Keep to One Subject Per Email

Has something like this ever happened to you? You need to write an email to your boss because you have a question-- let’s say it’s about the cost of some equipment. But she’s been on vacation for the past two weeks, so you figure you’ll earn some bonus points by asking about her trip. While you’re at it, you decide you’ll save time by writing just one email and ask her about throwing a going-away party for an employee who is leaving next week. So you write the following:

Lucretia--

How was your trip? I hear Sicily is lovely in August. Have you gotten over the jetlag yet? I did some pricing on the new copiers, and it looks like the cost is almost twice what we’re paying per page now. Does that seem outrageous to you? Also, next Friday is Freddie’s last day. Would the firm object if the department went to lunch early and didn’t come back? It’s awfully hard to work after a couple Margaritas.

Barney

Of course this is all very important, and you need a response right away. When you get one it says: “Yes.” That’s all. “Yes.” What are you going to do with that? Write your boss back and ask her to reread your email? Guess which one of your questions she was answering? Or apply it to each of your questions so you can take the half day on Friday?

Email may be a great medium for conveying information, but it’s not so good at dealing with a lot of questions or details all at once. Part of the problem is just due to email’s format. While books, word processors and newspaper columns are all set up so that only a certain number of characters fit on one line for easy reading, that isn’t true of email. A line of text in an email can be as long as your computer monitor is wide, which can make for difficult reading. But most of the problem is simply the result of email’s being perceived as a “fast” medium (which isn’t an oxymoron). People tend to write email quickly and they tend to race through when reading them, scanning rather than reading them thoroughly. They may even hit “Reply” and start writing their response after reading just the first sentence or two, which is why you get replies like Lucretia’s “yes” that don’t really respond to the entire email. Those curt, one word responses that aren’t very helpful are also inappropriate. But there isn’t much you can do to improve someone else’s writing skills-- especially those of your boss.

If you want to improve your written communications you’re going to have to do the heavy lifting, and one of the best ways you can do this is to limit your emails to one main topic. Sure, you can throw in a little chatter about the weekend or the weather, but keep to one issue that matters per email in order to avoid having to figure out what someone means by “yes.” Sticking to one topic can also help you avoid writing long emails full of questions (which often looks like polls) or facts (that can read like those tickers running at the bottom of the screen on the news channels) that, in all likelihood, aren’t going to be read all the way through. If you’ve asked too many questions, you probably won’t get all the answers you need. And if you’ve provided too much information all at once it’s likely to be ignored or put aside to be read “later.” Avoid all this trouble by sticking to one main topic and sending more than one email if necessary.

Always Think of Your Email in the Context of Office Politics

Chances are that someone is reading your email and you don’t even know it.

Over the years I’ve worked with more than one person who was sure that all of their email was being monitored. They were convinced because mail would disappear from their folders or because messages they were sure they hadn’t opened would be marked as “read.” One woman took me aside and warned me not to send her anything I didn’t want her email administrator to see because she was sure that he was monitoring her inbox. While she was probably a little nuts and flattered herself that the contents of her mail would be quite that intriguing to anyone, her advice was excellent. It’s true that you should never put anything in email that you wouldn’t want your email administrator or anyone else to read.

I know that sounds extreme-- and next to impossible to implement since most of us use email to discuss everything from our personal lives to employee compensation and confidential information about our businesses-- but every time you put sensitive information into an email you are all but making it public. While you may have the most ethical and incurious email administrator in the world, she’s far from the only person who might be reading your mail. Once you hit "send" you have lost the ability to control the information in your email and ceded it to your recipients. They can then forward it along to as many other people as they chose, whether they do so by accident or on purpose, innocently or out of malice.

This is where the idea of office politics comes in. Before you send anything important in your email you have to ask yourself if there’s anything in it that someone could take advantage of. Could they profit financially? Could they make you look bad? Is there juicy information that they’d enjoy sharing with the water-cooler crowd? Or maybe your trust your recipients. But do you trust them to never make a mistake and always check that they’ve forwarded your message to an appropriate address or distribution list?

There’s a great example of careless email usage and the havoc it can wreak in the workplace in the U.S. version of The Office. Michael Scott (Steve Carrell) has just returned from vacation in Jamaica-- with one dreadlock-- and wants to impress his loutish friend David Packer with the fact that he has secretly been there with his boss, Jan. Of course Packer doesn’t believe him, so Michael tries to send him a picture of Jan sunbathing topless to prove it. But Michael, who makes a career out of cringe inducing behavior, outdoes himself this time. Instead of sending the photo to Packer he sends it to the Packaging department. Michael’s first impulse is to get the message back, but of course it’s too late for that. Soon everyone in the warehouse, the office, and the company has pictures of Michael and Jan in Jamaica.

Once your email is out in the wild, it’s just about impossible to make sure that you have recovered or destroyed all of the copies. It might be sitting in someone’s inbox, on their hard drive, have been printed as a hard copy or posted on someone’s blog. In the case of The Office, it might even have been blown up to poster size and hung on the wall of the warehouse.

Be Aware Whether You Sound Casual or Careless

Because we compose, send and respond to email so quickly, it is generally treated as a casual means of communication. As I suggested earlier, it’s more like a phone call than a formal business letter and it’s not very well suited for “serious” discussions because of a variety of issues ranging from the difficulty of capturing the right tone to our inability to secure our messages. But that doesn’t mean that email is an “anything goes” format or that we should all be using instant messaging style shortcuts to save precious keystrokes. At the risk of sounding like a curmudgeon, I have to admit that I believe that all but the very most casual of our business emails should contain at least an approximation of proper punctuation and be written in complete sentences. If the point of email is to communicate, you can’t risk being misunderstood or forcing your correspondents to pull up an instant messaging glossary so they can figure out what your acronyms mean. Are you really saving time if you’re confusing people?

A group of people in one of my classes asked me what “EOM” meant, and I had to admit that I had no idea. Apparently one of their attorneys was signing off on all of his email with “EOM,” which was confusing people because those weren’t his initials. Since I had the computer right there in front of me I did a quick search and found that he must have intended this to mean “End of Message,” which is apparently something that is recommended to email writers so that their recipients know when the body of the text is done and that they don’t have to keep scrolling through the signatures, disclaimers and previous messages that might be attached. Not a bad idea-- as long as your readers know what it means. None of his, not even his secretary, had any idea.

One senior executive I know telegraphs all of his messages, condensing everything in his emails to a bare minimum-- nothing is ever capitalized, and punctuation is often limited to dashes that break up separate ideas. He also makes liberal use of what seem to be personally developed acronyms and abbreviations and the resulting messages often look more like a jumble of text than coherent thoughts until you take the time to sort out what it means. Of course, the reason he can get away with this is that he’s important enough that people are going to go to the effort of figuring it out. I know there are probably some of you out there who are offended that there are people (and emails) that are more important than others. But come on! No one would bother trying to decipher what I had to say if I wrote like that, except maybe the few unfortunate people I supervise and who feel like it’s their job to try to understand me.

Which brings me to an interesting phenomenon I’ve observed. Over time, people who work for sloppy writers start thinking that it’s acceptable for them to write the same way. You start to see entire working groups and whole offices that seem to have lost the ability to use their shift keys or end a sentence with a period. My advice to you is not to fall into this trap. Unless you’re way up there on that totem pole people aren’t going to give you the same sort of latitude or put the same amount of effort into figuring out what it is that you have to say. Worse, they may just give up trying.

Aim For a Professional, Conversational Tone

OK all you old-timers out there. Remember when we learned to write “professional” letters? How did they start?

Dear Sir or Madam:

To Whom it May Concern:

Gentlemen:

How would those look as the salutation in an email? As a rule, you don’t want to use those dry old greetings from business letters. “Hi” and “Hello” are generally fine. And as odd as it seems when you think about it, if you’re corresponding with someone you don’t know you might consider starting with “Dear:,” but even that sounds a little precious for a business email to my ears.

On the other hand, it’s important not to come across as sounding too casual or overly-familiar. A while back I was looking to fill a trainer position and some of the inquiries I got were just confusing. “Hey Corby,” one of them began, chatty as though it were from a friend. “I’ve been doing contract work for the last couple of years, and now I’m looking for a permanent position.” I had to look at the name on the resume a couple of times and search through the list of firms this trainer had worked for to make sure that he wasn’t someone I knew. He wasn’t, and the resume went in my trash can. If a trainer doesn’t know the appropriate tone to use when introducing himself to a potential employer, I didn’t want to take a chance on how he might present himself to a room full of lawyers.

Though finding the right tone for your emails is never going to be an exact science, my best recommendation is that a business email should generally be more formal that a phone call, but less formal than a letter. It’s a delicate balance that you need to consider-- if only for a split second-- each time you hit that New message button. You still want to include a friendly and appropriate greeting (more on that later), but you don’t want to err on the side being too stuffy, either. There’s no need to explain “This message is in reference to…” when you already have a working relationship with your correspondent. And there’s no excuse for using incorrect, overly formal language that usually seems intended to make the writer seem important.

I used to work with someone who always substituted the word “stated” when “said” would have worked perfectly well, as in “He stated that he was going to lunch early.” To me this seems appropriate only in court. The people who pull that are usually the same ones who replace “me” with the almost always incorrect “myself,” thinking that the more complex word is always better. It isn’t.

Think About Whether Your Tone Might be Misunderstood

Because it’s a format that is best at conveying hard facts-- not ideas that require discussion or subtle nuance-- it’s always important to consider whether there is anything in your email that could be misunderstood. Especially its tone. As we discuss the challenges inherent in writing email, we’ll return again and again to problems caused because of the difficulty in conveying tone in email. I’m not going to tackle that whole topic here, other than to say that it’s one of the most important things to consider as you’re writing. From my experience in teaching classes about email, I think that it’s something that most people are aware of. But I’m not sure that they’re actually giving it a lot of thought as they struggle to clear out their inboxes and fire off replies. One place where you will see people trying to make their tone clear is through the use of emoticons, those annoying, winking and smiling faces that pop up most often in the emails of young kids and elderly aunts. While I generally disapprove of them as too cutesy for business correspondence, they show that the writer is at least making an attempt to make their meaning clear. “Just kidding,” they signal when sarcasm or irony might not be apparent otherwise.


Sometimes the whole issue of tone can come down to how a sentence is punctuated. When there’s a problem, the exclamation point is often the offender. While a writer who uses emoticons is usually acknowledging the need to make their tone clear, the writer who uses an exclamation point often just muddies up theirs. Unfortunately we don’t all use or read exclamation points the same way, which can lead to misunderstandings. I’ve found that some people interpret any use of exclamation points in much the same way that they read ALL CAPS-- as though someone were angry or shouting at them-- while others simply use them to express enthusiasm. And then there are people like Elaine on Seinfeld, who is furious when her boyfriend writes down a message that her friend has had a baby but doesn’t use an exclamation point at all. In the Seinfeld universe, at least, a missing exclamation point is reason enough to end a relationship.


Just this week I found myself in an email exchange where I wasn’t sure what to make of an exclamation point. I was planning a presentation outside my office and corresponding with someone I barely knew but who I thought wanted to make a good impression on me. Though I was planning to take my computer with me, I was hoping that they might have a projector I could use so I wouldn’t have to lug one along myself. “Will there be a projector available in the training room?” I wrote after we had confirmed the date and time.


“Of course!” he replied. Just “Of course!” Now, there was probably nothing more to it than yes, they did have a projector available. The exclamation point was most likely intended to indicate enthusiasm, maybe even gratitude, that I was coming down to do training. Still, maybe it was just my mood, but I couldn’t help but wonder if he somehow felt that I was accusing him of not being prepared, or of being from one of those tiny firms that can’t afford a projector in the training room.


“OK, great,” I replied, not wanting to leave the conversation on that note. “See you next week!”

Select the Right Medium

If you’re having a hard time writing an email because it deals with a sensitive subject, start by thinking about whether email is an appropriate format at all and whether you’d be better off making a phone call, an in-person visit, or holding a meeting. Because sometimes it’s not what you have to say that makes the biggest impression, but the medium in which you choose to say it. There’s an episode of Sex and the City (of all things) that I often use to illustrate this point because it seems to have made such a big impression on so many people. Sarah Jessica Parker’s character Carrie Bradshaw has been dating a writer named Berger (played by Ron Livingston of Office Space and the Geek Hall of Fame). Their relationship has been rocky at best, and when he breaks up with her he avoids doing it in person or even over the phone. Despite the fact that they’re both writers, he doesn’t even send a letter. Instead, he leaves her a Post-It note. Carrie’s outraged that anyone would do this, but her friends all have similar stories of break-ups conducted in inappropriate formats. Miranda says that she was once broken up with by a boyfriend’s doorman. As much as she tries to contain her anger, Carrie herself reacts inappropriately by lashing out at friends of Berger’s she runs into at a club where everyone lounges on beds and she nearly gets arrested for smoking a joint in public. But Miranda manages to get Carrie off with just a ticket by explaining that she’s distraught over being broken up via Post-It Note. Even the police, it seems, understand how inappropriate and unfair that is.

When it comes down to it, Post-Its and emails are actually very similar formats. They’re both great for certain simple things, like delivering facts or messages. The cable guy will be here between 12:00 and 4:00. And they’re both lousy for conveying anything that requires finesse or might produce an emotional reaction. It’s not you, it’s me. But email lends itself to much more damaging reactions than you’d ever get with a Post-It. Break up with someone on a Post-It and they might show it to their friends or, at worst, to some cops on the street. Break up with someone over email and they can forward copies to everyone, with their own comment. It sure as hell was him.

Anyone who assumes that the emails they write at work aren’t capable of creating an emotional impact is making a big mistake. Though I can’t say I’ve ever hung out in a Manhattan nightclub drinking Cosmos in bed or been caught by the police smoking a joint, I have experienced the workplace version of being broken up with via Post-It Note-- the resignation by email. Several years ago I had an employee send me an email that basically said “I resign effective two weeks from today” and nothing else. No greeting, no “it was nice working here.” Nothing. And it wasn’t like I was out of the office at the time or as though he worked far away and couldn’t have just walked down the hall to tell me. He was sitting in an office two doors down from mine.

While I’ll admit that we weren’t particularly close as far as work relationships go, I hadn’t had any problems with him either. Which made the whole incident pretty shocking to me. Because whether he knew he was doing it or not, my former employee was conducting the same kind of bridge-burning as the law firm associate who wrote the “trophy husband” email. You don’t want to alienate anyone with what you don’t say (“it was great working here”), or with the format you use (email, Post-It Note). Even though we’ve all wanted to, it’s rarely a good idea to annoy someone you might need as a reference some day. Especially if you work in an industry as small as mine, where everyone seems to know everyone else. Because you never know what’s going to happen.

One more example. A good friend of mine worked for an arbitration company that wasn’t treating her very well and had restructured her commissions so she was making significantly less money. When she got a better offer, she jumped at the chance to leave. Even though she hadn’t done anything wrong, the fact that she’d left her old company for one of its major competitors made her former co-workers feel as though she’d betrayed them. What she didn’t know was that the two firms were engaged in merger talks. Within a couple of months she found herself back at her old desk, surrounded by people who treated her like a traitor and looking for yet another job. In today’s business environment, where mergers and acquisitions are announced every day, the same thing could happen to any of us. Building and maintaining relationships by observing the niceties of business writing-- saying the right things and saying them in the right format-- certainly can’t hurt. While email might seem like the easiest way to deal with difficult issues, it can come across as insensitive and as a cop out. (No offense to those Sex and the City police, who actually turned out to be quite sensitive.)

Understand that People Generally Like Personal Communication

Email is great for certain things. It’s especially good at quickly distributing easy to digest facts: the office will be closed Monday for Christmas; the price of a first-class stamp is going up (again!). But it’s not so great when it comes to dealing with topics that are open to debate or require some amount of discussion. How many times have you been involved in an email chain like this one?:

"Can you meet Thursday?"

"No"

"How about Friday?"

"What time?"

"Maybe 3:00"

"No"

This kind of communication just isn’t very efficient. Depending on how busy your correspondent is-- and what time zone they are in-- you might have waited hours between responses. By the third exchange you still haven’t accomplished anything besides identifying a couple of times that don’t work and ensuring that at least one of you is frustrated with the whole process. Especially since a quick phone call can often resolve an issue that might otherwise require hours of back-and-forth to accomplish.

But there’s an even better reason to pick up the phone or walk down the hall to talk to your coworkers: people generally prefer personal contact-- whether it’s face to face or on the phone-- to email. Sure, there are a few cyber hermits out there who would rather avoid human contact and deal with everyone via email if they could, but these are the same people who would prefer to never leave their houses and who went into extended periods of mourning when WebVan shut down and they found that they occasionally had to go out to buy food. I’m not sure I’m over it yet. Most people would rather deal with you than your email, however, and you’ll almost always get better results in person than you would with an email. Despite the hype surrounding social networking sites like MySpace and the odd wedding announcement you run into for couples who met online, it’s not very easy to build a working relationship via email. In fact, it’s probably much easier to get a date online than it is to bond with a colleague.

Certain things that are easy to do in person are very hard, if not impossible, to replicate in email. It’s difficult to chit-chat in email without it seeming forced or insincere, and it’s almost impossible to schmooze with your superiors if you’re not there in person for those "chance" encounters in the elevator or at the coffee station. It may seem a little superficial, but those opportunities to complain about the weather or feign interest in your coworker’s kids are valuable opportunities to build your work relationships. Don’t give them up by hiding in your cube.