Writing business letters can be tricky. You sit down to dash off a quick letter and boom, you're stumped right in the greeting. Writing to one person has enough issues if you don't know the person's name or gender. When you add a few people, the questions multiply. How many people are you writing to? Two, three or a crowd? Do you know them by name? Are they your close pals, or passing acquaintances? Fortunately, there are rules and guidelines for all these situations.

Writing to Two or Three

If you're writing to two or three, it's an easy answer: Simply write out their names. If you know them well and are on a first-name basis, you may use their first names, such as "Dear Will, Kiersten and Pat."

If you don't know them well, or you're not sure whether first names would be appropriate, use more formality: "Dear Mr. Sothers, Ms. Thompson and Ms. Crump." Generally, you won't be faulted for being too formal, but eyebrows will rise if you're too informal.

Writing to a Group

When you're writing to more than three people, spelling out names looks cumbersome. People tend to feel like they're just one of a long list. Better to use a group term like "Dear Team" or "Dear Colleagues." It's funny how spelling out a group's names can make them feel like one of a crowd, but "Dear Team" makes them feel like they belong to the group; they're part of the team. "Dear Colleagues," says you consider them worthy of being a colleague, an equal and a valued participant.

Do not, however, use "Dear Colleagues" when writing to people who are senior to you. Technically, they're your superiors, not your colleagues. But if they're on the team, too, then "Dear Team" would work well.

How to Name Names 

Write to people by name if at all possible. For example, if several people have written to you about a subject and you want to write back, make the effort to find and use their names. If you're applying for a job, or you're in another situation where you want to impress someone, finding out their names shows you would make extra efforts in your job, too, if hired. Do you know someone at the company who could find out the names of the human resources personnel involved?

Another idea is to go the organization's website and see if the department's director or manager is listed. If that's the only name you see, you could address the letter as: "Dear Mr. Burns and Colleagues" or "Dear Mr. Burns and Members of the Selection Committee." If you don't find specific names, writing "Dear Members of the Selection Committee" will do just fine. While you could write, "Dear Selection Committee," adding "members of the" gives it a special touch. "Members" acknowledges that you see them as individuals, not just as one big anonymous committee.

Getting Around Gender

With names like John, Maryann, Wayne and Daisy, it's easy to tell their gender. Other names can keep you guessing, like Cary, Adrian, Pat, Sam, Chris, Drew and Alex. Sometimes their spelling gives them away. For example, Adrian is usually a male, while Adrienne is a female. But names defy common rules of spelling, so if you don't know, don't assume.

If someone you know might know the person in question, you may be able to find out. Also, check the website to see if the person is written about and is referred to as he or she. A general internet search for the name might yield answers, too. If all that doesn't answer the gender question, it's acceptable to write "Dear Chris Trainor."

To Whom or Not

While "To Whom it May Concern" sounds stiff and very formal, it's still an accepted salutation to use when you don't have any clue to whom you are writing.

On the other hand, "Dear Sirs" is outdated. It's a grammar trap that is a leftover from the days when businesses were a man's domain. "Dear Sirs" is inappropriate today when your letter could very well be received by a woman. "Dear Sirs or Madams" at least acknowledges that a woman could be one recipient, but it still sounds old-fashioned. First of all, no one is addressed as sir or madam anymore, except perhaps by their butler or chauffeur. If you don't have names and don't have any idea of their gender, try something different, like "Greetings" or "Hello." These sound friendly and are gender appropriate.

Manners Matter in Email, Too

In all but the most formal cases, it's acceptable to send an email letter instead of mailing the letter. Many job postings suggest an email reply. Email is a more relaxed form of communication, but as in a cover letter, the rules of grammar and etiquette still apply. Errors and misspellings will be noticed and you'll be judged by them.

The same guidelines apply when writing to two or three people or a group. When sending an email, though, it's important to put the email addresses in the "bcc" field rather than the "To" field. Many people don't want their email addresses to become public knowledge, especially when it's so easy to forward an email with everyone's contact info in plain sight. "bcc," which stands for "blind carbon copy," means you can see the address but the other recipients cannot.