A few weeks back, we reviewed Ross Guberman’s terrific new book, Point Made: How to Write Like the Nation’s Top Advocates.

Ross graciously agreed to do an email Q&A. If I’d moved faster, we could have scooped SCOTUSblog. But I was paralyzed with self-doubt; nothing will make you question your own writing faster than trading emails with a legal writing guru.

Read on to see why. My questions are in bold, with Ross’ responses below.

Seriously: how many briefs did you have to read to write that book?

Let’s just say that my next book should be called How NOT to Write a Book. Or at least how not to write a book efficiently. I probably reviewed about 1,000 motions and briefs signed by well over 100 lawyers.

My mistake was in waiting too long to settle on a list of advocates and to limit the universe of filings. Only 50 lawyers and a couple of hundred filings made it into the final manuscript, though I enjoyed reading the others as well.

Can good legal writing be taught, or is it a talent?

Literary novels and poetry require talent. But persuasive writing can be taught, as long as the writer has a working command over sentence structure and a good ear for language.

Some people resist the idea that a well-written brief is a series of concrete techniques, and not a magical incarnation of God-given talent. Maybe “talent” seems sexier than “technique.” Maybe lawyers renowned for their writing want other lawyers to envy their supposed gifts. But the truth is, you can go line-by-line, heading-by-heading, example-by-example and explain what’s happening in even the most famous briefs by the most famous advocates.

Of course, just because something can be taught doesn’t mean that it’s easy. Golf and oil painting can be taught, too.

Point Made lists 50 writing tips. What are your 5 highest impact tips–what can a writer apply from your book right now to see the greatest immediate improvement?

How about these five:

  1. The Short List: Number your path to victory (Technique #2, for introductions)
  2. Back to Life: Center technical matter on people or entities (Technique #9, for fact statements)
  3. Russian Doll: Nest your headings and subheadings (Technique #12, for argument structure)
  4. The Starting Gate: The one-syllable opener (Technique #36, for style)
  5. Take Me by the Hand: Logical connectors (Technique #45, for flow)

That said, I don’t think you can learn writing techniques without seeing a lot of examples in many different contexts.

In addition to being an author, you’re also a legal writing consultant. Are there exercises that you recommend to lawyers who are looking to improve their writing? Hunter Thompson retyped Hemingway and Fitzgerald to learn rhythm and see what it felt like to write that well. Should lawyers be tapping out the Alaska v. EPA brief on their iPads?

I like your idea, though I bet that brief is longer than The Old Man and the Sea!

Let me make two other suggestions:

First, go to your grammar options and select “readability statistics.” Run a grammar check on a document you’ve written, and you’ll get a Flesch Reading Ease score between 0 and 100. Resolve to raise your score by ten points by (1) shortening some of your sentences, (2) breaking long paragraphs into two, (3) replacing long words with short ones, and (4) changing passive constructions to active ones. If you score 40 or higher, you’re doing better than most lawyers.

Second, spend five minutes a day analyzing a passage of your choice in the Wall Street Journal or The New Yorker or The Economist. Dig into the transitions, the word choice, the parallelism, and the variety in sentence structure. Then use those same techniques to write about something relevant to your own practice.

One of the things that makes Point Made such an enjoyable read is that it focuses on what great lawyers do right, not what mediocre lawyers do wrong. Let’s flip that around. What are the five worst mistakes that you see bad writers make?

So you want me to go off-message, as we say in Washington?

Let me answer your question this way. Here are five mistakes that otherwise good writers make when drafting motions and briefs:

  1. Starting too many sentences with “However,” “Moreover,” “Additionally,” “Therefore,” and “Accordingly.”
  2. Starting a new paragraph with “Moreover” or “Additionally” as an excuse to avoid linking the new point to the one before.
  3. Starting too many case discussions by reciting the facts of the case cited (“In Bush v. Gore, George W. Bush was born in Texas.”) rather than by linking the case cited with the current dispute.
  4. Distinguishing cases one at a time, in repetitive and excruciating detail, rather than explaining why the entire line of cases doesn’t apply (See Technique #24, One Fell Swoop)
  5. Overusing such words as “egregious,” “specious” “bald,” and “conclusory.” (Could the ABA’s Litigation Section just stipulate that your opponent’s assertions are always “conclusory” and their allegations always “bald,” so litigators wouldn’t have to keep saying these things over and over?) And if I can squeeze in one more thing, overusing the self-evident phrase “as a matter of law.”

How do good appellate briefs differ from good trial briefs?

The main difference is in overall quality. From a pure writing standpoint, few trial motions and briefs have the polished, finished feel and tight structure that you’ll find in many top appellate advocates’ briefs.

Exceptions do arise, especially when someone known primarily for appellate work writes a trial motion. I’m thinking, for example, of some of the trial excerpts in my book from former Solicitor General Seth Waxman or from Sidley’s Virginia Seitz.

Another observation: It’s no doubt easier to have a “theme” in a Fourth Amendment Supreme Court case than in a discovery motion in a commercial dispute. So I took note when someone like David Boies would start a routine filing with a line like “Defendants’ motion to compel is an excellent example of the axiom that ‘no good deed goes unpunished.’” That line isn’t going to win a Pulitzer Prize, but it gives shape to the entire argument in ways you rarely see at the trial level.

Of the 50 top advocates in Point Made, who’s the best?

My favorite brief is by my honorary 51st advocate, Thurgood Marshall, the only nonliving lawyer I include. Every law student should be exposed to the brief that he and his team filed in Brown v. Board of Education, for its conciseness and not just for its power and import. Incidentally, I recently came across the original complaint, which some of your readers may enjoy seeing.

But if forced to choose the “best” writer in the book, I’d say the Chief Justice. He’s a polarizing figure these days, but as a legal writer he has few peers.

On that uplifting note, I will thank you, Jay, for giving me this opportunity to discuss advocacy and Point Made.