David N. Greenwald began his career as a clerk to Richard A. Posner. He then joined Cravath,...
Michal Rogson is a Vice President in the Commercial Department of Skyward Specialty Insurance Company, and is...
| Published: | November 25, 2025 |
| Podcast: | Litigation Radio |
| Category: | Career , Litigation |
Have you ever thought about writing the perfect legal brief? Guest David N. Greenwald has, so much so that the retired Cravath, Swaine & Moore partner wrote a book on the subject: Sentence, Paragraph, Argument, Brief: Meeting the Four Challenges of Legal Writing.
The book is the culmination of a 30-year legal career, beginning with a clerkship and the lessons learned under the guidance of the Hon. Richard A. Posner, Chief Judge of the United States Court of Appeals for the Seventh Circuit. Reading, digesting, and understanding everything related to each brief proved to be the foundation of good legal writing, Greenwald says.
Throughout his career, Greenwald intentionally honed his skills, from writing briefs to eventually, as a partner, editing them. With each paragraph and edit, he focused on the construction and flow of each argument.
Writing, Greenwald explains, is a linear process, putting ideas and sentences in a logical progression. A brief, he says, is a special kind of writing that must be learned. It starts with a statement of fact or history, building a narrative. But it’s also a work focused on clarity, without surprises or suspense. Hear Greenwald’s discussion of the art, and science, of legal writing and the principles of a clear, persuasive argument.
Have a question, comment, or suggestion for an upcoming episode? Get in touch at [email protected] and [email protected].
Hon. Paul R. Michel, Chief Judge (Retired), U.S. Court of Appeals for the Federal Circuit on C-SPAN
Special thanks to our sponsors Relativity, ABA Section of Litigation, and Sovereign Discovery.
Michal Rogson:
Hello everyone and welcome to Litigation Radio. I’m your host, Mic Rogson My background is in insurance litigation, but I transitioned in-house over 15 years ago and I’m now vice President at Skyward Specialty Insurance Company where I manage their national court bond practice. I’m an expert in the litigation and fiduciary bonds that are often needed across the spectrum of litigation. On this show, we talk to the country’s top litigators and judges to stay abreast of developing trends in litigation and discover best practices in developing our careers and building a sustainable practice. If you’d like to stay up to date on future episodes, please be sure to subscribe to the podcast on your favorite podcasting app. This podcast is brought to you by the litigation section of the American Bar Association, which is where I make my home In the A BA. Not only is the litigation section an inviting and supportive community of highly talented litigators, it also provides litigators of all practice areas, the resources we need to be successful advocates for our clients. You can learn more at ambar.org/litigation. Today’s guest is a man with a passion for something that is important to any litigator in the trenches writing the perfect brief. David n Greenwald is a retired partner at Cravath Swain and Moore, LLP, who has lectured extensively on the subject of legal writing and has just published a game-changing book titled sentence paragraph argument Brief meeting the four Challenges of Legal Writing. Welcome, David.
David N. Greenwald:
Thank you, Michal. I’m so happy to join you from Cravath offices here overlooking the Hudson River.
Michal Rogson:
Well, I’ve got to say, when I first heard that we were thinking about doing an episode on a book on writing, I was like, okay, we’ve got half an hour, how are we going to fill it? And then I got to talking to you about the book, and I could have talked to you for two hours about it just in our planning meeting because it’s fascinating, and I wonder if we don’t all secretly have a passion for this that we just don’t realize. I was thinking just last night about how there are moments where I’ve been writing a brief and I write the perfect paragraph, and all I want to do is call someone and read it to them, right? And then of course I realize it’s 2:00 AM I’ve been working on it for six hours and no one else is as interested in it as me. But this is actually something that we are all really, really interested in. And I know that your book is game changing, so I’m really excited to share it with our listeners. I guess the first thing I want to ask you is how was the idea for the book born?
David N. Greenwald:
Well, the idea for this 200 page book was born, if you will. It had its origins, oh, a little over 30 years ago, really, in June of 1993, I graduated from the University of Chicago Law School. I was 25. The week later, I started work at my first job, not just legal job, my first job as one of Chief Judge Richard Posner’s, two judicial clerks and what followed for the following year. What ensued over the course of the following year was certainly the funnest professional year of my life. And I had many years that I counted fun, but as more relevant to our discussion today, it was also a magnificent, terrific introduction to legal writing. Now, why do I say that? Was it a great introduction to legal writing because I was writing all these draft opinions for the judge to review and give me great feedback on?
No, as I think most of your listeners know, judge Posner was one of the handful, maybe small handful of judges in the United States who wrote every opinion himself. And when I say every opinion himself, I mean every word. If you read even a citation or a pinsight in Poner opinion, you can be 100% confident that he typed that citation with his own fingers on his Macintosh computer. So no, it was not a great introduction to legal writing for that reason. Was it a great introduction to legal writing? Because even though we didn’t write opinions, we wrote carefully reasoned and analyzed and structured bench memos on every appeal that the judge heard? No, the judge and his two clerks read every single set of briefs and every appeal that he heard, not just the ones that, well, in every appeal that he heard, he read every one.
And my co Clark and I discussed every set of briefs with him a day before the oral argument, even if we weren’t planning to work on that particular appeal itself. And he thought it was, if I had offered him a bench memo, he would’ve been insulted because his position was, I’ve already read the briefs, why do I need some 20 something to tell me what the briefs say? So no, it was not a great introduction to legal writing for that reason. But here’s why it was, it was a great introduction to legal writing because we read a lot. My co clerk and I, we’ve read a lot. First of all, we read all the briefs in all the appeals he heard because the judge valued simply talking one-on-one about every appeal before he heard the oral argument. And so from that process of reading sets of briefs in probably, well, I don’t know, 250, 300 appeals, which means in an appellate context, 700 to 900 or so briefs, we or I learned how briefs read, what they looked like, how they were structured, how they sounded, how they sounded when they were, in my opinion, well-written, how they sounded, how they read when they were not so well-written.
And of course, the seventh Circuit, which is the circuit that hears appeals from the federal courts of Wisconsin, Illinois, and Indiana was a magnificent circuit because it drew in cases from really all of the layers of America, rural, urban, civil, criminal. I could go on it.
Michal Rogson:
It sounds like the point is that you had an opportunity really right off the bat to be the audience for the briefs, right? Most of us, our first opportunities are engaged in brief writing, but you had a really interesting opportunity right off the bat to experience briefs from both sides of an argument as at least one of its intended recipients before then proceeding to writing your own.
David N. Greenwald:
Yes. And that’s of course an experience that all judicial clerks have, and I think it’s one of the main, if not the main reason why clerking before you start your career, which isn’t done much these days, but it was standard when I was starting out, is such a valuable experience for future litigators. But there was another thing that we read in Judge Posner’s chambers that made it extraordinary. And that is that every morning at nine 30, like a train on the morning after every oral argument the judge would bring into the chambers for me and my co cochlear Larry Downs, a 10 to 20 page draft of an opinion he had written in one of the two appeals that he has signed himself to write the opinion in. Now, was this draft complete? Was it totally polished? No, but it was very polished, remarkably so for something someone had written overnight.
And from that and from the process of seeing him as he went through 2, 3, 4, sometimes five, never really more than four drafts of an opinion, what I was able to witness firsthand was, or not just witness experience, I’ll say Reed, the prose of someone who was, I put it mildly, a consummate legal stylist, the foremost legal stylist of his generation, the two flanking generations. Now, his opinions, they were famously conversational, famously informal, sometimes even playful. And that’s not something that I or even he thought thinks briefs should be. But if your goal was to get in your ear the sound of litigation, English, how to sound professional, how to use legal words properly in their proper context, if your goal was to understand how to write a long sentence and control it so that nobody thought it was too long, if your goal was to show or to see how a master of pros gets flow going in a paragraph properly, it was terrific. It was just terrific.
Michal Rogson:
But the fact is you didn’t write the book immediately after finishing your clerkship, so there was more involved.
David N. Greenwald:
Absolutely. No, I couldn’t have written the book at that point. What I did was I followed the conventional career path, which was a very good one. I started work at a law firm as a first year associate at the place. I had been a summer associate, Ava SW and Moore, New York, and there I immediately found myself writing a lot of briefs on tight timeframes and having them expertly edited by really a superb bunch of litigators. In those days, edits weren’t done with track changes. They weren’t sent over email in PDFs in those days, you put out a draft of a brief and you handed into the partner for whom you were working, and what would come back sometime later would be a set of hand marks, either line edits or what have you, and then you would talk about the draft, you would go over them face-to-face in person, and that was a wonderful experience too.
That’s where I really started, I would say started the process of learning to write briefs as opposed to just reading them. After a few years though, I felt I had written a lot of briefs, but like many, many associates then and now, I felt that there were some skill sets I needed to develop or wanted to develop, and they were oral skill sets. So I applied to be a prosecutor at the US Attorney’s Office for the Southern District of New York. And there I was fortunate to receive an appointment there as a prosecutor. And there the job, it was a lot of grand jury testimony. It was many trials, which were a lot of very fulfilling and fun to do, even appeals to argue. But still, despite all that, probably at least half of the job was just sitting at your desk and writing briefs. There are a lot of briefs. The conditions that were different at Cravath, there was a lot of supervision. There had to be, they had paying clients. And who was I? I was a 20 something associate at the US Attorney’s Office. Like most public law offices, there was a much less supervision that had its pluses and its minuses. But one of the pluses is you learned very quickly how to make your own decisions and live with the consequences. And that’s a great experience for any professional to have early in their career. And it was from you as will.
Michal Rogson:
And after that, you ended up going back to Cravath and being a partner, at which point you were the one who was doing the editing for the younger lawyers.
David N. Greenwald:
Yes. I returned to Cravath after a few years as a prosecutor, and I thereafter became a partner and then something changed. I was very comfortable writing briefs. I had written a lot over the course of the 10 to 12 years between the time I graduated law school, I became a partner. But then of course, the job of a partner, you are fundamentally a supervisor and you are not just a supervisor, but you are a developer of upcoming legal talent. So my job was now included editing, and I really didn’t know how to edit. I really didn’t. And truth be told, even today I prefer writing to editing. But okay, so what I got a job to do, stop complaining and do it. So I had to learn to edit. And I taught myself, I think, and the way I taught myself is this, I tried to find principles that permeated all the edits I was making principles governing what was I doing to sentences and trying to ask myself why was I doing these things?
Don’t just do them and throw back a track changes, try to analyze why did I just change this in the way it did? And similarly for the paragraph, and similarly, why was I moving around paragraphs in an argument if I was doing that, can I articulate this? And I wanted to do that not only so that I could understand the process better and do it myself more efficiently as any professional should want to do, but also importantly, so that when I went back to the associate who had written the draft, I could have a very meaningful and constructive conversation about why I did what I did. Because as anyone knows, getting back a draft that just has a bunch of marks on it and you don’t know why they’re there, it’s not always helpful and it’s often demoralizing, and I didn’t want that.
Michal Rogson:
Well, and I think that goes to the value of the book, which we’ll explore in just a moment. But as a young attorney, when you are getting feedback on your briefs, but the feedback is specific to that one brief and not necessarily formulated as a rule that you can then apply across future writing, it makes the learning process more difficult, right? It requires a certain amount of intuition and extrapolation, if you will. And one of the reasons that I really wanted to explore your background is because I think you bring a really unique perspective to the topic of legal writing because you began your career as in a role where you got to receive and be the audience for an extensive amount of briefs. And then you yourself had the opportunity to write both under supervision and unsupervised, and then you became a supervisor. So you had all of these different opportunities to engage in the writing process. It’s almost like a perfect storm. You were being set up to write this book.
David N. Greenwald:
Well, nal, I couldn’t agree more, and you’ve said it so beautifully, but I would even say that the perfect storm was even more perfect than that because on top of all that, about a year after I became a partner, the firm asked me to oversee the firm’s own internal litigation CLE offerings, which I was happy to do. I had that sort of bent. And one of the classes I developed was the brief writing course for incoming associates and for anyone else who wanted to watch, but mostly the attendance was incoming associates. And from that process of giving the course not just one year, but for the succeeding years, and I gave it throughout my tenure as a partner, I was forced like all teachers to really analyze, what am I saying? Why am I saying it? Is it right? And every year I gave the course the first name for the course because I was a prosecutor and I wanted to have a clever name.
I called it the sentencing guidelines, which is actually a pretty clever name I think. But over time, I realized that there was something more serious that I had to offer. So I called the course, I broadened the course to go beyond sentences to cover paragraphs and arguments, and I called it legal writing, a one dimensional approach. Why did I call it that? I called it not because I thought of legal writing as simple. I don’t, maybe we’ll get into this later, but I actually think brief writing is among the hardest types of writing anyone can attempt to do. It doesn’t get enough credit for that, frankly. My point being that I broadened it to bring in this idea that writing, whether it’s sentences, paragraphs, arguments, or briefs, is a linear process. It involves putting words in a line.
Michal Rogson:
If I was a young lawyer and I was seeing an array of different courses that I could take, I don’t know whether I would jump into the legal writing course straight up. I might be interested in exploring other areas of practice, et cetera. And broadening my knowledge from that standpoint with the idea that, look, I learned Iraq in law school, right? I personally, I was an English major. I had spent extensive amounts of my time writing. Do I really need to learn how to do it yet again? And so my question to you is I have to assume your answer is yes. You wrote an entire book, why is the answer yes?
David N. Greenwald:
Well, the answer is yes, because brief writing frankly shares very little with other modes of writing. And I’ll be more specific. I’ll break it down. A brief is essentially two modes of writing. There’s a statement of facts or a procedural history or both. That is essentially what we’ll call narrative. Now, narrative is a style of writing that’s very familiar to everyone. Narrative is what’s a fairytale? What’s say, what’s a novel? What’s a short story? It’s fundamentally it’s narrative. So in that sense, brief writing has some parallels to other modes of writing. But for reasons that I go into the book towards the end where I have a chapter devoted to nothing but statements of facts and background statement, it’s a very different type of writing than what you will see in literature that people want to read today. I think that, I don’t want to be misunderstood here, but in a sense, the perfect statement of facts in a brief is using narrative approaches that started to go out of fashion in the biblical era.
Why do I say that? Two reasons. First of all, the goal is to be transparent, to be explicit. You don’t necessarily want to build tension or suspense in a statement of facts in a brief, even though that’s the reason why Stephen King and Agatha Christie are the eternally successful writers that they are. The other thing though is that also like less modern literature, shall we say, your goal in the background statement of a briefs is to portray your client as totally white in a world that knows only black and white degrees of morality, if you will, and no shades of gray. I’m overstating things, of course, but you see where I’m going, and that’s antithetical to literature that modern people want to read. Okay? So that’s where there are some similarities with literary writing, but there are also very significant departures. But then we get to the meat of the brief, which is the argument section.
And there frankly, there is no parallel to legal argumentation in any type of writing that people want to read. And of course, as we all know, you can write the best brief that’s ever been written. No one will ever read it for pleasure. It does not happen, give up on that goal. If the argument section of a brief has a parallel to anything, and it’s a rather weak parallel, it might be to the mathematical proof, but clearly that’s not going to be helpful to people. They need different principles to help them write an argument section, and that’s what the book attempts to do.
Michal Rogson:
Let’s talk for a moment about audience, right? Because I mean, the distinctions that you are commenting on in large part is due to the fact that the audience for any other type of writing, right, whether it is a novel, whether it is an article, a piece of journalism, even an Iraq structured response on a law school exam is not aimed at the same audience that a brief is aimed at. That’s certainly one of the most unique things about briefs is you’ve got a very specific audience. So talk to me a little bit about how you direct the structure of a brief for the audience you’re addressing it to.
David N. Greenwald:
So as I hope the title of my book implies, I see brief writing as almost like construction. You have constituent parts and you have to build them up. Now, the sequence in which you design these constituents parts differs from the sequence that the book covers, but essentially, you have to write a good sentence, you have to write a good paragraph. You then have to put those paragraphs together to write a good argument, and ultimately, you have to put those arguments together to form a logical persuasive brief. Now, to do that, well, you certainly need to know substantive law deeply. My book doesn’t cover that. You also have to know intimately human psychology, cognitive biases. My book touches here and there on that, but that’s not the focus. My focus is just getting things in the right order. And it turns out that there are more or less turnkey principles and not all that many that can help you get these things in the right order.
Now, they’re all different. The principles for the sentence are totally different from the principles for the paragraph are totally different for the principles of ordering paragraphs in an argument. But they’re out there and they can be articulated, and most legal writing books out there will focus a lot on a sentence to a lesser extent on the paragraph. And then when it comes to organizing the argument, well, they’ll give you some Iraq or something, which is not bad, by the way. I don’t think I, Iraq is a bad thing, but it doesn’t give you anything close to what you need to structure the briefs that you’re going to encounter in the trenches of litigation. So just to take one example, if you to make a sentence sufficient, by which I mean easy to read, there are really five rules, only five rules, str and right will give you 25. Some people will give you even more, and I’m not saying that those rules are bad, but you can actually distill however many of those rules are into five, and my book does that. And then what the book does is show with a lot of examples drawn from actual briefs, how to apply those various rules in those various different contexts.
Michal Rogson:
Well, I feel like you’re teasing us. Do you want to share one or two of those rules?
David N. Greenwald:
Sure. I mean, for making a sentence sufficient, well, I won’t say the most important, but a very important one is just to keep related words together. Now, you’ll see this rule in any good book on legal writing or non-legal writing. Actually, you’ll see it more in non-legal writing books, Strunk in White, for example, pointed out. But what you see is that it has a special place in legal writing because legal sentences in briefs tend to have a lot of prepositional clauses tend to have adverbs, maybe sometimes too many, but that’s a whole other topic, and things can often get out of place. Even a simple word like only, which can be an adjective, which can be an adverb. This word often gets placed in the wrong place, generally doesn’t cause too much confusion, but it can over the course of a 50 page brief, slow the reader down a bit.
Another example, of course, is to eliminate unnecessary words, keep sentences short. And yes, you will see that in any good book, but in fact, it gets misapplied a lot because some people don’t appreciate that sometimes a word is necessary to give a sentence better rhythm or to make it flow better or to make it more persuasive, in which case that word is necessary and you need to keep it. Eliminate unnecessary words often also gets distorted into keep all your sentences short, which is actually a recipe for a brief that’s very hard to read because the paragraphs don’t read. Well, one of the two things, Richard Posner, and it’s not just Richard Posner, it’s any authority on writing will say is that in a paragraph, you want to vary the length of your sentences. I mean, you don’t want sentences to be more than 35, 40 words, but if you do nothing but follow the advice to keep all your sentences under 20, you’ll have paradoxically a written product that is harder to read. It’s very choppy, and it’s often hard with sentences that short to show the relations between each other in the course of a paragraph. So that just gives you a flavor. There’s a lot more to talk about, but that gives you a flavor of the types of things I’m talking about.
Michal Rogson:
How do you teach where it is useful to use certain words and where it is useful to eliminate them?
David N. Greenwald:
The basic principle I follow is that a sentence should be long enough, should be commensurate. I think the way I like putting is a sentence should be commensurate with the complexity of the ideas it’s trying to express. So for a simple idea, let’s just take an example for these reasons. The proposed policy is lawful. That’s a very simple idea. That’s a short sentence. I would phrase it that way rather than for the reasons recited in the foregoing five paragraphs, the proposed policy should be upheld as compliant with applicable law. That’s an extreme example of the point I’m trying to make though, which is just a variation of what Einstein said. Things should be made as simple as possible but not simpler.
Michal Rogson:
And do you offer examples like that in the book?
David N. Greenwald:
Oh, many. Look, another thing that distinguishes this book from nearly every other, I think every other one that I’ve encountered, and after I finished the first draft, I read a lot of the books in the area, is that my book adopts a, I call it the Extreme Makeover or the before and after example approach to teaching legal writing. What I did to write the book, yes, I had my ideas. I developed them over the course of decades, but before I wrote the book, I decided not to look at anything I had written, not to look at anything people in my firm had written or adversaries and cases had written, but instead to do literally, I used a random number generator to just identify, find appellate briefs, often state Supreme Court or US Supreme Court. I wanted to get briefs that were all things being equal better than others.
I found a random selection of a hundred sets, hundred briefs, and I read them, and from them I was able to pick out examples of sentences that exemplified all the points they were trying to make. And so throughout the book, almost on every page, you’ll find an example of the sentence as it appeared, and it’s anonymized. You won’t be able to tell who wrote the sentence, this is not personal. And then the book shows how to rewrite it. Now, there are books, a few in particular that are quite popular that give examples, a lot of examples from filed briefs, but only examples of briefs that the writer consider the author of the book considered to be excellent. And frankly, I feel that’s an inferior way to teach legal writing. It’s sort of like teaching harmony to a bunch of conservatory students by just showing them things that dub sea or Bach or Brahms wrote. It’s not good teaching material what you
Michal Rogson:
Need to do. It reinforces intuitive knowledge, but it doesn’t actually articulate the lesson, right?
David N. Greenwald:
Right. You want to show how is the sentence actually appear and how can we make it better? And that’s what the book tries to do on virtually, as I say, every page.
Michal Rogson:
That’s definitely unique. I don’t think I’ve ever seen anything like that, and I would’ve frankly loved to have something like that when I was starting out because that could have been incredibly helpful. Now, I want to take us back to something that you had mentioned earlier. You said it is all about sequence, and obviously we see this even in the title, right? Sentence, paragraph, argument, brief. These are sequences of things that lead into each other, and it sounds like that was your organizing principle when it came down to distilling the idea that you have about what it takes to write a good brief sequencing seems to be your theme. So can you talk to me a little bit more about why that is, how sequencing applies both to the brief as a whole and to its parts which you have parsed out into sentence, paragraph, and argument?
David N. Greenwald:
Well, I would modify what you said so well, just somewhat, and I’d say that it’s not everything. Sequencing is not everything.
There is substantive law, which I don’t cover. There’s also word choice. Word choice is important if you’re using the words, and my book addresses some of this in a chapter on how to write professionally, which is different from writing efficiently and persuasively, there’s something to be said. In fact, a lot to be said for speaking the dialect of English known as US, litigation English in a way that the judge will perceive you as a sort of a native speaker of it. However, I chose sequence as the unifying principle because it’s the area where I just thought I had the most to offer. I mean, I think somebody else not, I could write an equally important book about the importance of cognitive biases and psychology and how to use that effectively in not just your written advocacy, but your oral advocacy as well. I mean, that’s what makes great trial lawyers and appellate lawyers for that matter, the great oral advocates that they are. They have an instinctive expert knowledge of human psychology and biases, but that’s just not the, I mean, I don’t think I could write a convincing book on that subject. I just thought that this one dimensional, put one word in front of the other was where I could add the most value. And so that’s why the book is structured as used as it is. I would point out though that it’s hard to find other books in this very crowded field that have a unifying theme other than the simple one, how to write better briefs.
Michal Rogson:
Well, so I want to drill down just for a minute because I’m curious, and I want to understand this a little bit better. What is unique about how you would sequence a paragraph or sequence paragraphs, I should say, not a paragraph, but multiple paragraphs within a single argument or within a greater series of arguments that you are presenting in a brief? What is unique about that?
David N. Greenwald:
That is the topic I cover in the longest chapter of the book, the sixth chapter called The Order of Paragraphs. And I introduced that chapter by pointing out it’s frankly the hardest challenge. I believe in all of legal writing. The way I’ve tried to approach it is first of all, to identify some governing principles that I think should control how you outline an argument. One of them is, and I’ve just wrote an article about it, posted it on LinkedIn, teach First, nothing. Yes, think first. No teach first. Yes, definitely think first. No, teach first, argue later. Another important organizing principle is to group related contentions together. Now, that of course sounds commonsensical, and it is you would group related contentions together. But what you’ll find, and what I find when I was teaching this and writing it, is that there is no accepted classification system for contentions in US law that allows you to actually decide, well, what makes a contention related to another?
And really, you don’t need to go too deeply into this. Basically, there are presidential contentions, there are prudential contentions, and there are interpretive contentions. And I won’t go into detail to what they are, but these are the three basic classes of legal contentions that a brief writer has to organize in any argument. And so what this chapter of the book, this lengthy chapter of the book goes through with examples is how to classify contentions so that you can droop them together. And then further things like how do you sequence rebuttal and affirmative argument? That too is an important question. Most litigators do it instinctively. Some of them do it very well, but I think it should be done systematically according to easily communicable articulable principles. So the book does that. And then there are questions of how to deal with relying on cases that are factually analogous, et cetera, et cetera. There are other principles here, but those are the main ones. And give you a flavor of the approach that I would take in that all important chapter on how to organize paragraphs within an argument,
Michal Rogson:
Which again, I think is something that makes this book unique and different from some of the other books on the topic of legal writing. And it’s really focused on brief writing in a very, very unique and informative way. And what has struck me, I mean, I’ve read portions of the book. I’ve read some really stellar reviews of the book that are right out there on Amazon. And one of the things that seems to be a recurring theme is that they applaud the book, both for younger lawyers starting out and for experienced lawyers, which I think I found somewhat unexpected. You usually think of a book on legal writing as something aimed more for the younger attorney who is starting out needing to learn these. Why do you think it is that? And they do it offhand. They don’t necessarily go into it, but why do you think it is that the book is actually really helpful to experienced attorneys as well?
David N. Greenwald:
Because it not only teaches you how to write, it teaches you very clear, turnkey and reasonably easily applicable tricks, if you will. I won’t even say tips. I’ll say tricks for getting a draft that’s in less than perfect form and whipping it into shape as quickly as you can so that the client isn’t paying an exorbitant amount for what is simply editing of a single draft of a brief writing and editing. They’re clearly related skills, but there are some differences as well. And you can be an excellent writer. It’s often the case that excellent writers are so good at it that they can’t really edit well because they just know what they do and they don’t know how to fix it. You sort of see a, well, I wrote this book, yes, for law students, I hope that it achieves traction in that field because I think that’s the place where it can do perhaps the widest good. But I certainly feel that even the most expert experienced writer who I put it this way, any litigation partner or law firm who’s ever been received a first draft of a brief and his or her heart sinks thinking, how am I ever going to get this into fileable shape? I am optimistic that if that hypothetical real world litigator reads this book, their heart will sink a lot less.
Michal Rogson:
Well, it sounds to me like if you’ve got the newer associates using this book as a guide and you’ve also got partners who are editing their work, leveraging the same guide to give them the tips, you’re going to have a cohesive approach to brief writing that’s going to make everyone’s life, frankly, a lot easier.
David N. Greenwald:
Yes. I mean, even just the classification systems that I offer for paragraphs and then for arguments gives will give editors and writers
Michal Rogson:
A shared language,
David N. Greenwald:
A shared language,
Michal Rogson:
Exactly,
David N. Greenwald:
Which is so important for cooperative interaction.
Michal Rogson:
I mean, it would be a great help when receiving feedback and mentoring. There’s no question about it. I wanted to finish our discussion by reading one of the public reviews on Amazon that I think is an impressive testament to what you’ve achieved in endorsing your book. The Honorable Paul r Michel chief Judge, retired of the US Court of Appeals for the Federal Circuit, said as a federal appellate judge for 22 years, I read over 15,000 briefs. This book explains how to write the briefs I wish I could have drawn upon to help me resolve the hundreds of matters I adjudicated every year, drawing upon the author’s own decades of experience in writing and editing briefs and in teaching it to practicing lawyers. The book offers a new approach to brief writing that focuses on words, sentence, paragraph, and argument sequence. Unlike many other books in this field, it is rich with turnkey tips and generous examples. I know of no more helpful book on this underserved topic that is a pretty rousing endorsement for someone who is among the primary audience. We were talking about audience, obviously, the judges are the primary audience for the briefs, also opposing counsel, but predominantly the judges and writing an effective brief can make or break a case. So that is really remarkable praise.
David N. Greenwald:
Well, that appears on the back cover of the book is indeed a very meaningful endorsement for me. And I’ll tell you why. When I was in practice, I had several appeals before Chief Judge Michelle. He was, as some of you, maybe many of you listeners know, a leader of the IP bench or the federal circuit bench, which has a primarily, not exclusively, but primarily IP docket. And after a very distinguished career in judging, he retired at the young age, I think of maybe 75, but he didn’t go senior. He retired and has since then, since 2010 when he retired, had a very, very productive year in, excuse me, career, not productive career as a thought leader and doing various other things. So how did I come to meet Judge Michel? Well, by chance, he happened to attend about four years ago, A CLE on legal writing that I was giving at a firm.
He just by chance was attending and he was quite taken with my approach. He told me he’d never seen anything like it, and he thought it was right. And so from that developed, I would say a very mutually supportive professional friendship, if you will. And he’s followed my work. He was the one who encouraged me to start writing articles about what I was saying in these private CLE lectures, because that was not my intention to write. I just thought I would just do what I was doing at Cravath teaching CLEs, which I still do. And interestingly, when I teach them in the DC area, I frequently teach them with him. And I introduce all of those CLEs that we co-teach together by pointing out that this CLE will offer you the perspective of the wholesale producer and the wholesale consumer of litigation pros. And of course, those are two very important perspectives.
Michal Rogson:
Well, David, I want to thank you for joining us today and helping us think a little more analytically and strategically about what it takes to write a good brief. I know that brief writing is not considered the sexiest part of our job, but there is something really, really satisfying. I’m a word lover. I’ve always prided myself on being an effective communicator. And it’s funny because in our conversations, many of the rules that you lay out are in fact intuitive. They are things that I may have been doing intuitively throughout my career, but I never would’ve parsed out the rules. I don’t have your perspective on it, and I may also just not have the knack for that kind of breaking down of the rules. I’m more of an intuitive writer, I think. But the way that you break it down and the tools that you offer are really invaluable.
And I hope that litigators both young and old who are listening to this can sense the value that they can get from leveraging this together, experienced partners and young lawyers alike, because I really think it could be a game changer. Thank you again for creating this amazing resource for sharing the journey that brought you to writing it and for sharing all of the lessons that you’ve learned over the years and distilling it into, as you said, a mere 200 pages replete with the fascinating before and afters that I got to tell you I’m really enjoying looking through as I peruse. Thank you for joining us.
David N. Greenwald:
Thank you.
Michal Rogson:
Thanks to the litigation section, premier sponsor Roundtable group for sponsoring this podcast. Roundtable Group is an expert witness search and referral service with decades of experience and a comprehensive array of academic and industry relationships, as well as access to proprietary tools that further enhance the expert search capabilities of attorneys with no upfront fees. You only pay if you retain an expert referred by Roundtable Group. Learn [email protected]. And now it’s time for our quick tip from the a b ABA Litigation Section. I’m pleased to welcome back Lauren Williams, Lauren practices corporate law at Morgan Stanley in Columbia, South Carolina. Welcome, Lauren. What’s your quick tip?
Lauren Williams:
Today’s tip is less about strategy and more about our sanity. We’re officially in a season filled with gratitude and giving thanks. So this is a season where we can barely catch our breath between the deadlines, holiday invites, the yearend pressure, and whatever life’s throwing at us behind the scenes. And if you’re anything like most lawyers, I know your plate’s been full all of Q4, and somehow people are just going to keep piling more on. So this month’s tip is very simple, and it’s not always easy. No is a full sentence, and I mean it. There’s no extra explanation needed. No lengthy apology, no guilt, just a clear no. Now, we didn’t go to law school to become exhausted versions of ourselves. We didn’t sacrifice, hustle, climb, overachieve, just to become people who feel like we can’t ever rest or reset. However, I know that a lot of us say yes out of obligation, fear or pressure.
We may say yes for different reasons. We may want to be seen as easy to work with or that we feel like we may be the only one that can complete the task, or because it feels scarier to disappoint someone else than to disappoint ourselves. But I want you to think about what is costing you, whether it’s going to be your peace, your sleep, your presence in your personal life, your joy. Just know that every yes does have a price. And sometimes the most expensive thing you’ll ever pay for is the yes you gave when your soul just screaming, please don’t. No, I’ve learned that boundaries don’t make you difficult. They make you clear. And clarity is essential in leadership. So boundaries make space for you to show up with intention, not resentment. They create room for you to rest, for you to have peace, for you to just exhale.
And I always say that boundaries are very sacred because they protect your values, they protect your energy, and they protect your time. And some of that stuff you just can’t get back. And I’m not saying it’s always going to be easy, especially of those who are first in the room. You might be the first lawyer in your family. You might be the first black or brown face at the table. You might be the first woman, partner first, anything that weight is very real. But I want to give you this tip. You don’t have to prove your worth through burnout. You don’t have to say yes to feel valuable. You don’t have to show up for everyone else and forget about you. So practicing it with me, no. And if saying no, feel scary, flip it because every no is really a yes to something deeper. So it could be yes to your time, yes to your mental health, yes to your boundaries, yes to the version of you that doesn’t just survive the work, but you thrive inside and outside of it. So this November, while you’re giving thanks and you’re expressing gratitude, thank yourself too for making it for growing and just being able to rest and honor your boundaries. That’s your young lawyer tip this month, and I’ll catch you all next month. But until then, protect your peace and say no, like you mean it. Lauren, thank you so
Michal Rogson:
Much for sharing that. And that’s all the time we’ve got. I’d love to hear your thoughts about today’s episode, and if you have comments or questions you’d like for me to answer on an upcoming show, you can contact me at m [email protected] or connect with me on LinkedIn. You can also connect with the a b ABA Litigation Section on those platforms. But as much as I’d like to connect with you online, nothing beats meeting you in person at one of our next litigation section events. So please make plans to join us at one of our upcoming conferences such as the 2026 Women in Litigation CLE conference taking place February 11th through the 13th in Jersey City, New Jersey. This year’s theme launch and lead empowering women litigators to lead with purpose aims to ensure that all attendees leave feeling empowered, inspired, and equipped to accelerate their career trajectory.
For what it’s worth, I have always left the women’s conferences feeling inspired and empowered. So please consider joining us there. You can connect with litigators from across the country and hear from distinguished speakers like Desiree Rawles Morrison, McDonald’s General Counsel, who will be our keynote luncheon speaker. Now, don’t wait to register. Rates do increase after January 20th. And as always, discounted rates are available for litigation section members learn more and at ambar.org/lead her. If you like the show, please help spread the word by sharing a link to this episode with a friend or through a post on social and invite others to join the community. If you want to leave a review over at Apple Podcasts or a quick rating at Spotify, that’s incredibly helpful as well. And finally, I want to quickly thank some folks who make this show possible. Thanks, To Michelle Oberts who’s on staff for the litigation section. Thanks. Also goes out to the co-chairs of the litigation Section’s audio contact committee, Haley Maple and Michael Steger. Thank you to the audio professionals from Legal Talk Network, and of course, thank you for listening. See you next time.
Notify me when there’s a new episode!
|
Litigation Radio |
Hosted by Michal Rogson and Jim Reeder, Litigation Radio features topics focused on winning cases and developing careers for litigators.