Point Made: How to Write Like the Nation’s Top Advocates

Vicki Lowery Sam Gregory

Article by Vicki Lowery, research assistance by Sam Gregory Featured Authors

Posted December 17, 2016

Unlike sports or popular music, advocacy writing doesn’t evoke a hit list of heroes; but it if did, Ross Guberman would certainly be one of them. His must-read book Point Made: How to Write Like the Nation’s Top Advocates is not an ordinary legal writing book. It doesn’t tell you how to write better briefs: it shows you how to do it. Point Made offers step-by-step instructions that “reveal the craft” behind great legal writing.

Taking an empirical approach, Guberman identifies fifty of the most renowned and influential advocates and analyzes their writings. His list of super-star advocates includes John Roberts, Elena Kagan, Ruth Ginsberg, Frank Easterbrook, Barack Obama, Laurence Tribe, Ted Olsen, David Boies, Eric Holder, Maureen Mahoney, and Alan Dershowitz.

What makes their writing so persuasive? Guberman assures us that it’s more “science than art.” By dissecting hundreds of their motions and briefs, Guberman has spotted patterns in their work. In Point Made, he describes those patterns in specific, learnable techniques that demystify what makes good legal prose so compelling.

Guberman settles on fifty concrete techniques for more effective brief writing that span from the opening paragraph to the final footnote. The writing techniques are grouped according to the section of the brief where the techniques are most likely to be used. For ease of reference, each writing technique is listed separately in the Table of Contents.

Point Made is divided into five sections: (1) creating a theme and a compelling introduction (The Theme); (2) laying out the facts and crafting a narrative (The Tale); (3) structuring your argument (The Meat); (4) livening up your style (The Words); and (5) crafting a strong conclusion (The Close). In each section, Guberman offers multiple techniques for enhancing that portion of the brief as well as numerous real world examples of how those techniques have been used by some of the best legal writers in the nation.

To help you develop the theme of your case and craft a compelling introduction, for example, Guberman shares techniques in Part One (The Theme) like Brass Tacks, The Short List, Why Should I Care?, and Don’t Be Fooled. And, as another example, in Part Two (The Tale), Guberman offers several techniques to make the fact section more persuasive including Panoramic Shot; Show, Not Tell; Once Upon a Time; and Headliners.

Point Made starts out, logically enough, with four chapters on how to write a compelling introduction. It conveniently gives you a checklist:

  1. Brass Tacks. Start out by telling the court who, what, where, when, and why.
  2. The Short List. List the three or four points that you’d make to a judge who gave you sixty seconds to explain why you should win. And use the word “because” in each point (at least in your first draft) to make sure that you’re operating at the requisite level of specificity.
  3. Why Should I Care? Explain why the court should feel good about ruling your way.
  4. Don’t Be Fooled. Draw a line in the sand between two competing views of the dispute (e.g., “This is not a case about x.”).

But it’s in the details that Guberman truly excels. Concerning point three, Why Should I Care?, he identifies three fundamental judicial fears that an advocate can manipulate to grab the court’s attention:

  • The fear of misconstruing a statute or doctrine;
  • The fear of creating new duties, rules, or defenses; and
  • The fear of reaching an unfair result or causing harm.

He then gives multiple examples of superstar advocates skillfully using each technique in various briefs.

As one real-life example of a great opening Brass Tacks passage, Guberman spotlights Eric Holder’s brief in In re Chiquita Banana. Holder, then in private practice at Covington & Burling, litigated a high-profile civil case involving bananas, American missionaries, and extortion in Colombia. He started his introduction to a motion to dismiss with a Brass Tacks paragraph telling the court who the parties are, what happened to the plaintiffs and when and where it happened, when they brought their claim, what they want, and why they should get it. Holder also squeezes in what the claims are not, highlighting the weakness of the plaintiffs’ case.

Plaintiffs in this action are relatives of five American missionaries who were abducted for ransom and tragically murdered in the mid-1990’s by a communist guerilla group in Colombia, known as the Fuerzas Armadas Revolucionarias de Colombia. Now, more than a decade later, they seek to hold Chiquita Brands International, Inc. liable for those deaths under the Antiterrorism Act, and Florida and Nebraska tort law. There is no allegation, however, that Chiquita was involved in the kidnapping and murder of the decedents, that Chiquita intended that these despicable acts occur, or that Chiquita even knew about them until plaintiffs brought this lawsuit. Instead, plaintiffs allege that Chiquita is liable for decedents’ deaths solely because Chiquita’s former Colombian subsidiary made payments extorted by the FARC when this radical Marxist group controlled the remote banana-growing regions of Colombia in which Chiquita’s subsidiary operated.

Guberman also advises that the facts in a brief should read like narrative non-fiction, a bit like something you’d read in the The Atlantic or The New Yorker. As an example of effective fact writing that lets your facts “show, not tell,” Guberman offers the following example from Chief Justice John Roberts written when he was a practicing lawyer. Watch how Roberts explains the way the Red Dog Mine, the accused polluter in Alaska v. EPA, got its name:

For generations, Inupiat Eskimos hunting and fishing in the DeLong Mountains in Northwest Alaska had been aware of orange-and-red-stained creekbeds in which fish could not survive. In the 1960s, a bush pilot and part-time prospector by the name of Bob Baker noticed striking discolorations in the hills and creekbeds of a wide valley in the western DeLongs. Unable to land his plane on the rocky tundra to investigate, Baker alerted the U.S. Geological Survey. Exploration of the area eventually led to the discovery of a wealth of zinc and lead deposits. Although Baker died before the significance of his observations became known, his faithful traveling companion — an Irish Setter who often flew shotgun — was immortalized by a geologist who dubbed the creek Baker had spotted “Red Dog” Creek.

Guberman prompts the reader: Why would Roberts mention an Irish Setter? What does a shotgun-flying dog have to do with the Clean Air Act or administrative law? Roberts is litigating a classic federalism fight between the states and the federal government. Who knows what a mine means to nearby residents better than the local and state officials close to the ground?

In Part Three (The Meat), Guberman, also an award-winning journalist, notes that strong headings are like good newspaper headlines: they give you the gist of what you need to know and draw you into text you might otherwise skip. Guberman analogizes the headings and subheadings of great advocates to one of those Russian nesting dolls. As you open each wooden figure, you find a smaller version of the same doll inside. Similarly, as various headings and subheadings get “smaller” and more detailed, they build back toward their larger and broader siblings.

To see such nesting in action, Guberman offers an example from former ABA President Carolyn Lamm nesting three levels to explain why a parent company should be subject to personal jurisdiction in Virginia based on both its business activities and its relationship to one of its subsidiaries:

  1. Barceló GH is subject to personal jurisdiction in Virginia.
    1. Barceló GH conducts business in Virginia.
    2. Barceló GH is subject to jurisdiction in Virgina through its wholly-owned subsidiary and alter ego Barceló USA.
      1. The tribunal’s finding that Barceló GH is indistinguishable from Barceló USA should be given preclusive effect.
      2. Barceló GH’s corporate merger activities in Virginia are further evidence that is indistinguishable from Barceló USA.
      3. Overlapping corporate officers and directors underscore that Barceló USA is an alter ego of Barceló GH.

In this example of effective nesting: A and B prove I, while 1, 2, and 3 prove B. And these headings and subheadings pass the old test: Could a judge skim your headings and subheadings and know why you should win? Yes, definitely. Moreover, these headings explain where the brief is going and provide signposts along the way.

Another technique which focuses on structuring the paragraphs in each section of the brief is called Wish I Were There. Guberman instructs you to start each paragraph by answering a question you expect the court to have. According to Guberman, the best advocates “sense that judges have predictable questions” such as: What is the standard? How does it apply? Has any other court done what you’re asking us to do? What about the other side’s points? And what’s the bottom line? Guberman demonstrates that effective legal writing answers these questions using clear, comprehensible prose.

After writing the argument portion of a brief, consult Part Four (The Words). This section focuses primarily on language usage, sentence structure, and punctuation. The general consensus about legal writing — even substantively sound work — is that it is boring and hard to read. Guberman proposes four reasons for this perception: (1) law is dense and dry; (2) lawyers tend to adopt a haughty style; (3) tips on improving writing style are too general (e.g. “be clear”); and (4) writing tips are usually framed in the negative — avoid this, don’t do that, etc. — as opposed to empowering tips on how to write effectively.

To combat these flaws, Guberman offers seventeen techniques for improving your writing style. He offers tips to liven up the language in a brief to add colorful verbs, confident tone, figures of speech, and the like. “Hoodwink,” “pigeonholed,” and “thwart” are just some of the “zingers” pulled from excerpts of top advocates’ writings. Such language makes a powerful point and grabs the reader’s attention.
Another effective technique for catching a reader’s attention is use of analogies. Take the following excerpt from Nancy Abell’s brief in the case of Dukes v. Wal-Mart:

[T]he district court concluded that their pay and promotion claims were representative of those that might be asserted under Title VII by each and every female Wal-Mart store employee in the United States over a six-year period—more than 1.5 million women, a group that outnumbers the active duty military personnel in the Army, Navy, Marine Corps, and Air Force combined. The size of the putative class exceeds the entire population of at least 12 of the 50 States.

Paints a powerful picture, doesn’t it? Such analogies and illustrations can be added after the majority of a brief is complete.

Varied sentence structure is another technique Guberman has drawn from the top fifty advocates. Sometimes sentences have no choice but to be long, and Guberman cites examples of how to elegantly do so. But less is more in many instances. A short introductory clause or sentence may be all that is needed.

Every year in my appellate advocacy course, I stress this idea to students. I challenge students to tell a story in six words or less. One example I always give comes from Ernest Hemingway:

“For sale: baby shoes, never worn.”

The depth of this message compared to its brevity is astounding. Guberman has compiled nearly twenty excerpts using this technique in various legal settings. Many of the examples end with a short “pithy” sentence such as “That is false.” Or “That is not the law.” But short sentences can be used just as effectively in an opening remark such as “The jury got this case right.”

Point Made also highlights the topic of punctuation. First and foremost, punctuation must be used correctly. Even the most basic punctuation such as a comma can tremendously alter the meaning of a sentence if used incorrectly. A common example is “let’s eat grandpa,” versus “let’s eat, grandpa.” Obviously the latter was intended, but missing a simple comma can have grave consequences.

Beyond the basics, there are many other punctuation marks that are frequently used incorrectly. How to correctly use colons, semicolons, em dashes (“—”), en dashes (“–”), and hyphens (“-”) are all illustrated in Point Made. Guberman also shows how the nation’s top writers not only use punctuation correctly, but also to add a “dash of style” to their writing.

Guberman challenges you to gauge your brief’s readability. He instructs you to go to your Microsoft Word Options command and check “Show readability statistics” under the Proofing tab. To clarify Guberman’s instructions, I (eventually) discovered that the readability statistics will show up on the last pop-up screen after you run a Spelling and Grammar Check. Within these statistics, you’ll find all sorts of metrics you can use to make your writing more readable.

Aim for these numbers, and Guberman predicts your writing will approach that of some of the nation’s best technical writers:

  • Fewer than 27 average words per sentence
  • “Flesch reading ease” score above 30
  • Less than 20 percent of your sentences are passive

For comparison purposes, Guberman’s introduction to Point Made has eighteen words per sentence on average and a reading ease score of 60. And this book review has 18 words per sentence on average and a reading ease of 56.

So what’s the best way to use the book? The book is organized so that you can read it through as you might a novel from cover to cover, read relevant sections as you work on particular portions of a brief that are giving you trouble, or read the writing of particular lawyers that you admire. Having trouble approaching your statement of facts? Go to the index and look for the most fitting topic under The Tale. Struggling with how to distinguish the authorities cited by your opponent? Review the techniques under the heading Distinguishing such as Not So Fast: Show that the case doesn’t apply as broadly as your opponent suggests. Enamored with John Roberts’s writing style? Look for his name in the index. Whatever your goal, Point Made is sure to provide practical advice as well as inspiration.

Point Made is a must-have book for every litigator’s library. It should not be read once and placed on a shelf to collect dust; instead, it should be a constant companion when you are writing briefs. It’s the kind of book you will want to go back to again and again for guidance and inspiration.

Ross Guberman is convinced that if we learn why the best advocates write the way they do, we can import those same techniques into our own work. He offers fifty techniques which he promises will teach you “how to write like the nation’s top advocates.” He keeps his promise.