Don’t Be Part of the Problem

The most common mistakes people make when sending email aren’t premeditated or malicious; they’re simply a matter of not thinking things through—of not looking at email from the recipient’s point of view. If your guiding principle is to send only email messages you’d be happy receiving yourself, you’re already well on your way to being a better correspondent.

But what counts as email courtesy isn’t always obvious, so let me offer several specific tips:

• Use Bcc for lists: When my son was in preschool, I used receive email messages a few times a month sent to all the parents by a member of the parents’ association. And all 108 addresses were in the To field, which meant I had to scroll past them when viewing the messages on my iPhone before I got to the message body. It also meant I knew every other recipient’s email address, which not everyone is comfortable sharing publicly.

  When sending a message to multiple people—especially a long list, and even more especially when they don’t know each other—put your own address in the To or Cc field, and put all the recipient addresses in the Bcc (blind carbon copy) field (see Message Header). That way, each recipient’s address is hidden from the other recipients. And they’ll thank you for it.

• Be careful with Reply All and Cc: Suppose you’re the recipient of a message sent to multiple people, and their addresses are in the To or Cc fields. You might be tempted to click Reply All out of habit, but please think before you do. Does everyone else on that list really need to hear what you have to say, or just the sender? Or perhaps a subset of the recipients? You can individually delete email addresses when replying to all, and more often than not, replying to everyone on a long list amounts to unwanted clutter for most of them.

  Similarly, think before adding someone as a Cc recipient. People regularly Cc me on complaints, bug reports, and other matters that vaguely involve a book or article I’ve written, but really: I don’t need to be involved, and I assure you that putting my name on a message you send to Apple (or whomever) won’t lend it any more weight. Ask yourself whether the potential Cc recipient truly needs to be involved in a discussion.

• Don’t forward nonsense: Jokes, funny animal pictures, political screeds, and other such stuff that gets endlessly forwarded is nearly as bad as spam. You can’t stop someone from sending this material to you (although you can ask politely), but you can certainly make sure you’re the last link in the chain. Seriously, no matter how funny or apt you find one of these generic messages, your friends and family don’t need to read it.

• Use good subjects: When you’re scanning an Inbox full of messages to decide what requires your most urgent attention, it helps to have some clue what a message is about before you open it. And later, if you’re searching for a message, you’ll find it more quickly if the subject is descriptive. So, “Hi Joe” (an actual subject on a recent message to me) is not helpful, whereas “Question about shipping company” (the actual message topic) would have been. You don’t have to agonize over the subject, just give the recipient some idea about the topic.

• Reply promptly: If I had a nickel for every time someone expressed amazement at how quickly I’d replied to them (even if the person was a complete stranger), I could retire today. But this practice doesn’t seem unusually virtuous to me; it’s merely a natural byproduct of wanting to keep my Inbox empty. Not everyone checks their email constantly, and sometimes a proper, thoughtful reply requires hours or days to compose. But I can’t overstate the amount of good karma you generate with timely replies. If a response requires more time than you can invest at the moment, say so right away—something like “I need a bit of time to think about this, but I’ll get back to you in the next day or two” goes a long way.

• Avoid pointless replies: The canonical example of a pointless reply is “Me too,” where multiple people are discussing some topic and the only contribution of your message is that you agree. Once again, the question to ask yourself is whether the recipient(s) need to know what you’re saying—whether it will help them. If not, don’t send the message.

• Respect the recipient’s time: Although I’ve written some epic email messages in my time, email as a medium works best for relatively short messages—especially when you’re composing or reading on a mobile device. Messages that go on and on with needless details or elaborate stories are more likely to be ignored—or to have delayed replies. So, do your best to be concise but also include all essential information, because a series of back-and-forth “Wait, what did you mean by x?” messages wastes everyone’s time.

  And remember: even though you may have all the time in the world, the person you’re writing to may be extremely busy. Messages that cover a single topic, and do so in a compact and straightforward way, are the most likely to merit someone’s attention.

It seems kind of crazy to me that I should be giving a “do unto others” speech like this given how long email has been around, but judging by the email I get every day, far too many people still haven’t gotten the message (so to speak) that politeness in email is a virtue. So, practice and preach all these things, and it’ll raise the level of email interaction for all of us.

Those major points out of the way, I want to turn to a few issues that are a bit more mechanical in nature, such as choosing the best format for your message, being smart with message attachments, and quoting effectively.

Choose Formatting Wisely

When composing an email message, there are two potential formats you can use:

• Plain text: Plain text includes text only, without custom fonts, styles, or other formatting. Plain text is ideal when readability is paramount.

• Rich text: Rich text, which is Apple’s way of referring to HTML (the system of tags used to create webpages), gives you formatting options such as font, size, style, color, bulleted and numbered lists, and adjustable indentation. You cannot, however, manually edit the HTML code in your outgoing email messages.

In most cases, the simplicity and universality of plain text outweigh the creative control of HTML.

In iOS Mail, there’s no explicit switch; messages use rich text automatically if you add bold, italics, or other formatting—and plain text otherwise. Even so, incoming messages almost invariably look fine, because the formatting options are so limited.

In macOS Mail, I generally suggest sticking with plain text, because that way your recipient gets to decide which font, size, and style to display your message in. Every time I get a message written entirely in, say, green, 24-point Comic Sans—and believe me, it happens—I cringe. I know what fonts, styles, and sizes are easiest to read on my Mac, and I dislike messages that override those choices. If you want do your correspondents a favor, use plain text. It’s easy to do—simply avoid adding formatting! Even if your message format is rich text, it will be sent as plain text if you haven’t made any changes to the font, color, size, or other formatting. However, if you include any graphics or photos as attachments in a message (see the next topic), I recommend that you explicitly choose rich text format for that message, because the images are more likely to show up correctly for your recipient.

To switch explicitly between plain text and rich text for the current message, choose Format > Make Rich Text or Format > Make Plain Text. To set a default for all new messages, go to Mail > Preferences > Composing and choose either Rich Text or Plain Text from the Message Format pop-up menu.

If you insist on using rich text, please don’t use wacky fonts, sizes, or colors. Stick with standard fonts in black, at reasonable sizes, because that will make your messages more readable. (Recently, someone sent me a series of messages in Courier, with black text on a dark gray background, which was so lacking in contrast that I could barely make out what it said. It took considerable restraint not to reply with a lecture on email etiquette!)

Use Attachments Judiciously

An earlier edition of this book had a topic here called “Avoid Attachments,” in which I advised readers not to attach files to messages at all if it could be avoided. Now that Mail Drop is part of Mail, several of my objections to attachments are moot. In particular, you no longer have to worry that a mail server will reject a message due to excessive attachment size, nor do you have to go through a multi-step process to send a link to a file stored in the cloud.

That said, it’s still my opinion that attaching files to email messages is not the best general-purpose file-transfer method, even with Mail Drop. Consider these factors:

• Each email app (and user) does things a bit differently. Mail assumes that the program receiving the messages it sends will be at least as intelligent and capable as Mail is, but that may not be the case. Mail also assumes you always want attachments to appear in what it deems the “prettiest” manner, and your idea (or the recipient’s idea) of “pretty” may not match Mail’s.

• The experience of downloading and viewing attachments on a mobile device is often poor, and while iOS can display many file types natively, many others can be displayed only on a computer.

• Attachments (even when sent via Mail Drop) count against your monthly data transfer limits—often a bigger deal with cellular data plans than with home broadband—and chew up valuable storage on your device.

• One or two smallish attachments may be fine, but when attachments get up in the multi-megabyte range or higher, that uses a lot of storage space on my devices and eats into my IMAP storage quota. (Remember, Mail Drop doesn’t even kick in until attachments reach about 20 MB in total, but having tons of 18 MB messages is still a problem.)

• Most email servers have limits on the sizes of attachments (iCloud’s limit, for example, is 20 MB, but some servers have a limit as low as 5 MB). If you go over that size when sending from an iOS device or the Mail web app at icloud.com, Mail tries to send the message but fails, eventually displaying an error message. (And even if your outgoing mail server accepts an attachment, the recipient’s incoming mail server may have a lower limit and reject the message.)

• Larger messages take longer for you to send and the recipient to download.

• As a recipient, I generally dislike having to deal with attachments, so I try to extend my recipients the courtesy of not having to either.

Now, none of this is a big deal if you email your friend the occasional 100 KB PDF document. However, if you’re in the habit of emailing files frequently, emailing lots of files in a single message, or emailing multi-megabyte files that are nevertheless too small to trigger Mail Drop, I’d like to suggest that you stop doing that and adopt an alternative approach that’s better for you—and better for your recipients.

What I recommend is basically the manual version of Mail Drop: put the files you want to send in a cloud-based storage system such as Dropbox, Box, or Microsoft OneDrive—a process that’s normally as simple as dragging the file to another folder—get the link to that file, and email your recipient the link. Admittedly, that requires more steps than using Mail Drop, but if you’re using Mail on a Mac, you can pick up Mailbutler, a Mail plugin that automates the entire process.

All that said, if for any reason you can’t or aren’t willing to email links instead of actual files, at least meet your recipient halfway by following these tips.

Quote Effectively

The final pointer I want to offer involves quoting the text of a previous message when replying to or forwarding a message.

Broadly speaking, there are two models for quoting previous text:

• Top-posting (or bottom-quoting) is the default in Mail and most other modern email clients. You hit Reply, and the entire text of the previous message (along with any earlier messages in the thread) is quoted. Your reply goes at the very top, and the earlier portion of the conversation is below, for the recipients’ reference.

• Bottom-posting (or top-quoting) is the reverse. The original message (or, more often, a brief excerpt from it) goes first, and the response goes underneath. If the message contained several questions or points, there may be alternating blocks of quoted text and replies.

I get why people tend to prefer top-posting: it’s much easier—for the sender. It requires no thought or effort; you simply type your response and put the burden of reading the context on the recipient. And that’s an entirely reasonable approach if, and only if, the response is brief and it’s entirely obvious to the recipient(s) what you’re responding to. But beyond that, please be kind to your recipients and go to the tiny extra effort to put your replies after their questions or comments.

In macOS Mail, first go to Mail > Preferences > Composing and make sure the “Include selected text, if any; otherwise include all text” radio button at the bottom is selected. Now, whenever you reply to a message, select just the text you want to quote—I suggest including just enough of the original text to provide context for your reply—and click Reply. Then type your reply after the quoted text.

In iOS Mail, bottom-posting is more awkward, but here’s how you can do it (and think how much pain you’ll save the recipient):

1. While viewing the message you want to reply to, double-tap and hold over the portion of the message you want to quote. Adjust the selection handles to select the desired text.

2. Tap the Reply icon. Mail opens a new message, addressed for a reply, but with only the selected text quoted.

3. Delete the extra return(s) at the beginning of the message, move the insertion point after the quoted text, and begin entering your reply.

iOS Mail always puts your signature at the top, above any quoted text, even if you quote only a selection. To avoid this, you can:

• Cut and paste your signature from the top of the message to the bottom—admittedly a bit awkward.

• Turn off Mail’s automatic signature (see Change Account Settings) and use the iOS Shortcuts feature (Settings > General > Keyboard > Add New Shortcut) to quickly insert a one-line signature wherever you want it to go.

• Use a third-party virtual keyboard, such as TextExpander + Keyboard, to type your replies, entering previously configured custom signatures on the fly.