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Ask Lisa C. Tang about the most irritating e-mails she received as a psychology teaching assistant, and she's quick to respond.

"I got a lot of e-mails from students asking if they had to buy the textbook or even if they had to attend class," says Tang, a sixth-year student in clinical psychology at Michigan State University. "And students would often e-mail me with questions about information that was already on their syllabus."

Demonstrating such lack of understanding may be the most egregious violation of e-mail etiquette, but it's certainly not the only one. And the way you correspond electronically can harm — or enhance —your career, warns John Suler, PhD, author of the online book The Psychology of Cyberspace and a psychology professor at Rider University in Lawrenceville, N.J. Although most students use e-mail effectively, he says, some need help learning how to make a good impression.

Fortunately, there's now an entire book devoted to the topic: Send: The Essential Guide to Email For Office and Home (Knopf, 2007). It offers many do's and don'ts, including:

  • Respect the niceties. When you're writing to professors, supervisors and the like, politeness counts. Use proper grammar, correct spelling and a tone of respect rather than slangy informality. With friends, anything goes.

Don't annoy recipients with outrageous requests. "Some students who miss a class ask the professor to summarize the whole class," reports Suler. E-mails that are overloaded with questions or multiple requests are also annoying.

And don't forget to identify yourself. "Some students send messages from personal rather than university e-mail accounts and fail to place their names at the end, which leaves the professor scratching his or her head," says Suler.

  • Make it easy for recipients. Since most people just scan e-mails, keep your paragraphs short and skip lines in between paragraphs.

"When I first started using e-mail, I'd write big, long paragraphs," says Tang. "I found that my respondents would often miss questions I had asked."

If you're making a request, make it early in the message and make it stand out: Give the request its own paragraph.

  • Don't expect an immediate response. Remember that some professors came of age in a different generation and aren't as obsessed with e-mail. "They don't check their e-mail constantly like I do, so they can take a few days to respond to a message," says Tang.

Give your recipients extra slack if you've sent your e-mail in the evening, over the weekend or during the holidays.

  • If you wouldn't want your whole department to read it, don't click "send." As many have learned the hard way, recipients often forward e-mail. That means your message could end up in the inbox of the very person you were just venting about.

Confidentiality is a special concern. At Tang's internship site, for example, colleagues use initials to identify patients and are vague about identifying details in case an e-mail goes astray.

Remember there are legal considerations, too. In addition to being easily forwarded, e-mail creates a permanent, searchable record of your correspondence.

  • Remember e-mail's not the only option. Just because you have e-mail doesn't necessarily mean you should use it.

If you've got a delicate problem, need to reach agreement on a thorny question or have a similar situation, a face-to-face meeting might be a better option. Because of the lack of visual cues and nuances of voice, e-mails can be difficult to interpret and easy to misunderstand.

And if the message is really urgent, remember that there's a device called the phone.

Rebecca A. Clay is a writer in Washington, D.C.