The Essential Guide to Crafting a Work Email

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You, like me, probably rattle off emails quickly, all day (and sometimes all night) long. And that means the people receiving your emails are doing exactly the same thing. Whether this is good or bad for us, generally speaking, is an open question. But until we all get better at dealing with email overflow, how do you make sure the ones you send get noticed – and for reasons other than an unfortunate Freudian typo?

First, the basics. They may seem obvious, but they’re easy to forget.

Text

Enough with the lower-case “i” and lack of periods. Even the little things, like using proper capitalization and punctuation, can help your messages stand out in an inbox full of acronyms, fragments, and misspellings. And as business writing expert Bryan A. Garner says, “It takes less time to write a clear message the first time around than it does to follow up to explain what you meant to say.”

– However, there are occasions when an emoji or typo may be appropriate. A smiley face could work if you’re mimicking the style of the person you’re communicating with, says Harvard Business School PhD student Andrew Brodsky. And a strategic typo might be smart if your message requires a high degree of authenticity (to make it seem like you’re not carefully crafting your message), especially if you’re in a position of power. But before hitting sned (see what I did there?) make sure you ask yourself whether it’s “important in the situation to seem more emotionally authentic (by making errors) or competent (by making no errors)”?

Can people actually read your green cursive font? Probably not. Remember that an email is, aside from a piece of communication, a designed experience. A distracting font, or more than three types of fonts, can take away from your message (or cause someone to hit “delete”). Some good choices include Arial, Helvetica, Lucida Sans, Palatino, and Verdana, according to social entrepreneur Dan Pallotta.

– Don’t forget a subject line that’s short and descriptive. If you need the recipient to do something as a result of your email, include a clear call to action.

Length

– No one will read huge blocks of text, says Pallotta. You can break them up by visually highlighting key messages, explains Bridgespan Group’s Katie Smith Milway, or stick to the rule of composing a single screen of reading or less.

– But even if you trim the fat, keep the meat intact, instructs Garner. “Consider your message from their perspective. They aren’t as immersed in your project as you are, and they probably have many other things going on. So remind them where things stood when you last sent an update, and describe what’s happened since then.”

– Above all else, get to the point quickly. No need to butter anyone up (though an authentic compliment here or there is probably OK) in order to get the job done.

Revisions

Yes, there are rules for this. Generally speaking, the number of recipients dictates how many revisions you should do, according to author David Silverman:

  • 1 to 5 recipients = 2 to 4 revisions
  • 5 to 10 recipients = 8 to 12 revisions
  • Company-wide or to Executive Committee = 30 to 50 revisions

The crux of his advice is that no email should be clicked-to-send without revision. Other suggestions from Silverman include deleting anything written in the heat of moment or that seems especially amusing or clever, and allowing a day to go by before hitting “send” – who knows, the issue that provoked your typing may be resolved outside your inbox. (According to Milway, even setting a two-minute delay on your email can make a difference.)

Timing

In general, avoid sending emails at the end of a workday or on the weekend (there are exceptions, of course, which I’ll talk about in a moment), or when you know people don’t have the time to read and answer them.

Recipients

The usual rules apply: Don’t include anyone who might be confused about why they’re on the email, and avoid using BCC unless you’re sure it’s necessary, says Garner. ” It could get you a bad reputation as being indiscreet.”

And when you’re on the receiving end, please don’t be that person who starts the “Reply All” chain from hell. 

Aside from the basics, there are a whole bunch of email tips that apply to specific circumstances. Here are a few to use in tricky situations.

When there’s a conflict or bad news. For the most part, these are best dealt with in person. Email, while great for some things, can be a bad place to handle a touchy issue because it’s incredibly difficult to predict how emails will be interpreted by the recipient. Andrew Brodsky says there are a couple of reasons for this: first, people infuse their own emotions into a message, regardless of the sender’s intent; and, second, there are a lot of contextual factors (how long you’ve known someone, for example) that come into play.

Whenever you can, he says, put yourself in the recipient’s shoes before hitting “send.” It’s also a good idea to explicitly state your emotions to prevent frantic guessing on the other end of the message.

Author Joseph Grenny advocates for asking yourself the following question before considering an email about conflict or bad news: “Can I do this well without seeing her face — and without her seeing mine?” We gather important information from faces, he notes, and we tend to be more ethical and empathetic when we’re looking someone in the eye.

An email could be OK when you have a long history with someone and have a good grasp of their emotions. But you should approach your note by stating your intent before delving into the message and immediately change mediums if things start to get emotional. Pick up the phone or use Skype when tension arises.

When you’re unsure of how to respond. We’ve all gotten tricky emails about “a complex negotiation, or a politically sensitive situation. Or maybe it’s just from a person who unnerves you,” writes CEO Anthony Tjan. He first recommends buying some time, either with a short “got your message” or by not responding for 24 hours (“not responding is its own kind of response, which can often work to your advantage”).

Then he suggests employing what he calls the “Four C’s” as you consider how to respond: Context, content, contact, and channel.

When you’re emailing someone powerful. It can be terrifying to email a high-powered executive from any company — or even your CEO. Yet sometimes it’s a good idea, according to writer and entrepreneur Peter Sims. Most higher ups, he says, crave insight from the front lines of their companies. And even though it’s fairly likely you won’t get a reply, there are well-documented incidents of cold emails opening up a productive conversation or being the start of real change within an organization. Sims also offers some tips for when the best time to reach a busy executive is, and rules of thumb on persistence.

Of course, much of the advice above applies, including keeping your message brief and to the point.

And finally, a reminder: While email is something we do constantly, don’t let it become a mindless pursuit. It’s not the only method of communication at your disposal — even if it is the default.

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