Did you watch Lost? I was a big fan of the show, which ran on ABC from 2004 to 2010. The series required quite a commitment from its viewers, since it had a large ensemble cast and was a true serial — you really couldn’t miss any episodes. After the third season, the producers made the unusual announcement that the series would definitely conclude at the end of the sixth season. Since so many elements of the show remained a mystery until the very end, it became a guessing game as to whether the writers would be able to tie everything together into a satisfying ending.

Toward the end of the final season, the show revealed a location that we’d never seen before that was crucial to explaining the Island’s secrets. (I’m not giving anything away here if you haven’t seen it.) But the location, a glowing cave, was rendered with cheesy special effects that looked like they’d been borrowed from the original 1960s “Star Trek” series. The bad effects were so jarring that they took the viewer out of the story, causing you to say, “What’s with the cheeseball special effects?”

What the heck does this have to do with improving your legal writing? Find out after the jump.…

You see, you never want your audience to get jolted out of the story you’re trying to tell. Whether your audience is a judge or a client or an opposing counsel, your writing is supposed to convey a persuasive message. That’s the story you’re telling. But when you do something that distracts the audience, they suddenly focus on the medium rather than the message. Which means you’re failing at your job.

Typos and misspellings and grammar mistakes are the sort of thing that can jolt your audience out of following your message and make them pay attention to the medium. Which means that your ability to persuade has just diminished, even if only a little. They may get right back on track, and might even forget about the hiccup. But you’ve lessened your chances of winning. Why take that risk?

Main characters of Lost

Bet they knew how to use hyphens.

The mistake can also have another effect. It might make your reader lose confidence in your abilities, fairly or not. If the reader suddenly sees that you’ve made a typo or misspelling or grammar mistake, she might wonder whether you’re really as smart as she thought. Or she may wonder whether you really pay attention to detail. Neither of these two possibilities is good for you or your client. When the Lost producers used the cheesy special effects, it made me wonder whether they were just phoning in the end of the six-year journey. Unfortunately, given how the series ultimately ended, that feeling never really went away.

Typos and misspellings are usually just lapses in concentration and editing. Reading and rereading your work and having a good dictionary handy are the way to avoid these problems. On the other hand, grammar mistakes take more work. First of all, you need to know what the rules are.

“Now wait,” you say. “Most of my readers also suck at grammar, so they probably won’t notice my mistakes.” That’s certainly true. But what if the judge or client or other reader is one of the few who don’t suck at grammar? Let’s say that only ten percent of judges truly understand grammar. Do you really want to take that ten percent risk that you’re going to annoy the judge with your sloppy prose?

Some people (including me) believe that you can learn a lot about a person from their his or her writing. (OK, commenters: I’ve teed it up for you.) How they write tells me how smart they are and how careful they are. For example, many times over the years I’ve correctly been able to tell when an attorney has ghostwritten a letter for an employee. I can usually tell what kind of a lawyer the writer of a demand letter is. And as I’ve written about previously, a candidate’s cover letter can tell me whether to bother interviewing him or her.

One of the things I look for is how they use or misuse hyphens. Why a hyphen fetish, you ask? Because I believe that hyphens are the cause of more writing mistakes in American English than anything else, except maybe commas. Even more than apostrophes and quotation marks. If you properly hyphenate in your writing, more likely than not you know what you’re doing.

Here’s what The Chicago Manual of Style (16th ed.) has to say about hyphens:

7.77 To hyphenate or not to hyphenate. Far and away the most common spelling questions for writers and editors concern compound terms — whether to spell as two words, hyphenate, or close up as a single word. Prefixes (and occasionally suffixes) can be troublesome also.

The two main areas where hyphenation questions arise are compound (or phrasal) adjectives and prefixes. Most people fail to hyphenate compound adjectives, and most people put hyphens after prefixes. And most people are wrong both times.

Bryan Garner, who happens to be the editor-in-chief of Black’s Law Dictionary, states the rule for compound adjectives in his indispensable Garner’s Modern American Usage:

Here’s the rule: if two or more consecutive words make sense only when understood together as an adjective modifying a noun that follows, those words (excluding the noun) should be hyphenated. Thus, you hyphenate special-interest money, but only because money is part of the phrase; if you were referring to this or that special interest, a hyphen would be wrong.

So you write high school, but high-school student. (Otherwise, you might momentarily think that the student had been inhaling.) It’s popular music, but popular-music critic. (Otherwise, you might think it’s the critic who’s popular, not the music.) It’s to spare your reader these momentary false starts — what Garner calls “miscues” — that we use hyphens. As Garner puts it, it’s all about having empathy for your reader, and “to make reading easier and faster.” Many writers bristle at peppering their writing with all those hyphens, thinking that they’re cluttering up their writing with little black lines. Garner disagrees: “Some writers — those who haven’t cultivated an empathy for their readers — would omit all those hyphens.”

There are a few exceptions to the phrasal-adjective rule (see what I did there?). If the phrasal adjective begins with an adverb ending in -ly, you don’t hyphenate (for example, the rapidly falling temperature). If the phrasal adjective is borrowed from a foreign language, no hyphen (prima facie case). If the phrasal adjective is a proper noun, no hyphen (United States Government). And if the phrasal adjective follows the noun, it’s usually not hyphenated (a much-needed solution but the solution was much needed). Your dictionary will tell you if the phrase is always hyphenated. Use an excellent dictionary like the New Oxford American Dictionary, which is available free on every Mac. Don’t use Microsoft Word’s junky spell-checker dictionary.

The other main area for hyphens is with prefixes. The general rule is simple: don’t hyphenate after prefixes. Thus pretrial, noncompete, antiterrorism, postjudgment, and coworker; not pre-trial, non-compete, anti-terrorism, post-judgment, and co-worker. There are two main exceptions. One is when the noun or adjective after the prefix is a proper name: anti-American, post-Bush, pre-Vichy. The other is where the lack of a hyphen would create confusion, either because of strange vowel combinations (anti-inflammatory, extra-administrative, co-opt), or because it would look like a different word without the hyphen (re-sign vs. resign, co-op vs. coop).

That’s hyphenation in a nutshell. There are other minor rules on things like fractions and numbers. Chicago is the place I turn to for those questions. Keep Garner’s, Chicago, and a good dictionary by your side. I probably use them a dozen times a week to check on hyphens. But that’s only because I want my readers to think I’m a careful writer. Don’t you want your readers to think that, too?

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Jay runs Prefix, LLC, a firm that helps lawyers learn how to value and price legal services. Jay Shepherd also spent 13 years running the Boston management-side employment-law boutique Shepherd Law Group. He writes the ABA Blawg 100 honoree The Client Revolution, which focuses on reinventing the business of law, and Gruntled Employees, a workplace blog. Follow Jay on Twitter at @jayshep, or email him at [email protected].


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