I posted this piece a few weeks back for Jezebel. I am not a credentialed etiquette expert, but just someone who receives a lot of email. By the way, if you'd like to read my review of a TV show called "Whisker Wars" ("whisker," not "whiskey") go here. Also, today I contributed to a piece called "Eating the enchanted fortune cookie: 16 comedically convenient magical movie items."
Thanks to Facebook and Twitter, our pool of professional connections is as expansive as our list of friends. While it's savvy to make use of your list of contacts when asking for a work-related favor, it's important to remember that your "friend" online is a more than just a pal when you're asking him or her for a professional favor. Here are some suggestions for the next time you shoot an email requesting help from someone you know (or someone who someone you know knows).
Say please and thank you.
"Who doesn't say please and thank you when asking for a favor?" you ask. To which I say, "You'd be surprised." I am as guilty as anybody of shooting off emails without carefully proofreading them, but when you're asking someone to help you out with something, basic manners are essential. One of my patented ways-in-which-I'm-becoming-my-mother-and-I-don't-even-care is that if someone asks me a favor and neglects the P and TY, I'm inclined to ignore it. Without please and thank you, it reads as if you expect assistance, and aren't requesting it.
Explain why you're asking this person this particular favor (if necessary)
Recently I was sent a book to blurb, with no explanation whatsoever how the author knew me or why I was being asked to read and comment on the book. Was it for my humor writing? My nonfiction? The fact that I'm a woman? I figured I'd be a nice guy anyway and follow up with the author's publicist, asking about the deadline. I was given a deadline, but after I asked why the author requested my blurb, I received no explanation as to why I was asked to do this. So I'm skipping it, half because I don't know what they really want from me, and also because if the publicist can't be bothered to return my email, I'm not inclined to spend time reading a book and crafting a response to it.
On another occasion, a writer emailed me asking me to read and provide comments on his novel. He finished his pitch with something along the lines of "I have to admit I don't know who you are or anything. I guess I should have googled you first lol." I gently told him, for next time, you should at the very least not tell the person you're asking to do a time-intensive favor that you know nothing about her. (He then wrote back asking if I did know someone who could help, to which I did not reply.) Telling the person you're writing "I'm asking your input because I know you're well-versed on the topic of ___" or "I really enjoy your pieces at ___ and was wondering if you knew whether they were open to new writers" isn't just flattering—it shows that you know what you're talking about. On that note, though, be mature about it. Don't say "Because you kick ass and you're a rock star, I thought you could help me." That means nothing.
Indicate that you know it's a favor
This goes along with "please" and "thank you." Someone recently asked me to help her with something and she indicated that she knew I was really busy, but figured she'd ask anyway. I am busy, but I like her and her work and the fact that she didn't assume I'm sitting on my ass all day waiting for things to come to me was thoughtful. Noting a person's busy schedule, or the fact that they may need to stick their neck out for you might soften the blow if they in fact can't do what you're requesting, or, at the very least, makes you sound polite and gracious in your request. Sometimes I say something like "If this isn't a good time, I understand but I figured I'd ask just in case!" It's a fine line though between being deferential and undermining yourself: you don't want to say something like "You probably can't help me with this, but just in case..."
Be judicious with the follow-up
So you never heard back after sending your polite request for assistance. Did the recipient of your email purposefully blow you off or did they just lose track of the email? You may never know (do not send a request for an email receipt. That is annoying.) Go with your gut: if you got an "I'm out of my office" message when you sent the email and then never heard back, by all means follow up again a few days after you know the person returns and he or she has time to get caught up (when I'm gently nagging someone I say something like "I just wanted to send this again in case the original email got lost in cyberspace: if you're simply too busy at this time, I understand.") If you know someone in common, it might not hurt to ask whether your recipient is the kind of person who just needs a gentle nudge or whose silence is their answer. I can tell you this from experience: don't send a passive-aggressive email saying something along the lines of "Sorry for bothering you. I guess I'll just find help somewhere else." That reads simultaneously as defeatist, guilt-tripping and nagging.
I'm not indicating that you transcribe your "Can you help me out?" email on thick stock and seal it with wax. But make your words count. Starting your email with "Hi Claire" is fine but finishing with "If you can help me with this I'll be your best friend forever and give you my firstborn" is just...nothing. It's not going to spike your request necessarily but the empty hyperbole won't add anything to your request.
Really, when it boils down to it, asking an online contact for a favor isn't that difficult. Use your manners, include details (is your request time-sensitive?) and be a decent human being. This all seems like it'd be common sense, except for the fact that there are people out there who don't seem to know this, so if you follow these guidelines, you'll come out ahead and probably one day be like me, getting annoyed by other people's rude emails and building a reputation as a crabby old lady who only helps the polite.