Ed. note: The Rainmaker is a new Above the Law series highlighting attorneys who have built distinguished practices by excelling not only in the courtroom and at the negotiating table, but also in business development, mentorship, and leadership. Each installment will feature candid reflections on what it takes to succeed as a rainmaker in today’s legal industry. Our first featured rainmaker is Neal Katyal.
About 20 years ago, I wrote a piece for Legal Times arguing that law schools fail to teach what matters most: how to work in groups. Fresh from the Justice Department, I had learned the hard way that brilliant legal arguments mean nothing if you can’t bring people along with you. I thought I understood that lesson.
I was wrong. Understanding it intellectually and living it daily are entirely different things.
Here’s the paradox of building a thriving Supreme Court practice: you succeed not by being the smartest person in the room, but by making everyone else in the room smarter. Supreme Court lawyers aren’t exactly known for their humility—we’ve built our reputations arguing before nine justices who can eviscerate your reasoning with a single question. Yet the rainmakers I’ve observed, and the practice I’ve tried to build, succeeds precisely because it inverts that stereotype.
The Improv Principle
For years, I’ve been studying improv comedy, and it’s transformed how I think about legal practice. The cardinal rule of improv is “yes, and”—you accept what your scene partners offer and build on it. You don’t say “no” or shut down their contribution. You make your partners look good, and in turn they make you look good.
This sounds soft. It’s not. It’s the hardest discipline I know.
In a meeting, when an associate offers an idea that seems off-base, the instinct is to correct them, to show why you’re the experienced lead counsel. The improv instinct is different: find what’s valuable in their contribution and build on it. “Yes, and we could take that framework and apply it to the jurisdictional question.” Suddenly, the associate isn’t embarrassed—they’re energized. They’ve contributed something real. They’ll work twice as hard for you, and next time, their idea might be the one that wins the case.
This isn’t artificial, it’s definitely not about giving false praise. A smart associate, after all, will see through that in a second. It’s rather about trying to find the diamond in the rough, the insight that the associate has and that can be built upon. I kind of stumbled upon that idea when I did my first case, challenging Guantanamo. At my side were a dozen law students – and they would all have various writing assignments and my duty was to sort through all their insights and build a coherent product out of it. Many were off-the-wall, to be sure, but many were brilliant, too. It just took work to find those flashes of brilliance and to build upon them. That kind of “bottom-up” strategy is one I have taken to heart – so much so that today I routinely take advice on crafting arguments from my Researcher at Milbank. My Researcher is someone who has graduated from college and yet has not attended law school.
This isn’t just about associates or your internal team, it’s just as much about clients. When a client pushes back on your strategy, you could dig in and explain why you’re right. Or you could listen—really listen—to what’s driving their concern. Usually, they’re telling you something important about their business reality, their risk tolerance, or their board dynamics. “Yes, and given that constraint, what if we structured the argument this way?” Now you’re not just their lawyer; you’re their partner.
Why Clients Return
Twenty-three years ago when I wrote that piece, I thought clients hired you for your legal brilliance. They don’t. They hire you because you make their problems smaller, not bigger.
I’ve represented the same clients through multiple Supreme Court cases, not because I won every time (I haven’t), but because they trust that I’ll listen to what they actually need. Sometimes what they need is an aggressive cert petition. Sometimes what they need is someone to tell them that the case isn’t worth the institutional risk of taking to the Court. The clients who keep coming back are the ones who know you’ll give them the second answer when it’s true, even though it costs you a major case and significant fees.
This requires a specific kind of humility: the humility to know that the client understands their business better than you do, and that your legal judgment is in service of their goals, not the other way around. Supreme Court lawyers can struggle with this because we’re trained to think about doctrinal purity and legal architecture. But clients don’t care about your elegant theory of administrative law. They care about whether they can build the project, launch the product, or avoid the devastating liability.
The best piece of advice I ever received came from Eric Holder, who mentored me at the Justice Department in my first stint there, right after my clerkships. He watched me fail to persuade senior officials of a position that I was absolutely certain was right. Afterward, he pulled me aside. “Your analysis was perfect,” he said. “But you didn’t listen to their concerns. You tried to convince them you were right instead of understanding why they were worried. Next time, start by understanding their perspective.”
That lesson echoes through every client relationship, every oral argument, every brief. Start by understanding their perspective.
Building a Team
The legal market is full of brilliant lawyers. What’s scarce is brilliant lawyers who other brilliant lawyers want to work with.
I’ve been fortunate to attract extraordinary talent to our practice at Milbank, and I’ve spent a lot of time thinking about why. It’s not compensation—plenty of firms pay well. It’s not just interesting cases, though we’ve had our share. It’s that people want to work in an environment where their contributions matter, where they’re not just executing someone else’s vision but actively shaping the strategy.
This means involving associates and junior partners in client conversations earlier than might be traditional. It means crediting their ideas explicitly in meetings and briefs. It means creating an environment where someone can say “I think we’re missing something” without fear. The best legal work happens when smart people feel safe being honest about uncertainty, about gaps in the argument, about weaknesses in the case. That safety only exists when egos are checked at the door.
In my 2002 piece, I argued that law schools, which focus on solitary exam writing, send the message that “to succeed I had to work as an island unto myself.” The most successful practices do the opposite. They’re archipelagos—distinct talents connected by shared purpose and mutual respect.
Other Firms
Here’s what surprised me most about building a practice: some of our best work comes from other law firms bringing us in on their cases. This seems counterintuitive. Why would a major firm want to split fees and credit with us?
Because we’re not a threat.
When you build a reputation for collaboration rather than competition, for making others look good rather than claiming all the credit, firms trust that you’ll enhance their client relationship rather than trying to steal it. We’ve been brought in on dozens of cases where the referring firm maintains the client relationship, handles most of the case, and brings us in specifically for the appellate-like stage, which is most often at the trial court. Everything from dispositive motions like motions to dismiss to issue preservation. We do the work, share the credit, and strengthen their relationship with their client.
This only works if you genuinely believe that there’s enough success to go around. The scarcity mindset—that every case is a zero-sum competition for prestige and credit—is poison to a sustainable practice. The abundance mindset—that by helping others succeed, you create more opportunities for everyone—is what builds a practice that lasts.
The Long Game
None of this is fast. You don’t build trust with clients, teams, and co-counsel through a single brilliant performance. You build it through hundreds of small interactions where you consistently choose collaboration over ego, listening over talking, “yes, and” over “no, but.”
The paradox of rainmaking is that you succeed by focusing on something other than success. You focus on making others successful—your clients, your team, your co-counsel. You build a practice where people want to return not because you won (though winning helps), but because working with you made them better at what they do.
Is this the only way to build a successful practice? Of course not. Plenty of rainmakers succeed through sheer force of will and brilliance. But I’ve found that the practices built on collaboration tend to last longer, weather storms better, and—ironically—attract more business than those built on individual genius.
The real world works in groups. Twenty years after writing that, I’m still learning what it means.
Neal Katyal is one of the nation’s foremost attorneys and former Acting Solicitor General of the United States. He is a partner at Milbank’s Washington, DC office, and serves as the Paul Saunders Professor of Law at Georgetown University, where he was one of the youngest professors to have received tenure and a chaired professorship in the university’s history. He has argued 52 cases at the Supreme Court, including landmark cases on gene patents, Guantanamo, the Voting Rights Act, and corporate law. He received the highest honor the Justice Department can bestow on a civilian, the Edmund Randolph Award, and has won all sorts of other awards, including being named one of GQ’s Men of the Year. He has performed in both Netflix’s House of Cards and Showtime’s Billions (both times playing himself).
The post The Rainmaker: What 20 Years In Supreme Court Practice Have Taught Me appeared first on Above the Law.
Ed. note: The Rainmaker is a new Above the Law series highlighting attorneys who have built distinguished practices by excelling not only in the courtroom and at the negotiating table, but also in business development, mentorship, and leadership. Each installment will feature candid reflections on what it takes to succeed as a rainmaker in today’s legal industry. Our first featured rainmaker is Neal Katyal.
About 20 years ago, I wrote a piece for Legal Times arguing that law schools fail to teach what matters most: how to work in groups. Fresh from the Justice Department, I had learned the hard way that brilliant legal arguments mean nothing if you can’t bring people along with you. I thought I understood that lesson.
I was wrong. Understanding it intellectually and living it daily are entirely different things.
Here’s the paradox of building a thriving Supreme Court practice: you succeed not by being the smartest person in the room, but by making everyone else in the room smarter. Supreme Court lawyers aren’t exactly known for their humility—we’ve built our reputations arguing before nine justices who can eviscerate your reasoning with a single question. Yet the rainmakers I’ve observed, and the practice I’ve tried to build, succeeds precisely because it inverts that stereotype.
The Improv Principle
For years, I’ve been studying improv comedy, and it’s transformed how I think about legal practice. The cardinal rule of improv is “yes, and”—you accept what your scene partners offer and build on it. You don’t say “no” or shut down their contribution. You make your partners look good, and in turn they make you look good.
This sounds soft. It’s not. It’s the hardest discipline I know.
In a meeting, when an associate offers an idea that seems off-base, the instinct is to correct them, to show why you’re the experienced lead counsel. The improv instinct is different: find what’s valuable in their contribution and build on it. “Yes, and we could take that framework and apply it to the jurisdictional question.” Suddenly, the associate isn’t embarrassed—they’re energized. They’ve contributed something real. They’ll work twice as hard for you, and next time, their idea might be the one that wins the case.
This isn’t artificial, it’s definitely not about giving false praise. A smart associate, after all, will see through that in a second. It’s rather about trying to find the diamond in the rough, the insight that the associate has and that can be built upon. I kind of stumbled upon that idea when I did my first case, challenging Guantanamo. At my side were a dozen law students – and they would all have various writing assignments and my duty was to sort through all their insights and build a coherent product out of it. Many were off-the-wall, to be sure, but many were brilliant, too. It just took work to find those flashes of brilliance and to build upon them. That kind of “bottom-up” strategy is one I have taken to heart – so much so that today I routinely take advice on crafting arguments from my Researcher at Milbank. My Researcher is someone who has graduated from college and yet has not attended law school.
This isn’t just about associates or your internal team, it’s just as much about clients. When a client pushes back on your strategy, you could dig in and explain why you’re right. Or you could listen—really listen—to what’s driving their concern. Usually, they’re telling you something important about their business reality, their risk tolerance, or their board dynamics. “Yes, and given that constraint, what if we structured the argument this way?” Now you’re not just their lawyer; you’re their partner.
Why Clients Return
Twenty-three years ago when I wrote that piece, I thought clients hired you for your legal brilliance. They don’t. They hire you because you make their problems smaller, not bigger.
I’ve represented the same clients through multiple Supreme Court cases, not because I won every time (I haven’t), but because they trust that I’ll listen to what they actually need. Sometimes what they need is an aggressive cert petition. Sometimes what they need is someone to tell them that the case isn’t worth the institutional risk of taking to the Court. The clients who keep coming back are the ones who know you’ll give them the second answer when it’s true, even though it costs you a major case and significant fees.
This requires a specific kind of humility: the humility to know that the client understands their business better than you do, and that your legal judgment is in service of their goals, not the other way around. Supreme Court lawyers can struggle with this because we’re trained to think about doctrinal purity and legal architecture. But clients don’t care about your elegant theory of administrative law. They care about whether they can build the project, launch the product, or avoid the devastating liability.
The best piece of advice I ever received came from Eric Holder, who mentored me at the Justice Department in my first stint there, right after my clerkships. He watched me fail to persuade senior officials of a position that I was absolutely certain was right. Afterward, he pulled me aside. “Your analysis was perfect,” he said. “But you didn’t listen to their concerns. You tried to convince them you were right instead of understanding why they were worried. Next time, start by understanding their perspective.”
That lesson echoes through every client relationship, every oral argument, every brief. Start by understanding their perspective.
Building a Team
The legal market is full of brilliant lawyers. What’s scarce is brilliant lawyers who other brilliant lawyers want to work with.
I’ve been fortunate to attract extraordinary talent to our practice at Milbank, and I’ve spent a lot of time thinking about why. It’s not compensation—plenty of firms pay well. It’s not just interesting cases, though we’ve had our share. It’s that people want to work in an environment where their contributions matter, where they’re not just executing someone else’s vision but actively shaping the strategy.
This means involving associates and junior partners in client conversations earlier than might be traditional. It means crediting their ideas explicitly in meetings and briefs. It means creating an environment where someone can say “I think we’re missing something” without fear. The best legal work happens when smart people feel safe being honest about uncertainty, about gaps in the argument, about weaknesses in the case. That safety only exists when egos are checked at the door.
In my 2002 piece, I argued that law schools, which focus on solitary exam writing, send the message that “to succeed I had to work as an island unto myself.” The most successful practices do the opposite. They’re archipelagos—distinct talents connected by shared purpose and mutual respect.
Other Firms
Here’s what surprised me most about building a practice: some of our best work comes from other law firms bringing us in on their cases. This seems counterintuitive. Why would a major firm want to split fees and credit with us?
Because we’re not a threat.
When you build a reputation for collaboration rather than competition, for making others look good rather than claiming all the credit, firms trust that you’ll enhance their client relationship rather than trying to steal it. We’ve been brought in on dozens of cases where the referring firm maintains the client relationship, handles most of the case, and brings us in specifically for the appellate-like stage, which is most often at the trial court. Everything from dispositive motions like motions to dismiss to issue preservation. We do the work, share the credit, and strengthen their relationship with their client.
This only works if you genuinely believe that there’s enough success to go around. The scarcity mindset—that every case is a zero-sum competition for prestige and credit—is poison to a sustainable practice. The abundance mindset—that by helping others succeed, you create more opportunities for everyone—is what builds a practice that lasts.
The Long Game
None of this is fast. You don’t build trust with clients, teams, and co-counsel through a single brilliant performance. You build it through hundreds of small interactions where you consistently choose collaboration over ego, listening over talking, “yes, and” over “no, but.”
The paradox of rainmaking is that you succeed by focusing on something other than success. You focus on making others successful—your clients, your team, your co-counsel. You build a practice where people want to return not because you won (though winning helps), but because working with you made them better at what they do.
Is this the only way to build a successful practice? Of course not. Plenty of rainmakers succeed through sheer force of will and brilliance. But I’ve found that the practices built on collaboration tend to last longer, weather storms better, and—ironically—attract more business than those built on individual genius.
The real world works in groups. Twenty years after writing that, I’m still learning what it means.
Neal Katyal is one of the nation’s foremost attorneys and former Acting Solicitor General of the United States. He is a partner at Milbank’s Washington, DC office, and serves as the Paul Saunders Professor of Law at Georgetown University, where he was one of the youngest professors to have received tenure and a chaired professorship in the university’s history. He has argued 52 cases at the Supreme Court, including landmark cases on gene patents, Guantanamo, the Voting Rights Act, and corporate law. He received the highest honor the Justice Department can bestow on a civilian, the Edmund Randolph Award, and has won all sorts of other awards, including being named one of GQ’s Men of the Year. He has performed in both Netflix’s House of Cards and Showtime’s Billions (both times playing himself).
