1. Proofread — and be businesslike. Let's get real. You don't actually proofread all your messages before sending them anymore, do you?Gotcha! Get back in the habit. Spell-check is swell but far from fail-safe.Messages should be concise and accurate. Do not waste recipients' time or attention. (For more on avoiding basic e-mail mistakes, see these tips.)And don't paste in cutesy cartoons, your toddler's artwork, your favorite epigram from college, memory-hogging graphics, wacko fonts or all the rest of the endless and poignant attempts to stand out from the crowd. That goes for forwarding such things as well. Just be straightforward. Please."E-mail has become your electronic stationery and business card," says Leah Ingram, a Certified Protocol Consultant based in New Hope, Pa. "If you aren't presenting a professional image in your e-mail, then what does that say about the rest of your business dealings?"You can efficiently customize messaging manners, including using salutations, templates, e-mail signatures and the like, by utilizing the features offered by Microsoft Office Outlook 2003.

2. Consider your e-mails company records. At most businesses, even the owner or chief executive cannot be guaranteed complete privacy when it comes to company e-mail.More and more companies are monitoring employee e-mail, according to a 2005 American Management Association survey. That includes telecommuters who work on company networks and PCs. The association found that nearly two-thirds (60%) of companies surveyed now rely on some type of snooping software to monitor employee e-mail, up from only 47% a few years ago. Monitoring software is inexpensive, too.Take steps to protect yourself and your business. Installing surveillance software is a preventative measure. But periodically remind everyone that it's in place, so employees remain careful. And set a good example yourself.(Remember Harry Stonecipher? He was the Boeing chief exec installed to help restore the company's reputation for ethics. Yeah, well. As you may recall, Stonecipher reportedly sent an explicit romantic e-mail to his employee inamorata over the company network. That message was intercepted via surveillance software and publicized just about everywhere. The upshot? A likely career-ender.(My word to the wise: Don't set policies that apply to everyone else but you.)

3. Know the kind of e-mails that will backfire. Experience has taught most of us that e-mail isn't meant for certain kinds of humor, sarcasm, ironic asides or critical assessments. The medium is way too literal and fast moving for nuances. There are, natch, tons of exceptions to this rule for the recipients who know you well and can "hear" your tone via e-mail. However . . .Certain topics should be entirely forbidden. In business, don't ever use e-mail to send off-color jokes or to comment on anyone's sexual, racial, religious or ethnic characteristics. Do not ever send messages about someone's age or disability. Do not ever trash a colleague's professional capabilities or performance or job history. Some of this can be legally actionable. Any of it could severely damage your reputation and business.

4. Know the kind of e-mails that will annoy. We've all downloaded our fair share of e-mail that's annoying, offensive, amazing (in all the wrong ways), weird, unnecessary, confusing, incomprehensible — should I go on? I'm not talking about spam or phishing — I'm talking here about simple daily business e-mail.Use these experiences as object lessons. Put yourself in a recipient's place and, before hitting "send," ask yourself: "Would I want to receive this message?" It's miraculous how well this works.The corollary: "Don't write it if you wouldn't say it," advises executive coach Leslie Ungar, who runs Electric Impulse in Akron, Ohio.

5. Utilize automated security features for confidential or sensitive e-mails. Outlook 2003 now offers a combination of technologies called Information Rights Management (IRM) that can prevent any recipient of the messages you send from forwarding, copying from, or printing the message. Basically, the recipient can read the message and that's it.With Information Rights Management, you can limit the distribution of sensitive e-mails, warding off office gossip-mongers, busybodies, and careless co-workers. But IRM is not a silver bullet in terms of keeping information secure. For more on what it can and can't do, see this page.

6. Know when e-mail just isn't the best vehicle. Face-to-face communication is alive and well. "Don't use e-mail to avoid an uncomfortable situation or to cover up a mistake," says Laura Stack, productivity expert based in Highlands Ranch, Colo., and author of "Leave the Office Earlier."(For more on e-mail tips for bosses, see this article.)

7. Don't be unrealistic. Today, roughly half of all online holiday shopping is conducted at work, according to market researcher comScore Networks. Plus, millions of workers send e-mail to family and friends every day. The point? E-mail is now an integral part of everyday life. If you try to ban all personal use, you'll lose.Go with the flow here. Understand that personal and work lives are blurring, especially when it comes electronic communications. Set reasonable standards for personal e-mail use that suits your needs and productivity. Just make sure to enforce them.

8. Don't put policies in place and walk away. Times change. Technology improves. The company grows. And employees turn forgetful. All such factors have an impact on e-mail. Set up and monitor e-mail etiquette appropriate for your business, then make sure to review and, if need be, re-jigger the standards at least once a year.For help in drafting smart e-mail policies, check out The Electronic Communications Compliance Council (www.TE3C.org). An alliance of IT industry companies and consultants, TE3C provides best-practice advice about the evolving issues of electronic communications.These days, understanding e-mail etiquette goes way beyond keeping messages short or avoiding all caps. It could make the difference between profit and loss.