I recently went one-on-one with Robert Giuffra, Co-Chair of Sullivan & Cromwell.
Adam: What compelled you to become a lawyer?
Robert: My father was a lawyer, so I always tell people I went into the family business. He was a litigator and a trial lawyer, and when I was probably nine or ten years old, he would take me to court, and I would watch him. I also remember at dinner, he would tell stories about the cases he was handling and the trials he was working on. When I was going to Little League practice, he would be sitting in the stands, going through his papers, getting ready for the next trial. He was a very hard-working person, and I think I got my work ethic from him. There was also a bit of Perry Mason coming to life for me.
I was a competitive golfer in high school and into college, and I sometimes think I might have been a teaching pro if I had stayed with that. But my natural aptitude was to be a lawyer. When I think about other things I could have done, maybe investment banking or business, law was the profession that suited me best. I’m verbal, I can write well, I can analyze things, I can think through problems, and I’m very good at strategy and taking complicated issues and simplifying them. I genuinely like being a lawyer. You often hear that some lawyers don’t like what they do, but I really love it and always have. I also think a law degree is a great degree because you learn how to think and solve problems, and lawyers have always played a central role in how this country is structured. We’re a very law-driven country.
Adam: How did you become a great lawyer?
Robert: There are a few things. One of the most important, which people don’t focus on enough, is having great mentors. Law is a profession where one generation trains the next, and you can’t really learn it from a book or a classroom. I went to Yale Law School, where the teaching is very theoretical, but to become a great lawyer, you have to watch other great lawyers. I was fortunate. I clerked for William Rehnquist, the Chief Justice of the United States. I worked on a case with Robert Bork for three years. I clerked for Ralph Winter on the Second Circuit, one of the great appellate judges. At Sullivan and Cromwell, I worked with some of the best lawyers in the world. You learn by watching what they do well and incorporating it into your own style.
You also have to love what you do and be willing to work hard. Hard work can take you a long way, but you also need common sense and leadership ability. As you get more senior, you’re leading large teams, and you need to understand what people are good at and put them in the right roles. Some people are great writers, some are great in court, some are strong at analyzing facts, and you have to bring that together into a team. There’s also an element of grit and perseverance. All four of my grandparents were immigrants who came through Ellis Island, and my grandfather was listed as a peasant on official records. Now I sit in a corner office at Sullivan and Cromwell overlooking the Statue of Liberty, and that perspective matters. Litigation requires resilience. You may lose multiple times before you win. I worked on a case for Goldman Sachs that lasted over a decade and went all the way to the Supreme Court. You have to believe in your position and stick with it.
Adam: Can that immigrant mentality, grit, and work ethic be taught, or is it purely innate?
Robert: I worry about that a little bit. As people become successful, you want your kids to have things maybe that you didn’t have. You want them to go on nice vacations, live in a big house, have help at home. I had a housekeeper growing up, and I’ve always been relatively neat, but there’s something to be said for discipline in small things. There’s that idea, I think it was Admiral McRaven, about if you want to change the world, make your bed. There’s truth to that.
I don’t make my bed anymore, and I don’t know if my kids ever made their beds, but my children are hardworking. They all went to top schools and did well. My oldest daughter works at Goldman Sachs as an analyst, which is not a place for slackers. But it’s different when your grandparents came through Ellis Island and didn’t speak much English, and none of them went to college. That experience shapes you.
I do worry that when kids grow up with privilege, with nice apartments, nice houses, and exposure to wealth, it can be harder to instill grit. And grit and perseverance are incredibly important, especially in litigation. I’ve had cases where I lost multiple times before eventually winning on appeal. I worked on a case for Goldman Sachs that lasted over a decade and went to the Supreme Court. You have to be willing to stick with something when you believe you’re right.
Adam: When you’re building your team, when you’re hiring people, and then when you’re looking at who are going to be the next leaders within your organization, who are the people you want?
Robert: I always tell people that if I had a choice between someone who is a high EQ person or a high IQ person, I would take the high EQ person every time. You want someone with common sense, especially in what I do, where you’re constantly interacting with people and trying to persuade them. Someone who is very smart but can’t explain their ideas clearly, or ends up confusing people, is not going to be a great lawyer.
The best ideas are simple ones. The key to being a great communicator is to simplify ideas, not to complicate them. If you look at great communicators, they simplify ideas and repeat them again and again. That’s a big part of being a great litigator. You figure out the winning strategy, and you repeat it consistently to your audience, whether that is the client, the judge, or the jury. Even if you lose at one stage, you have to be prepared to keep pressing forward. Litigation is not a straight line, and persistence matters just as much as intelligence.
Adam: When you say the best ideas are the simplest ones, is there an example that stands out?
Robert: There are many examples. One that stands out is when I represented Volkswagen in their emissions scandal. This was one of the most iconic brands in the world, and they were accused of cheating on emissions tests in the United States and globally. You could have tried to litigate that case for years and years at enormous cost to the company and its reputation. I made the decision early on that the right strategy was a fast, global settlement. We accepted responsibility for what had happened, compensated customers, and worked to resolve the matter as quickly as possible. We settled the U.S. cases in record time, within about a year. The goal was to put the issue behind the company.
It was a simple strategy once defined, and it was easy to explain. I’m also currently representing Argentina in a very large case, and one of our core arguments is straightforward. Why should a U.S. court decide a dispute that involves Argentine law and should be litigated in Argentina? There’s complexity behind it, but the core idea is simple. I find that bad lawyers tend to complicate things, while good lawyers simplify and get to the core issue. I often say that if you can’t explain why you should win in a minute, you probably don’t deserve to win. And you should be able to explain it to someone who is not a lawyer. If you can’t explain it to your kids, you probably don’t have a clear enough argument.
Adam: How do you develop a successful legal strategy?
Robert: I basically think about cases along a continuum. At one end, there are cases that nobody can win. At the other end, there are cases that anybody can win. And then there are the cases in the middle where being a really good lawyer can make the difference. So the first thing I try to do is figure out where on that spectrum the case falls. From there, I look at whether we are actually in the right. I look at the equities, which matter more than people think. People assume law is just about statutes and precedent, but fairness and perception matter a lot. I analyze the facts and the law as deeply as possible.
You never want to be in a position where you don’t know the facts better than your opponent. And you have to look at everything in a clear-eyed way. You can’t put on rose-colored glasses, and you can’t just tell the client what they want to hear. A lot of lawyers do that. They tell clients what they want to hear until things start going badly. I believe in expectation management. If you’re realistic with the client from the beginning and then perform at or above that expectation, you build trust. I would much rather under promise and over deliver than the other way around.
Adam: How can anyone find great mentors and develop successful mentor-mentee relationships?
Robert: I think you have to be open to it and keep your eyes open. Everyone has a different style, and unless you’re working for a solo practitioner where you only have one option, you’re usually going to have multiple potential mentors. You have to figure out who you connect with and try to work with those people. Most senior people actually like having really strong junior people around them. If you’re smart, hardworking, and make their lives easier, they’ll want to invest in you.
But one thing I feel strongly about is that I don’t like yes-people. I don’t want people who just agree with everything I say. I want people who will challenge me and tell me when I’m wrong. It’s much better to hear that internally than to have a judge point it out later. You also can’t ignore weaknesses. If there are bad facts in your case, you have to deal with them directly and figure out the best explanation. If there is bad case law, you can’t pretend it doesn’t exist. You have to address it and explain why it doesn’t control your situation. That’s part of being a strong lawyer and part of learning from the people around you.
I don’t actually think you should only look for people who are just like you. If you do that, you end up reinforcing the same habits and perspectives. I think you should be open to working with different kinds of people. For example, there are lawyers who are very aggressive, what you might call pit-bull litigators. They can be very effective in certain situations, but that approach can also backfire. I’ve worked with those types of lawyers, and I’ve learned from them. I’ve also worked with people who are more big picture and less focused on details. From them, you learn strategy. Then there are people who are extremely detail-oriented, and from them you learn precision and discipline.
Some lawyers are great oral advocates, and you can learn how to present in court from them. Others are great writers, and you learn how to craft arguments on paper. Some people can do all of these things, but I think it’s important to expose yourself to different styles so you can develop range.
One thing I pride myself on is having different gears. I can adjust depending on the situation. That’s becoming less common because specialization has become so dominant. Many lawyers focus on a very narrow area. I believe in a more generalist approach. In my career, I’ve handled a wide range of matters. I’ve represented professional sports teams like the Giants and Jets. I’ve worked on cases involving the America’s Cup. I even handled a case involving retired thoroughbred racehorses. I also work across trials, appeals, and government investigations. Many lawyers only do one of those. I think having that range gives you a broader perspective and allows you to solve problems more effectively.
Adam: How can a lawyer become a great generalist?
Robert: It’s hard, and it’s one of the biggest challenges we face. It’s much easier to take a young lawyer and have them do the same thing over and over until they become very good at it. But that can be limiting if that area later declines in importance. I remember during the financial crisis, I interviewed someone who had spent ten years doing real estate securitization. That market collapsed, and suddenly their expertise wasn’t as valuable. They hadn’t developed a broader skill set.
Looking ahead, a lot of repetitive work is going to be replaced by technology. AI is already changing the legal profession and will continue to do so. There will likely be tools that can draft briefs, create presentations, and even outline arguments. As that happens, the value of being able to think broadly and adapt will become even more important.
We make sure people don’t do the same thing again and again. We push them outside their comfort zones and give them opportunities to work on different types of matters. The idea is to challenge them while still providing support. We often put younger lawyers into situations where they’re dealing with more senior lawyers on the other side. That can be intimidating, but it’s how you grow. I had those experiences myself when I was younger. You get better by being tested and by handling difficult situations.
You can’t become a great lawyer if you stay in your comfort zone. It can be stressful to work on something for the first time, especially when the stakes are high, but that’s part of the process. Over time, those experiences build confidence and capability.
Adam: What is your process when it comes to preparation?
Robert: I’m big on getting a lot of input from different people and really understanding the details. I want to know the facts inside and out. At the same time, I’m focused on identifying the winning theme, the winning strategy, or the core narrative. I don’t believe in walking into court with fifty different arguments. I want two or three that really matter and that I can explain clearly and simply.
When you get a question from a judge, especially a hard one, you need to be able to answer it directly and then use it as an opportunity to reinforce your argument. We do a lot of moot courts where we simulate the courtroom environment. We have people act as judges and ask difficult questions. The first time you go through it, you’re not as good. By the second or third time, you improve significantly. By the time you get into the actual courtroom, it feels more familiar. It’s like batting practice. You wouldn’t expect someone to face major league pitching without preparation. The same applies here.
The problem is that the first time you see a curveball, it looks like it’s coming at your head. And when someone throws really fast, it’s hard to track. You have to respect how skilled those athletes are. Someone like Aaron Judge can see a ball coming at a hundred miles an hour and still make contact. That takes incredible timing and reflexes.
Adam: I was great in the batting cages because I knew exactly where the ball was coming and at what speed. But in actual games, it was a completely different story.
Robert: Exactly. In practice, you know the speed and location. In a real game, everything is unpredictable. The same is true in court. You have to prepare for that unpredictability. You can’t assume everything will go according to plan.
I’ve won cases where the judge clearly didn’t like my client. I’ve been in courtrooms where things didn’t go the way I expected. You have to be ready for anything. Even small things like technology can fail. I’ve had situations where everything was working perfectly until I stood up to cross-examine a witness, and suddenly the system stopped working. You have to adapt in real time.
Experience matters a lot because the more situations you’ve seen, the better you can handle unexpected developments. Most people aren’t great in court the first time. You make mistakes, you learn from them, and you improve. You also have to be willing to step outside your comfort zone. That’s where growth happens.
Adam: What are the keys to building strong client relationships?
Robert: The most important thing is not to oversell. It’s much better to under promise and over deliver. You also have to be honest with clients. Some lawyers tell clients what they want to hear, but that doesn’t help anyone. Listening is critical. You need to understand what the client is going through and what they care about. There’s also an element of empathy. In some cases, especially criminal cases, the stakes are incredibly high. A person’s freedom and reputation may be on the line.
Another challenge today is that people communicate less face-to-face. A lot happens over email or messaging, and while that’s efficient, it’s not always effective. Being able to read people and understand their reactions is an important skill. Communication is not just about talking. It’s also about listening and observing.
Adam: How can anyone become a better communicator?
Robert: Simplification is key. The older I get, the more I believe that. You need to be able to take complex ideas and express them clearly. You also need to communicate in a logical way, moving from one point to the next in a coherent structure. I also believe in using visuals where appropriate. In court, we often use graphics, documents, timelines, and charts. People process information both visually and verbally, and combining those can be very effective.
Another important point is not to rely on reading from notes. If you’re just reading, you’re not engaging with your audience. You need to make eye contact and connect with people. And repetition matters. You often have to say something multiple times before it really sticks.
Adam: How do you approach understanding your audience and tailoring your message?
Robert: It depends on the situation. If you’re dealing with a jury, you can do jury research and testing to understand how people in that jurisdiction think. You can also observe the jury during the trial to see how they are reacting. If you’re dealing with a judge, you can research their background, their prior decisions, and their tendencies. At higher levels, like the Supreme Court, people generally know where the justices stand on various issues, and you can tailor your arguments accordingly. Ultimately, it’s about understanding who you’re trying to persuade and shaping your message in a way that resonates with them. You can’t just go in and talk without thinking about your audience.
Adam: How can you build and ultimately protect your reputation?
Robert: It’s becoming increasingly hard in the world we live in. I’m a big believer in being straightforward with people. I never raise my voice in court, and I don’t raise my voice with adversaries. If I tell someone we’re going to do something, we do it. I don’t play fast and loose with the facts, and I don’t overstate things in briefs or in arguments. I don’t lie. If someone wants that, they can hire someone else.
I try to stay within the facts and present things in a rational and logical way because it’s more effective. If you exaggerate or make statements that are not accurate, your opponent will expose that. I actually prefer going against lawyers who yell and scream because it’s not effective. I don’t rely on that style. I don’t like the overuse of adjectives or dramatic language. It doesn’t help your case. I also try to treat people the way I would want to be treated. I don’t believe in being a bully. That kind of behavior might have worked decades ago, but it doesn’t work today. It’s much better to come across as calm, measured, and credible. You want to sound like someone who is presenting the facts clearly, not someone who is trying to overwhelm the room.
Reputation is fragile. You can spend years building it and lose it very quickly. That’s even more true now because of the internet. People can say anything, and it can spread quickly. So you have to be careful. And when you make a mistake, you have to own it and correct it.
Adam: What are the key pitfalls that people should look out for?
Robert: Social media is a big one. You can get yourself into trouble very quickly. You have to be aware of where the lines are and try to stay within them. It’s also important to avoid situations where you could be compromised. In law, you also have to be careful because you’re relying on clients. A client might tell you something that is not accurate, and you have to verify what you’re saying before you present it as fact. You can’t just repeat something without doing your own diligence. I try to stick to the facts and the law and avoid anything that could be misleading. And if we make a mistake, we acknowledge it and fix it. That’s important for maintaining credibility.
Adam: How do you develop the conviction to stay the course, especially when there is pressure to change direction?
Robert: You have to recognize that judges and juries are human beings. They have their own perspectives and biases, and that can affect outcomes. There’s a saying that a good lawyer knows the law, and a great lawyer knows the judge. There’s some truth to that. There are times when you believe strongly in your position, but you lose at the trial level. You have to decide whether to keep going, whether to appeal, and whether the client is willing to continue. I’ve had many situations where we lost in a lower court and then won on appeal. And sometimes you can lose again and have to keep going.
There’s always an element of uncertainty. You can do everything right and still lose because of the decision maker. That’s part of litigation. You have to be prepared for that and have the confidence to continue when you believe you’re right. One concept I often talk about is landing the plane. A good lawyer always has multiple strategies and is thinking ahead. If something unexpected happens, you need to adjust and find another path to a successful outcome. It’s like playing multiple games of chess at once. Every move has consequences, and everything is connected.
Adam: You have taken on many high-profile and controversial cases and clients. How do you decide whether to take on a case or a client?
Robert: One of the first questions is whether I think the client is in the right, or at least whether I think I can make a meaningful difference. There are situations where a client has done something wrong, but the goal is to achieve the best possible outcome under the circumstances. At this stage in my career, I’m less interested in certain types of work, like cases where there is very little strategy involved, and the outcome is largely predetermined. But if a case raises important legal issues or has broader implications, that’s something I’m more likely to take on.
People sometimes forget what lawyers do. Lawyers are supposed to represent clients who have problems. Historically, great lawyers have taken on difficult and controversial cases. They are not defined by their clients. They are defined by how they handle the work. I’ve represented many clients who are not popular, and some of the most interesting cases I’ve worked on have been in that category. If it’s an important case and there is an opportunity to make a real impact, that’s something I’m interested in.
Adam: How do you approach managing and motivating people on your team?
Robert: It’s challenging, especially in a large organization. I’m not just managing, I’m also actively practicing law. I try to lead by example. I stay involved in the work, and I think people learn by working alongside me and seeing how I approach things. A big part of leadership is putting people in positions where they can succeed. You need to understand their strengths and give them opportunities to develop. I also focus on maintaining a positive environment. I don’t believe in yelling or creating fear. That’s not effective.
Delegation is very important. You can’t do everything yourself. You need to trust your team and give them responsibility. At the same time, you need to be available to guide them and step in when necessary. I also think it’s important to recognize people’s contributions. A simple thank you goes a long way. People want to feel that their work matters and that it’s appreciated.
You have to put yourself in their position and understand what motivates them. Different people respond to different things. You also need to be good at matching people to the right tasks. That’s something you get better at over time. I try to keep people in a positive mindset and create an environment where they feel supported. I don’t see much value in being harsh or overly critical. You get better results by being constructive.
I also spend a lot of time reviewing work and giving feedback. For example, I mark up briefs in detail. With tools like Track Changes, people can see exactly how I’m thinking and how I would approach something. That helps them improve. I prefer face-to-face conversations when possible. It’s much more effective than long email chains. You can resolve issues more quickly and communicate more clearly.
I’ll also say something that might be a little controversial. I think being busy is generally better for your mental health than having too much free time. If you have too much time on your hands, you can end up watching too much television, spending too much time on social media, and overthinking things. If you’re busy and engaged, you’re interacting with people and focusing on meaningful work. That tends to put you in a better mindset. I’m not saying that applies to every situation, but in general, staying active and engaged is helpful.
I also believe in small habits that add up over time. For example, I always take the stairs instead of the elevator if it is just a few floors. Over the course of a career, that adds up. Living in a city like New York makes it easier to stay active because you can walk places. In other cities, you have to be more intentional about it.
Adam: For a lot of lawyers, the challenge isn’t staying busy; it’s managing that busyness. How do you manage your time?
Robert: That’s one of my biggest challenges. I have a lot going on at any given time, and I could easily fill more hours than exist in a day. One of the most important things is delegation. I try to push as much work as possible to talented people on my team so I can focus on the areas where I add the most value. If I get a draft of a brief that is already very strong and needs minimal changes, that’s ideal. If it needs more work, I’ll step in and help shape it. I also try to structure my day in a logical way, so I’m not constantly moving between unrelated tasks or locations.
Technology has made it easier to work flexibly. Sometimes I’ll work from home in the morning to get focused work done. I also have a great executive assistant who helps manage logistics, which frees up time and mental energy. Structuring your life so you can focus on what matters most is very important.
Delegation is critical because if you can’t delegate, you can’t scale. There is no way to handle complex matters alone. The cases I work on often involve large teams, sometimes dozens of people. You need to rely on others and trust them. At the same time, you have to make sure people feel valued and that their contributions matter. That’s part of leadership. People want to know that their work is appreciated and that they are part of something important.
A lot of it comes down to confidence. You have to trust that your team can handle things, and you have to be willing to step in if needed. Sometimes the first version of something is not great, and that’s fine. You give feedback, and the next version is better. That’s how people learn. I’ve had many situations where a draft was not strong initially, but after feedback, it became excellent. That is a win for everyone. The person improves, and the work product improves. Over time, you build a team that can operate at a very high level.
Adam: How can someone develop emotional intelligence?
Robert: I think part of it is being aware of other people and paying attention to how they react. You need to be able to read a room and understand different perspectives. Listening is a big part of that. So is empathy. Some people are naturally better at it than others, but I do think it can be developed. You can improve by interacting with a wide range of people, observing how different situations unfold, and learning from those experiences. People who are very high IQ but lack interpersonal skills often struggle in this profession. You need to be able to connect with people, communicate clearly, and build relationships. That’s just as important as technical ability.
Adam: What advice do you have around taking risks?
Robert: Every day involves some level of risk. The key is being willing to step outside your comfort zone and take on new challenges. That’s how you grow. In my case, I didn’t take big career risks in terms of moving around a lot. I spent most of my career at the same firm. But I took risks in the cases I chose and the way I approached them. I was willing to handle complex, high-stakes matters and figure things out as I went.
Not every risk pays off, and luck does play a role. For every success story you hear about, there are many people who took similar risks and didn’t have the same outcome. But if you’re not willing to take on challenges, it’s hard to reach a high level. You have to be comfortable with uncertainty and willing to put yourself in situations where you might fail. That’s part of the process of building a successful career.
Adam: Is there anything else that you would share with anyone who wants to become a great lawyer or a great leader?
Robert: I think one of the most important things is discipline. Discipline in how you work, how you prepare, and how you conduct yourself. This is not a profession where you can just show up and wing it. You have to be prepared, and you have to be consistent over a long period of time. I also think integrity matters a lot. Your reputation is everything. If people trust you, that opens doors. If they don’t trust you, it doesn’t matter how smart you are. You will not be effective. So you have to be honest, you have to be straightforward, and you have to do what you say you are going to do.
Another thing is you have to be willing to learn continuously. The law changes, the world changes, and the way people communicate changes. You can’t just rely on what you learned early in your career. You have to keep adapting. And I would say, don’t be afraid of hard work. There is no substitute for it. There are a lot of very smart people out there, but not everyone is willing to put in the effort. If you combine intelligence with hard work and good judgment, you can go a long way.
