The Rainmaker: What 20 Years In Supreme Court Practice Have Taught Me; Above The Law, September 30, 2025

 Neal Katyal  , Above The Law; The Rainmaker: What 20 Years In Supreme Court Practice Have Taught Me

"The Improv Principle

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...

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."

THE LIBRARIAN OF CONGRESS AND THE GREATNESS OF HUMILITY; New Yorker, February 19, 2017

Sarah Larson, New Yorker; 

THE LIBRARIAN OF CONGRESS AND THE GREATNESS OF HUMILITY

"The new Librarian of Congress, Dr. Carla Hayden, is highly motivated to make this library, and all libraries, a favorite object of the people. Hayden is the first person of color, and the first woman, to lead the Library of Congress; she is also the first actual librarian to lead it since 1974. Her predecessor, Dr. James Billington, a distinguished Russia scholar appointed by Ronald Reagan, was beloved for his intellect but criticized for mismanagement; he neglected, for many years, to appoint a chief information officer, which was required by law, and he also didn’t use e-mail. Hayden, a former head of the American Library Association, revitalized and modernized Baltimore’s twenty-two-branch Enoch Pratt Free Library system. President Obama nominated her, in 2010, to be a member of the National Museum and Library Services Board, and, last year, to become Librarian of Congress...

Like many librarians, Hayden is a big believer in the rights of all people to educate themselves, and in the importance of open access to information online. (This inclusive spirit has become more urgent nationally in recent weeks: see “Libraries Are for Everyone,” a multilingual meme and poster campaign, created by a Nebraska librarian, Rebecca McCorkindale, to counter the forces of fake news and fearmongering.) In September, Hayden gave a swearing-in speech in which she described how black Americans “were once punished with lashes and worse for learning to read.” She said that, “as a descendent of people who were denied the right to read, to now have the opportunity to serve and lead the institution that is our national symbol of knowledge is a historic moment.”...

I thought of the drafts of Lincoln’s first Inaugural Address that a curator in the Inaugurations exhibit had shown me. Lincoln had originally ended his speech with a challenge to the South: “Shall it be peace or sword?” William Henry Seward had suggested an edit that pushed Lincoln toward a more conciliatory tone, and the phrase “guardian angel of the nation.” Lincoln turned that into the sublime “better angels of our nature,” an appeal to our common humanity. Our greatest President was also, possibly, our greatest reviser—a cutter and paster who questioned his imperfect ideas, accepted input, made them better, and kept all of his drafts, so that history could learn not just from his speeches but from the workings of his mind. The contents of the library, like Hayden herself, often directed my attention to the systems by which progress is made and recorded."