the client’s problem? What was your role? How did you spend your time on it?

TK: I had a case a bit outside of my ordinary practice. We advised a company that had been threatened with a whistleblower suit. We worked closely with colleagues from multiple practice groups, including employee benefits, capital markets, and M&A, to develop a deep understanding of the matter’s background, while assessing the relevant legal issues that could come into play. We were ultimately able to place the client in a strong negotiating position, which led to a successful resolution of the dispute pre-litigation.

LM: On a white-collar enforcement matter, the client had identified concerning conduct by one of its employees and was very quickly trying to understand what had occurred, how far it extended, and how to take the necessary steps to remediate any live issues. I was lucky enough to join the case when Cleary first got the call to get involved; it was extremely busy, and sometimes stressful, but always exciting. My role was helping to investigate what happened, assess the potential enforcement and litigation consequences of the issue, and help the client think through how to remediate it.

“The fact that we were ready to march into court gave our client credibility to push for what they wanted in the negotiations.”

My latest case was an M&A related matter. Our corporate colleagues had negotiated a transaction, but the buyer was indicating that it might refuse to close. So we had to quickly learn the details of the transaction and analyze the strength of potential arguments. But because it takes some time to get papers ready, we were simultaneously drafting a complaint. We also prepared talking points for the client to use in negotiations, so we could build a favorable record. Fortunately, they worked out a business resolution, so we did not have to actually file the papers. But the fact that we were ready to march into court gave our client credibility to push for what they wanted in the negotiations.

CA: What’s the most interesting litigation case you’ve worked on?

JK: It’s nearly impossible to pick a single case. I’ve worked on a number of incredibly interesting (and fast-paced) investigations, often involving interviews and reviews in multiple countries, for clients who need quick answers in order to make decisions to resolve a possible crisis. It’s particularly rewarding to have the opportunity to work closely with clients in those circumstances, and hopefully to guide them to an effective and satisfying resolution of whatever problems they are facing. I also love the opportunity we get as litigators to spend time on a regular basis learning about a new industry or business since we need to understand how our clients operate in order to represent them.

VR: One of the most interesting litigation cases I have worked on involved representing Brazilian oil company Petrobras in a securities fraud class action litigation and dozens of individual actions in connection with one of the largest corruption scandals in history. It was really exciting to work on such a high-profile international matter involving cutting edge issues of securities law, and we won an appeal to the Second Circuit.

TK: I would be lying if I said that my very first case didn’t have a special place in my memory. We teamed up with the Southern Poverty Law Center to challenge a conversion therapy organization’s practices on the grounds that they had violated a consumer fraud statute. Even beyond the personal passion I had for the work, the case was an incredible opportunity to develop skills that would serve me throughout in my career – including taking a deposition, drafting briefs, and arguing contested motions at trial.

LM: As a junior associate, I worked on a matter that involved a large health care company that had been sued derivatively by a shareholder after the company settled a number of regulatory investigations into an alleged kick-back scheme. In addition to the specific facts of the case, I got the opportunity to learn about the health care industry and board members’ fiduciary duties, both of which I found interesting and useful.

CA: What are the current trends in litigation?

JK: Whether we are talking about civil litigation or white-collar defense and enforcement, litigation continues to be very active. From my perspective as an enforcement litigator, one current (and significant) trend that I see is the continued growth of multi-jurisdictional investigations, as more non-U.S. authorities become active (for example, in connection with corruption investigations).

“Clients and judges have begun to push for more diverse teams.”

There is related growth in civil litigation in the U.S. and elsewhere connected to these investigations. For example, a securities class action litigation in the U.S. can be based on the stock drop associated with a significant new enforcement investigation. Civil litigation has also changed over the last few years with the growth of third-party litigation funding, which aids plaintiffs in bringing (and funding) long-term litigation.

VR: One major trend affecting litigation right now is how much technology is revolutionizing the practice. It touches everything we do, and it is very important to keep up-to-date and to adapt to changes. Better technology also means that clients demand their litigators to be extremely responsive and as efficient as possible.

LM: One trend that I’ve noticed is that judges and senior practitioners are looking to give juniors lawyers more opportunities to speak in court. This is a welcome change that will greatly benefit the next generation of practitioners (and their clients).

CA: What would you say the future of practicing litigation looks like?

JK: It’s always difficult to predict the future, but for now, I think the litigation and enforcement practice will continue to grow. On the enforcement front, there is always a question with a new administration whether there will be a change in the government’s approach. But so far at least, the U.S. authorities and regulators continue to be very active.

VR: I hope the future of litigation practice looks more diverse. Clients and judges have begun to push for more diverse teams, and Cleary has been extremely proactive about recruiting and mentoring diverse associates. I am hopeful that those efforts will pay off.

“You need to think about what will be persuasive and compelling for the decision maker, be it a judge, jury, or arbitrator.”

Cases are only becoming more complex. Plaintiffs and defendants are pushing the boundaries of legal theories and doctrines, exploring the contours of a statute or line of cases to find a novel angle that might give their client the edge. Being on the leading edge of that creative thinking is exciting and a constant motivator for enhancing my own skills.

CA: What personal qualities make for a good litigation lawyer?

TK: A good litigator will be curious, tenacious, and have excellent strategic and creative thinking. It’s also important to think about how your target audience will receive what you’re working on. What questions or concerns will they have, and how might you implicitly respond to those questions (or allay those concerns) in your work product?

VR: Empathy affects your work in so many ways. You need to take the time to really understand your client’s goals, fears, and priorities because that will change your legal advice and recommendations. You need to think about what will be persuasive and compelling for the decision maker, be it a judge, jury, or arbitrator. And finally, you have to figure out the best way to motivate and inspire your colleagues because you need everyone on your team to be working together to deliver exceptional work product.

LM: Attention to detail is critical for an effective litigator— particularly when you are researching and thinking about legal authority and when you are preparing work product. Being able to think both as an impartial analyst and an advocate for your client is very important, and being able to get up to speed quickly on the facts of a case, and the relevant law, serves a litigator well.

JK: I think the most successful lawyers are more than just smart and thoughtful individuals with strong advocacy skills. They are proactive, engaged strategic thinkers with excellent judgment. They also care deeply about their clients and are able to establish close personal relationships with them and truly understand their businesses.

CA: What can students do to prepare themselves for a career in litigation?

JK: There are certainly some important classes that students should take, such as evidence, that will be helpful to future litigators. More importantly, I think students should do everything they can to get real-world, on-their-feet experience, both for the experience itself and to get exposure to different areas of the practice. This might take the form of a law school clinic (such as for a legal services organization, or a U.S. Attorney’s Office), or by volunteering for an organization.

“Read widely, and not just legal stuff. Litigation is about telling a compelling story, and there are lots of ways to do that.”

Students can also look for opportunities to get similar experience during their first-year summer. I recommend taking trial practice (or moot court) classes as well – again, it’s helpful to get as much of this kind of experience as possible!

VR: Read widely, and not just legal stuff. Litigation is about telling a compelling story, and there are lots of ways to do that.

TK: I would encourage students to seek out any opportunity they can to write from a persuasive viewpoint. So much of what we do is writing – whether it’s emails to partners, clients, or adversaries, or the many types of work product we create every day. Being able to write persuasively and concisely is critical to being a successful litigator and, as with all skills, it takes practice.

CA: What makes the field of litigation unique?

VR: Litigation is unique because most of your clients don’t want to be involved in it. Litigation is stressful and distracting for the parties. As a litigator, you can help to guide your client through an awful situation and make them feel like they are in good hands.

TK: Because our clients can become embroiled in litigation in almost any circumstance, we’re constantly being asked to learn and advise on new and interesting factual scenarios – and often through the lens of new legal issues.

LM: Litigation weaves together so many different skills sets and components, but it is primarily about thinking carefully, critically, and creatively, and especially being able to tell an effective story on your client’s behalf.

CA: Could you describe the opportunities unique to Cleary?

JK: Our matters are endlessly interesting and challenging. Many of our litigation matters are cross-border, and we work closely with our colleagues in Cleary’s offices outside of the United States all of the time. In addition to offering all of our lawyers the opportunity to work on these global matters, our litigation group is also very flexible, and our associates get the opportunity to work in all areas of the practice depending on their interests.

VR: Litigation at Cleary is special because we get to be generalists, and we aren’t expected to choose a major early in our career. That means junior associates can try lots of different things and work with lots of different people. I get to work on all kinds of cases and have had opportunities to develop a wide variety of legal skills.

TK: When I think about my first few years at Cleary, what strikes me the most is the presumption of competence that permeated every assignment I received. I felt instantly trusted by my colleagues to do substantive work with real-world applications. I always pushed to do my best but never felt like I was being made to prove myself before given “real work.” In my experience, and I think in the experience of our associates generally, that presumption enables you to get excellent experience very quickly, and to build on the experience much earlier in your career than I think is typical.

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