Willy Jay leads the Supreme Court and Appellate Practice at Paul, Weiss. He's led hundreds of appellate matters, and in this conversation he explains what he means by being a technical lawyer: understanding how courts actually work, what limits them, and what they can realistically be persuaded to do. We talk about choosing between a high-probability outcome and a long-shot ideal one, about writing a brief before you know which judges will read it, and about explaining technical material to judges who are smart but not experts in your client's field. Willy also describes the short-term, medium-term, and long-term approach he takes to business development, and the specific things he's still trying to get better at after decades near the top of appellate practice.
Top Insights
- Appellate strategy is often a choice between a high-probability "A-minus" outcome and a much less likely "A-plus" one, and knowing which one actually serves the client matters as much as the legal argument itself.
- The argument that won at trial doesn't always work on appeal, because appellate judges are constrained differently than juries or trial courts.
- Since you often don't learn your appellate panel until the morning of argument, Willy writes briefs that can persuade across different judicial philosophies rather than betting on one type of judge.
- Good appellate advocacy depends on reading judicial constraints accurately: what a court can realistically be persuaded to do, more than what it technically has the power to do.
- Willy splits business development into three tracks: short-term (someone just lost and needs help now), medium-term (a live case that might need an appeal down the road), and long-term (staying visible to industries and repeat litigants who may need him someday).
- After decades of practice, the skill he says he's still working on is not letting an ignored pitch discourage him from sending the next one.
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Full Transcript
Khurram Naik: All right, Willy. I'm really happy to have you here, because I think this is going to be a great opportunity to get into the nitty-gritty of appellate law. I'm excited to jump in.
Willy Jay: Yeah, I'm excited to be here. Thanks for having me.
Khurram Naik: So Willy, in our conversations, a theme that's been consistent is your approach to appellate practice and how you think about your work. And the term you used in our first conversation is "technical lawyer." That's a term I think needs some defining. Can you help us understand what it means that in your practice you were a technical lawyer?
Willy Jay: So when I was a brand-new associate working in an appellate practice, someone described Justice John Paul Stevens, who was then an associate justice on the Supreme Court, as a great technical lawyer. And I'm sort of using it in that sense: understanding the ins and outs of how courts do their work, and what limits them in getting to particular results. Some of that could be summarized as what you learn in a Federal Courts class in law school, the limitations on federal judicial power and on the power of federal courts. And some of it is more like what you learn in a Legislation and Regulation class, which is about how judges read statutes and how judges understand precedent. Those things come together in a complicated case when human judges, especially a multi-member appellate panel, are trying to figure out: What do I have to decide? What order do I have to decide it in? And how do I reconcile what I want to do with what the precedent, the statutes, and the other limitations on what I do tell me I can, must, or must not do?
Khurram Naik: So starting with a trial court decision of some kind that's appealable, and you have a client with a desire, a goal, how do you take that raw material and shape an appellate strategy? Maybe there's an example of how you do that.
Willy Jay: Sure. I think a lot of appellate strategizing is understanding what has a chance of success and what the client wants to get out of the appeal. And those don't always match up. The thing that would benefit the client most might be something that has only a 20% chance of success, either because of the facts of the case, or because of the difficulty in getting an appellate court to take up this kind of issue, if it seems like it's second-guessing a jury, or second-guessing the trial court on something that's really more in the trial court's discretion. Whereas sometimes your more purely legal arguments might be really appealing to someone who's just grading in the abstract, how good an argument is this, does this seem right, but the client might say, "That's great, but if we got an opinion saying that, it means we have to do the whole case over again in some other venue, and that's not what I'm looking for. I'm looking for a different outcome, business certainty, or a final resolution." So having the world's best venue argument might not matter to the client if the client needs this case to be over, not relitigated in a different venue. And on top of that, judges understand the same thing, and an argument that a court should tear up an entire final judgment and send a whole case back to square one is a bigger ask than correcting a judgment based on a fairly straightforward legal error.
Khurram Naik: So as a minor aside, it sounds like you're saying appellate judges also think about judicial economy. Thinking about, hey, if we really get this right, even if it's, quote, the right answer, it's an expensive answer. Is there a less expensive answer from a judicial-resources and appellate-interest perspective?
Willy Jay: Yeah, I think they think about it. Is this something I must do? And if it's not something I must do, then judicial economy, I think, weighs in on whether it's something I should do, and in what sequence. Not just what you decide, but perhaps in what order you choose to decide the issues.
Khurram Naik: So in terms of client objectives, clients may have objectives that need to be aligned with the constraints of how judges decide. Are there instances where you've reframed objectives for clients, where you say, "It seems your objective is this, but actually I think there's a more powerful objective you can achieve through an appellate strategy"?
Willy Jay: All the time we encourage clients, and our co-counsel who tried the case or got it as far as the appeal, to let go of particular issues and think about what the case is now going to be about on appeal, which may or may not be the same thing you told the jury or the trial judge the case was about, because of the limitations on what federal appellate judges, or state appellate judges, are able and willing to do. So a case that was once about winning a complete victory might, on appeal, wind up being about getting a do-over, because that's the most realistic possibility. A client might want to shoot for a hundred percent, the A-plus, shoot-the-moon outcome, but if that's not realistic, you may handicap yourself from getting an A-minus outcome as your fallback if you spend all your time on the unrealistic pursuit of the ideal one. Each case is different, and there are cases where clients say, "I realize it's an uphill battle, but what I need is the 20% outcome. Be really good at your job, beat the odds, and get me that." But in other cases clients decide to play percentage ball and say, "I'd be satisfied with this A-minus outcome, which has a much larger probability. Let's go for that. Let's reframe the appeal as pursuit of that." It can be hard to do both, because you can only capture an appellate judge's attention for a limited time. A lot of appellate judges will say, if you tell me you have seven issues, you're really telling me you have no issues. They want more focus on what the real issues are, more distillation of what went wrong and what you want them to do about it.
Khurram Naik: I feel like the stereotype of an appellate lawyer is someone who lasers in on one specific matter, on the legal issues, and is totally wrapped up in the particulars of fashioning a strategy. Is it ever the case that you're zooming out, saying, "Are there patterns in this industry, or with this type of company, that I've observed across appellate matters, that direct my guidance for this particular client"?
Willy Jay: There definitely are types of cases, for types of clients, in particular courts, where you can see patterns. In the IP litigation space, there definitely are patterns. Where a life sciences patent has been upheld by the Patent Trial and Appeal Board and there's no claim-construction issue, I think you can regularly say this is probably not going to be easy to overturn on appeal. In the tech space, for example, there's statutory immunity for online companies, if you're familiar with Section 230, which protects internet service providers from liability. There are a lot of judges who really hate Section 230 and think it's grown like kudzu beyond where it was originally planted. So being able to understand whether you're facing a court that's on a mission to cut back whatever doctrine or statute you're relying on, or a court that's resigned to the precedent and willing to say, "I don't like the precedent, but it sure seems like we immunize a lot of things under Section 230, and I'm just going to follow it," that can be a strategic understanding as well. A lot of things go into judicial decision-making, and resignation, making your peace with precedent, can be one of them. So your question was about industry-specific knowledge. Yes, up to a point. But judges, just as they don't spend all their time on bankruptcy or environmental law or copyright, don't spend all their time with litigants in a particular industry either. It's a question of how many reps this appellate court has had with this issue and this type of client. Do they see a lot of products-liability cases for companies that make consumer products? A lot of IP cases in the high-tech space? You're always asking what the judge knows about this case compared to what the lawyers know, because the lawyers usually know their clients and the legal framework a lot better than the judge does, at least to start. A judge who's very experienced with a particular type of case gets up to speed on the facts much more quickly. Whereas if you have to explain what a bankruptcy doctrine does, why we have it, how it works, how many times the circuit's precedent has considered it, what the statute says, when it changed and why, before you even get to the facts of your case, that's just, as a practical matter, less advocacy you can do about why you should win.
Khurram Naik: So maybe this is a zero-sum aspect of how much you have to explain, how much background you provide, versus making it clear to the judge why you should win, why you must win. What are the constraints the appellate judges are operating under?
Willy Jay: Right. If I were saying to the District of Delaware, "This is a Hatch-Waxman case," I probably don't need to say any more than that, and they'll understand what kind of case this is. If I were saying to a judge hearing an antitrust case about patent settlements, "This was a Hatch-Waxman case," I probably have a lot more explaining to do before that judge is up to speed.
Khurram Naik: On that note, judges sit by designation, and that can be bidirectional, say, between the Federal Circuit and a district court. Judges see perceived value in that, and broadly speaking I think we'd agree it's useful. Have you ever found that useful in your practice? Is that something you'd want to try, if you haven't, like a trial?
Willy Jay: I have been to trial, but very consciously as the appellate lawyer who went to trial. So I don't talk much. When I talk, it's not in front of the jury. It tends to be about jury instructions, preservation of error, standing objections, things like that. No one is likely to hire me to examine a witness. But I do think understanding enough about how trials operate, how trial judges operate, and why the evidence comes in the way it comes in makes you a better appellate lawyer. Someone who's never had any contact with the trial-court process is probably not going to be as effective, no matter how good a writer, how good a technical lawyer they are. But I've never said a word to a jury.
Khurram Naik: And you don't plan to, it sounds like.
Willy Jay: I don't plan to.
Khurram Naik: Is there something specific you can point to? Maybe at some point in your career you were very focused on appellate work, particularly at the Solicitor General's Office, where you're obviously not really working on trial-court issues, but then in private practice you get pulled into it, since that's the bulk of what any practice is doing, trial-court practice. As you learned more about trial-court proceedings, is there a specific example of how that influenced your appellate work?
Willy Jay: When I was an associate at a firm, I got a lot of encouragement to do a lot of different things, don't just be an appellate lawyer, in part because you need to work with more people, but also because it'll make you a better lawyer to have done work in trial courts. Sometimes that meant things as mechanically simple as: get this case removed, write a motion to dismiss, get it granted, the end. Writing-heavy tasks about federal jurisdiction, preemption, statutory defenses, or the elements of a cause of action, things people who focus on written and oral advocacy can be good at. When I went to the Solicitor General's Office, all of a sudden essentially a hundred percent of my work was appellate. I never had to think about whether that was the right mix, because that was what I was hired to do, and what came into my inbox every day. So when I left government, that was what I was good at, what I'd spent the last several years doing full time, and what the market was looking for from me primarily. So that's what I focused on. But trying to understand as much about the litigation process from soup to nuts, in order to give better advice and develop better strategy, matters too. You might well walk into a court of appeals and have one of your three judges be a visiting district judge who has no appellate experience but knows very well how a trial should run. Being able to sound notes that resonate with that person, especially if you didn't have much notice, in the Fourth Circuit, the Seventh Circuit, the Federal Circuit, you find out your panel that morning. If you have the visiting district judge, maybe it's a surprise, but being prepared for that, and having the vocabulary to talk to those people as well as people who have a million reps on the jurisdictional doctrine we're discussing, that can be really important.
Khurram Naik: I want to return to that in a moment, but I think we're onto something interesting here. A district judge sitting by designation happens, but it's rare, and generally you don't know until the day the panel is announced, as you mentioned. That makes you think about edge cases. It sounds like you found value in being prepared for edge cases like that. How much time do you spend preparing for edge cases versus focusing on the core?
Willy Jay: I think one of the most important things about being a good appellate lawyer who argues cases in appellate courts is understanding who your audience is, or might be. In the Supreme Court, it's the same nine justices every time, and you know from the moment the Court grants your petition that it will be heard by those nine. I've had a few cases where there was a surprise, or a recusal, during the briefing process, or even right before argument, but short of a surprise like that, in the Supreme Court you know who you're talking to. That doesn't happen in the courts of appeals. You write the briefs in complete ignorance of who the audience is. So you have to think about who the possible audience is. Am I unjustifiably putting all my chips on getting a certain type of judge? What if we get two or three of that kind? What's that person going to get out of my brief that they agree with? That tends to produce briefs that are hedged in some respects, that speak on multiple layers, because the audience may be listening for different notes in the harmony. Some judges may be moved by something that seems more discretionary, and some by more technical arguments, the sort of thing a young lawyer would give an A-plus but the client would find impractical. Judges are the same way. Some are more pragmatically skeptical of a particular reading of a statute or a record, and others may be more open to it. Understanding the range of decision-makers you may be talking to is helpful. I wouldn't say I go into argument with, "This is what I'd say to Judge X, this is what I'd say to Judge Y if she's on the panel." It's more like, if we get a panel heavily interested in this, or a visiting district judge, or judges who are young and more likely to be savvy about this particular technology versus judges who are 85 and not known to be tech-savvy, that affects what kind of explanation I'm giving and what kind of vocabulary I'm using.
Khurram Naik: It seems like one of the canonical questions in appellate lore is what kind of call you're making, and there are different layers to that. But it seems like what you're describing, with this hedging, is that you can maybe have your cake and eat it too. Maybe you make a call that one issue is the most important, the thrust of your brief, but there's a skillful way to hedge, where the secondary argument is strongly appealing to a numerically larger number of judges. Is that a dimension to your practice, or does it make things too complicated?
Willy Jay: In the Supreme Court, where you know who the personalities are and what commitments they bring to deciding your case, I think you have to think about that, and that's one thing amicus briefing is consciously used for. There are cases where, if you're going for a majority that includes Justice Thomas but also justices with very different sensibilities, you might or might not be able to cram into your brief everything that would persuade Justice Thomas while still leaving room for the very different considerations that might persuade Justice Sotomayor and Justice Jackson. I've seen people write basically two sentences for Justice Thomas: "Please see the brief filed by originalist historians in support of us," thirty pages of historical sources Justice Thomas will find persuasive. In a Supreme Court case, the justices only decide about 60 or 70 cases a year, and they will go and read the amicus briefs. Especially if your methodology calls for looking at history or text in particular ways, presenting those sources, even in an amicus brief, is a legitimate strategy. That's a lot harder in a court-of-appeals brief, because it's just your brief. You don't have, say, 14,000 words, and you don't know who all the possible readers are. Writing two thousand words for an idiosyncratic judge who might not even be on your panel is pretty hard.
Khurram Naik: So returning to technical lawyering, I think a useful question is: technical lawyering as opposed to what? This goes back to what we were talking about at the beginning.
Willy Jay: I think there are a lot of lawyers who are really excellent in their chosen fields, whether that's litigation or some substantive area of the law. There are true experts in bankruptcy, or in particular aspects of environmental law, for example. When I've worked with people like that, the discussion we have about how we're going to win the case is often: they focus on, "This is the right answer, this is where we need to get to, this is the answer that best fits with the seamless web of bankruptcy law." And my job is to nitpick and say, how are we going to get a federal appellate court, in this posture, to agree with that? Sometimes the disagreements we have are about arguments that we think might serve our appellate colleagues, that I think are good readings of the statutory text, but that a subject-matter expert would say we can't make, because it doesn't fit with the agency common law that's grown up over forty years. The question becomes: what's persuasive to the audience we're in front of? Is it three young appellate judges who grew up being taught statutory interpretation in law school, more read-the-text, damn-the-consequences decision-makers? Or are they sympathetic to, "I don't know what I'm doing, I'm not an environmental lawyer, I don't want to accidentally upset the applecart, I want to move very cautiously through this difficult and unfamiliar area"? Sometimes it's a mix. If current practice is on your client's side, then warning the judges not to upset the applecart can be a powerful message. But you might be on the other side, saying, "The best argument for us is the words on the page. You might think our argument is too simplistic, or that it ignores all this history, but this is how the judge who doesn't know all that history is going to think, and it's the best way to get the outcome our client needs."
Khurram Naik: How does that operate at the level of oral argument versus briefing?
Willy Jay: Some of it is both, in briefing and oral argument. It's the art of the possible, understanding what the court is willing to do, and what constraints make certain arguments low-percentage arguments. At oral argument, I think it's being prepared to deal with the oddball question. Sometimes the question is about a jurisdictional doctrine that comes out of left field, and just understanding federal jurisdiction can prepare you for that. I got a question in the Federal Circuit once about why my client had standing to appeal a particular type of decision. No one had raised that, and opposing counsel wasn't prepared to deal with it. If it's the kind of thing you go into argument thinking about, you can be prepared to answer it on the fly. But I think more often it's when a judge is spitballing a question, saying, "What if we decided this, and this, and this," being able to understand in real time what the consequences would be, and whether the court has the power to do that, whether you'd want to agree that it does, whether that would trigger some other doctrine, mooting the case, or triggering some abstention doctrine, or raising a question of whether this is federal or state law. Understanding the architecture the federal courts operate on can prepare you to answer, on the fly, a question about how to decide a particular case, and explain why the judges shouldn't, or can't, do that, and why that solution won't work. Sometimes it's recall, but I think more often it's having a good understanding, from hundreds or thousands of reps, of what will work in federal appellate courts.
Khurram Naik: Is technical lawyering an end or a means? Is it something you're inherently drawn to, or something you find to be an effective technique for accomplishing client objectives?
Willy Jay: It's a technique. I find it interesting, in part because I spend so much time looking in depth at the power of federal courts and the limitations on that power, and then appellate courts specifically. But no one is going to hire me to write a brief about getting a case removed to federal court and then say, "Well done, you got the case removed, congratulations." We're getting the case removed to federal court because we want to litigate it there. Understanding where we can litigate, under what circumstances, what we need to allege, what the limitations are on the court's power to hear our case, all of that is about getting to a good result. If I'm working with a bankruptcy specialist or an environmental lawyer, we're very likely both focused on the same finish line the client wants to get to. It's more a matter of being aware of what the roadblocks are, and which avenues are blocked and which aren't.
Khurram Naik: Something you mentioned before is that at the Solicitor General's Office, there's necessarily more of a direct form for how cases are practiced, just by being in that environment, a center of gravity for how you argue. But in private practice you're free to shape your practice so much more. Is there a reciprocal relationship between technical lawyering and choosing to specialize? Technical lawyering seems to lend itself well to being a generalist. In the example you gave, bankruptcy and environmental lawyers are, of course, specialists. Is there a relationship between those two components? I'd note that for a number of years you've had a generalist practice, but with a strong IP focus as well, so it hasn't necessarily lent itself purely to being a generalist.
Willy Jay: Yeah, I think the technical part of my practice is just what I and the judges have in common. It's the thing the judges know in depth, more than they know environmental law or copyright. If you've done a lot of challenges to federal action, or lawsuits against unconstitutional state legislation, or appeals from jury decisions, some of the mechanics of when something can happen, how it can happen, what the limitations are, some of that is the reps in my world, but it's also the reps the judges are most familiar with, whereas they don't have as much exposure to copyright. But each case is about something, it's about substance, and you mentioned I've done a bunch of IP cases, which really wasn't that different from the very technical other types of cases I did in government. What they have in common is you have to learn highly technical subject matter much better than the judges are ever going to understand it, and be able to explain it to the court in a way that accomplishes your client's objectives, being scrupulously accurate about what the judges don't know and need you to explain, because it's your job to help the court while helping the court see that your client is right, in ways that don't drive the true experts crazy, because it's always a dialogue in getting ready for argument about how we describe this, whether it's a set of clean-air regulations or the technology described in a patent. Appellate judges aren't jurors. They have a different level of sophistication. They're not lay people, but what they're good at is reading written words and declarative English sentences. They don't necessarily understand the scientific content, so explaining the science in plain English, and understanding which pieces actually matter to how the court is likely to decide the case, not burdening them with gratuitous explanation of things they don't need to know, I think that's what makes a good appellate advocate a good translator. Someone who explains the jargon in ways the court finds accessible but accurate. I feel like I've done my job well if the true experts on our team say, "Yeah, that's a good, simple way of putting it, that's accurate," as opposed to, "That's a ridiculous oversimplification, we have to do another iteration of that."
Khurram Naik: Can you take the other side, say, someone very focused on IP appellate issues, with a strong command of different technologies and of Federal Circuit and Supreme Court jurisprudence on IP issues. Can you speak to what someone like that does skillfully, as a trade-off from what you do? If someone focused on some other aspect of appellate lawyering, what would they be able to do very skillfully that's different from what you do, but that you'd regard as a skillful approach to appellate practice?
Willy Jay: IP is a little unique, because a single appellate court decides most patent cases, and does so all year round. Even though some judges on that court weren't patent practitioners before becoming Federal Circuit judges, now they're fully engaged in patent litigation all the time, which isn't true of a regional appellate judge hearing a trademark, copyright, or trade-secrets case. So patent is a little different in that sense, and there are lots of very good patent lawyers who've gotten good results at the Federal Circuit. Every good appellate lawyer wants to know his or her case, so I resist the dichotomy you're setting up a little, because in preparing for argument, you also want to fill your brain, at least for this case, with a very deep understanding of every aspect of the substance, who said what at trial, what the patent says, how the technology works, how the client's business works. But then you set that aside and move to the next case, in a way you don't set aside the legal architecture we were talking about. People who have a really deep understanding of their client's technology, in a case where the judges are willing to give them a little space to explain, can often do a very good job. But the question is whether you can convey that as effectively if the judge doesn't understand the relevant technical terms, or is more impatient and the clock is ticking and they need a legally focused answer rather than a paragraph-long technical explanation.
Khurram Naik: In technical lawyering, it seems there are different tools in your tool belt for achieving client objectives. You use a concept of sequencing, what an appellate judge is going to decide first, whether there are ways they can put off a hard decision, maybe for judicial-economy reasons. In developing those tools, it seems a technical lawyer could become a specialist in certain aspects of appellate lawyering. Maybe you become a specialist on issues of standing. Has that ever been part of your practice? Is that something you considered and ran with, or rejected?
Willy Jay: Standing is a good example. No one's going to hang out a shingle saying, "Hire me for your Article III standing challenges," except people who work for the United States government, who think nobody has standing. That's part of the Civil Division's standard playbook: nobody has standing, and the case isn't ripe. Kidding aside, standing does come up a lot, in class actions, in challenges to agency action going straight to the court of appeals, from the PTAB, for example, in Hatch-Waxman-type cases, where there's a question about whether a particular type of exclusivity is harming a competitor. Being conversant with those concepts is important, but ultimately most of the time those are table-stakes issues, about getting into court, but they can be fatal. Understanding them is a way of navigating some of the mines in the minefield, but ultimately getting your client standing only gets you part of the way. Defeating the adversary's standing can sometimes be a trick in the bag of tricks people don't think of, and being able to spot that a bunch of plaintiffs in a plaintiff class aren't actually injured can wind up producing good outcomes through creative lawyering. But ultimately standing is fundamental, because it's about what courts have the power to decide and when, though for our clients it's usually only part of the journey, except when it's something you've deployed to get rid of the case.
Khurram Naik: And more generally, is it possible, or beneficial, for a technical lawyer to specialize in some component of technical lawyering?
Willy Jay: Honestly, no. I think being a good appellate lawyer is having a really good understanding of the technical architecture of the judiciary. But if you can't also write and communicate orally what the case is actually about, the substance, why your client should win, then your understanding of the technical stuff won't really avail you much. There's a reason they don't just make federal-courts professors top litigators. The people who write the Hart and Wechsler federal courts casebook are more knowledgeable about these doctrines than I'll ever be. But you'd need more than that to be successful at appellate practice, because ultimately it's about using written and oral advocacy to get good results within the art of the possible in the federal or state judiciary.
Khurram Naik: My recollection of going through Civil Procedure in law school was how eye-opening it was to understand the procedural aspects of law. Lay intuition is that cases are largely about substantive issues, but you come to understand how much of litigation is about procedure, when things should be decided, the process for resolving a dispute, and how much strategizing is involved. It seems to me appellate work is like that too. For clients used to trial-court issues, but for whom appellate issues are less common, how do you educate them about that landscape? How do you get them to rely on your judgment rather than their intuition about how things should shake out?
Willy Jay: Ultimately, I think what a lot of clients want to hear from outside counsel, and this is true of litigation counsel generally, is, "I've seen this many times before, and here, in my judgment, is what's likely to happen." If you're thoroughly familiar with how courts of appeals review particular types of decisions, you can give a client that advice with confidence, rather than, "I opened the statute book and it turns out there's a rule that lets you appeal class-certification decisions, so we should do that." Understanding that some circuits are very skeptical of discretionary review, and what considerations a court of appeals weighs in deciding whether to accept a case for review, often requires experience. I think that's what clients are looking for. You may not always be right, your judgments are ultimately predictions, judges are human, and you don't know who your judges will be. But having a deep enough understanding that you can give good advice and good judgment based on your opinions, rather than a ChatGPT-level assessment of the options.
Khurram Naik: So you've built a destination practice, meaning work flows to you not just from your firm but from other firms as well. That seems unique to appellate lawyers, that your clients are not just businesses or other entities, but also outside counsel with trial-court issues. Can you talk about how you came to develop a destination practice, and what alternative you considered, if any, or was it emergent from the way you were working?
Willy Jay: I think there are people who work at large firms where everything tends to flow through the firm, because it has a well-integrated litigation practice and enough demand for appellate services to keep the appellate group busy. But because appellate work and trial work call for different skills, and because many clients want the top people to litigate their cases, and because the top trial-court person and the top appellate person might not work at the same firm, it's an option to think about changing counsel after something has gone wrong, or at least come to a conclusion, in the trial court. It's not always a switch. A lot of clients tell me they hire lawyers, not firms. When I've gone to trial, it's sometimes been with people from other firms, and my appellate team plugs into the litigation team, working cooperatively with the people standing up in court examining witnesses. Our job is different, but we all have the same goal, serving the client. So it's not surprising that when people get a bad result, their instinct is sometimes to change counsel. But I think the reasons to change counsel are often just as strong when you win, because the point isn't that your lawyer messed up, often the lawyer didn't. The point is you're now speaking to a different audience, and you need people with experience talking to that audience. That's just as true whether you're the appellant or the respondent, as if you're the petitioner.
Khurram Naik: Let's keep talking about business development. Something you mentioned is the concept of short-term, medium-term, long-term business development. I think for a lot of people, the reaction is that appellate business development is a contradiction in terms, a rarefied breed that just waits for cases to come to them. But you shared that you take an active approach, in three buckets. Can you talk about that?
Willy Jay: Sure. It would be great if I could just count on Google or AI to send people to me when they type in "Supreme Court lawyers" or "appellate lawyers," but there are a lot of excellent choices. Short-term business development means things like: someone has lost a case, we might be able to help, let's look at what we'd do and propose a strategy. That's, in a sense, the easiest, because you're talking to people who know right now they need an appellate lawyer. Long-term business development is more like being in front of people in the industries and repeat-litigation lines that will use the type of service you provide. They might not need it today, or tomorrow, or in a year, but being regularly in front of the right audiences, and showing that you understand the types of problems clients like theirs face, and the judgment calls involved in appeals, that's long-term business development, and some of it may never pay off. But I've had cases where I've been in front of an audience talking generally about topics like the ones you and I have discussed, and people said, "You seem to know what you're talking about, as it turns out, I have this case that might need to go up on appeal someday, let's talk about that." That's the medium term, a case that's not yet on appeal, but you might need appellate counsel someday. You hope not, you hope it gets resolved, you hope you win a smashing victory and there's no appeal. So it's possible for a litigant to say, "I'll cross that bridge when I get to it." But being better set up for ultimate victory often means having appellate counsel involved in time to have the record be what you want it to be, the arguments be what you want them to be, the jury instructions and objections be what you want them to be, and, frankly, to know your case really well. In a case I mentioned earlier, where I was sitting in the back of the courtroom, never spoke to the jury, another firm did the trial work, it was immensely helpful to learn the technical issue from the trial lawyers while getting ready for trial. It made it much easier to write the appellate brief accessibly, because I'd learned all of that earlier and saw how the trial experts portrayed it. So your appellate lawyers can do a better job for you if they get started earlier. Not every case calls for that. This medium-term business development is about identifying people who may legitimately need an appellate lawyer for something concrete down the road, and starting the conversation in ways that make you a valued counselor, advisor, and strategist on the team.
Khurram Naik: For the three buckets, are the patterns different depending on whether your audience is more general counsel versus more trial counsel?
Willy Jay: I think most of the time it's the client who decides. One nice thing about how my practice has gone since I left government is that I have a number of cases where trial counsel say, "We've recommended you to our client as appellate counsel." Sometimes that's strategic, "We want to stay involved, and we'd rather have you come in than someone whose instinct is to try to seize the whole case." But part of it is just being user-friendly, collaborative, and respectful of clients' desire to hire lawyers rather than firms. If that's how the client sees the team, it's imperative that all the lawyers see it that way too, plugging in seamlessly, treating everyone respectfully, not reinventing the wheel, and not revisiting the hard work trial counsel put in to get to that point. At the same time, having a fresh enough perspective that you're not just letting them fill your brain with, "This is how we've decided to litigate this case, and that should continue on appeal." You're hired to bring a fresh perspective, and the client wants to hear that. Sometimes that means an awkward conversation, "I don't really think we made the right argument in the trial court, so we need to pitch it differently on appeal." But the number of times trial counsel have said, "Our client wants to pick you, they'd rather work with you than some of the other options," has been really gratifying, and I try hard to be as collaborative as possible, to earn that trust and hopefully earn second and third chances with the same trial counsel.
Khurram Naik: Of these buckets, is there one you find most rewarding or gratifying?
Willy Jay: Honestly, the medium one is a chance to be really helpful. The short-term one is more transactional, there's an appeal, let's go get hired for it. The medium one calls for judgment and a calibrated approach to client service, you're not trying to take over the case, but you're trying to help steer the client to avoid making mistakes, or, if the court's going to make mistakes, to help make sure those can get reversed on appeal. Sometimes that's a very small amount of work. Sometimes it requires a lot of learning and thought that generates a very short email. Reconciling the budget and the amount of thinking that goes into doing it well can be hard, but ultimately the client, I think, tends to feel that you've got their back, and your job as their appellate lawyer is to help them avoid making mistakes. I don't expect to see you blabbing the most in team meetings, you have a role, you have a lane, stay in your lane, but do your absolute best work in it. So that's what I find gratifying, we're not even on appeal yet, but you're helping a client. You're potentially making yourself irrelevant if the strategy pays off, but that can be really gratifying, a few hours of my time wound up avoiding a major problem.
Khurram Naik: And how much of that bucket is cold versus warm outreach?
Willy Jay: Warm outreach is always easier than cold outreach. It's been interesting to see how much stranger-to-stranger communication there is, and that goes in both directions. When there's a big loss in trial court, lawyers reach out to clients, and sometimes my phone rings and clients are reaching out to lawyers. If we don't know each other, sometimes that's the result of a referral. I literally had one person tell me that ChatGPT told him he should contact me for this type of case. But it's only cold until it warms up. By the end of a pitch, where we've spent an hour having a substantive conversation about your case, often the prospective client and I will have a better sense of what makes each other tick, and what it would be like to work together. I've had cases where we lost the pitch but formed a friendship or a professional connection, so the next pitch is a warm pitch, not a cold one.
Khurram Naik: And is that cold pitch through a defined mechanism, like an RFP, or more like emailing a GC directly, doing some upfront work, distilling it into a short email, saying, "I have some thoughts about this matter, I recognize the high stakes, and here are some solutions"?
Willy Jay: It's easier if you know where to send it, so it's not a complete, over-the-transom, "Dear Sir or Madam, please hire me as your appellate lawyer." The coldness refers to the fact that nobody asked for this, we don't really know each other. Sometimes that's finding a connection who says, "Oh yeah, I know they had litigation." But sometimes, for Supreme Court matters, it's working directly through the lawyers who handled the case in the court of appeals, people who recognize their client needs Supreme Court counsel, don't plan to do that themselves, but know their client and their case and plan to be heavily involved advising on Supreme Court counsel. One of my younger colleagues landed a Supreme Court case doing exactly that, by impressing the counsel who handled it in the court of appeals. They got fifteen or sixteen outreach messages, and chose my partner as their colleague for the Supreme Court, because he cared the most, had done the most and the best thinking, and they recognized he'd be easy to work with. They chose him, and we wrote the petition. It was granted, and we won. Happy ending.
Khurram Naik: How do you allocate time, given you're so busy with day-to-day work? How do you allocate time on a weekly and monthly horizon for business development?
Willy Jay: I told myself when I first came to private practice that I was going to have a block on my calendar for BD time. Life comes at you too fast for that to be literally true, in the same block every day. But I try to stay aware, there's a saying about not letting the urgent crowd out the important, having a sense of how much time you've put in today, this week, this month, on the truly important things. Sometimes that's more like a task list, and sometimes it's an open block of time: what have I done to help get the word out about the successes our team has had for clients? What can I do to remind clients we haven't worked with in a while that it might be good to have a chat about what kind of problems they're facing? Some of that requires space and time, and it's easy not to make the space for it, because there's a lot of urgency to whatever's going on, and practice leadership can crowd out business development too, because it's time-consuming, not in a bad way. But there are only twenty-four hours in a day. The one-sentence business-development lesson I learned when I became a law firm partner is: people spend a remarkably little time thinking about you. So you have to remind people that you exist, more often.
Khurram Naik: You mentioned practice leadership. I'm curious about the relationship between that and your work. Is there a translation of lessons from one to the other?
Willy Jay: One nice thing about being a practice leader with multiple talented people in the same line of work is that you can learn from other people's approaches, even really young people who have great energy, great ideas, and great talent. If you're just on your own, building your own practice, you're focused primarily on what you yourself are good at, what you have to sell, and who might be interested in buying it. But as part of a more integrated team, you get to see that there are other people who either do the same thing in different ways, which might be sellable to different people, or who do different things that complement you, and that you're stronger together. That's definitely shaped how I think about business development and approaching clients. Sometimes I'm not the right person to put in front of a client, for whatever reason, and having the responsibilities of a practice leader makes it easy to say, "This should be an opportunity for this other person instead of me," because that serves the client better and serves the overall interest of our practice.
Khurram Naik: A lawyer who's worked with you complimented you once on your editing skill, and what this lawyer said was that your approach is less about reworking something and more about editing while keeping the spirit of the approach, finding the high-ROI changes that can be made. Was that a function of the constraints of time in practice leadership, or were those skills you were bringing that led you toward practice leadership as well?
Willy Jay: I haven't really thought about those things as connected, but I think my editing is less driven by "I'm busy, so I only have time to do X," and more by the fact that the client is already invested in having this talented younger person draft this filing, and it's good. I might say some of it differently, but the client wants a coherent product that doesn't sound like it was written by committee, it doesn't necessarily have to sound like it was written by me. There may be high-ROI edits I can make, some of which might be taking things out, some of which might be saying things a little more concisely. What I like about working in a group with other talented people is that those same people may edit my work just as effectively as I edit theirs. It's very difficult to edit yourself, to make judgments about what word choices are good, what resonates, what's a good, snappy way of saying something, if you're also the person who had to write it from word one. So a lot of what I do in editing is shaving things away, making it crisper, finding a common-sense, accessible way to encapsulate the point we're making. And when I'm the person who's written the draft, somebody else could always do the same thing to me.
Khurram Naik: I'm interested in how lawyers skill up, particularly lawyers who've already achieved success in their domain. We've talked about three categories, the work of appellate law, practice leadership, and business development. What's the next dimension for each, the thing you want to skill up on? Maybe we can start with practice leadership. Is there something about practice leadership you're attuned to, or interested in cultivating in yourself?
Willy Jay: I think ultimately part of being a practice leader is getting people to work hard as a team, because they care not just about the clients but about each other. Building that kind of spirit requires everyone, not just people in leadership, to show appreciation, show understanding, have a deep understanding of what makes our different teammates tick, what motivates them to work hard, what motivates them to stay late and spend another half hour finding that perfect turn of phrase. Being a good listener is part of it, having a good human understanding of your teammates is part of it, but ultimately I think being good about showing appreciation and providing motivation, separate from the wins themselves, I'd like to learn to do better at that.
Khurram Naik: And let's turn to business development, what's a dimension there you're looking to skill up on?
Willy Jay: Honestly, I think one can be too easily discouraged. If you send in a pitch and it's ignored, or you never hear anything, does that mean you did a bad job and should stop doing it? Probably not, probably you should do another one and hope the next one works out. But in a business where much of what you do ends with somebody winning and somebody losing, it's easy to think about business development the same way, we won this pitch, we lost this pitch. Sometimes we weren't the right fit, sometimes for reasons beyond our control, and sometimes it's, "I liked three of you and chose this one, it's not even a loss in that sense." But if it discourages you from doing the next one, then you're not succeeding. So what I want to skill up on is not being discouraged, and cheerfully tackling the next thing quickly.
Khurram Naik: I like that, because there's an interesting parallel. Whether in trial court or appellate court, a lay characterization is, "It's about winning and losing," and then with more experience you say, "No, it is about winning and losing, but there's subtlety to that too," we win on infringement, lose on invalidity, or whatever. That's a good, subtle approach to accepting outcomes that don't go your way.
Willy Jay: Sometimes you get asked, literally, from the bench: if you're going to lose, how would you like to lose? It's a serious question, even though it tends to produce a kind of gallows humor, because if your client is a repeat player, and the decision in this case is going to govern not just this case but many cases brought against them, or by them, in the future, then what rule the court writes could be quite significant. If the reason you're going to lose this case is something case-specific and fixable or avoidable in the future, that's a much better outcome than a sweeping holding that forecloses the client's options for the next case, and the next twenty-five cases. So sometimes you can win by not losing as badly as you could.
Khurram Naik: So, to pause on skilling up, and to run with what you're saying, I think part of it is: to a degree, the client is looking to make new law. That relates to the question of what these appellate judges are likely to do, are they likely to take this on and make new law, or sidestep it and address some other issue? To what extent is that part of your counseling for clients, how much they want to make new law?
Willy Jay: In high-level, sophisticated litigation, it's pretty rare to find a precedent that just dictates the outcome. There's usually some room at the margins, to make the facts different, or the law a little different, the previous decision didn't consider this particular aspect. One of the Jedi masters of the appellate bar, who's helped hundreds of lawyers prepare for Supreme Court arguments, likes to say: if you're relying on a case, I can distinguish that case, whatever it is. That may not be true if you're an AUSA or a federal defender dealing with the type of criminal-law issues that come up a thousand times a year in the federal system, there may in fact be a precedent that says a sentencing guideline does or doesn't require a greater sentence under exactly these circumstances. But it's pretty rare for cases to drive the answer a hundred percent. So it goes back to what we were discussing earlier, what's going to make the judge make the decision? Sometimes it's precedent, but there's still a layer of checking whether this case is like that one, and you have an opportunity to persuade the court that, for some real reason, and not just because that case was decided on a Tuesday, this case should be distinguished. When I get a draft that says "that case is distinguishable," I think, well, yes, but why will the appellate court want to distinguish it? Explaining that is important. But our clients more often face cases where there's no clear answer. One side says, "You should infer from these six data points, statutory language, precedent, analogous cases, persuasive authority, you should reach this conclusion," and the other side says, "No, you should weigh these six other things more heavily to reach the opposite answer." Ultimately, judges sometimes have to decide, as Justice Scalia used to say, whether this rock is heavier than that line is long, it's not a one-to-one comparison. You have to decide if this piece of textual evidence, or precedent, or legislative history, is more persuasive than that piece over there. Since they're not always drawn from the same column, that's where judges are really making judgments, and anticipating what kinds of judgments these judges make, and what they think about in making them, that's our job.
Khurram Naik: And turning to written advocacy, what is it you're looking to skill up on there?
Willy Jay: I've been doing this too long to make huge changes, but I recognize that I tend to try to have a conversational style, to lock eyes with the judge and establish that we're having a conversation, I'm trying to help you, I know the record and the law, I'm going to give you straight answers, trying to advance my client's position, but my goal is to help you reason your way through this so you can write an opinion. Not all judges respond the same way, and I probably could have a different set of lead-ins, or a different kind of preparation, for certain types of cases where the incoming fire may be hotter, and part of the task is lowering the temperature before you can get into the conversation about the law.
Khurram Naik: What are some techniques for lowering the temperature?
Willy Jay: I don't know that I've figured that out definitively, but some of it is being respectful and responsive, even when the question is incredibly hostile, taking it seriously, latching onto the appropriate portion to answer. I think that's something appellate lawyers have gotten good at, especially during the period Justice Breyer was on the Supreme Court, sometimes his questions would be so long you could choose which portion you wanted to answer, or where to begin. If he thought you weren't focusing on the load-bearing part of his question, he'd tell you. So if you get a super-hostile question, you try to figure out what part of the case it's really getting at, and respectfully and constructively try to give the best answer from your client's position. And you recognize that, on a multi-member court, one judge's hostility doesn't necessarily mean you're totally cooked with the other two.
Khurram Naik: Is there a category of hostile question that's the most difficult to handle?
Willy Jay: I don't know if this is what you meant by a category, but where the judge not only doesn't want to hear your answer, but doesn't want her colleagues to hear it either, and just keeps interrupting early on. Sometimes, to be fair to the judge, they think you're not answering, that you're tap-dancing to get away from the question, and they want to focus you on actually answering it. There's at least one federal circuit judge who really likes the formulation, "Answer my question," and you should. But if the judge wants to talk, and say, "I disagree," and talk over you while doing that, that's very difficult. One of my younger colleagues had an argument earlier this year where she took that model, was respectful and persuasive when she got airtime, and front-loaded her points so that if she got interrupted, she'd at least communicated the substance to the other two judges. Then she'd get a question like, "You started to say to Judge X that you had two points, one about the text and the other about the regulations, you didn't get to the regulations, would you mind giving that answer?" So another judge can sometimes throw you a lifeline. She won that case two to one, with the hostile judge dissenting.
Khurram Naik: I think another lay conception of appellate lawyers is that they're tracking things like circuit splits, maybe pet issues they're tracking until an issue reaches the Supreme Court, counseling clients on what matters to bring, what the ideal posture is to get an issue like that resolved. It seems to me your lawyering is different, less about a substantive legal issue and differences among judges on that. But are there procedural aspects of different appellate courts, and how they're evolving, that you're tracking? Procedural developments in appellate practice?
Willy Jay: There are quite a few. Let me say at the outset that the type of technical issues we were discussing earlier often make great circuit splits and cert petitions, and the Supreme Court has taken a number of such issues in recent years, about jurisdictional doctrines, arbitration procedure, things like that. But to your question, different circuits tend to approach both emergency matters and discretionary matters differently, and sometimes those are the same thing, because you might be deciding whether to grant mandamus and whether to grant a stay at the same time. So there's a level of, is this something we're going to take up at all, and if so, on an emergency basis? Cases against the federal government, of which there are a great many, are in a different category. A lot of the emergency litigation has come up in cases brought either against or by the federal government on various hot-button issues of the day, and I think the courts of appeals have approached that set of cases differently than business-versus-business emergencies, where it's more like, "We need review of this certified class judgment, and we need a stay, because we won't be able to post a bond for the full amount and we won't get to appeal."
Khurram Naik: We're getting close to time here, so I think we should land on a final question. I'm curious, what's a piece of received wisdom in appellate law that you disagree with?
Willy Jay: I thought about this, and I don't love the answer I came up with, because it's more like consensus than received wisdom: "don't use humor at oral argument." I think that's generally good advice, so it's not that I disagree with it as received wisdom, but there's a difference between "don't use humor" and "don't be good humored." I think it's possible to set a positive and cheerful tone in oral argument, even when you're dealing with serious, high-stakes matters clients care a great deal about. Sometimes the judges think oral argument is fun, sometimes they're making fun of you, and that's not great, but sometimes they're having an enjoyable exchange with counsel and enjoying it themselves, and setting a positive tone, acting like you're enjoying it too, can honestly make the argument go more smoothly. So I wouldn't make jokes, I've winced more than once in the audience when people bring in their prepared joke about the particular venue the case came from, or something like that. My own attempts to deploy humor have generally fallen flat. But I'd say: be good-humored, act like you're happy to be there, and that this is a productive conversation.
Khurram Naik: My reaction is there are two aspects to that. One is, it seems very risky to make a joke, it's surprising that appellate counsel, who are so careful and measured, would choose to do something like that. There's just about nothing riskier in a professional context than a joke.
Willy Jay: That's pretty much why it's received wisdom not to make jokes, but I've seen people do it, and I'd say it doesn't have to be a career-ender.
Khurram Naik: Yeah, I think the other thing about "don't make jokes" is that it seems like a meritocratic approach. I'm very far from the Supreme Court bar, functionally speaking, about as far as a non-lawyer. But it seems to me a joke can be a flex of insiderness, which I recognize is of value among repeat practitioners like yourself, and generally in our legal system, it's both a benefit and a cost, the kind of thing that gets thrown off between lawyers, and sometimes in front of judges. Adam Smith said every meeting of a profession is a conspiracy against the laity. I think there's some of that, but I like your approach, because it encourages parity among practitioners.
Willy Jay: Without criticizing anyone, I do think it can come across as a flex.
Khurram Naik: Okay, Willy, I learned a ton. I certainly had some understated ideas about appellate law and some perceptions about how the work is done, and I think you've reframed the work in a very interesting way. You made a persuasive case for the value of technical lawyering, which, given that your purpose was to persuade, was itself persuasive of the value of this approach. I really enjoyed it.
Willy Jay: You asked really great questions and made me think. I appreciate the chance to have this conversation with you.