We've asked Cleary’s litigators to tell you about the benefits of playing devil's advocate; 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.
Alex ‘Lenny’ Leonard, associate: It is any formal process of dispute resolution that pits one side against another, and where there is a neutral party (e.g. a judge or jury) that will decide the outcome. Litigation can also cover regulatory and enforcement work, such as internal or governmental investigations, though at Cleary the enforcement work is viewed as somewhat distinct from the litigation work, even though the same lawyers tend to do both types and all are part of one litigation group.
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.
“It is any formal process of dispute resolution that pits one side against another, and where there is a neutral party (e.g. a judge or jury) that will decide the outcome.”
AL: The partners generally oversee the case. They have the primary interaction with the client to discuss strategy, goals, scope of work, and cost of work and billing issues. The partners also manage the team and have ultimate say in strategy within the firm. However, the partners will usually delegate the majority of the legal work to associates, at least in the first instance. Partners will sign important documents, such a court briefs or other official submissions, and usually will be the ones to speak at important court hearings or meetings; however, depending on the particular circumstances of a case, sometimes associates will take the lead at hearings or in important meetings. Partners will supervise the work of the associates, but the scope of authority delegated to associates will vary depending on the case, the partners and associates involved, the particular stage of proceedings, and the comfort of the particular client involved.
CA: What do the senior associates do?
AL: Senior associates manage the team and make sure everything runs smoothly and important deadlines are met. They tend to participate in strategy planning with the partners and, sometimes, the client. They also serve as a resource to more junior associates and make sure they are aware of and are involved with the broader strategy. Senior associates will usually revise work product, such as briefs, that more junior associates draft before the draft goes to a partner for review.
Senior associates also serve as an important point of contact for clients to go to with questions or requests. Similarly, they can interact extensively with counsel for other parties in litigation or, in the case of government investigations, with attorneys for the government. During discovery in litigation, senior associates will be involved in ensuring productions run smoothly and working with experts and may be involved in taking and defending depositions.
CA: What do the junior associates do?
VR: Junior associates usually take the first crack at legal research, but junior associates also get opportunities to draft briefs, participate in interviews, and interact with the client. I took my first deposition as a third year associate!
Richard Freeman, associate: Junior associates have a range of experiences at Cleary. As a junior associate, I researched and drafted briefs, communicated the team’s legal advice directly with clients, attended hearings, and managed sub-teams.
AL: Junior associates do the first-level work on a case. For example, they will do research, will draft the first cut of sections of a brief or a memorandum, will be responsible for knowing the documents and may do some document review, will help draft interrogatories and other discovery documents, will help prepare for depositions, and may take or defend some depositions.
Junior associates may also be involved in discussing strategy with the partners and senior associates, and, depending on the case, may also have contact with the client.
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.
AL: The litigation at Cleary also frequently involves travel as much of our work involves international companies, so you might spend time preparing for a trip to meet with key witnesses or to visit an important site. There is also frequently an effort to resolve cases through mediation or settlement discussions, so you might spend your day working on arguments about the merits of the case or potential liability to assist in those discussions.
“Winning is obviously a high – it feels pretty great when a judge grants your motion!”
For enforcement work, you might spend time working on a presentation to a regulator about the findings of an investigation or drafting an internal report to the client. You might also spend time meeting with a pro bono client or working on a brief or submission for his or her case.
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.
AL: Put simply, the highest of highs are when you achieve the resolution that your client wants, and the lows are when you fall short in that effort. Specifically, if you spend months working on a brief and you win on the issue that you drafted the argument for, that is a big high – and a bonus if the judge writes an opinion specifically using your language.
“...a cartel bribed a few corrupt executives at the company in order to secure favorable bids on projects.”
VR: 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.
RF: Winning cases is a ‘high’! But so is the team camaraderie as we figure it out together. I spend most of my time with a particular team that has been working together for a number of years on active cases. We have a set of shared experiences and humor that has developed over time, which makes my daily life at Cleary more fulfilling.
CA: Describe your latest case: what was the client’s problem? What was your role? How did you spend your time on it?
AL: My latest case was an enormous securities class action (In re Petrobras Securities Litigation) and related opt-out cases that we litigated for about three years before finally settling at the beginning of this year (it is still subject to final court approval). The client was accused of making material misstatements in its financial statements arising out of a multi-year corruption scheme wherea cartel bribed a few corrupt executives at the company in order to secure favorable bids on projects.
As an associate on the case, I worked on everything from motions to dismiss, to opposing class certification (so document discovery), to preparing for, taking, and defending depositions, to working with experts, taking an expert deposition, and beginning preparation for trial. When we appealed class certification, I also worked on drafting the appeal to the Second Circuit and helped the partner prepare for oral argument.
“The fact that we were ready to march into court gave our client credibility to push for what they wanted in the negotiations.”
VR: 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.
I was the senior associate on the team. I supervised junior associates, drafted and revised the papers, conducted witness interviews, participated in strategy sessions with the corporate and litigation teams, prepared talking points for negotiations, consulted with local counsel, and so much more. It was a great opportunity to use a wide variety of legal skills.
RF: I have been working on an appeal for a sovereign client (after we won a motion to dismiss an investor’s claims relating to the client’s bonds). My role was to coordinate researching and drafting our briefs in the district court and in the court of appeals, to provide case updates to the client, and to help moot the partner arguing the case.
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.
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.
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.
“It helps to be good at playing devil's advocate.”
CA: What personal qualities make for a good litigation lawyer?
AL: You have to be smart, driven, a hard worker, client-oriented, a good writer, a quick thinker, and have the ability to see things from multiple points of view. It helps to be good at playing devil's advocate.
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.
RF: Empathy, patience, perseverance, a healthy degree of skepticism, and an ability to imagine oneself in the shoes of a client, of an adversary, of a judge, and of a teammate.
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.
AL: You can prepare by just learning to analyze and critique cases, working on your legal research and writing, and by learning how to be organized and manage your time effectively. Practicing public speaking and thinking on your feet will also help.
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.
AL: Litigation is unique because companies or individuals can have disputes over anything, so you never know what kind of case you might be asked to take on, and it’s likely that the types of cases you will work on in your career will vary considerably (at least early on).
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.
RF: Litigation itself is not necessarily unique, but practicing as a litigator at Cleary is. Of course, Cleary grapples with the high-pressure demands that challenge the dynamics of any corporate workplace. But, the firm articulates a set of values around inclusiveness, collaboration, equality, dignity, and intellectual curiosity, while delivering the highest quality legal work to its clients. Those messages and values matter. They give lawyers at the firm a license to prioritize those values and to advocate for them. Litigators operate in an adversarial system, so being conscientious of our collective values – and of how we respect each other – is especially important in this line of work. Although some of our efforts play out more gracefully than others, I’m proud to be part of a law firm that strives to do more than just deliver great results, but to do that in a noble way.
AL: Cleary is unique in that there is a strong emphasis on making sure each associate has exposure to many types of litigation and enforcement work early on. Throughout your time as an associate you’ll get to work on both large and small litigations and large and small enforcement/investigation matters. You can also work on bankruptcy or international arbitration cases.
Cleary is also unique in that the practice is so international that you will be able to travel and be exposed to a variety of different companies and clients around the world. This can make the work more interesting than that at some of our peer firms, where the focus tends to be a bit more exclusively on domestic financial institutions.