Plan Before You Start Writing

Let’s say that you are an HR administrator at a large company and you need to communicate an important change in benefits to all of your employees. I know that sounds scary, but it’s all hypothetical at this point. Unless you really are an HR administrator. Sorry about that. Anyway, you have to tell your employees about these changes and there are lots of things to think about before you actually send them an email. The first question I’d suggest you ask yourself is whether email is even the appropriate format for conveying something so important-- there are few things that people take as seriously as their compensation. If it’s good news that you have to share with them-- maybe everyone is going to get an extra week of paid vacation during the holidays-- it’s easier. But if it’s bad news-- maybe you’re doing away with their pensions-- you have to be considerably more careful. In a case like that an email is most likely going to come across as a heartless and impersonal way of communicating information that is going to have a major impact on people’s lives. If it’s at all possible, I strongly suggest that this is a case where personal contact is much better and less likely to alienate your employees. I’d even go so far as to say that it’s generally a bad idea to convey bad news in email since having someone there in person and being able to ask questions can often go a long way toward cushioning such a blow. Heck, why stop there? The personal touch is usually best for all kinds of emotional issues. Why waste the good news about that extra week of vacation in an email? Why not have a party to announce it and bask in the love and gratitude?

Whether email is even the right format for your communication is just one of the things you should think about before you write or send that message. Admittedly, not every email you write is going to require a lot of thought. If your best friend sends you a note at work asking if you want to have lunch, just say “YES!” (here the caps are perfectly appropriate in the sense of YES, GET ME OUT OF HERE!) and don’t worry about going through a checklist of rules to consider. But for anything more formal you should at least consider whether your message requires a little more thought and planning. For guidelines on what you should be thinking about as you plan those important emails, see below.

Strategy

Having a strategy for your email doesn’t mean that you’re trying to pull something sneaky, though sometimes that’s exactly what you want to do. Sure, there are times when you want to wait to send out an important message until the end of the day Friday so you don’t have to deal with a whole bunch of annoying responses. It’s Friday and you’re ready for happy hour-- bring on the nachos! But most of the time having a strategy for what you’re writing just means taking a couple of seconds to think about what you’re doing so you don’t make mistakes. Taking the time to ask yourself a few questions can make all the difference between a good email and an embarrassing one. What is it that I’m trying to say? Who needs to know about this? How are they likely to react? Have I taken the time proofread and run spellcheck on my message?

So the first and single most important step in the SEAR program is:

SEAR

These days, it seems that everything needs an acronym. But while acronyms used to exist to make complex terms and phrases (Self Contained Underwater Breathing Apparatus) into words less terrifying (SCUBA) and easier to remember, sometimes it seems that they exist today just to bewilder and embarrass us. Maybe it’s because more and more technical terms are leaking into our everyday language. Maybe it’s because so many of them (HTML, SQL, IEEE 1394) don’t even look like words and give us no cues as to how we are supposed to pronounce them. Or maybe it’s because our clever and secretive teenagers seem to write in a new language that consists of little more than a series of acronyms strung together with smiley faces. IMHO a combination of all these factors has done a lot of damage when it comes to making everyday writing easy to understand.

Just the same, I’m going to go out on a limb and introduce an acronym of my own in the hope of making it easier to remember the key elements that I think are most important when it comes to writing clearly and effectively. I hope that mine is more reminiscent of the days of clear and helpful acronyms (CARE) than the muddled-sounding efforts (UNIFEM - which sounds like an evil supercomputer with a female voice but actually stands for United Nations Development Fund for Women) that people have been resorting to lately. I wanted to come up with a real acronym, something that you could recognize as a word and didn’t have to struggle to pronounce. Above all, I wanted something that you could remember and would help you to recall the four points that I wanted to emphasize as key to successfully writing business email.

What I came up with is SEAR, which is, I think, pretty good. Not only is it a real word, but it’s a verb-- an active, forceful word. It’s a command, for crying out loud! This is an acronym with a lot going for it! Creative writing teachers will always tell you that in order for your language to be memorable you should engage as many of your reader’s senses as possible. SEAR is just the kind of word to do that. It evokes the bright heat of a flame; you can practically hear the sizzle of the fire in its long, sibilant “S”. To make it even more memorable, take the mental picture a step further and imagine that it’s a nice steak that you’re searing. You can practically smell it, can’t you, your mouth watering as you almost taste that first bite?

“Alright, enough of the acronym,” you say. “We remember it already! You’re making us hungry! But what does it mean? How are those four letters going to help me with my writing, and why are the letters arranged in that order? Why is it SEAR and not EARS?”

So here we go. Here are the four things you need to think about when you sit down to write, in the order you should generally think about them:

Strategy-- Basically the idea here is to do a little planning before you start to write. Take the time to think about whether email is really the right format for your message. Have you clearly worked out what it is that you have to say, or are you still struggling? Have you given yourself enough time to write and to write well? Is there something in your email that could get you in trouble down the road?

Emotion-- Believe it or not, feelings play a crucial role in the overall success of your writing. As I mentioned earlier, email that is loaded with emotional content can cause you more severe problems than any other issue. And most of the time emotions get stirred up unintentionally because we are simply better at communicating in person than we are in writing. Email is notorious for lacking the cues to tone and meaning that we share in our everyday person-to-person conversations. Because of this, it’s often hard to tell if someone is kidding or if they’re really angry with us. Are they just being brief, or are they upset? And the truth is that we don’t always take the time to be good readers, either, which makes it even harder to communicate clearly. But we all need to take a little more responsibility for our writing to make sure that it isn’t going to stir up emotions unnecessarily. Is the message you need to convey something that’s loaded with emotional content? If so, maybe you would be better off considering another, more personal format. Do you have a history of conflict with the person you intend to write? Are they likely to react badly to this particular topic? If so, you might want to reconsider using email and pick up the phone instead. Better yet, walk down the hall and see them for a change.

Audience-- This idea really builds on the topic of emotion. It’s critical that you always think about who you are writing to. How are they going to react to your message? Do they even know who you are? If not, you’ll need to introduce yourself. How are you going to get their attention when they get hundreds of emails every day? What are they interested in and what information do you have that they are going to care about? It’s important to make sure that your message is modulated for this particular audience. Are you using the right tone? If you’re writing to the president of your company in the same tone that you use to write to your best friend, you should probably reconsider-- unless you’re also a VIP. Is the person you’re writing to a stickler for spelling and grammar? If so, you’d better run that spellcheck and proofread one more time.

Rules-- The rules really have to be followed to make sure that all of your other hard work isn’t wasted. So far I’ve played down the importance of correct grammar and punctuation, which is why I’ve made this the last of my four topics. But the fact is that you can do everything else well and still lose all of your credibility if your readers are put off by typos and missing punctuation. There are still lots of people out there who will judge your intelligence and ability based on the mechanics of your writing, whether or not that is fair. Know who those sticklers are and do your best to weed out the mistakes in your messages to them. But really, why not do your best in all the emails that you send? The rules of grammar and punctuation only exist to make language clear and easy to read. When you write poorly you increase the chance that your message will be misunderstood or not read in the first place. After all, if you can’t take the time to write clearly, why should your reader struggle to make sense out of what you have to say?

Those are the headlines, the big ideas from what follows. Read on for the specifics.

Pay Attention!

If you think email has made communication easier, think again. I’m focusing primarily on email because it is overwhelmingly the way we communicate at work, but much of what you’ll find here are simply suggestions for maintaining good communications. And I’m not just talking about written communication-- email has also taken over for much of the conversation that we used to do in person and on the phone. Think about it, how often do you send email to the person sitting at the desk next to you rather than just getting up and going to talk to them? And much of what I have to say about email can also be applied to other forms of written communication. Unfortunately, the problem of short attention spans, the expectation of an immediate response and generally poor communication skills apply to all of our writing these days.

As much as we’d like to blame the format of email itself for all of our communication problems, much of the time we have nothing to blame but ourselves. Even though it has probably never been harder to get and keep someone’s attention, there are also a lot of things we do all the time that make people stop reading what we have to say and effectively shut down our communications. This is what happens when you send someone one of those long messages that they have to wade through to find your point. Or when they can’t figure out how your email is relevant to them in the first place. It happens when you send them a message that’s full of typos and makes them feel like you didn’t take the time to proofread it. If the message wasn’t important enough for you to run spellcheck on it, they may (rightly) think, why should they take the time to read it? They’re likely to stop reading if you haven’t made yourself clear and they find themselves struggling to make sense out of what you have to say. Why should they have to do all the work? But the very worst thing you can do is send them something that makes them angry, whether you’ve done it intentionally or not. If you make someone angry you run the risk of shutting down not only your current communication, but any future contact as well. Because when you make your reader angry they aren’t exactly going to be receptive to anything you send them in the future, either. So much for that relationship.

That’s the focus here, helping you to make sure that people pay attention to what you have to say, that you don’t sabotage yourself and make them stop reading. While learning the rules of grammar and punctuation are important in helping you write clearly and professionally, they only occupy one section of my tips here. My broader goal is to help you overcome the modern obstacles that make written communication more and more difficult. It’s to help you write persuasively and in a manner that will give you credibility at work and anywhere else writing is important. It’s to ensure that people pay attention to what you have to say and that you are able to share the information that is vital to your work. It’s to make sure that you don’t go around pissing people off unintentionally. If pissing people off is your goal, that’s another thing entirely. Still, there are some good examples of ways to do that later in the book. Keep reading!

Is Anybody Out There?

Never mind what the perfectionists and amateur English teachers would have you believe; grammar and punctuation aren’t even close to being the biggest problems in writing today. I have no doubt that the number one problem people have with their writing is simply getting someone else to read it. I’m not talking about selling that novel you’ve been working on since college. I mean just getting your coworkers to take the time to read the business email you send them at work. The speed and ubiquity of communications today have made it extremely difficult to get and keep anyone’s attention.

Part of my job as a training manager is to send out announcements about upcoming training. Some of it is for routine stuff, like the 300th Excel class we’ve offered for the year, but some of it is considerably more important and has a direct impact on the way we practice law. We recently rolled out a metadata scrubber, for example, that is designed to help protect us from unwittingly sending out sensitive information that can be concealed within the documents we create for clients and share with opposing counsel. Ultimately, we bought it to help avoid being sued. So when it came time to roll it out to our users we sent our typical training notice, but we also sent out other information that included references to articles about the dangers of metadata and stories from The Wall Street Journal about how other firms had gotten into trouble by sharing hidden metadata. This was important stuff. It seemed to me that this was exactly the sort of topic attorneys should be interested in and that we were doing a great job of promoting the training. But out of approximately 150 attorneys in our San Francisco office, we had exactly one show up. Pretty sad, but typical.

Another frustrating problem that I often encounter is that we send out announcements that we will be rolling out a new product, conduct the training for the few people who manage to make it, and then I start to hear complaints once people notice the new application on their computers. “What is this thing?” they demand. “Why weren’t we offered training!” (There’s often a “hell”, “damned” or worse thrown in there somewhere). One of the nice/scary things about email is that it keeps track of everything you do. So I can go into my Sent Items while I still have the caller on the phone and pull up the training announcement that we sent to all of our users. “The first training announcement went out on November 2nd, and there were two more after that,” I can tell them. “Would you like me to forward you a copy?” When I can tell them the date we sent it, they don’t usually ask for a copy. What usually does happen after that causes me endless despair.

“Oh, I don’t read email that comes from you,” they’ll say. Sometimes they substitute “trainers” or “IT” for “you.” This really doesn’t make me feel any better.

But it’s hard to blame people. We all get so much stuff to wade through that it can be overwhelming. It’s no secret that many of us receive hundreds of emails a day, and it piles up at an alarming rate. Go on vacation for a couple of weeks and you’re done for. I’ve seen Outlook inboxes with more than 30,000 items in them. Some of it-- the Nigerian scams, the email generated by viruses, the come-ons for various physical enhancements-- is clearly junk and can be deleted right away. Unless you’re like me and are entertained by these things. (If you’re not, find a good spam blocker. They can save you a huge amount of time managing your email.) Other messages are basically junk that we’ve asked for-- ads from online retailers where we’ve ordered things in the past, word-of-the-day emails, news summaries from The New York Times-- that can be dealt with (or not) when we have time. Then there are the administrative messages that contain information that might actually be important, but that we habitually ignore: the notices from HR about our benefits, the emails about what support services will be available on weekends and holidays, those pesky emails from the training department. They might all be useful, but the sheer bulk of the messages that we receive makes it difficult to pay attention to any of them. Where I work there is a large group of people who get what we call “staffing notices.” A staffing notice is generated whenever someone leaves or joins the firm, changes their title or their name, even when they switch desks. If you follow the staffing notices closely you can learn a lot: who has gotten married (or divorced), who finally made good on their threats to quit, who has been promoted. But the volume of them-- dozens a day-- means that very few people pay attention to them. When I was teaching classes on email etiquette, the staffing notices were specifically mentioned as “spam” more than any other kind of email.

Even if you get your readers to notice your email, they aren’t necessarily going to read the whole thing. When I talk to groups of people and ask them to name the single most annoying thing about email, what they talk about most often is that email is too long. It turns out that most people don’t want to receive email that looks like a letter, memo, or report. What they want is “just the facts.” The general consensus that I’ve seen is that anything more than three sentences is too long. I’m not saying that’s a good thing, but that’s probably the way most of your readers feel, too. Unfortunately, many of them will react to your message based entirely on its subject line and won’t ever read the body of its text at all.

Never Write a Book About Writing

Even the people who put themselves forward as the defenders of the language, the cranks who love nothing more than spotting someone else’s errors, the maniacs who would dare to write books about writing, get caught up in the complexities of English. Take the example of Lynne Truss’s shockingly popular-- for a book on grammar and punctuation-- rant, Eats, Shoots & Leaves. Truss characterizes herself as the ultimate language crank, turning what is basically despair over misplaced or missing apostrophes into the basis for a whole (if slim and wide-margined) book. It’s entertaining in the way rants often are and she provides some funny examples. Still, the impression Truss creates is that she isn’t exactly someone you’d want to share an email exchange with. Chances are she’d rather grade your message rather than read it, then she’d use it as an amusing example in her next book. Which is probably why the response of so many critics was to take out their red pens and mark up her prose. The toughest response may have been that of Louis Menand, writing in The New Yorker, who doesn’t get very far before digging in the long knives:

The first punctuation mistake in “Eats, Shoots & Leaves: The Zero ToleranceApproach to Punctuation” (Gotham; $17.50), by Lynne Truss, a British writer, appears in the dedication, where a nonrestrictive clause is not preceded by a comma. It is a wild ride downhill from there. “Eats, Shoots & Leaves” presents itself as a call to arms, in a world spinning rapidly into subliteracy, by a hip yet unapologetic curmudgeon, a stickler for the rules of writing. But it’s hard to fend off the suspicion that the whole thing might be a hoax.

A non-restrictive clause not preceded by a comma! Oh my! Menand goes on to provide a catalog of Truss’s sins:

The preface, by Truss, includes a misplaced apostrophe (“printers’ marks”) and two misused semicolons: one that separates unpunctuated items in a list and one that sets off a dependent clause. About half the semicolons in the rest of the book are either unnecessary or ungrammatical, and the comma is deployed as the mood strikes. Sometimes, phrases such as “of course” are set off by commas; sometimes, they are not. Doubtful, distracting, and unwarranted commas turn up in front of restrictive phrases (“Naturally we become timid about making our insights known, in such inhospitable conditions”), before correlative conjunctions (“Either this will ring bells for you, or it won’t”), and in prepositional phrases (“including biblical names, and any foreign name with an unpronounced final ‘s’ ”). Where you most expect punctuation, it may not show up at all: “You have to give initial capitals to the words Biro and Hoover otherwise you automatically get tedious letters from solicitors."

So what’s one to do when “experts” on punctuation and grammar, people with book deals and (presumably) professional editors available to them, can’t keep things straight? How are we supposed to get the commas right in our correlative conjunctions if they can’t? What the hell is a correlative conjunction, anyway? Truss’s first mistake was to set herself up as an expert in the first place. Anyone who puts themselves in this position is just asking for trouble because they are going to have to watch every comma they use for the rest of their lives. Because Truss’s biggest problem is that she sets her rules of punctuation down in black and white, then proceeds to break them. Most of us won’t ever find ourselves in this position and don’t even have to worry about memorizing all of the rules and their oddball exceptions. What we want to do is gain a basic understanding of the rules and try to be consistent. Unless it makes your writing hard to read and understand, it’s probably not the end of the world if you abuse an apostrophe or indulge in a superfluous comma every now and then. As long as you’re not writing a book on grammar and punctuation, that is.

Rules and Exceptions

Still, the dynamic and open nature of English causes problems for any of us who try to write in it. Not having an “official” set of rules means that it’s often hard to understand how the language should work. There are plenty of places you can go for advice-- the trick is trying to get these sources to agree. You can consult dictionaries, grammar books or newspaper and wire service stylebooks for guidelines, but you are likely to come away confused by their very different opinions. The New York Times writes the plurals of CD and DVD as CD’s and DVD’s, for example, while The Wall Street Journal writes CDs and DVDs. The rules and the exceptions to them can be maddeningly confusing, even within one source. Take the example of the rules for punctuating possessives, which might cause more errors than anything else in written English (and contributes to the confusion when the Times writes CD’s and DVD’s). Strunk and White’s well-worn Elements of Style is generally a model of clarity and simplicity, but the details of its guide to punctuation can be harrowing. They tell us to form the possessive singular of nouns by adding 's, regardless of the final consonant. Except when you’re writing about Jesus (Jesus always seems to get an exception). Or other ancient proper names ending in either -es or -is as in Moses’ or Isis’. And common phrases like for consciences’ sake and for goodness’ sake. Oh yeah, and possessive pronouns (hers, theirs) don’t get apostrophes. How are we supposed to keep this stuff straight without having to memorize all the rules and their exceptions?

The truth is, the “rules” most of us were taught in school aren’t nearly as firm as we were led to believe. Sentences must include a verb. Really? You can’t start a sentence with and, but or because. And what will happen if I do? Because I do it all the time. Many of these rules were given to us by our English teachers in the hopes of helping us develop more complex thoughts and sentence structures. But others are simply rules transplanted from Latin by people who wanted to impose a little order on the chaos of the English language. Many of these rules, like not ending a sentence with a preposition or not splitting an infinitive, have become more like conventions than hard and fast rules. We only need to be bound by them as long as they help make our writing clearer and easier to read, especially since the stylebooks of major newspapers often can’t agree on how something as basic as the plural or possessive is formed.