How to write an email?

What’s next? A post on how to tie your shoes?

I know, I know. Email is such an ubiquitous part of our lives that you might think that people would naturally have it down pat.

But having received thousands of emails over the past four years, I can say with certainty that frequency does not necessarily beget proficiency. Which is to say: a lot of people out there are pretty clueless about how to compose a good email. Even those hired as professional PR reps!

No matter how basic a life skill, it’s something you still have to learn. And unfortunately, nobody seems to be teaching young folks the components of an effective email, despite the fact that it forms the backbone of modern communication. Knowing how to write a good email—one that will actually get a response–is crucial to your success: it can make the difference between whether or not you get a job, find a mentor, get funding for an idea, or receive potentially life-changing advice.

You see, each email is essentially a pitch, even if you’re not literally selling a business idea. What you’re pitching is the idea that you’re worth responding to—and that can be a tough sell. The person to which you’re writing may get dozens, even hundreds of emails every single day, and they can’t possibly give every single email the same time and attention. So just like with face-to-face pitches, these people develop ways of slotting their emails into two tracks—those that get a response and those that get kicked to the trash folder. What determines the track you get funneled to is whether or not you raise one of the recipient’s red flags; an email can be your first impression with someone, and since the recipient doesn’t have much to go on, he or she will be looking for little, subtle clues as to whether they should hit reply or delete. These red flags can be really small things—things that may not seem at all fair to you–but they’ve probably found that 8 out of 10 people who exhibit those characteristics aren’t worth responding to, as it ends up being a waste of their time.

The blog Think Simple Now did a great job of outlining the way the sender of the email and the recipient of the email have very divergent perspectives:

Observing the Receiver Gets a lot of email.

May receive compliments regularly, if they are a public figure.

Regularly gets asked a standard set of questions and favors.

Does not have a lot of free time.

Does not mind helping you, if it is fast. Observing the Sender Spends a long time crafting the ‘perfect’ (-ly long) email.

Believes that their request is original, unique, and special.

Believes that they are the first to ask for such favors.

Cannot imagine why anyone would turn them away.

Desires to tell the whole story, explained from every angle, so that the listener can understand their point of view.

The key to getting a response to your email is to put yourself in the recipient’s shoes and tailor your email accordingly. How do you do that? Well below we outline some of the things we look for in determining whether or not an email is worthy of a response. Now, the language may seem a little harsh. But this is not one man’s personal’s pet peeves—these are the same things that business owners, agents, and newspaper editors have told me they use in evaluating their emails; these are the things folks already say behind your back, and there’s no use in keeping it from people for the sake of being “nice.”

Note: These guidelines are only for emails that you write when you’re hoping for something from the recipient, even if it’s just a response. If you’re just dashing off a quick note to pass along some information or share your appreciation, or are corresponding with someone you’re very familiar with, the rules really don’t matter very much.

Respect the recipient’s time and make sure the email is even necessary. Everyone’s time is precious. When you send an email, what you’re saying is, “What I have to say is worth five minutes of your time, time you could be spending on your business or with your family.”

So don’t waste the recipient’s time with a question that you can figure out yourself. Exercise some self-reliance! I’m amazed at the number of questions I get that could easily be answered with a 10 second Google search (indeed, it is tempting to respond with “Let me Google that for you…”). After you exhaust Google, search the person’s website. Check out their past articles, their FAQ, and their About page.

On AoM we accept guest post submissions, and right above our contact box we have a link to the “Write for AoM” page that describes all of our guest posting guidelines, one of which is:

“Submit your guest post using the form below. Don’t email us asking if you can write for us. It will just get deleted. If you’d like to write a guest post, write it up, and submit it using the form on this page.”

And yet day after day we still get emails from guys that say, “Hi! I was wondering if I could write a guest post for you.” I used to still respond to these emails, but I found that 9 out of 10 of the people who couldn’t be bothered to read the instructions, couldn’t write a good guest post, either.

Begin with a salutation. Starting straight off with the first sentence of your email makes you sound abrupt. Instead, begin with “Dear ____” (for a more formal email), or “Hi _____” for a more casual one. But not “Hey ____” unless you’ve already established a rapport and history with the recipient.

I think the tendency to leave off the salutation is strongest when using a contact form to submit your message. But keep in mind that even when you use a contact form, it arrives in the person’s inbox looking like any other email.

Type your email address correctly in the contact form. This probably seems like a complete no-brainer. But people will ask me for advice, I’ll spend 20 minutes thinking about their question and writing a thoughtful reply, and then when I hit send, I’ll get a delivery failure notice. Arg! That’s 20 minutes of my life that I’ll never get back.

Address the email to a specific person(s). Do your best to find out the name of the person who will be reading the email instead of saying just “Hey everybody” or “To Whom It May Concern.” Using a person’s name builds rapport since it makes your message seem more personal and less like spam. If there are a couple of people in charge, address the email to both of them. Since Kate and I run the site together, people who address their queries to “Brett and Kate,” instead of just “Brett” automatically get extra points.

Spell the recipient’s name right. Again, a no-brainer, right? Yet we get emails addressed to “Brent and Kay” all the time. Misspelling someone’s name kills your rapport with the recipient before they’ve even read the body of your email. It tells the recipient that you either don’t know much about them or aren’t very detail-oriented. And if you follow the spelling error with, “I’m such a big fan of yours,” you come off as rather disingenuous.

Build a bit of rapport before getting down to business. Just as in any kind of pitch, you want to create a bit of rapport with the person before you start talking business. It makes the recipient of your email a little more inclined to like you, hear you out, and want to help you. Keep it short and authentic. Here are some examples of rapport-building intros:

“I am a loyal fan who has been reading your website for three years. Because of AoM, I now take James Bond showers, shave with a safety razor, and write weekly love notes to my wife.” “I have been a customer of Jim’s Sporting Goods for the past 20 years. My dad bought me my first mitt there when I was 7.” “I am a great admirer of your research on the howler monkey. Reading your book made me want to come to this university and major in biology. Which is why I’m writing to you today…” “As a fellow native of Austin…”

Something I’ve been noticing PR people do lately is to say something like, “You have a great site. I really enjoyed [article I clearly just picked off the front page one minute ago].” When rapport-building is obviously phony, it backfires. You want to say something so specific that the recipient knows you’re not sending the exact same generic message to lots of other people and that your interest in them is genuine.

Keep it short and to the point. Again, everyone’s time is precious. Don’t send someone a wall of text. Don’t give them your life story. Get right to the point in as few sentences as possible. You might think that giving the recipient as much detail as you can will make it more likely that he or she will respond to you, but the opposite is true. A giant block of text makes the recipient feel overwhelmed; they’d rather just delete it than deal with taking ten minutes to read and digest your tome. If your idea isn’t interesting enough to grab someone in just a few sentences, then you need to work on your idea, and if the advice you need requires multiple paragraphs to explain, you either need to do more research yourself first or it’s simply not a question you should be asking a stranger over the internet.

Make your request crystal clear. Even though you want to keep your email short, be sure to make whatever it is you’re hoping to get from the recipient as clear and specific as possible.

This is my least favorite kind of email:

Hi AoM: I really enjoy your site. I feel like it is a great fit with what we do. We should do some kind of partnership or something. What are your ideas on how we can do that? Sincerely, Vague Vinny

Of course I don’t have any ideas about how we can work together…you just entered my mind ten seconds ago! If you are contacting me, it is your responsibility to take a look at the kind of things we already do and then come up with an idea you think we might like—a clear, concrete proposal. Give the recipient a pitch they can say yes or no to. If you’re asking a question, make that question as specific as possible, one that it won’t take the recipient very long to answer.

The shorter your email and the easier it is for the recipient to answer your question, the more likely you are to get a response.

Don’t be a tease. Now for my other least favorite email:

Hi Brett and Kate- I have an awesome idea that can help you improve your website. Write me back if you want to hear more! XOXO- Huckstering Harry

Why would I waste my time writing you back if I don’t know whether or not I’d even be interested in your idea? Automatic delete.

If you have a website, link to it. Don’t tell me about your blog or website without linking to it. I know it would only take me 5 seconds to Google the name of your biz, but I’m not going to do it. It’s just one of those deal-breakers. Make things as easy as possible for the recipient.

And when you link to your site, make sure it’s up and running! Numerous times people have pointed me to their site, and when I clicked on it, the site was down for maintenance. Delete.

DON’T USE ALL CAPS. The universal sign of the crazy man. Using all CAPS make you seem like you’re shouting. Automatic delete.

or all lower cases. Yeah I know it’s 2012, and capitalization is so 20th century. And maybe someday the young people of the world will rise up and do away with capitalization altogether. But until then, when you’re dealing with 29-year-old geezers like myself, you should capitalize things that need to be capitalized, otherwise you seem lazy and dopey. If you can’t be bothered to take the time to push the shift key on your phone, I can’t be bothered to take your email as seriously as other people’s. I know, it’s not fair, but 8/10 emails from people who don’t capitalize are, in fact, pretty dopey emails.

Proofread and spell check. Read the email over a few times to make sure everything is right. Remember, this is your first impression with someone—make it a good one. I know a newspaper editor who throws a press release away as soon as she sees a mistake. Personally I’m not looking for perfection—I’ve thought some of my own emails were flawless when I sent them, only to look at them later and see egregious errors. But do the best you can, and at least spell words that are important to the recipient correctly. “I want to write about manlyness” won’t get you very far.

Close with a valediction. Ending your message without a valediction and your name makes you seem brusque. Close with “Sincerely _____,” or “Best __________.”

Return the favor. If somebody takes time out of their day to offer you free advice, do whatever you can to support their website or business! For example if somebody runs a shoe blog and sells shoes too, and you ask him all sorts of questions about what shoes to wear with what, and he kindly answers you, then buy your shoes from him! Only a scalawag asks for advice from a small business owner who’s willing to talk to him and then takes his business to some giant impersonal website to save a few bucks.

Follow-up once. But just once. If you still don’t get a response, they’re not interested.