Sunday, August 24, 2008

Respect the Privacy of Others. Assume that You Have None.

One of the professional organizations I belong to sponsors several incredibly helpful listserves where members can send messages to everyone who has signed up and ask questions they need help with, offer technical expertise, request a reference for a particular product or vendor or air whatever else they have on their mind. It’s a great resource and a wonderful example of how people from across the country and around the world can come together to as an online community. Unfortunately, online communities aren’t immune to the same kinds of problems that we see in other groups. Though these listserves specifically exclude vendors from joining and members are frequently reminded that all that all conversations are confidential and should not be shared with anyone else without permission, every so often it seems that we have to go through a blowup when it becomes clear that the vendors have been keeping up with our discussions.

It happens like this; I send out a message asking if anyone has been having trouble with the XYZ Corporation’s doohickeys and mention that I haven’t had much luck with their customer support, either. Lo and behold, I almost immediately get a call from my XYZ representative, who I haven’t heard from in years but insists the call is purely part of their normal program of keeping in touch with clients. I call the listserve administrator, who assures me that there are no vendors on the group list, so one of my fellow members had to have forwarded my message along. Maybe they thought they were doing me a favor. Maybe they have a close relationship with someone at XYZ Corp. But this is exactly the kind of thing that you should never do without permission and why you need to assume that your email exchanges are never private. A big part of the problem is that you may have a very different idea of what information is appropriate to share than the original sender of the message. And you might not even have enough information to know what’s appropriate to forward along and what’s not. I’ve been surprised more than once to find that people I really like are close friends with people I can barely tolerate and been immensely relieved that I haven’t bad-mouthed one to the other. Imagine if you’ve put those feelings down in writing….

The wise thing to do is to always ask permission before forwarding along someone else’s message. If you can’t ask for permission, delete anything that the third party doesn’t need to see from the original message, even if you think it’s innocuous. That’s right, you can edit someone else’s message and forward it along—which is another reason to be wary of email. Because you can’t rely on stopping these sorts of leaks, don’t put anything in email you don’t want other people to see, whether it’s racy vacation pictures, financial information or criticism of someone else. You need to assume that someone may violate your trust and privacy, whether they intend to or just don’t know any better.

Monday, August 11, 2008

Be Aware of Your Employer’s Email Policy

Remember that towering stack of papers you pretended to read and then signed? No, not the ones you signed without reading when you bought your house—the stack of papers you signed without reading when you started your job. Somewhere in there was information about your health insurance (or lack of it), something affirming your citizenship status and probably an acknowledgment of how as an at-will employee you could be fired at any time for any reason—or for no reason at all. If you signed all of that paperwork in the last five or ten years chances are that one of the pieces of paper you ignored was your company’s email policy. Now might be a good time to go back and read that. Even if you have no idea what you did with all of those orientation papers you can probably find the policy on your company’s intranet site. If worse comes to worse, ask your HR person for a copy—though they might wonder what you’re up to.

Odds are your policy says something close to what mine says. No one likes to write these kinds of things from scratch and companies tend to borrow liberally from each other. It's likely that your firm’s policy says something along the lines that all your email is the property of your firm and that while some personal use is permitted it is expected that it will be kept to a minimum. It probably also says that everything in your email is subject to review by the company. There’s no room here to claim that your email is private; unlike in the UK, where personal privacy rules are much more stringent, there are no laws in the US protecting the privacy of email (or voicemail, for that matter) in the workplace.

If you really must have private email conversations at work or need to provide an email address for personal transactions like banking or shopping it’s an excellent idea to set up an email account through one of the free services like Hotmail or Gmail. Although some companies block these sites to prevent viruses from sneaking into their systems, many will allow you to use them. That way you have a place to keep your personal messages that you can access when you need to but is out of the hands of your employer. In all likelihood, your firm doesn’t want your personal mail anyway. Since it can ultimately be held responsible for any mail on its system, your company can—at least theoretically—be sued if you use your email to stalk a co-worker or bilk Nigerians out of their life savings.

Realistically, you’re going to use your work email to make dinner plans and receive confirmations from your travel agent. But use a personal email account for anything that’s less than innocuous.

Sunday, August 10, 2008

Don’t Depend on Recalling Messages

“Recall” is one of those features that I’m really inclined to say that you should never use. But “never” is an awfully tough rule to live with and people tend to resist when you tell them they should “never” do anything. So rather than have you throw on your old black leather jacket and start recalling messages just to prove that you’re an email rebel, I’ll suggest that you avoid using recall as much as you possibly can. I’m sure that your email administrator would tell you that it’s a feature that you shouldn’t use—she’d probably turn it off altogether if it were up to her—because of the havoc it can wreak on your mail server. Trying to recall a message from a large number of recipients can slow, or even crash, an entire email system. While it’s amazingly easy to accidentally forward an inappropriate joke to everyone in your office (all you have to do is pick the wrong distribution list), it’s much more difficult for your email system to go back once the message has been sent, search through all of the mailboxes and messages they contain and retrieve all of the copies of the one you wish you had never sent.

I’d tell you not to use “recall” for another reason. It usually doesn’t work. What do you do first when you receive one of those messages saying “so-and-so would like to recall the message: My boss is a big fat jerk”? You think to yourself, “well this must be something interesting” and you open and read it, don’t you? That’s what everyone does. Attempting to retrieve a message usually just draws attention to it, which causes your recipients to open it and makes the email impossible to recall any longer. Even if your correspondents aren’t sitting at their desks waiting to thwart your recall attempts, chances are you still won’t be successful. If you’re sending to someone outside of your own email system the other one may not be compatible with recall or may have the feature turned off. Even more of a concern these days is the preponderance of BlackBerrys and other mobile devices in the workplace. Once a message has been received on one of these they can’t be recalled—though attempting to do so will generate one of those attention-grabbing emails pointing out that you’ve attempted to recall the message. Good luck with that.

Saturday, August 9, 2008

Avoid Using HTML Stationary, Graphics, Excessive Color and Odd Fonts

The pile of bad resumes that I’ve received over the years has been far more valuable than I ever imagined. It turns out that there are many lessons to be learned about bad writing from the mistakes people make with their resumes. In addition to my encounters with the boastful guy (“I was their best trainer ever!”), the inappropriately-familiar-for-a-stranger guy (“Hey Corby!), the woman who included a Glamour Shots portrait of herself and the people who are hopelessly unable to proofread (almost everyone), I’ve run across the woman who prints her resume on lavender paper with gold flecks. While that might be appropriate for something (wizarding school applications?), it sure isn’t going to help you find a job with me.

Unfortunately, it’s way too easy to make the same mistake in email. Outlook and other email programs provide you with their own forms of “stationary” that too often includes busy backgrounds and brightly colored fonts that make it hard or impossible for your readers to make out what you’re trying to say. Even worse, although it often seems that Microsoft’s domination of the office software market must be nearly complete by now, there are still lots of people out there using other emails programs who won’t be able to open your message at all if you send it to them on the cute stationary with the kittens frolicking around the borders that you downloaded from spyware.com. Many web-based email programs and handheld devices simply won’t be able to deal with the kind of message. Some won’t get through because they’ll be blocked as suspicious attachments. Others will arrive with your text, the background and any other graphics all as separate attachments that your readers will have to open one at a time in order to find what you have to say. Since many of your readers are worried about the security threats posed by opening unknown attachments they just won’t do it. And a few of them will be so confused by a blank message with a whole bunch of strangely-named attachments that they just won’t click on them. In the end it’s just not worth the trouble of using the cute kitties and risking that your message won’t be read, even if you don’t take into account the impact that the less-than-professional look of your message might have on your readers. It’s never a good idea to make them work harder than necessary.
And don’t even get me started on what the dog people will think about those kittens….

Some other formatting issues to consider:

Avoid pictures and clipart for the same reasons you should avoid email stationary. Not everyone will appreciate them and they can balloon the file size of your messages, filling up inboxes and taking a long time to download over remote access or on handheld devices. If you just can’t live without them, save images in a lower resolution to reduce the file size.

Make a habit of using the most common fonts in all of your messages. It’s really best to stick to the basics when writing business email despite the temptation many people feel to personalize their work. Some fonts and colors can be difficult to read, especially when light colored text is used against a white background. To be safe, use a sans-serif font like Arial and choose black text on a white background. Ten or twelve point text is also best so your text isn’t too small that it can’t be read or so big that it looks like you’re shouting at your readers.

I know, it’s a little boring, but writing business email really isn’t an exercise in creativity. Your goal is to make sure that people hear what you have to say.

Wednesday, August 6, 2008

Read the Whole Message Before Responding

This issue is the flip side of something I wrote about earlier when I suggested that you Keep to One Subject Per Email. The point that I made there is that many recipients just don’t take the time to carefully read all of a message before they hit “reply” and start writing their response to you. They’re in such a hurry to get another message out of their inbox that they answer one of your questions but don’t notice that there is a second one. Or they assume that they get the gist of your message from reading the first sentence or two and ask you a cranky question that’s answered in your third.

Just as it’s your responsibility as a writer to construct clear and efficient messages, it’s also your responsibility as a reader to read the entire text of an email and make sure you understand it as best you can instead of firing off a response that’s based on a cursory reading of the first few words. It’s important to remember that while you and I might be trying to be good citizens of the email ecosystem, limiting ourselves to one topic per message and putting the most important information at the beginning of our email, not everyone else is as thoughtful or has our good training. You may work with someone, even your boss, who still subscribes to the “murder mystery” school of writing and likes to save all of the most important stuff for the last line of her messages. Ta-Dah! Help her—and help yourself—by making sure that you understand everything she has to say as well as you can before making a decision or responding. You’re never going to understand everything perfectly (bad writing creates all kinds of mysteries and confusion), but it’s worth the effort. Why bother? As usual, because you don’t want to look stupid—and being a bad reader can make you look stupid just as easily as being a bad writer.

Tuesday, August 5, 2008

Let Recipients Know the Nature of Attachments

Even though most of our workplaces now outfit our computers with spam and virus blockers that do a pretty good job of protecting us from all of the nasty junk bouncing around out there on the internet, malicious emails still manage to slip through every now and then. So if you want your message to get through to your recipients and you want your readers to be confident enough to open and read it make sure to give them a clear idea of what they’ll find inside. A quick description (“Here’s an Excel spreadsheet with the May sales figures”) will assure them that the file is actually from you and let them know what program they need in order to open it. I’ve even seen some people include links that their recipients can use to download free programs like Adobe Acrobat when the files are in a format such as PDF. What a thoughtful gesture!

On the other hand, an attachment that comes with a generic description or no explanation at all may be ignored by your correspondents or automatically relegated to a spam folder where it will be hard to find and recognize as a legitimate file. Because spammers and virus writers have become very good at “spoofing” or faking email addresses, it’s not enough that your message says that it’s from you. I find emails in my spam filter all of the time that look just as though I’d sent them to myself despite the fact that they’re hawking Viagra knock-offs (Viagrow, anyone?) or trying to get me to adopt bulldog puppies from Africa. In order to overcome the uncertainty this creates you need to make your readers confident that your message is from you and that your attachment is safe to open.

Of course some people take caution too far and wind up living in fear of opening every email or clicking on every link on the web. You don’t want to become one of them, terrified that every interaction you have with your computer is potentially sending your credit report to Buglarian mobsters or will cause your PC to start smoking and melt into a pile of plastic and circuit boards. People who are scared of or intimidated by their computers rarely learn to make efficient use of them. Just the same, you don’t want to go around opening things will-nilly. Emails about certain topics-- Anna Kournikova, Viagra, the entire country of Nigeria-- should set off alarm bells in your head and be treated like the potential landmines they are. Unless you’re involved with professional tennis, work in the pharmaceutical industry or are expecting a big inheritance from Nigeria, messages related to those topics should probably be deleted ASAP.

Monday, August 4, 2008

Attach a Word Document Rather than Compose a Lengthy Message in Email

While email is great for many things, it isn’t really well suited for the composition of lengthy messages.  Unlike Word (or any other modern word processing program) email isn’t designed to automatically wrap text to the next line and keep each of them a readable length.  Instead it just keeps going until it reaches the right end of your screen, the window you have open, or until you hit “enter” and start a new paragraph.  As more and more of us work on larger and larger monitors this means that lines of text get longer and harder to follow.  Because of this-- and because you can never be sure what email client people are using to read your message-- there’s really no way to know what the message is going to look like when it reaches the other end.  Depending on whether your readers are set up to receive mail in HTML, Rich Text or plain ol’ Plain Text, all of your fancy formatting and the images you’ve included might not even show up.

Do your readers a favor and compose long messages with lots of text and formatting in your word processor and attach them to your email.  Not only will they be easier to read but you can make use of the far superior tools included with the word processor to refine your document and make it more accurate and attractive.  You’ll also save yourself some of the heartache that comes when you’ve been working on a long email, the program crashes and you lose all your work.  I can’t tell you how many attorneys I’ve worked with who have lost hours of work this way and expect to be able to retrieve text that’s now long gone.  Word processors do a far superior job of automatically saving documents as you work and recovering them when you crash—though you should still make the effort to hit that “save” button occasionally. 

I know, it’s a lot of effort.

Saturday, August 2, 2008

Help Your Readers by Letting Them Know the Importance of Your Message

No, I’m not talking about adding those exclamation points. 

But don’t leave your correspondents guessing about how important an issue is to you.   Leaving them guessing is likely to lead to their guessing incorrectly and there can be a huge difference between needing something ASAP, needing it tomorrow and needing it eventually.  It can also give certain people an excuse not to reply in a timely manner or at all-- “Really, you wanted those numbers this year?” I’m not saying that you need to create a fire drill every time you send out a request, but do try to give a realistic sense of your expectations.  If something actually is an emergency, let your readers know.  If the rush is your fault, feel free to apologize; you might be surprised how much that can help.  On the other hand, don’t create false deadlines or exaggerate the importance of your issue.  Once people figure out what you’re doing (and you can bet that they will) you’re likely to find that they’re much less willing to help you in the future.  Anyone who is in a position to ignore your requests most likely will do so if they believe that you’re crying wolf again.  Those who aren’t will just be resentful. 

It’s also a good idea to consider the time of day and whether it’s realistic to expect an immediate response at all.  Now that many of us work every day with colleagues across the country and around the world, we’re often still in the office when our co-workers are at home, in bed or enjoying a well-deserved holiday.  Believe it or not there are still a few people out there who don’t pay close attention to their email on evenings and weekends—I hear that there’s even the occasional Luddite who doesn’t have a BlackBerry or access to email outside of work. Being aware of the schedules and habits of your correspondents can help you avoid misunderstandings, rushes and missed deadlines.  I’d also suggest that it’s a good idea to avoid sending anything that needs an immediate response late in the day if it can be avoided.  But, if you find that you have to, be sure to let your recipients know if their answer can wait until the next day (or Monday if it’s the weekend).  I promise that they’ll be grateful. 

Monday, February 11, 2008

Reply in a Timely and Appropriate Manner

There are few things that annoy people more than not getting a response in a timely manner. The problem is that ideas of exactly what “timely” means vary from person to person and situation to situation. Way back when I used to manage an IT help desk I treated all of my business-related email much the same as I would have answered a help desk call, lobbing back a response as soon as I could come up with an answer. I think that’s the way many of the people at my firm, used to dealing with attorneys who treat everything as an emergency and expect white glove treatment, tend to deal with their email. But now that I’m focused on managing trainers I’m operating under a much more relaxed paradigm. There just aren’t that many training-related emergencies. The rule that I’ve set for myself is to respond to every message within half a day. So if I get a message in the morning I’ll reply to it by that afternoon. If I get one late in the day I’ll make sure to respond by early the next morning.

Of course there are exceptions. If someone has a simple question I can answer immediately I try to do so. If they have managed to come up with one of those rare training emergencies I get back to them right away. If someone important needs something they go to the top of my list. This isn’t brown-nosing, it’s covering my own ass. And if you don’t think there are VIPs in you workplace who require special attention I’m guessing that there are some office dynamics that you don’t understand and would benefit from studying.

There will still be some questions and requests that you can’t deal with in as timely a manner as you’d like. Maybe you’re tied up in a meeting and have to consult with someone else or crunch some numbers before you can provide an answer. If that’s the case, at least reply and let the sender know that you’re working on their request. That way you let them now they’re not being ignored and you can save yourself from dangerous hard feelings. I once put in a request with one of our software developers to see if he could help my group by developing an application to track attendance in our classes. By the time I heard back from him six months later we had already researched and bought software from an outside company. I guess I did get a response, but it wasn’t helpful or timely. I had to wonder if he’d been thinking about the issue all this time or if he was just six months behind in reading his email.

The most important thing you can do when answering email in a timely manner is to ask yourself when your recipient needs or expects a response and try to fulfill their expectation. Of course, some people believe that all of their emails are mission critical-- you’ll have to figure out how to deal with them yourself. Personally, I tend to ignore those people as long as I can. But I’m a bit of a jerk.

Saturday, February 9, 2008

Don’t Get Caught in a “Thank You” Feedback Loop

It’s nice to be nice. Except when it’s not. If someone is able to answer a question for you, does you a big favor or sends some juicy gossip your way by all means send them a quick thank you. But that’s where it should end. Don’t keep volleying “thank you”s and “no, thank you”s back and forth in an endless game of mutual appreciation. It’s nice to say “thank you.” But saying it once is enough.

Friday, February 8, 2008

Don’t Reply to a Message with Many Recipients Unless a Reply is Clearly Expected or You Have Something to Contribute

Some messages to large groups of people require a response from everyone. “Please let me know if Wednesday or Thursday works better for you,” for example. Others are clearly fishing expeditions for information and don’t require a response from all the people on the distribution list. “Has anyone seen my red stapler?” would be such a message. But there are some people out there who don’t seem to understand the difference and will reply to every single email they receive. I’m talking about the people who get a broadcast email that was sent to large number of people with a question like “does anyone know a good divorce lawyer in Las Vegas?” and feel obligated to hit Reply to All and respond with an answer like “No.” Maybe they do this to make themselves feel relevant or useful, but there’s no excuse for generating meaningless email. These people are one of the reasons why our email inboxes are full of junk and why so many of us have a hard time focusing on the messages that really are important. They must be stopped.

The first step in making sure you don’t commit such crimes is to take a second to think about whether a reply is really expected. If a message is addressed just to you it’s likely that you’re expected to respond. And of course you need to reply when someone directs a question at you personally. But the more people who are on the distribution list the less likely it is that you’re required to chime in or do anything. When you do have something to contribute the best approach is often to simply reply to the sender of the original message rather than inundating an entire group with information they don’t need. The organizer of a meeting may need to know that you aren’t available on Thursday because you’re going to your chiropractor, but everyone on the attendee list doesn’t. And it’s almost never a good idea to use Reply to All when you change the topic of discussion-- especially when you change it to something personal. I can’t tell you how many times I’ve seen Listserve discussions go bad when one person sends out a perfectly businesslike question to a large group of people and one of them replies to everyone with something like “Hi, how have you been? I haven’t talked to you since your husband left and you went into rehab! Did you run into Britney there?” Distribution lists and Listserves make the Reply to All button especially dangerous because it’s easy to forget how many people are included in them.

Thursday, February 7, 2008

Make More Than One Draft of Important Messages

None of us get everything right on the first try. Not even attorneys.

Chances are pretty good that you learned to make more than one draft of writing assignments in high school. Why wouldn’t you make at least as much effort with your email messages when your dignity, reputation or career might depend on it? Give yourself enough time to write more than one draft of important messages and set them aside for a while if you can before sending them. Editing your own writing is always more effective if you can take a little break before evaluating it. Even better, get a trusted friend or colleague to proofread critical messages for errors and to make sure that your tone is appropriate. It can be very difficult for us to hear how our tone might be interpreted by others, so borrowing someone else’s ear can be incredibly useful.

Wednesday, February 6, 2008

Understand That You Have No Control Over Your Email Once It’s Been Sent

I’ve already covered a lot of the scary reasons why you need to understand the fact that you have no control over your email once it’s been sent, but this seems like a good time to gather up a bunch of them in one place. What kind of trouble can your email create after you hit the “Send” button and think that you’re done with it?:

It can be forwarded along in an endless chain to anyone in the Universe who has an email account. Some clever person can forward it to your boss, to your boss’s boss, to your boss’s boss’s boss. It can wind up in the hands of your ex-husband, your priest, or the girl who beat you in the 8th grade student body president election. It might be of interest to the Securities and Exchange Commission or amusing to any number of strangers who simply enjoy laughing at you.

Your message can be permanently posted someplace such as the blogs and websites where you can find copies of the angry associate’s goodbye message or the fight between the two secretaries over the makings of the ham sandwich. If you think that the fast-paced nature of the web means that these things disappear quickly, you’re wrong. Many websites are still available even when they’ve been shut down or altered. Still not convinced? Check out the Wayback Machine (www.archive.org), which keeps an archive of websites just the way they looked in the distant past-- 2001 for example. Go ahead and take a look at an old version of your company’s website. You’re bound to find something embarrassing there. Web design sure seems to age quickly!

Anyone with a copy of your email can edit it and forward it along to someone else as your original text. While there are methods intended to thwart this kind of tampering, it’s generally quite easy for someone to create a forgery out of your email if they are really determined to mess with you. Really, the best thing is to avoid making enemies in the first place. But if that’s already a forgone conclusion, try not to send those people anything that would tempt them to make a tiny little change that could make you look really, really bad. By the way, I don’t feel guilty about editing someone else’s message if I’m going to forward it along if doing so cleans up errors in the original message or removes sensitive information that other people don’t need to know. But it’s always a good idea to ask permission before forwarding anyone else’s message. You can never be completely sure what’s sensitive and what isn’t.

Monday, February 4, 2008

Think Of Your Email as Eternal

While they aren’t usually as romantic, email messages, like diamonds, are forever. Of course you wouldn’t think so from the way they are hastily composed, cursorily read and quickly deleted. But the truth is that deleting an email is seldom enough to get rid of it. Chances are that there’s a local copy on the machine of the person who wrote it and another on the computer of anyone else who received it. It may be lurking in the “deleted items” folder of someone who doesn’t know the “deleted items” folder even exists or in that of one of those nuts who use “deleted items” as a filing system. There may be copies of every email you’ve ever sent on the backup tapes your company makes so that your mail system can be restored in case of disaster and copies on the servers of any email service used by you or your correspondents. And those are just the copies that are created automatically. There are people out there like me who keep examples of bad emails so they can write about them and others who will forward them to their friends so they can say “can you believe what an idiot so-and-so is?” and feel superior. These are also the kind of embarrassing emails that get forwarded ad infinitum, posted on blogs and turned into funny news stories. Remember that law firm associate who sent the angry email as he was leaving his firm ("I am no longer comfortable working for a group largely populated by gossips, backstabbers and Napoleonic personalities") and then tried to recall his message once he realized his mistake? He never had a chance of recovering all the copies of his message because it had already been forwarded beyond the reaches of his firm’s email system. You can still find copies online.

It’s not just your dignity that you have to protect. It seems like every week there’s a new story about a company or governmental agency getting in trouble for the way it keeps (or doesn’t) records in its email system. Morgan Stanley was ordered to pay more than $1.5 billion in response to a lawsuit (though this was overturned on appeal) because, despite the fact that it filed an affidavit saying it couldn’t produce subpoenaed documents related to a business deal gone bad, those very documents kept turning up on backup tapes that Morgan Stanley had asserted were lost but kept turning up. Some of them were found in a janitor’s closet. Both the Bush and Clinton administrations, which are required by law to maintain archives of all of their email, have found themselves facing investigations for not adequately keeping track of their correspondence. In order to deal with the challenges posed by keeping email records, many companies are struggling to come up with policies covering what messages they keep and how long they keep them. Many organizations are effectively deciding to keep everything despite the fact that it effectively means maintaining an enormous volume of data forever.

My firm has implemented a system where every message older than sixty days is moved from an Outlook user’s inbox and stored in an archiving system where it will presumably be available as long we have electricity to power our computers. And we’re not just talking about client emails. Since there’s no way to know what’s important and what isn’t, we’re saving everything; the emails from mom, the Viagra solicitations, the pictures taken at the alcohol-fueled holiday party. One of our secretaries expressed concern that some of her mail that would be archived might not be business related because she “occasionally” received personal messages at work. “If you don’t want it archived, delete it within 60 days,” I told her. “Otherwise it’s going to be around forever.” I didn’t have the heart to tell her that it probably would be anyway, and I wasn’t foolish enough to suggest that she not use her work account for personal email. That doesn’t mean that you shouldn’t think at least twice about what you put in your email at work. In addition to my general warning that you shouldn’t write anything you wouldn’t want your mother to see in email it’s also a good idea not to write anything you wouldn’t want to show up in court. Because your email belongs to your employer and they are responsible for what you write, everything you produce can be subpoenaed.

Besides the threat of the law, you should be very careful about putting down any strong opinions or emotions-- especially if you might ever change your mind. Remember those diaries and love letters you wrote as a teenager? Imagine them being reproduced and distributed to everyone in your high school yearbook. That’s the kind of potential for embarrassment you get with email. The fact that email-- just like your yearbook-- is more or less permanent is also a good reason to take the time to write well and try not to embarrass yourself as much as possible. You can’t go back and do anything about that Flock of Seagulls haircut in your senior picture, but you can make an effort so that your email is as smart and charming as you are.

Wednesday, January 23, 2008

Give Yourself Plenty of Time to Write

Not a lot of planning goes into the writing of a typical email. And that’s OK. Frankly, most emails don’t require a whole lot of preparation because they are either quick questions or quick answers to questions. It’s when you’re dealing with more complex matters that contain a lot of text, explanation or uncertainty that you need to take the time to plan your message. Which means you literally need to set aside enough time to make sure that you are able to write a message that accomplishes your goals, that you state your case clearly, that you get the attention of your readers, that you don’t offend them or make yourself look bad by sending something that’s riddled with errors. Overall, the more important your message the more time you should devote to writing it.

The first step for important messages is to make sure that you’ve given yourself enough time to draft your email. Then make sure you can take the time to proofread what you’ve written and edit your message to make any changes. If what you have to say is likely to cause confusion or an emotional response, get someone else to proofread your message for errors and (especially) for tone. If you find yourself writing an emotional response to someone else’s message, put your reply aside for a while so you can cool down before sending it. After a little break you may find that you don’t want to send it after all.

Of course these suggestions are appropriate for any writing that you do, but they are even more important for email because we tend to treat it as such a casual, offhand means of communicating. But don’t let those smiley faces fool you, email and the responses it provokes can be extremely serious.

Tuesday, January 22, 2008

Use Headings, Lists and Bullet Points to Make Information Accessible

People in my email classes are often surprised that I recommend using lists and bullet points as a way to quickly convey information in email. I suspect that they assume that I’d think that using bullet points is cheating, that I wouldn’t approve because bullets don't use complete sentences and paragraphs. But the biggest challenge in email communication is often just getting your message heard and using bullet points or lists can be a highly effective way to condense what might otherwise require several sentences or paragraphs of text-- which would likely go unread-- into a few bullet points that can be easily scanned and absorbed.

As is often the case with good ideas, there are a couple of caveats. Like email itself, bullet points and lists are great for passing along information but they would be an extremely insensitive way to convey emotional or otherwise sensitive information. Please never send anything like this:

Dear Bill:
  • Layoffs
  • You're fired
  • Two weeks severance
  • The guard will escort you from the building


Of course, personnel issues aren’t a good topic for email anyway. But most things that are appropriate for email and contain a lot of facts, steps, dates, etc. can make effective use of bullets.


That doesn’t mean you can totally ignore the rules of grammar and punctuation. Bulleted lists need to be introduced by phrases that combine with each individual item to create a complete sentence and they should be set off by a colon. They also need to use parallelism, which means that each bullet uses the same tense and follows the same basic construction-- which is easier to show than to explain. One place that I often see problems with parallelism in bullet points is in resumes. People will list their qualifications by saying something like:

In ten years as a sales manager I:

  • Supervised a staff of 12
  • Managing customer relationship database
  • Excellent communication skills


My example is pretty obviously wrong, but it’s the sort of thing people do all the time. Whether you’re writing an email, a resume, a PowerPoint presentation or anything else with bullet points, you should always go back to review your list to make sure that it’s made up of similar items and that they use the same tense. The first place to look is at the verbs you are using. In the example above “supervised” is in the past tense and “managing” is a gerund. (Don’t worry what that means, just look for the “ing” ending.) The third bullet point, “Great leadership skills,” doesn’t even have a verb, so we’re clearly in trouble here.


Another way to check to make sure that your list makes sense is to read the introductory phrase with each of the bulleted items to check that they form a coherent sentence. In our case “In ten years as a sales manager I supervised a staff of 12” passes muster, but “In ten years as a sales manager I excellent communication skills” doesn’t exactly instill confidence. To fix this problem we need to make sure that each bullet point has a verb and that we choose a consistent tense. Something like this works:

In ten years as a sales manager I:
  • Supervised a staff of 12
  • Managed our customer relationship database
  • Demonstrated excellent communication skills


Headings and lists work the same way as bullet points (which are really just a kind of list) to organize your message and make it easy for your readers to scan your email and pick out the pieces of information that they can disregard or that they need to pay further attention. Both require the use of parallelism in order to make sense. Headings allow you to organize long or complicated messages thematically, while lists allow you to serve up several ideas or pieces of information quickly and in an easy to digest format.


As with just about anything, you run some risk when you use headings, lists and bullet points in email. One danger is that you may be trying to do too much in email to begin with and that you overwhelm your readers. If your message is so complicated that you need to use headings you should probably think about whether email is an appropriate format to begin with. But in some cases you have no other choice. Another potential problem is that all of the items in a list tend to look as though they carry the same importance, so you need to be sure that you’re clear about anything that’s absolutely critical. Finally, reducing anything that is emotionally involved to bullets will trivialize what you have to say and is likely to alienate your readers. Think of the example of the layoff notice that I used earlier, or check out the PowerPoint version of the Gettysburg address (http://norvig.com/Gettysburg/) for a supreme example of why you should be careful about reducing important topics to bulleted lists (and why PowerPoint isn’t the proper tool for every task).

Monday, January 21, 2008

Don’t Address Important Messages Until They Are Ready to Send

There are good reasons that the first thing most of us do when we create a new email is to address it. But that doesn't mean you should do it that way.

The best reason to address your email first is because it helps you to think strategically; addressing your message helps define your audience, what you have to say to them and the tone you use to say it. But, realistically, I think that most people address their messages first for no better reason than that they are used to filling out forms and that the “To” field is the first one they see in the top left-hand corner of a blank email. After choosing the recipients in the “To” field they move on and consider whether they need to “Cc” or “Bcc” anyone. By the time they get to the subject line they often seem to be too worn out to think of a good headline and are so eager to jump into the body of the text itself that they settle on something lame like “hi.”

I’m here to tell you that addressing your message first is a bad idea-- especially if your message is an important one. There are just too many thing that can go wrong and you don’t want your important message to go out before you’re sure that you’re done with it. Several years ago I was testing some of the early ultra-portable laptops for my firm. They came with small screens, no floppy or optical drives, and tiny cramped keyboards. There was one that I liked a lot, especially for carrying back and forth between home and the office. But its keyboard was a fatal flaw for me because the keys were too small and weren’t tactile enough to differentiate between them. I was constantly making typos. But the real deal-breaker was that I’d be in the middle of typing an email when something would happen and Outlook would send the message before I was done. It took me a while to figure out what was happening-- I was accidentally hitting the combination of the “Alt” and “S” keys, which is the keyboard shortcut for “Send” in Outlook. My goofy initial workaround to prevent this problem was to type some garbage characters at the beginning of each of my important emails so that spellcheck would stop them from being sent accidentally before I was ready-- which only works if you have spellcheck set to run automatically. But the whole thing is a little more Rube Goldberg than necessary. The better solution is just not to address your message until you’re done with it.

The worst thing that happened to be because of my premature emails was that I sent out typos and ideas that were left unfinished mid-sentence to a couple of people. But none of them were particularly embarrassing. It could have been far worse if these had gone out to an entire office or a group of senior directors. Or if I were venting by writing out an emotional reply to an email that I never intended to send.

Addressing your message last gives you the added benefit of making you think about the appropriate audience for your email once it’s done rather than before you’ve started. I’ve found that the audience for a message often changes while it’s being written, but people often neglect to rethink their list of recipients when they’re eager to get their email out the door. It’s always a good idea with any important email to take a look at the list of recipients and make sure your message is appropriate for all of them before you finally pull the trigger and hit send.

Sunday, January 20, 2008

Change the status of a high priority message when you forward it

Here’s an easy way to look stupid. You get a “high priority” message from a summer associate asking if anyone knows a good dry cleaner in the Marina. Of course she’s sent the message to everyone in the firm and Blackberrys are buzzing all over the building, disrupting countless conference calls and vibrating themselves off the edges of desks like little rectangular lemmings. You’re so annoyed that you forward a copy to your best friend Doris, who works in the next building over. “Are these kids stupid, or just self-absorbed?” you ask her. “It’s hard to believe they’ve made it this far without learning how to use email. So maybe they actually think their dirty clothes are important enough to bother partners.” Your message, which has inherited the “high priority” status of the original, arrives in Doris’s office via the internet’s series of tubes while she’s on a conference call with her boss and starts her Blackberry vibrating in its particularly grating way before it dives off the desk in embarrassment.

Unless it really is critical, change the status of a high priority message before forwarding it. Otherwise you’re committing the same crime as the original sender. But hey, at least you didn’t hit “Reply to All” by mistake. Did you?