Ask the Author: Interview with Ross Guberman

By Conor McEvily
on Mar 24, 2011 at 4:37 am

Oxford University Press recently released Ross Guberman’s new book, Point Made.  Through an empirical approach that draws heavily on the writings of the country’s fifty most influential lawyers, the book shows how the nation’s top advocates write.  Guberman kindly agreed to an interview on the book for SCOTUSblog.

There are a lot of books about legal writing out there; what separates this one from the others?

The book focuses on what goes right, not what goes wrong.  It crystallizes 50 concrete writing techniques through hundreds of bite-sized, timely, and diverse examples from recent high-profile cases and appeals.  It ferrets out how the most in-demand advocates write differently from other lawyers.  Finally, it’s styled as a trade book, so it’s written as a one-on-one conversation with what I hope is a personal touch.

Your book draws on the writings of the nation’s fifty most influential lawyers.  How did you settle on these fifty, and who are some of the advocates that you wish you could have included?

It was hard but fun.  Thirty or so were no-brainers; the other 20 “slots” were tougher.  I took a free-market approach, identifying nationally known lawyers retained to handle one prominent matter after another.  I also consulted third-party sources like Chambers & Partners ratings, which reflect client satisfaction. I sought diversity in all senses of the word, and I tried to spice things up with some icons and thought leaders.

I ran my final list by several judges, academics, and other experts to make sure that no one was conspicuously absent from my list.  I would typically hear something like this: “You could have included so-and-so, but I can’t say that you should have included so-and-so.”

As for those I would have liked to include, many other advocates have equally sterling credentials and reputations, particularly on the appellate side.  I have also heard from a few lawyers who insist that they’re the “real” writers of some of the examples in the book, and not the more-famous lawyer to whom I attribute the excerpt.  In one instance, two different lawyers have claimed ownership of the same filing!  Many of these lawyers are younger, and I hope to include some of them in the next edition.

I would have also liked to recognize more plaintiff-side trial lawyers, and I’m open to suggestions for other superb advocates as well.

All that said, at the front of my mind while writing the book was how I could help my readers apply these techniques and write more effectively, not which lawyers to include or which lawyer first typed which sentence.

In your book, you use both appellate briefs and trial motions to provide examples of good writing and the tools that good legal writers use.  Is persuasive writing at the appellate and trial level pretty much the same thing?  If not, what are the primary differences that distinguish them?

From a pure writing standpoint, the skill set is similar: streamlined introductions, fact sections that are more persuasive than argumentative, varied sentence structure, liberal use of examples and analogies, clean transitions between points, eye-pleasing formatting, and smooth integration of authorities.

The main difference, frankly, is in overall quality.  The top appellate and Supreme Court advocates finesse every word and turn of phrase—their prose is great writing, not just great legal writing. But with few exceptions, you just won’t find that level of attention to detail in even the greatest lawyers’ trial motions in even the most high-profile cases. For trial filings, I had to dig deeper to find excellent examples.

What makes persuasive writing so hard?

To succeed, you have to imagine a highly skeptical, highly impatient reader who will never care as much about your case or appeal as you do—and then ask yourself how you can somehow grab that reader’s attention and sustain it page after page.

I just don’t think that most advocates—legal or otherwise—imagine an actual person reading their work, let alone think about how to sway that person to their cause. That may be one of the reasons briefs used to be better when lawyers dictated them.  Dictation is at least one step closer to actual communication.

You also have to channel whatever passion you feel into clarity and creativity, not into the anger and self-righteousness that drive so many motions and briefs.

Finally, the apparatus of brief-writing—the citations, record cites, defined terms, footnotes, and case discussions—can easily mask flaws in the prose and in the logic itself.

In your book, you write that advocates should “show, not tell,” in their facts statement, letting choice details speak for themselves.  Why is it important to let the reader come to her own conclusions about the facts?

The people who read lawyers’ work—judges and other lawyers—are highly educated and often cynical.  If your fact section sounds like argument, they’ll dismiss it as spin.  Fiction readers don’t want to be told that March 1 was a warm day in Washington, DC.  They want to be shown that the plaintiff’s clothing stuck to his skin just seconds after he stepped outside his apartment. Judges are similar. They don’t want to be told in a fact section that the defendant engaged in dilatory tactics throughout discovery. They want to be shown that on four occasions, defendant missed a discovery deadline and then provided incomplete responses requiring weeks of further delay.

Bottom line: We are inclined to believe our own conclusions, but we resist conclusions that someone else is trying to shove down our throat.

Apart from using the writing techniques you share in your book, what other things can advocates do to become better writers?

A great exercise is to take an editorial that cuts against your politics and write a rebuttal based on pure logic, with no rhetoric or name-calling or “meta-commentary” on how flawed the editorial is.  So liberals might pen a response to the Wall Street Journal, conservatives to the New York Times.

Another useful tool: Take a typical BigLaw “client alert” on a hot legal or regulatory issue, and then see how the writers at the Journal or the Times or The Economist address that same issue.  I’ll let you decide which is more compelling and evocative and why, but when I travel, I see businesspeople reading a heck of a lot more Wall Street Journal articles than law-firm client alerts.

I would also play around with the readability statistics I discuss in one of the book’s Interludes.

You provide a very comprehensive list of excerpts from outstanding legal writing, but what about non-lawyers?  Are there any journalists or essayists whose style you particularly admire, and who might have something to teach advocates?

Certainly. James Stewart, Dahlia Lithwick, Stuart Taylor, Linda Greenhouse, Adam Liptak, Jeffrey Toobin, and others all write about the law in a fresh and vivid way.

As for general-interest publications, I’d recommend analyzing the writing in The New Yorker, The Economist, The Wall Street Journal, The New York Times, and The New Republic.

If you’re willing to look at op-eds as writing and not as polemics, I’m always impressed by the Washington Post’s Eugene Robinson and Charles Krauthammer here in my hometown of Washington, DC.  The Times’s Maureen Dowd and David Brooks are worth a read as well, though their writing styles couldn’t be more different.

Has legal writing changed over the years?  And if so, for the better or for the worse?

I hate to mythologize the past, but legal writing is changing for the worse.  The advent of technology has ushered in an era of cutting-and-pasting that makes the finished product often read like a patchwork quilt, or as what Judge Ruggero Aldisert famously called a “promiscuous uttering of citations.”

Of course, I think that many of the great examples in my book are exceptions that prove that rule!

As a writing instructor, what is the biggest problem you see with legal writing today?

Psychologically, the biggest roadblock is that lawyers hear “legal writing” and think it’s all about eliminating legalese and the passive voice.  To begin with, that advice is too simplistic: You need to distinguish between legalese and terms of art, and you also need to know when the passive voice is appropriate, if not preferred.  But more important, so many other writing skills and techniques make a lawyer a standout advocate; avoiding legalese wouldn’t even make my Top 10.

As for the finished product, at the upper echelons of the profession, the biggest problems are (1) on the strategy side, a failure to explain the dispute as a clash between competing views and (2) on the style side, choppy transitions between sentences, paragraphs, and thoughts.  I’m about to run some workshops with judges, so I’ll add that the same observations hold for many judicial opinions as well.

At several points in your book, you note that lawyers are prone to convoluted syntax and confusing prose.  Why are lawyers so bad at “plain talk”?

Probably because we think that the only way to make the law understandable is to dumb it down, and then the reader will think less of us. The opposite is true: If you want readers to think you’re smart, make your readers feel smart.  That reminds of one of my favorite bits of writing advice: “If it reads easy, it wrote hard.” And vice versa.

Part 4 of your book exhaustively lists devices that can “liven up your style.”  But are judges really all that susceptible to these persuasive techniques?  Can’t they see through persuasive writing methods and easily assess the merits of your argument?

In an ideal world, I supposed that style wouldn’t or shouldn’t matter.  But in the real world, it most certainly does.

Most lawyers overestimate how much time and effort that judges and even clerks can devote to deciphering the many briefs that cross their desks each week.

So here’s what judges will tell you off the record: although they may not assess style consciously, when the word choice is precise and evocative, the sentences are vivid and varied, and the writer shows some personality or pizzazz, the arguments become all that much easier to understand—and to accept.