LEGAL BLOG & NEWS

Practical Legal Writing from the VTLA Annual Convention

By Jay O’Keeffe 

Chief Justice Lemons likes to say that an advocate develops three oral arguments in each case: the one they planned to give, the one they actually gave, and the one they wish they’d given.

Last Friday, I was honored to speak at the VTLA Annual Convention. My topic was practical legal writing. Below is the speech that I planned to give. Two caveats: First, this is not the speech that I actually gave (let alone the speech that I wish I’d given); the actual speech was more of a structured improvisation and was, uh . . . way better? At least more lively and profane. The text below is just what I used to plan my slide deck. Second, the presentation was accompanied by a written outline with loads of citations. I tried to give credit where credit was due in the outline but couldn’t cite all the sources orally in real time because that would be the most tedious presentation ever. I’m not claiming original ownership of the ideas below.

Anyway, here you go:

Thanks, and good morning. I’m grateful to be here for all the usual reasons, but especially because I get to talk about my favorite part of our job: Writing. As lawyers, we get to be professional writers. We are paid to write. That’s a dream come true for some of us. And it only gets better, because people have to read our stuff, even if they’d prefer not to. The judge has to read our briefs; our clients have to read our memos; opposing counsel has to read our letters. We’re blessed with a captive audience. That makes us some of the luckiest people—and even some of the luckiest writers—on the planet.

But those blessings come at a cost, because we as lawyers face pressures and obstacles that other writers never have to consider. It’s not just the timing and economic pressures of a law practice—although that’s a big part of it, and something that we’ll talk about today. Those pressures are compounded by a challenge unknown to the writing profession at large: On every single project, on every single case, there is always some asshole on the other side trying to make us fail. Trying to make sure that our words are discounted or misunderstood. Other writers have to cope with the demons in their heads—fear, self-doubt, procrastination, perfectionism, all the forms of self-sabotage that stop them from doing their work. And to be sure, we have to deal with those, too. But we get the added bonus of opposing counsel.

Add it up, and you’ve got a welter of factors working against us, and keeping us from delivering the type of top-notch, professional writing that our clients deserve. So for the next 30 minutes, I want to talk about practical strategies to help us get the work done. And to get it done right, at the level our clients need. So I’m going to focus three ideas: Preparation, Process, and Product.

Let’s start at the beginning, with preparation. What’s the apocryphal Lincoln quote? “Give me six hours to chop down a tree and I will spend the first four sharpening the axe.” In our preparation phase, we’re sharpening the axe. We do that first by reading good writing. That doesn’t have to be legal writing. In fact, it probably shouldn’t be legal writing. If you’re looking for a good composition, you’re better off reading The New Yorker, or The Atlantic, or anything by Michael Lewis, Malcolm Gladwell, or John McPhee. These authors are mechanically excellent. They know how to tell a story, frame an argument, and engage an opposing position. They use structure to develop themes. And their prose sings. That’s because they’ve mastered rhythm, word choice, sentence structure, and variation. You can’t learn this stuff by reading law review articles.

But there’s more to it. These folks learned the secret of what makes writing interesting: precise, concrete examples. Malcolm Gladwell says that you see this when you talk to an interesting person about a subject they care about. So borrowing from Gladwell, Trey Smith is interesting, and he loves Aretha Franklin. But he doesn’t just say, “I like Aretha.” He’ll talk about a specific progression in a specific song that she recorded in Muscle Shoals in 1967 that he first heard in 1987 and where he was when he heard it and how it changed his life. That’s interesting. And the trick isn’t limited to popular nonfiction. Who here has read John Roberts’s brief in Alaska v. EPA? Consensus pick for the best brief ever written? What do you remember about that brief? The Irish Setter in the airplane. That detail had nothing to do with the brief’s merits, but everything to do with its themes. It set the brief apart from the hundreds of others that the Court and its clerks read.

One last thought about reading: When you read this stuff, read it critically—the way an NFL quarterback watches game film. Think about the choices the writer made. Try to figure out why she made them. Run them back in your head and play out what would have happened if she’d made different choices. Hunter S. Thompson retyped passages from Fitzgerald and Hemingway to see what it felt like to write like them. He typed up The Great Gatsby more than once, in its entirety. That’s professional.

A second thought about preparation: Know the rules—grammar, civil procedure, local rules, standing orders, rules of court. There’s no easier way to lose credibility than by making a small, dumb mistake. If your audience can’t trust you with the small stuff, why should they trust you with the big stuff? They shouldn’t. And if you get the little stuff wrong, people are guaranteed to catch you. Almost no one will notice if you misconstrue an obscure case about the First Amendment rights of protestors, even though it’s a substantive mistake. But absolutely everyone will notice if you leave the “l” out of “public forum.” Even though it’s a nonsubstantive error, it will erode their trust. The little mistakes will kill you.

That brings us to our second major point: Process. Every good process starts with the end in mind. So at the outset, we identify our document’s goals. We ask some basic questions

  • Who is our reader?
  • Do we want to persuade or inform?
  • How much do they already know?
  • How much more do they want to know?

And consider the messages and themes that we want to convey

  • Do we want to present the case as easy or hard?
  • Novel or routine?
  • Fact-bound or law-driven?

The answers to these questions will color every choice that we make, from structure to typography.

And I’m serious about that. Let’s say we have a case that’s really strong on the law, but maybe with some unsympathetic facts. We want our argument to feel logical. Inevitable. Like math. And maybe we want our brief to feel as much like the Restatement or a treatise as possible. So we’ll pick a font like Century Schoolbook. We’ll use heavy boldface type for emphasis—just like the “black letter law” that shows up in the Restatement. We’ll use lots of syllogisms. Structurally, our brief will focus on the law. We’ll adopt a dry, detached tone.

Or consider the opposite scenario: We have a case with sympathetic facts that will require an expansion of the law. What now? Well, if our strength is our client’s story, we want our brief to feel like a story—like something a judge might find on her iBooks or Kindle. Maybe we pick an airy font like Palatino. Maybe we adopt a more conversational tone. Structurally, our brief will be weighted toward the narrative. We might even adopt a non-chronological structure, like a novel, to emphasize themes or particularly compelling facts.

But just identifying goals doesn’t get us from a blank white screen to a 50-page brief. To do that, it helps to have a system. Indulge me for a minute. If you watch sports, you’re probably sick to death of hearing people say “trust the process,” right? It’s tired, it’s faddish, it’s cliché. But there’s a kernel of truth in there. Think about a seven-pass sequence in a soccer game. You’re looking at between 10 and 20 touches on the ball. Each touch requires every one of the 22 players on the field to make a decision, and each of those decisions requires every else on the field to make decisions. So you have a geometric progression. In 10 seconds. And a soccer game isn’t measured in seconds; it’s 90 minutes long. Teams play dozens of games over the course of a season. No player or coach can manage all that information. It would paralyze them. They focus instead on offensive and defensive systems—principles of play and rehearsed, choreographed movements—that reduce the cognitive strain. After all, there’s no sense making 100 decisions when 1 will do. And implementing systems lets each player focus only on his immediate task—this touch, this pass, this shot—without having to account for the 21 other players on the field.

Same thing with writing. Getting from a blank page to a 50-page brief is a huge cognitive lift. Just picking the first word is a big deal. I mean, there are something like a million words in the English language? How do we know which one to use? It’s tough. So we follow a process break it down into manageable chunks. How we do it in practice can and should be idiosyncratic. But if we’re going to be maximally efficient, we need to both isolate and make room for each stage of the writing process because we don’t have the bandwith to do everything at once. Imposing a system reduces decision fatigue, fights writer’s block, and it gives us more space to be creative.

Bryan Garner has a handy mnemonic for this: Madman, Architect, Carpenter, Judge. Each character represents a phase of the writing process.

The Madman phase is wild, nonjudgmental brainstorming. Try to think of all possible approaches to your writing task. Write them down, by hand, on a notepad or dry-erase board. Do some legal research, and then brainstorm some more. The Madman thinks of hard questions, even if he can’t answer them. The Madman’s work product is a bunch of notes. His goal is to be very sloppy and very productive.

The next phase is the Architect. She works from the Madman’s notes. She spots connections and imposes structure. She takes the madman’s ideas and produces a linear, full-sentence outline.

The Architect then hands things off to the Carpenter. He does the actual writing—which should be easy, because the Madman and the Architect have already done all the hard work. The Carpenter is basically filling in the blanks from the Architect’s outline. He is writing quickly, without editing along the way. He can leave out precise case citations and quotations with a note to fill them in later.

Finally, the Carpenter lets his draft sit for a day or two, then turns things over to the Judge. The Judge is our internal editor. Most lawyers have a highly overactive Judge. If we let her run free, she will stifle the writing process. She will look over the Madman’s shoulder and say, “This is garbage.” That will hurt the Madman’s feelings. He will shut down, and we will be less creative. And you know what? The Judge is right. The Madman’s stuff is garbage. It’s supposed to be garbage It’s not supposed to be good yet. That’s how writing works. You can’t compare your first draft to, say, Steven King’s published work. Stephen King can’t compare his first draft to Stephen King’s published work.

So we need to keep the Judge in a box until it’s time for her to do her thing. And when it’s time, we just give her the keys and let her roll all.

This raises another interesting question: How do we edit? My natural tendency is to sit down and start marking up a draft—line edits, proofreading, big thoughts—correcting every mistake that I see. I mark it up and run and the changes. Print out the document and mark it up again. Lather, rinse, repeat. The editing process expands to fill all available time between completion of my first draft and delivery of my final document.

That is a deeply stupid way of doing things. It’s infinitely long, it’s impossible to plan, and it is hugely demanding because it requires me to do a million things at once.

Here’s a better way I’ve found to do it: Break the editing process up into a series of passes over the document. Each pass has a specific objective. I do it right, once, and then I’m done and I never think about it again. So depending on how large the project is and how much time I can devote, I can do a number of passes, reviewing at increasingly granular levels. But I’ll probably want to make at least 3 passes: a big-picture pass, a structure and coherence pass, and a line-edit pass.

And we can simplify those line edits even further because sentences are like apples: They’re all about chunks and cores. “Chunks” are bite-sized pieces of information. I have a 10-year old who loves Legos. He builds all sorts of cool Star Wars ships and buildings. And when he does that, his Lego blocks are the irreducible unit of construction. We can break his project down, but not any further than the individual Lego.

That’s how chunks work in writing. They’re the irreducible, idea-level unit. You can’t break things down any further. And the trick to editing sentences is managing your chunks. We can do this a number of ways:

  • Dividing longer sentences into shorter segments.
  • Organizing those segments to reflect the order of our thinking.
  • Placing important information in its own sentence or, failing that, at a more chunkworthy place in the sentence. After all, a standalone sentence is more important—and gives an idea more emphasis—than an independent clause, which is in turn more important than a dependent clause, which is more important than a prepositional phrase, which is more important than a modifying phrase. You get the idea.
  • Putting old information before new information.
  • Presenting your argument before the bad guy’s rebuttal.

And sentences, like apples, also have cores: a subject, a verb, and an object. So when we edit, we think about those cores. We try to put the subject, verb, and object close together. We try to put the core of the sentence’s content in its grammatical core. We try to put the sentence’s most important action into its verb. And when it doubt, we put the core near the start of the sentence because it’s just easier to read that way.

When I talk about process, lawyers tell me: These steps are nice in theory, but I don’t have time for them. My clients can’t afford them. I need to get paid.

I disagree. These are the essential steps of the writing process. Trying to cut one out makes all the rest harder. So they take longer, and your brief isn’t as good. And let’s be very clear: I am not saying that you need to spend 5 days on each phase of this process. If you only have a few hours to crank out a brief, fine. That’s all you’ve got. But use it intentionally. Spend part of it brainstorming, part of it outlining, part of it writing, and a lot of it editing. That’s PROCESS.

I want to shift gears now, and spend a little time speaking about the final PRODUCT, and what makes for effective legal writing. And in doing so, I want to touch on three concepts:

  • Providing focus before detail;
  • Avoiding unnecessary suffering; and
  • Developing a sense of style.

Let’s start with focus before detail. Emory professor Timothy Terrell argues that most technical writing—including legal writing—fails at the macro level because it delivers too much information without offering any context or structure. His basic analogy is that if the information in a writer’s head is a liquid, too many writers just dump that information onto their readers, without giving them a container to collect it. Professor Terrell stresses the need for “meta-information” in legal texts–signposting, structural cues, and the like. The trick to good technical writing, in his view, is to make complicated information seem straightforward and accessible.

One of his mantras is focus before detail: Help your reader understand what we’re discussing before going in for a deep dive. We do that in the introduction—before we get to anything else—by making the reader smart, attentive, and comfortable.

First, we make the reader smart. Before digging in, we forecast the information that we’re about to provide. We do this in three ways.

We label: We tell the reader what the document is about, so she can put it in context. For example, “This is a breach of contract case that turns on a single issue: Whether the trial court erred by admitting parol evidence of blah blah blah . . . .”

We map, previewing the document’s structure. For example, “Summary judgment is appropriate for three reasons. First, blah blah blah . . . .”

And we point: We let the reader know what she should be looking for as she makes her way through the document.

But in addition to making our reader smart, we want her to be attentive. To keep her focused, we’re very clear about the bottom line: We tell her precisely what’s at stake. Our powerful, syllogistic reasoning compels a favorable result. But we want to make sure that the reader understands, from the start, why that result is important. So we connect it to her circumstances. For example, “If the Court upholds this sanction, it will effectively eliminate blah blah blah . . . .”

To keep the reader attentive, we also want to be efficient. We want to show her that we will not waste her time. So we’re not repetitive or verbose. We don’t present irrelevant information.

Finally, we want to keep our reader comfortable. And we use two techniques to do that. First, we use plain English and a classic prose style—as opposed to, say, shrieking italics and bitter ad-hominem attacks—to put her at ease.

Second, we’ll appeal to ethos. We’ll show why the result we seek is just and fair, so the judge feels better about ruling in our favor.

And that’s focus before detail.

Our next rule is do not inflict unnecessary pain on your reader. Seems fair enough. What are some things that inflict pain? One obvious culprit is repetition and verbosity. All lawyers know that we often face express page limits. But we often have to navigate more subtle—and more important—limits on the length of our work. That’s because as lawyers, we’re generally writing for readers who are

  • Very smart,
  • Very busy, and
  • Already behind on a ton of reading.

As a result, they have extremely limited time, energy, and patience. We squander those resources at our peril. At best, adding words dilutes the force of our writing. At worst, it leads to unnecessary mistakes. This all goes back to Justice Scalia’s golden rule, which is the very first thing in our outline: Whatever doesn’t help hurts.

What else inflicts pain? Anything included to show how smart you are, or how hard you’ve worked—string cites, superfluous citations, clever wordplay. You don’t get points for that. Intelligence and hard work are assumed as the price of admission. Cut the showboating.

You know what else causes unnecessary suffering? Block quotations. It’s bad enough when you find yourself in the hands of a writer who doesn’t appreciate white space, and who writes paragraphs that go on for pages and pages that go on for days. But it gets even worse when she starts using block quotes: The text gets single-spaced and indented, the font gets smaller, and everything runs together. Block quotes are an abomination. But sometimes you do need to work with the controlling text. When that happens, I’ve got three tricks to help.

First, you can tell the Court what the block quotation says in your own words in your lead-in. That way, even if they skim or skip the quotation, they’ll get the point.

Second, you can break the quotation up into forty-nine-word chunks. Quote the first one. Then say, “The Court went on . . . “ and quote the second chunk. Continue until you have used all the words. This will trick the judge into reading the whole quotation.

Third, if you are quoting from a document that has been produced in the case—maybe a contract or email—you can use the Snip Tool to capture the relevant text. Create a table in your brief with two vertical cells. Past the text into one of the cells. Use the drawing tools to highlight or mark it up as you see fit. Use the other cell to label it “Figure 1.” The table and the pretty colors will trick the judge into reading your quotation. They will also make your brief look professional.

What else is sure to give your reader a headache? Snark, meta-analysis, and personal attacks. Look: If we’re writing a brief, we are trying to help the judge, not hurt our opponent. The judge is just trying to get to the right answer. She doesn’t care if opposing counsel is Mother Theresa or Michael Avenatti. She just cares about the strength of their arguments. So she certainly won’t be impressed when, for example, you call out the irony of your adversary’s position. Irony is a literary device, like metonymy, synecdoche, or alliteration. A legal brief is not a literary critique.

And those cheap shots can backfire for at least two reasons. First, anything that your reader perceives as a personal attack on your opponent will cost you credibility. Professionals attack ideas, not colleagues. Second, the judge is just trying to get to the right result. It’s in your interest to assure her that your friend across the courtroom has presented the opposing argument in its strongest possible form. Because if she doubts opposing counsel’s work product, the judge will assign a  clerk to do his job for him. That’s bad for us. The clerk is probably at least as smart as opposing counsel. She’s less experienced, sure, but she’s got way more time on her hands and much more credibility with the judge. We want to avoid this scenario at all costs. So we play nice.

And that brings us to our last tip: cultivate a sense of style. Stylish writing captures the reader’s attention and lures them into your argument. Of course, we can’t all be Hemingway. Otherwise there’d be no excuse for compelling Friday morning CLEs about legal writing. But we can fake it. The outline has tips courtesy of Mark Hermann. Here are the big ones.

  • Write in short sentences. If the sentence runs for more than 3.5 lines, break it in half. Make it two sentences.
  • Write in short paragraphs. Two or three to a page, and make sure that they have topic sentences.
  • Start sentences with little words and familiar concepts, and build momentum as you move into longer words and harder concepts.

That’s all I’ve got. I love to talk about this stuff, and would be glad to meet you at the coffee station if you want to continue the conversation.