AI Secrets of the Best Briefs

• do NOT fare better on traditional readability metrics like the Flesch index or grade-level score. • do NOT vary their sentence length more than other lawyers do (though they are likelier to follow an unusually long sen- tence with an unusually short one). • do NOT use the word “that” at a lower rate—in fact, they do so at a higher rate. • do NOT use shorter words (but see below). • do NOT use more active voice (but see below). • do NOT use fewer adjectives and adverbs (but see below). Before you denounce the data as sacrilege, consider that what readers experience as overly long sentences could be the occa- sional gargantuan sentence (writers like Chief Justice Roberts draft those, too) floating amid a turgid document. And when read- ers admire short, crisp, declarative sentences, they’re probably not counting words, computing means, and diagramming syntax. Clarity and conciseness are still worthy goals, of course. It’s just that if you believe in data and want to induce that “short and to the point” sensation, the best brief-writers have more nuanced and productive ways to break the mold. Let’s start with substance. Language analysis can yield insights into what kinds of arguments lawyers make and how, not just into what words they use to do so:

Also bridging style and substance: data on headings, defined terms, parts of speech, types of words, and even punctuation.

TOP BRIEF-WRITERS ARE MORE LIKELY TO . . .

RANDOM BRIEF-WRITERS ARE MORE LIKELY TO . . . Use slashes. Use semicolons to join two clauses.

TABLE 2

Punctuation Use em dashes to expand on a point. Use colons to explain a point. Conventions Include headings (though they’re no more likely to include subheadings).

Define parties in more than one way, as in “Defendant”

or “Employer”. Use acronyms.

Parts of Speech

Use pronouns like “it,” “she,” and “they” (but not “he” or “him”). Include the relative pronoun “that” after a verb. Use verbs. Use adjectives and adverbs (but see below).

Use prepositions, especially “at,” “by,” and “of.”

Now let’s turn to pure writing style—what you can most read- ily adapt. Here’s how I broke down the style data:

• Analyzed the relative rates of unigrams (a single word or punctuation mark) along with bigrams and trigrams (combi- nations of two or three). • Looked for meaningful differences between the two sets. • Looked for patterns in those differences and then grouped them into nine coherent factors. Here are the nine factors. Factor 1: Speed Up The legal-writing punditry has focused so much on fighting “legalese” (see below) that it sometimes neglects the many bu- reaucratic, heavy-handed, or cumbersome terms that belong to modern English but can drag down a document. To that end, this factor consists of 176 correct-but-ponderous terms that are less common in top-notch briefs.

TOP BRIEF-WRITERS ARE MORE LIKELY TO . . .

RANDOM BRIEF-WRITERS ARE MORE LIKELY TO . . .

TABLE 1

Write “the Court must.”

Reasoning Use language like “for

example” or “for instance” to introduce examples. Address the court in the second person: “Consider,” “Suppose,” and so forth. Use language like “it is true that” or “to be sure” to concede a point. Use a parenthetical for a single-sentence quotation. Quote from authorities within sentences rather than as a full sentence or a block quote. Include language like “some courts” or “many courts” to synthesize case law.

Have a high ratio of cases cited per word. Use “ id. ” Use See also or other signals introducing similar cases on the same point.

Case Law

RANDOM BRIEF-WRITERS ARE MORE LIKELY TO . . .

TABLE 3

Cumbersome Sentence Structure Follow a semicolon with a conjunctive adverb like “however” or “therefore.” Start sentences with wind-up, throat-clearing phrases like “It is apparent that.” Wordy Phrases Use wordy expressions like “with respect to,” “the fact that,” “are obligated to,” “exists to,” and “in the event that.” Long Words Use long words that have shorter alternatives like “absence,” “characteristic,” “initiated,” and “regarding.”

Published in Litigation, Volume 46, Number 4, Summer 2020. © 2020 by the American Bar Association. Reproduced with permission. All rights reserved. This information or any portion thereof may not be copied or disseminated in any form or by any means or stored in an electronic database or retrieval system without the express written consent of the American Bar Association. 3

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