Oops, Didn’t Mean to Send That: Essential Email Etiquette in the Library Workplace

Book review of
David Shipley and Will Schwalbe’s Send: The Essential Guide to Email for Office and Home. NY: Alfred A. Knopf, 2007.

Email is a crucial productivity tool, but we have all had an “oops” moment when we wish email had never been invented. Common email mistakes include forgetting to attach a document, sending a blank message or saying something you wish you hadn’t.

Breaches of communication etiquette can have personal and professional consequences. For decades, etiquette books like Emily Post’s have guided us on socially acceptable means for written and telephone communication. In my opinion, the best guide to email etiquette is David Shipley and Will Schwalbe’s Send: The Essential Guide to Email for Office and Home (2007).

Why do we have “oops” in our email life, and what can we do about it? Shipley and Schwalbe argue that the core problem is “email’s unique character – or lack thereof . . . a message written without regard to tone becomes a blank screen onto which the reader projects his own fears, prejudices and anxieties.” For example, “Will you bring that report you’re working on?” might be a simple request, or it can indicate that the sender doesn’t trust you have it done or to remember to bring it. Email communication leaves us without much ability to monitor the emotions and reactions of the person we are communicating with. Also, the speed of email communication compounds the problem and increases the amount of communication you send and receive. Shipley and Schwalbe argue that “email has vastly increased the amount of writing expected of us…as a result, we all complain about the sheer quantity of emails we receive, but what’s often overwhelming – and overlooked – is the quality of the messages we exchange.” They have identified the “Eight Deadly Sins of Email”, the types of email that really shouldn’t happen:

  1. Vague (“Remember to do that thing!”)


  3. Criminal (“Please tell them that I asked you to sell that thing when it hit $70”)

  4. Cowardly (“Here’s the thing: you’re being let go”)

  5. Endless (Re:Re:Re:Re:Re:Re:Re; that thing)

  6. Sarcastic (“Smooth move on that thing. Really smooth!”)

  7. Too casual (“Hiya! Any word on that admissions thing?”)

  8. Inappropriate (“Want to come to my hotel room to discuss that thing?”)

There are many reasons why sending an email is a good idea. It is an excellent means for exchanging essential information. It also reaches a lot of people quickly and over time and geography rapidly. Unlike phone conversations or handwritten letters, emails provide an easily accessible and searchable record. But there are eight reasons where email may not always be the best choice:

  1. The ease of email encourages unnecessary exchanges: we email too often because it is so easy to do

  2. Email has largely replaced the phone call, but not every phone call should be replaced: if you need to reach an agreement or find common ground, choose to call or to arrange a face-to-face meeting

  3. You can reach everyone, but everyone can reach you: emails have a democratic nature, a sense that we are somehow equals when communicating. This opens us up to (1) emails from people we don’t even know or want to communicate with and (2) social and professional blunders because the hierarchies we really should respect (employee to boss; son-in-law to father-in-law, etc) get blurred.

  4. Email defies time zones, which means it can defy propriety: when at work, you may not be able to tell if an incoming email is worth opening and reading. Shipley and Schwalbe note that it takes about a half-hour to recover and return to an original task when interrupted like this.

  5. Email provides a searchable record, which means you can be held accountable for your electronic correspondence. Shipley and Schwalbe note there are two kinds of “office creatures” to be aware of in this instance: (1) the ones who delight in saying “I told you so” and (2) the ones who try to pass the buck by burying an important piece of information (information time bomb?) in an otherwise barely important email message.

  6. The ease with which an email can be forwarded poses a danger: forwarding email is too easy. It is best to assume everything you send will be forwarded

  7. With email, your words can be changed. This can be done without your knowledge by others who use the forwarding function. So, if you are sending sensitive documents via email, send it in an Adobe .pdf format.

  8. Email attachments don’t just come with baggage, they are baggage. This is more than just a problem with viruses. Attachments take up a lot of server and computer space.

Essentials of Composing an Email Message

We have discussed some of the core issues about sending emails, but many of the problems of poor email etiquette come from how an actual message is composed. Too often we neglect the mechanics of the email itself. Shipley and Schwalbe note that  “because the To, Cc, Bcc fields and Subject line are built into our email programs . . . we consign them to a default model: simply hit one of the Reply buttons, and everything is filled in for you.” Relying on a default is convenient, but can encourage thoughtlessness. Here are some of the most important dos and don’ts when composing your email.


The “To” field may seem so straightforward that you don’t need to worry about it. But the consequences of entering or replying to the wrong recipients in the “To” field can come back to haunt you, or at the very least be seen as unnecessarily clogging the email ether. Too many people in the “To” field can cause others to judge that you are not taking them seriously if the email wasn’t really important to them or shouldn’t have been sent to them at all. Our sense that we want to cover our bases may be taken by the “also included” as a waste of their time. The person(s) who can act on the email is the most important one to be in the “To” field. Others should be consigned to the “Cc” field or not at all. Also, some evidence suggests that a better response rate comes when fewer people receive the email. Response rate drops drastically when too many people are in the “To” field, even from those you want responses.

“Cc,” or Carbon Copy

The “Cc” field is usually the way you keep people in the loop of information you are passing on or accomplish the professional slang acronym “CYA”. However, Shipley and Schwalbe say, “Nobody likes to be left out. But you can’t include everyone on everything. This is why Cc’s are among the most troublemaking aspects of email” (p. 72). Also, Cc can be seen as “picking sides.” Being careful about whom you include in a Cc is one of the most important details that needs attention. Ask yourself who should be in the loop (as opposed to who needs to act on the message). When in doubt, check with someone else to confirm who you think should go into the Cc field.

“Bcc,” or Blind Carbon Copy

The blind carbon copy, or Bcc, is another potential minefield. Shipley and Schwalbe argue that “Bcc’s should almost never be used . . . for the simple reason that you don’t want to talk behind the backs of people with whom you work. On rare occasions, though, Bcc’s are a defensible way of signaling your faith in a colleague” (Shipley & Schwalbe, 2007, p. 76). It is best to only Bcc your most trusted confidants.


The “From” field is very straightforward and rarely an issue. However, if you have one of those creative, crazy email names for your personal email, it is best to be careful to whom you send an email from that source. To a boss, it may look very bad.


Crafting a good subject line is often overlooked, but it can be one of the most effective forms of communication. Imagine getting an email you don’t even have to open because all you need to know is in the subject line. Think of an ideal email subject line like a Tweet in Twitter, in which an entire idea must be communicated in fewer than 140 characters. The absolute worst subject line is the blank subject. Many people will not open an email with a blank subject line for fear of it being spam with a virus. While that may be obvious, just any old subject line can be as much of a problem as the blank one. Here are some “useless subject lines” from Shipley and Schwalbe:

  • RE: FYI

  • Great news!

  • Urgent

  • Tomorrow

  • How is this?

  • Quick question

A good subject line (1) is informative; (2) represents the entire content of the message, not just the beginning; and 3) doesn’t sound like spam.Turn “Committee meeting” into “Planning Committee meets today, noon, room 123, brown bag”. The recipient will not only know which committee is meeting, but also the time, place and that attendees are expected to provide their own lunches, all in 50 characters. The small difference in typing time makes a world of difference in effective communication. Another note: avoid subject lines that don’t live up to their hype. Some subjects may sound great before you open the email, then be a downer after you read the message, e.g., “Great news!” only to read in the email “I’m going home for the day”. Be sure the subject matches the message.

Concerns about font, spelling and grammar may seem petty or obvious, but neglecting details can hurt you. It may seem cute or creative to choose a less common font style (Old English Text may appeal to the literary crowd), but for effective communication, choose a legible font. And double-check your grammar and spell check: the grammar and spelling you use in correspondence shape the impression others have of your education and intelligence.


A word on deliberately hostile emails, also known as “flames”: extreme emotions expressed in an email can have an even more devastating effect than if expressed in other forums. The best advice about flaming? Don’t do it. It’s not only rude, it can haunt you for a very long time. Shipley and Schwalbe advise that there is a time and place to express anger in emails, but to be aware of potential consequences: “expressing anger tends to upset the social structure. So before you explode, make sure it’s worth it… you also need to be aware that your outburst may well be forwarded to a much larger community.”

Email is the essential form of communication in the library workplace and will probably remain so for the next generation. Being smart about how to email will make you a more effective member of your library staff.