How To Write Emails That Lead To “Yes”

An 8-step program.
November 20, 2013

One of the golden rules of writing is: Respect the reader’s intelligence. This rule gets magnified by a factor of 10 when it comes to composing unsolicited emails.

Most people who receive any significant quantity of email in a day have developed extremely refined B.S. detectors. They can identify an impersonal templated email in 0.5 seconds, and they can spot a time-wasting “let’s explore the possibilities” ask from a mile off.

In short, getting someone that you don’t know to pay attention to you—and respond—is a delicate art. One that requires craftsmanship, charm, concision, and a lot of self-editing.

Based on years of drafting, redrafting, observation, and misfires, here are a few pointers to keep in mind when composing an email “ask”:

Step 1: Make it easy to say, “Yes.”

When it comes to giving good email, making it easy to say “Yes!” is objective number one. Sadly, it’s also where most people fall down on the job.

I frequently receive emails from people who are interested in some sort of knowledge exchange but never clarify how they would like for me to take action. Do they want to have a coffee? Do they want to do a phone call? It’s unclear, which means that instead of saying, “Yes!” I have to respond by asking them what they’re asking me for in the first place. Or, not respond at all.

If you are asking someone to take the time to answer you, it should be very clear what you are asking for. Look at your email and ask yourself: “Can the recipient say ‘Yes’ without further discussion?” If the answer is yes, you’re doing well. If not, you need to redraft.

Step 2: Write an intriguing subject line. 

Composing a good email subject line is akin to writing a great headline. If you’re cold-emailing someone you’ve never met, it’s important to strike a balance between being direct and being interesting.

If I were asking someone to speak at our annual 99U Conference, for instance, I might use a subject like: “Jessica + Behance’s 99U Conference?” (Analysis: Using someone’s name feels personal; mentioning Behance in addition to 99U gives more chance of name recognition; and the question mark gives a sense of possibility/ creates curiosity.)

Keep in mind that while it’s always good to be clear, you also don’t want to give anyone a reason to dismiss your email before reading it. For that reason, you’ll want to avoid stock or cookie-cutter phrases that might get your email lumped in (and glossed over) with others.

For instance, for a speaker ask for the 99U Conference, I typically avoid run-of-the-mill phrases like “speaking opportunity” or “speaking invitation,” because they can turn people off before they’ve really assessed my particular opportunity.

Step 3: Establish your credibility.

“Why should I care?” is the tacit question hovering in most people’s minds every time they open an email from someone they don’t know. This is why establishing your credibility is crucial. Tell your reader why you are different, why you are accomplished, and why they should pay attention to you.

If I’m contacting someone about contributing to 99u.com, I might share stats on our monthly page views and social media reach to do this. If the ask is related to one of our events, I would share audience size, years sold out, and a power-list of past speakers.

If you don’t have “data points” to share, you can also establish credibility by being a keen observer of the person you are contacting; you could tell them how long you’ve followed their work, how you enjoyed the last blog post they wrote, etc. As long as it’s not fawning, most people appreciate being noticed.

Step 4: Be concise and get to the point.

Never assume that someone is going to read your entire email. You should make it clear from the get-go exactly what you are asking for. That means clarifying why you’re reaching out in the first sentence or two, and no later.

However, sometimes everything you need to say can’t be explained in one to three sentences. If this is the case for your ask, go ahead and say your piece (as concisely as you can) but assume your reader will be skimming it. This means using bolding, bullet pointing, and so forth as much as possible.

If it’s necessary to give some backstory prior to the ask, I like to just go ahead and break out the ask in paragraph two with a bolded preface that reads, “The Ask:” If you’re asking for something, there’s no point in beating around the bush. Make your objective clear.

Step 5: Give a deadline if you can.

People are often shy about including deadlines in emails, especially when cold-emailing. While it’s never a good idea to come off as presumptuous, deadlines do have great utility. In fact, most busy people like them. Bear in mind when you are emailing someone that—surprise!—they are probably also getting tons of emails from other people.

Most of those emails fall into one of two categories: 1) Things they have to do, and 2) Random requests for things that they might like to do, time permitting. Chances are, your email falls into group two. Which means it’s really important to know when something needs a response by. In other words, do whatever you can to help the receiver put the requested task on a timeline and prioritize it.

Step 6: Be interesting and interested.

At the most basic level, this means do not ever send anyone a templated email. If you are asking someone to take the time and energy to reply to you, make it clear that you actually know who they are.

That doesn’t mean being obsequious and singing their praises, it does mean talking to them like you are one human talking to another human. It’s nice to articulate why you’re interested in them. It’s also nice to articulate why they should be interested in you. Try to have a voice and say something funny, meaningful, or thoughtful—preferably all three!

Step 7: Never ever ever use the word “synergy.”

No single word lights up the experienced emailer’s B.S. detector like the word “synergy.” No one worth their salt wants to spend their time talking about exploring synergies. Emails with this language typically mean that the person asking for something hasn’t really thought through their ask enough to offer any specificity. If you want someone to take a chance on you, show them respect by thinking through what you are asking for and being up front about it. Otherwise, you’re just wasting your time and theirs. 

Step 8: Preview your email on a phone.

You probably write most of your “ask” emails on a desktop computer. Bear in mind that your recipient will be receiving and reading your email on their mobile phone in almost all instances. And what looks “digestible” on a desktop computer looks like an epic poem on a mobile phone.

As per point 4, you may think you have already confirmed that your email is concise. But is it still concise on an iPhone? Once you check, you will probably realize there are a few more things you can remove. Edit your email again, and then send.

This article originally appeared on 99u.com.

Jocelyn Glei is the editor-in-chief of 99u.com.

Photo: Shutterstock