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.

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).

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.

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?