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My Approach

Write a Brief Like the Chief—And 49 Other Top Advocates

If you’re an ambitious golfer, you might analyze the swing of Phil Mickelson or Annika Sorenstam. If you want to appear on Top Chef, you might devour books by Julia Child or Thomas Keller. But what if you aspire to be a first-rate brief writer? Who does it best—and how?

Here’s one way to answer those questions: dig into the work of the profession’s most sought-after writers, unearth how they write differently from others, and then turn those differences into techniques that you could apply yourself.

To test out this approach, let’s take a lawyer who is more revered for his advocacy skills than perhaps any other lawyer alive: Chief Justice John Roberts. After all, even Justices Kagan and Ginsburg and Democratic Senator Chuck Schumer have all stated publically that Roberts may be the greatest advocate alive.

And let’s pick not just any old John Roberts brief, but a brief that the Justices said at the time was the best they’d seen in decades—the brief Roberts filed for Alaska in a high-stakes environmental case against the EPA.

At stake was who gets to decide which technology is “best” for controlling air pollution: the state of Alaska, as Roberts claimed, or the EPA, as the federal government claimed. Arguing for the state, Roberts suggested in a now-famous passage that determining the “best” technology for fighting air pollution was bit like asking people to pick the “best” car:

Mario Andretti may select a Ferrari; a college student a Volkswagen Beetle; a family of six a mini-van. A Minnesotan's choice will doubtless have four-wheel drive; a Floridian's might well be a convertible. The choices would turn on how the decisionmaker weighed competing priorities such as cost, mileage, safety, cargo space, speed, handling, and so on.

I have shared this passage with lawyers all over the world. “Brilliant,” exclaim some. “Look how he gets his point across,” say others. But they all agree on one thing: “Writing like that is an art.”

And yet there’s plenty of craft behind that art. In fact, when I unpack Roberts’s famous car passage, I see at least three concrete writing techniques that Roberts and other top advocates use time and again—techniques that you can use as well:

1. That Reminds Me

When most lawyers discuss regulations, they fall into an abyss of detail. Roberts, by contrast, offers up the familiar analogy of choosing a car. Why is this car analogy so effective? First, it’s concrete and even memorable—everyone understands how your car preferences change as you age and move. Second, it plays into Roberts’s theme about deferring to the states: it’s no coincidence that in a brief about how the “best” technology might be different in Alaska than it would be in California, Roberts contrasts a Minnesotan’s “best” car with a Floridian’s “best” car. And third, the analogy is provocative: it’s hard to avoid thinking about your own favorite car.

Advocates with a knack for coming up with analogies like this tend to be generous with examples as well. Roberts is no exception. When most lawyers use abstract phrases like “competing priorities,” they stop there. Roberts, on the other hand, adds examples of competing priorities, like “cost” and “cargo space,” so you can identify with his point right away, nodding your head in agreement.

Such techniques are priceless for getting your points across. But what if another one of your goals was to write varied and compelling sentences that inspire the court to keep reading? Here, too, the Chief Justice has much to teach us.

2. Parallel Lives

Let’s consider Roberts’s sentence structure. How would most lawyers join “Mario Andretti may select a Ferrari” and “a college student a Volkswagen Beetle”? By chopping up their point into two sentences and starting the second one with “However.” Not Roberts: He uses a semicolon to join the parallel clauses as one sentence, highlighting the contrast.

In the list of various “best” cars, he also drops words like “and” and “select,” creating a rhythmic effect through techniques known as conjunction deviation and verb ellipsis. You can hear how adding these words back in would kill the effect:

Mario Andretti may select a Ferrari; a college student may select a Volkswagen Beetle; and a family of six may select a mini-van. A Minnesotan's choice will doubtless have four-wheel drive and a Floridian's might well be a convertible.

Sentence-level techniques like these add variety and elegance to the prose, making the writing engaging and even memorable.

3. What a Breeze

Finally, the Roberts passage stands out at the word level: he favors fast and crisp words when other lawyers would pick slow and soggy ones. Case in point: How many lawyers would write “the choices would turn on how,” as Roberts did? Most of us would type something flat and dreary like “the choices would be contingent upon the manner in which.” But as with many of the techniques Roberts uses, the results don’t just fall from the sky. They happen when you condition yourself to make different writing choices and to employ ever-more-specific techniques.

More Techniques, More Advocates, More Examples

If you find annotated bite-sized examples like these helpful, my Point Made: How to Write Like the Nation’s Top Advocates will give you hundreds more examples from Roberts and 49 other advocates who have mastered these and others that can boost your career and help you win more cases.

The book offers a step-by-step guide for navigating the many challenges you’ll face as a written advocate, from the introduction to the final footnote.

“I love this book and recommend it to everyone,” says Ron Marmer, the chair of the ABA’s Section of Litigation. “An indispensable tool,” says Yale Law School Professor Dan Kahan. “A tour de force” says the publisher of SCOTUSblog, Tom Goldstein. “Practical, trenchant advice,” says NAAG’s Supreme Court Counsel Dan Schweitzer. “A must for the library of veteran litigators,” says Stephen Shapiro, one of the nation’s top Supreme Court advocates. “Guberman’s exemplars demonstrate again and again how to transform an otherwise ordinary case into a morality tale,” says Judge Thomas Penfield Jackson, who presided over U.S. v. Microsoft.

Order your own copy here.

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