Writing to Persuade -- Author Ross Guberman on What Professionals Need to Know

The most important quality in an employee is integrity, but the most important ability is effective communications. Ross Guberman's new book Point Made is directed at lawyers, but is essential reading for anyone who wants to create written or oral presentations that are clear and persuasive..

Continue for Guberman's thoughts on making writing vivid, phrases and constructions to avoid, and what you can learn about writing from Barack Obama.

Making writing punchier »

Punch it up
Many of your techniques are designed to make written communications more vivid and concrete, even when they deal with abstract policy or legal issues. Why is that important?
The best writers know that even the most pressing policy matters can daze and confuse: "important" doesn't always translate into "interesting."

Great writers know that, and so they do whatever they can to evoke concrete images reactions in their readers' minds. I hate to quote Stalin here, but he was on to something when he said, "One death is a tragedy; a million is a statistic." That insight is why the crack writers at the Wall Street Journal often start complex business or policy stories with a vivid anecdote or a catchy turn of phrase.

Let me share a quick legal example with you. In a nasty dispute over Calvin Klein jeans, a team led by Brendan Sullivan (lawyer for Lt. Col. Ollie North and for the late Alaska Senator Ted Stevens), claimed in a brief that Calvin Klein had for a long time been content to profit from royalties it had earned from sales of its jeans at Sam's Club and other discount retailers.

In Sullivan's rendition, Calvin Klein "was only too happy to pocket" those royalties. Through just that one word "pocket," the star-studded Sullivan team conjured up an image that made an abstract accounting move sound suspect or worse.

Are those sorts of choices what people mean by "punchy" writing?
Yes. Punchy writing, legal or otherwise, is long on vivid verbs, parallel constructions, varied sentence structure, sharp contrasts, one-syllable sentence openers, smooth transitions, concrete examples, and evocative analogies, and other techniques that great nonfiction writers have used for centuries.

So when is it appropriate to use vernacular in written communications? How do we balance enough formality to be respectable and credible with enough informality to be engaging?
Pick up the New York Times, the New Yorker, the Wall Street Journal, the New Republic, or the Economist. Those publications get the balance just right. The writers and editors meet twin goals: to appeal to busy and impatient readers with fresh prose -- but without dumbing down the language or condescending to their audience.

As I always tell lawyers, if you want to find the gold standard in professional writing, look at what your busy clients are reading on the airplane. When those clients want to know the latest in derivatives regulation, they pick up the Wall Street Journal, not some big law firm's latest Client Alert.

Why good lawyers are bad writers »

Why good lawyers are bad writers

Of course, some lawyers do get the balance just right. A simple but telling example: In a brief that has become legendary, Chief Justice John Roberts once wrote that "the choices would turn on how the decision-maker weighed competing priorities." I'm not saying that his turn of phrase deserves a Pulitzer Prize, but most lawyers would have written something like this instead: "the resulting choices would be contingent on the manner in which competing priorities were weighed by the decision-maker." Both versions mean the same thing, but the second one falls flat. Small tweaks make a big difference.

So the right tone is direct but not sarcastic, conversational but not casual, clear but not patronizing. Imagine looking a smart but impatient reader in the eye, and engaging the reader so effectively that the reader is nodding after every sentence. That's the image you want.

That brings me to another question. Why are so many good lawyers such bad writers?
Those are fighting words! But I'm sure you've noticed that when people say, "You write like a lawyer," they always mean it as an insult, not a compliment.

I can think of many reasons the insult may be warranted, at least in part.

First, the law is dense and dry, and even in a single paragraph, lawyers often cull their information from several sources. All that makes for choppy, muddy prose unless you have an arsenal of writing weapons at your disposal.

Second, when lawyers think and talk about writing, they mostly discuss "legalese" and "Plain English" -- in other words, whether the profession should continue to use words like "heretofore" or whether recitals in contracts should still begin with the word "whereas." To me, the legalese discussion is something of a red herring. Far more important are classic writing skills like flow, structure, conciseness varying sentence structure, integrating authorities, and using creative examples and analogies. These get short shrift.

Third, and I'm just reporting the news here, just as most Americans think they're above-average drivers, most lawyers think they're above-average writers.

The fourth reason is a dirty little secret I've learned in my training and consulting business: many otherwise brilliant law students graduate with honors from elite law schools with a weak command of grammar and with little experience writing professional-quality prose. Law students are graded and recruited based on exam-taking skills, not based on writing skills or other practical abilities.

Learning from Barack Obama »

Where schools fall down
Speaking of schools, what do schools fail to teach us about writing?
I see problems on two fronts.

First, and this is not exactly news, the Millenials were raised to believe that writing isn't about rules and principles but about self-expression. The problem is it's hard to express yourself effectively if you don't know how to construct a paragraph and if you panic at the thought of using a semicolon. Please spread the word: Writing rules liberate more than they constrain!

To be fair, I'm seeing something of a backlash against this "anything goes" mentality, at least anecdotally and in my own kids' public schools, and I believe that the SAT's new multiple-choice writing section is helping in this regard.

On the other end of the spectrum -- the universities and professional schools -- students are not exposed to enough dissected models of great nonfiction prose. The law schools are the worst offenders; nearly all students graduate thinking that all lawyers and judges are poor writers. That's one of the reasons I wanted my book to stress what goes right in persuasive writing, not what goes wrong.

You use Barack Obama as one of your examples of excellence in advocacy. What made him effective as a lawyer?
One aspect of Obama's life has received surprisingly little attention: his work during the 1990s at a prominent Chicago civil-rights firm. While there, he signed several briefs in Voting Rights Act disputes and in other cases related to his academic focus at my alma mater, the University of Chicago Law School. As the junior member of the team, he presumably did much of the drafting, and although I can't prove that he wrote every word, I recognize some style traits from his book Dreams of My Father.
I included in my book a few excerpts from one of those briefs. That particular filing is on an issue dear to Obama's academic heart, the Voting Rights Act, and he makes great use of hypotheticals, the rhetorical device known as "antithesis," and other techniques that I thought would be useful to Obama-lovers and Obama-haters alike.

Can you give some good and bad examples of the use of graphics?
I'd be happy to, and my advice here will be decidedly nonpartisan.

The good: Tables, charts, lists, bullet points, graphs, or timelines -- when in doubt, use 'em. For some great advice on such issues as fonts, spacing, and margins, check out Matthew Butterick's new book Typography for Lawyers. I'm sure Matthew won't mind my saying that it's full of great advice for all professionals, not just lawyers.

The bad and the ugly: Avoid underlining and italicizing for emphasis. Don't use too many fonts in any one document. And avoid all-caps in headings or anywhere else.

A "hit list" of words and sentences to ban »

Words and sentences to ban
Are there some words or sentence structures you would ban forever?
You better shut me up on this one, Nell, or I'll go on for days. Here are a few ideas for you:

Words and phrases to avoid: "egregious," "clearly," "notably," "as such," "the fact that," "provided that," "attached please find" ("enclosed please find" was considered old-fashioned even in the pre-computer era!).

Sentence structures to put to rest:

First, try not to start too many sentences and clauses with "however." So not "I am hungry; however, I don't have time to get a snack" (a favorite construction of lawyers) but "I am hungry, but I don't have time to get a snack" or "Even though I'm hungry, I don't have time to get a snack." In his terrific new book on sentences, Stanley Fish devotes an entire chapter to this sort of "subordinating sentence" pattern and offers many helpful examples.

Second, avoid this horribly common pattern as well: "The Court did not address the merits of the case. Additionally, the Court did not indicate when it would." Try "The Court did not address the merits of the case. Nor did it indicate when it would" or "The Court did not address the merits of the case, nor did it indicate when it would."

What's the most important priority for organizing an argument?
To start with something newsworthy rather than circular. Let me explain. Many people start a letter with something like "I am writing to explain why I think the settlement offer is in your best interest." And then the writer is off and running. But if you are skeptical of an offer, hearing that someone thinks it is in your "best interest" isn't going to help you or budge you one bit: the writer is assuming what must be proved.

Far more effective would be to start by acknowledging the reader's skepticism and committing to addressing it in concrete ways: "Although I know you're skeptical about this offer, I believe it's in your best interest for these three reasons." Then you list those reasons in a row before breaking them down and supporting them in detail.

In the legal world, a Supreme Court advocate named Maureen Mahoney (famous for winning the Michigan affirmative action case and for reversing the Arthur Andersen conviction) is one of the best at frontloading arguments with such detailed and thoughtful lists.

In day-to-day correspondence, one way to organize your arguments in this way is to ask yourself, "What three things do I want the reader to do, believe, or understand by the end of this letter or document?" Then list those three things up front.

How do the techniques of legal advocacy apply to other forms of business communication like memos and presentations?
They apply very well. Of the 50 techniques in my book, for example, 17 focus on how to have more interesting, varied, and flowing sentences -- a goal of almost all writers.

Writers of memos and presentations can exploit other techniques related to introductions, narrating facts, and organizing complex arguments.

In the end, great legal writing is simply great writing that happens to be about the law.

Image via Flickr user Unhindered by Talent, CC 2.0