As a member of Gen Y, you (hopefully) already know the most important rules of email etiquette: Keep it short and sweet, and don’t put anything in an email that you wouldn’t want forwarded to your grandmother, your boss, or your significant other.

But sometimes, the stickiest part about writing an email isn’t the content at all—it’s how to begin and end it. Especially in the workplace, it’s not always as simple as starting with “Dear Joe” and signing off with “Thanks, Kelly.”

So when you’re crafting a message to a hiring manager, an executive, or even your boss, here’s how to make sure you’re putting your best cyber-foot forward—from beginning to end.

1. An Email From Who?

First things first: It’s time to retire your “CrazyGal@woohoo.com” email account. Really. It’s not cute or creative, it’s unprofessional. If you're using an email account for any other reason than chatting with your college friends, use an address that incorporates your first and last initials or name and leave it at that. Also, be careful when using the numbers 0 or 1 in your email address; it can be hard to tell them apart from an uppercase letter O or lowercase L.

2. Avoid Greeting Gaffes

Choosing the first word of an email is easy—“dear” or “hello” both work in nearly any situation. But it can get tricky after that. In regular workplace communications, addressing the person by his or her first name is usually fine, and using titles can make you look overly formal, stuffy, or juvenile.

But there are exceptions: some upper-level execs prefer “Mr.” or “Ms.” so it’s worth keeping an ear out to hear how other people normally address him or her. And it’s a safe bet when you’re meeting a medical doctor or professor for the first time that they would prefer to be addressed as “Dr.”

When sending emails for your job search, it’s best to use titles. But if you don't know the gender of the person you're contacting, don’t guess—go with the first name only. Yes, Christina “Chris” Brown might forgive you for calling her Mr., but the last thing you want to do is embarrass yourself before you get into the heart of the email.

Finally, if you don’t have a specific name for the recipient (e.g., you’re sending a job inquiry to a central HR address), a simple “hello” is perfectly sufficient.

3. Close With Courtesy

You might have your favorite email closing line, but you should always consider your relationship with the correspondent and the reason for the email when signing off. Here's a quick peek at some commonly used taglines and the message they convey:

Sincerely: This is a universal closing sentiment and 100% appropriate in most situations, but it can be seen as a bit stuffy or off-putting for correspondence with someone you know well.

Best regards: This phrase is professional, but with some warmth. It’s common for business emails that are less formal, such as between co-workers who work together somewhat frequently. This can be shortened further to "Regards" when emailing someone familiar.

Best: This sign-off is widely debated and is seen as everything from sincere to trite, depending on the filter of the recipient. It’s simply a shortened version of "Best regards" and can connote positive feelings. But, it can also be misconstrued as inauthentic if you don’t have a previous one-on-one relationship with the person you’re emailing.

Respectfully: This is a formal sendoff that’s appropriate when emailing the CEO, Chairman of the Board, or a high-level company executive.

Fondly: This is definitely a social closing, not a professional one. It sends the message of friendliness and genuine interest—but with a level of familiarity that’s best kept out of professional correspondence.

Warm regards: This is a more formal version of "fondly," but it's still best suited for social emails.

Yours truly: Often considered a bit stuffy for email, this closing may be best used for more formal correspondence such as a printed letter.

4. Make Your Signature Useful

Make sure your signature line lists the basics: your full name, title, company name, and contact information, including phone numbers and email. A company logo can also be an aesthetically-pleasing addition.

When you’re sending job search-related emails, use your name and contact information. Be thoughtful about what contact info you give, though—if you don’t want potential employers calling the line your receptionist sometimes picks up, then don’t give out that number. And if you use Facebook, Twitter, and LinkedIn professionally, it’s fine to include that information as well.

You’ll sometimes see emails including quotes or witty asides as part of the signature—but proceed with caution before you go thinking yours needs this kind of upgrade. Business emails need to contain just that: business. Your signature is not the place to tout your personal beliefs or interests.

When you go to craft an email, be sure you pay as much attention to your opening and closing line as you do the rest of your content. Don’t let an avoidable packaging blunder annoy or distract the recipient before he or she gets to the most important part of your email—the message.

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