Interview: Ross Guberman

Ross Guberman is the President of Legal Writing Pro, a company that helps lawyers and judges write more effectively. He has written several books about legal writing, including “Point Made: How to Write like the Nation’s Top Advocates” and “Point Taken: How to Write like the Nation’s Top Judges.”

My questions are in bold; his answers are in plain text.

What were you like as a teenager?

I was really into music. I went to a boarding school for music, and I had every intention of becoming a professional musician. The viola was my focus, and I was pretty devoted to it. I spent a lot of time on auditions and competitions and practicing. I was also into academics, and I was fairly social too. But my mind was mainly on music. If you told me I was going to go to law school one day, I would’ve laughed in your face.

How did you become interested in the law?

There were quite a few steps in between music and the law. My initial jump was from music to academia – linguistics and literature and philosophy. I got some degrees in those fields, and then I started a PhD at Yale as well. But quickly after starting the PhD, I decided once again to change direction. I had some friends at Yale Law School who seemed passionate about what they were doing. They advised me that I’d be happier and more fulfilled not being in academia, but maybe going off to law school. So I took their advice, and I dropped out of my PhD program early on to attend law school.

Why were your friends so sure that you would like law school?

A lot of it was probably my extroverted nature. One thing I used to complain about in graduate school was how isolating it was, and how people were in their own minds. I was craving more interaction with other people and some connection to reality. And I was always fascinated by their stories of their classes. I distinctly remember — this is going to show you how old I am — my friends were jetting off to Haiti to meet with Aristide, the leader back then, and I was stuck reading some incredibly obscure literary theory article in a journal that no one had ever heard of. It woke me up.

Before we move past graduate school, I’m curious: who were your favorite fiction writers that you studied? And did they tend to have something in common?

One unusual thing about me, among people who do graduate work in literature, is that I was always interested in nonfiction. This actually isn’t a huge surprise, given that what I prize now is crisp, clear writing about reality. But the literary writers and fiction writers that I liked the most tended to be 19th century French novelists, and that’s what I wrote my masters thesis on at the Sorbonne.

In a recent interview, you said that you “focused a lot on writing” when you were in law school. Could you elaborate on what that means?

I was very drawn to my legal writing class. I instantly loved my legal writing professor, and even in the early months of law school, I was easily distracted by what I would see in opinions wording-wise when I was supposed to be concentrating on the holdings. It sounds obvious now, but I didn’t realize then that I was taking what I liked about academia and applying it to law school.

Because on the other hand, law school was so alien to me. I had no exposure to the law, and I didn’t know any lawyers beyond my Yale Law School friends. I probably found refuge in the parts of the first year that I found comfortable and inspiring. Later, when I

gained more autonomy, I was able to focus more on writing in briefs, articles, and the like.

When you read opinions, and you were distracted by the writing quality, which opinions jumped out to you as especially well written?

Part of not knowing anything about the law when you go to law school is that you don’t know the names of any judges. And to be totally blunt, I probably knew even less than the usual person who stumbles into law school. I didn’t know, for example, that Justice Scalia was famous for his writing, let alone who Justice Scalia even was. It’s more like I would notice patterns that I found noteworthy. The one that I remember very distinctly is that judges, and even students in my legal writing class, would start sentences with “further” in a way I’d never seen before. It struck me as odd and clunky. Decades later, this is still one of my main crusades: to get people to stop starting random sentences that simply add onto a previous point with “Further.” [laughs]

One advantage of having a hardcore literary background is that, even though I didn’t know anything about the law, I was able to understand which terms were legal terms. Some words and phrases were normal; then you had this middle ground of words and phrases that weren’t legal, but were still peppering all the opinions I read.

Chief Justice Roberts has said that “the best teachers of writing are good writers whom you read, and you kind of absorb [their techniques] when you read them.” In that sense, who inspired your writing style?

Even in graduate school, I always prized very clear, direct, straightforward academic writing. And I noticed, not just in the humanities but in the sciences and social sciences as well, that the truly influential academics — the ones that commanded the public’s attention, like Stephen Jay Gould — were able to adopt that sort of direct, clear, economical style. So I was inspired by that going into law school.

And then again, I told you that I appreciated well written narrative fiction. In law school itself, I latched on pretty quickly to Justice Scalia’s style once I figured out that he was someone of note. Also, maybe because they taught at Chicago while I was there, I admired the writing of Judge Easterbrook and Judge Posner. So I had them to go by. And then, when I was a summer associate and when I had other positions, there were lawyers I learned a lot from as well. But I wouldn’t say I came out of law school with a specific person or people in mind to emulate.

I did go to school at the Sorbonne for a while, which has a much stricter and somewhat less satisfying approach to literature than we have in the United States. And that’s one of the things you would do there — you would have to actually imitate, not just a writer’s style in general, like Proust, but a single paragraph, and then try to reproduce the structure and the feel and even the rhythm using different words. But I didn’t have anyone like that. Which is funny, because I first became known in the field for focusing on Chief Justice Roberts’ writing style.

But you don’t try to imitate his style. You point out parts of his writing that people may want to imitate for themselves.

I actually have, for my own purposes, tried to imitate the style of someone like Justice Kagan or Chief Justice Roberts or Paul Clement. I don’t necessarily recommend that other people do; I’m not sure that’s a good use of their time. But I have done the things that one does, like type it up — you may have heard that advice. You take something like a Hemingway novel and you type it up first, word for word, until you start to get the feel. Your brain and your mind merge, and you feel like you’re writing like Hemingway. So I have done that, but I don’t think it’s nearly as helpful as what I do try to teach, which is breaking things down into specific concrete techniques and patterns that you can internalize. Because it’s not realistic or possible to truly imitate somebody else’s style word for word.

It’s quite hard to imitate them, too. It takes time to replicate Justice Kagan’s conversational style.

There’s a great interview Justice Kagan did at Harvard Law School with the new dean where she uses that very word you just used — “conversational” — and she contrasts that with “informal.” She talks about how hard she feels she works to get to that sweet spot, where writing is conversational but not informal. So I guess it’s reassuring to know that even someone who’s as gifted as she is has to work at it.

Do you think that a somewhat anguished writing process is necessary to produce good writing?

I have a very unpopular view on that. The right answer is supposed to be “yes,” but I just haven’t found that to be true and I don’t want to lie. So it isn’t really true for me, personally. I don’t believe in suffering. When I write my books, I certainly procrastinate like anyone else. But when I’m actually writing, I don’t find it painful or miserable. I don’t necessarily believe that everything requires twenty rewrites, and that every sentence has to be checked and reborn. Again, maybe my experience is unusual or my advice is unrealistic, but I don’t endorse the prevailing view that unless you’re suffering, and unless you’re rewriting everything and reconsidering everything, something’s wrong. I just haven’t found that to be the case. Obviously I can’t speak for Justice Kagan and her process, but I can’t imagine that she’s suffering over every character and syllable and word and phrase and sentence. Once you get what’s often called a voice, which is already a term I’m a little bit leery of, and you stick to that approach and you hone that approach, writing really shouldn’t be that painful.

But again, I’ve noticed that Appellate Twitter loves this idea: that everything takes ten times as long as it’s supposed to, and you’re supposed to suffer, and it’s okay if you have to rewrite everything. I think it does make a lot of people feel better, but I also wonder if the corollary is that if you enjoy writing and you don’t struggle over everything, that you must suck. And I just don’t think that’s the case.

I wonder if people feel like they’re supposed to be anguished. So if you open up a Word document, and you already have it in your head that everything’s going to be hard and time-consuming and everything you write is going to be revisited, I wonder if it becomes a self-fulfilling prophecy for some people. I don’t know.

When you open up a Word doc, what’s the first thing you do? How do you organize your writing?

I hate to say that I do what I teach, because we never truly practice what we preach – and I’m no exception. But I at least try to do what I teach, which is not treating something as an intimidating amorphous challenge, but really breaking it down. First, what is the number one most important point I want to get across to the reader? Obviously this is different if you’re writing a book or magazine article, as opposed to a brief or a motion. But that’s always my first step. If I only wrote one sentence, and that one sentence would remain in the reader’s mind, what would it be? It’s challenging in a good way to settle on a single sentence, but once you figure it out, everything else is easier.

Then you go from that to “Now I have one goalpost. I now want to make sure that I can encourage the reader to adopt that point.” So I’ll break it down to three more points to support my idea. Then I type those up. If it’s a brief, you have your heading and the three most important paragraph openers of your section. And then you go back to those three and you ask, “How many logical steps along the way until we get there?” If there are two, three, four internal steps, you type those out. That’s a little bit pat-sounding, and I’m probably not being realistic, but that’s what I’ve done when I’ve coached partners or federal judges who are great writers with huge process or efficiency issues. Almost overnight, they cut their time by two-thirds.

That reminds me of what you said in either “Point Made” or “Point Taken.” You mentioned that Laurence Tribe might spend two hours working on the framing of his first sentence, or Scalia would work on one main question. Afterwards, their writing fell into place pretty easily.

That’s a great and somewhat dramatic example of what I’m saying, because something like an issue statement is so hard to get just right. And you sort of know when you have done so. But that work pays off, because the effort it takes to truly encapsulate an issue is going to help you later on. And yet that’s not how most people write. What most people do nowadays, wherever they are, is they open up a document and they just start typing random things. And then they get lost and overwhelmed.

When you wrote about framing in “Point Made,” one of your examples was the Chief Justice’s brief in Alaska v. EPA. I understand that you’ve studied this brief quite a bit. What have you learned?

I’ve learned so many things, and in some ways, it’s responsible for expanding my reach career-wise. Honestly, I hate to overhype things, but it all comes back to that one brief. One big thing I learned was a little bit controversial, which is the idea that sometimes you really do need to include facts that aren’t legally relevant – they can help the reader see a complete narrative that would be disjointed otherwise. Or they seem like unrelated facts, but they actually end up sounding legal themes that someone like Roberts will return to later.

An example in that brief would be the way he talks about the regulated mine, and the dog — it was an Irish Setter — that would greet the miners. The dog reference seems to people who are a little rigid in their approach, I think, to be superfluous or gratuitous. But he’s making the point that the state and local officials know things like, “This is a mine that people really value, that employs people in this sparsely populated area of Alaska.” The image of the Irish Setter meeting the miners suddenly turns it from a polluting, abstract mine into something with a warmer association. That was a hugely important technique that I learned.

Probably the last thing I’ll mention is the unbelievable, pristine approach he has to words and sentences. Everything is short and crisp and concise, with apt transitions. A lot of lawyers use convoluted subject matter like the Clean Air Act as a crutch, an excuse for our style, when it’s actually entirely possible to marry the two.

Is that the same brief that talks about “best available technology”?

Exactly. There’s this horrible lingo, Best Available Control Technology, known as the BACT standard. And he has this beautiful passage in there about the word “best.” You know, listen, he didn’t win the case, which is important to note. And I was of course fully aware of that at all times. But he took what is objectively a very difficult case and got at least three votes, which is a miracle in itself.


If you could build the perfect legal writer from Justice Scalia, Justice Kagan, and the Chief, which elements would you take from each?

That’s a great question. If it were a recipe, and I were to use parts of the three people you mentioned, I would take the basic core approach to words, phrases, and sentences that Chief Justice Roberts has. And then I would take from Justice Kagan her knack for provocative examples and analogies and hypotheticals. And then I would take from Justice Scalia his ability to show appealing parts of his personality in his writing without getting sidetracked. They’re all pretty great as they stand. But I think if you actually had all that together, the whole would be even greater than the sum of the three parts. And there really is a lot of overlap. I think people would be surprised to hear me compare Scalia to Kagan, but the truth is, if you look at his opinions as opposed to his dissents, they don’t contain his “Pure Applesauce” language. His diction in majority opinions is much more like what you’d see from Roberts or Kagan.

Some parts of writing seem more teachable than others. Anyone can learn to start their sentences with conjunctions, cut out vague passive voice constructions, and stop using legalese. Are humor and vivid hypotheticals equally teachable, in your view?

I think it’s all harder than people than realize, and yet easier than people realize. It dependson how you look at it. There are a few challenges with examples and analogies. One is: you have to know when it’s a good idea to include an example, analogy, or hypothetical. That already rules out a lot of people who tend to be too confident in the abstract exposition of their thoughts. What I believe Justice Kagan is doing is that she’s either making a point that’s dense, controversial, or both, and using that realization as an impetus to come up with an analogy. It’s not like you do it every seven sentences. It takes some judgment about how receptive the reader’s going to be to a certain point.

The second problem is, to be honest, that a lot of good examples of analogies and hypotheticals have already been taken. Or they’re trite. And then the third one is, if you try to be memorable or creative, you run the risk of coming up with something that sounds forced. Or it might sound clever in isolation, but it doesn’t really fit the point you’re trying to make. I suppose some of that requires a gift; some of it, though, is probably teachable. So I think it’s a combination.

I don’t think that writing clear and concise sentences is quite as teachable as people want to believe, though, because it requires a certain type of thinking. There’s a certain approach to linking the thoughts in your head to the words your fingers produce that you can’t accomplish just by learning different style tips. It’s teachable to a point, but not 100%.

So anyone can become a better writer, but not everyone can become Chief Justice Roberts.

I don’t know if it’s impossible to become like him, but I would say that speaking empirically, it’s extremely hard. Because I show people all the time what I think are bite-sized techniques from the three justices you mentioned. They nod, and they say, “This is much easier than I thought.” But rarely do I see them actually able to integrate the techniques into their writing in a way that seems as natural.

A lot of people in my realm think that unclear writing from lawyers and judges is on purpose; lawyers try to be convoluted to justify their high bills, or the judges try to keep things really confusing so they can’t be reversed. I see that narrative’s appeal, but I don’t find that to be the case. Because I’ve worked with so many lawyers who write unclearly, but who otherwise have brilliant resumes. Believe me, their unclear writing isn’t on purpose. It really is hard to write about something as abstract and complex as the law.

What are some of your favorite hypotheticals or analogies that you’ve seen over the years?

Well, let’s go back to the best available control technology. I’ve always been struck by what the chief justice did there: “Choosing the best technology is like choosing the best car. Mario Andretti would choose a Ferrari; a family of five a minivan. I always thought that was an incredible example that on the one hand spoke to people’s own experience, and really provoked them in a way that might feel personal. And yet, after people are swept away by that analogy — and I notice many people are, including liberals who wouldn’t normally want to agree with him — they tend to forget that it’s really not that great of ananalogy. Because emissions are quantifiable, and car choice is inherently subjective. So I think that’s a terrific accomplishment if you’re an advocate.

And then, what I also really appreciate from Justice Kagan is that she likes second-person hypos. She’ll say, “Suppose a city imposed a 0.0000001 cent tax on people of a certain religion.” So she’ll come up with these hypotheticals and sort of insert you into the world of the hypothetical by addressing you in the second-person. And one thing I’ve pointed out and I get people to agree on this, regardless of their ideology is that either her example is unfair, or the majority is wrong. It has to be one or the other. You’d have to actually say that her example doesn’t match the fact pattern in the case, because if it does, then the majority is wrong and the dissent is right. Now, that doesn’t mean people are going to agree. But as a logical matter, I’m telling you the truth. That’s how she crafts these hypotheticals.

Justice Kagan and the late Justice Scalia seem to have that in common. They speak the same way they write, which makes their oral argument questions especially effective.

Yes. I think that explains why people who don’t agree with Justice Scalia ideologically admire his writing; it makes them think. A lot of conservative law students enjoy reading Justice Kagan, too. They present their points and hypotheticals, and you’re intellectually engaged.

And their opinions are clearly written — maybe unlike some other materials in law school.

Absolutely! That’s another reason law school students like those two justices — because they’re so grateful to read something they can actually understand, which is much rarer than it probably should be.

You wrote some terrific blog posts a couple of years ago about Justice Gorsuch’s writing in the lower courts. What are your thoughts on Justice Kavanaugh’s writing on the D.C. Circuit?

Shortly after he was nominated, I did go back and pull a lot of his decisions from the D.C. Circuit. I had already looked at his writing when I wrote “Point Taken,” as he was pretty well known on the federal bench for being exceptionally strong. Obviously we don’t know how his style on the Supreme Court is going to be because he hasn’t written anything. His style is probably closest to the Chief Justice’s — a spare style. No unnecessary syllables, words, or phrases. But also, at least in what I’ve seen from him on the D.C. Circuit, there’s not a lot of risk-taking. Very, very few metaphors or figures of speech or elaborate analogies. Also, no harsh rhetoric — even when he’s dissenting. No asides. Nothing “fun.” Just what most people would prize as excellent, straightforward, clear writing on difficult topics, but without anything particularly memorable or idiosyncratic.

This is quite nerdy, so bear with me. But in your Gorsuch cheat sheet, you said that he sometimes uses “she” to refer to something generic, like a user. And you said that this wasn’t so common for conservative judges. A few weeks ago, I attended an event at Princeton with Judge Thomas Hardiman, and I noticed that he did the same thing as Gorsuch: he used “she” pronouns to refer to a generic judge. I thought that was kind of interesting.

That is interesting. It might seem like a nerdy point, but it does matter. Because you have to make those choices when you write; you have to choose whether you’re going to have a generic masculine pronoun or a generic feminine pronoun, or try to avoid it, or not try to avoid it. I don’t think those choices are random, and I don’t think they’re related solely to grammar or writing. My general advice — because this is actually a very common question I get from judges and lawyers — is to try to make the problem disappear by putting a lot of sentences in the plural so you don’t have to write he or she or he/she.

Your advice is really helpful, because it can get awkward – and certain pronouns may be seen as a political statement.

It probably shouldn’t be, because I think most people operate in good faith. But just as you say, these are seen as political choices. And not doing them is also seen as a political choice. Not so much nowadays, but there used to be many people who only used “he.” They believed, and still believe, that this debate is preposterous and everybody understands “he” to be the universal pronoun. I also notice that a lot of law professors only use “she.” I do believe when you’re a lawyer, and to a large extent a judge, you have a duty to avoid distracting your readers as much as possible. So, fair or not, these kinds of things do rile people up in different directions. If it’s possible to avoid the issue, I think we should at least try.

How often do your kids ask you for writing advice?

When they need to. Or, you know, when they have a standardized test. But I try not to interfere in how they’re taught or what they learn.

Actually, it’s funny, because you would think someone in my position would be very critical of how writing is taught or how literature is taught. But based on my limited experience, I’m really impressed. My daughter’s AP Language and Composition seems really great – I think there’s a nice mix of hardcore instruction on mechanics, which is not so popular, and there’s some attention to vocabulary, and attention to writing essays, and attention to analyzing essays and looking for rhetorical devices.

The hard part, of course, is making all this enjoyable. Grammar’s not inherently interesting, I will admit, and literature can seem alienating as well. So if you have a good high school English teacher, I’d say it’s priceless.

How was your English instruction in high school?

I had great teachers later on in life. But believe it or not, I didn’t care that much about academics when I was in high school. I did very well, but I didn’t care. My strength was actually in math. [laughs] And it’s funny: I’ve always been good at grammar since I was a little kid. But not so much literature. I didn’t love even the kinds of things you read in high school, which is very unusual for someone who ends up starting a PhD in the humanities.

Which books on writing would you recommend to teenagers?

A pretty fun book, relatively speaking, with a lot of great before-and-after examples, is called “Style” by Joseph Williams. I think that’s really good. Again, it’s not talking about writing in the abstract; it’s giving lots of sentences before and after in ways that may stick.

I mean, there really aren’t a lot of fun books on writing that would be appropriate for college students, let alone high school students. I think a lot of ambitious high school students are sometimes asked to read Orwell’s “Politics and the English Language.” That’s more of a thinkpiece on language, and it’s controversial. There’s always “Elements of Style” by Strunk and White, which is also controversial.

“Elements of Style” is controversial?

Yeah. It had a milestone recently, and there was a symposium on it. People pointed out that when Strunk and White wrote it, they didn’t really expect it to become a bible. And that the authors didn’t necessarily have the linguistic background to pull it off. A lot of sentences they shared in the passive voice are actually not, and vice versa. And it treats, in a somewhat random way, certain points of writing and not others.

On the other hand, it’s the best-selling book in the world on writing. And a lot of people are just jealous, so they want to knock it down. They think their books should be the go-to guide.

So if I taught high school, which is never going to happen, I would teach writing the way I teach lawyers and judges – through activities and exercises so you really learn it by doing it. I would find some great essays, and then I would take a lot of the precise, interesting verbs and replace them with boring ones and try to have the high school students think of more clever ones. I think that’s much more useful than reading books about writing – which is kind of funny, because the main criticism I’ve gotten of “Point Made” and “Point Taken” is that they have too many examples and not enough discussion of what makes for great writing. But I’m not backing down. I’m glad that I give readers many examples, because you can get a real false sense of security in reading abstract thoughts about writing that you will agree with, but that will not change your actual approach one iota.

I also think the idea that you should read great writing and it’ll just soak through is overrated. I know you’re in high school, and you’ve probably read several Shakespeare plays – voluntarily or not. But you wouldn’t be any better at writing a play after reading Macbeth than you were before. It’s not nothing, but it’s not everything. I think it’s much more important to interact with text, to create it, to break it up, and then to put it back together. That’s more enduring than passively reading great writing.

How can teenagers improve their writing?

I always appreciate it when I see teenagers blogging on Twitter or other social media sites. And I don’t mean Instagram, where you re-post pictures of spring break. I just think that for teenagers, including teenagers who may be isolated in a small town somewhere, there are so many great mediums and venues now to practice their writing and to express their thoughts and ideas. I even know of teenagers who read something in the Wall Street Journal or New York Times, and they write substantive comments that other people see and reply to. That’s a wonderful feature of our world. And of course I’m very well aware that it’s also a dangerous feature, because there’s so much nastiness. But I think that these social media avenues can be a great way for teenagers to hone their skills and sharpen their thoughts.


Other interviews conducted by Anna Salvatore: UChicago law professor Justin Driver, former Solicitor General Neal Katyal, court artist Art Lien, New York Times Supreme Court correspondent Adam Liptak, UCI Law Professor Leah Litman, litigant extraordinaire Fane Lozman. former Court writer Linda Greenhouse, Georgetown professor Shon Hopwood, NPR reporter Carrie Johnson, Fix the Court Director Gabe Roth, IU Maurer Law Professor Ian Samuel, and Lawfare editor-in-chief Benjamin Wittes. 


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