A Guide to Cold Emailing

Cold emailing is harder than most communication for two reasons. You have no relationship with your audience yet, and you lack non-verbal feedback, so you can’t modify your approach in real time. As a result, most cold emails fail. But they can work well. People have built careers and launched start-ups with little more than cold emails. (By the way, I am not talking about sales emails, which tend to be sent in bulk. This article is about cold emailing a specific person.) There isn’t much research on cold email, though Shane Snow did an interesting experiment for his book Smartcuts. He sent 1,000 cold emails to executives and got almost no response. So he tried again with a smaller slice of the same group and got better results by applying a few principles that line up with my extensive cold email experience and some great advice from people like Wharton psychology professor Adam Grant, and entrepreneurs Tim Ferriss and Heather Morgan. An effective cold email does five things. It should: 1. Tailor the message to the recipient. You need to do your research. But there’s a right way and a wrong way to do that. I’ve received about 25,000 cold emails since 2004 (yes, I do keep track). Many of them make a generic mention of something on the first page of Google results for my name, then launch into a ridiculous, tone-deaf request, like “Hey, can you read my 300-page novel, give me extensive notes, and then get me an agent?” That is not personalization. Personalization means that you’ve thought about who this person is, how they see the world, what interests them, and what they want — you’ve developed a “theory of mind” about the recipient. This shows them you have put work into understanding them. You also make it clear why you are emailing them as opposed to anyone else. Research shows that people are far more motivated to help others when they feel uniquely qualified to do so. By outlining precisely where they fit in, you can tell a story that makes sense to them. You and Your Team Series Business Writing Bad Writing Is Destroying Your Company’s Productivity Josh Bernoff How to Improve Your Business Writing Carolyn O’Hara What You Miss When You Take Notes on Your Laptop Maggy McGloin It’s also important to make sure your request isn’t easily fulfilled another way. I cannot tell you how many emails I get asking for advice on how to write a book, even though I literally wrote a book on that exact subject. Through personalization, you avoid that, because you’ve read up — you know the book’s out there. 2. Validate yourself. When we meet a stranger or get an email from one, we want to know who that person is and why that person matters to us. Remember that when you’re the stranger. You’ve already done a bunch of research on the people you’re emailing, but they don’t know anything about you. You need to show them you’re credible and they can trust you. Knowing someone in common is the strongest form of social proof you can offer. If you have any direct connections, mention them. A mutual friend means you are no longer a stranger. Lacking that, if you have any authority, credibility, or social status that is relevant to this person and your request, mention it quickly — a line or two should do it. The more “important” you are, the more likely you are to get a response. If you have no real status, that’s fine. Find a commonality. Being part of the same group, especially if it’s a personal group, is a core human attraction. Look for unexpected connections, like hometowns and unusual hobbies. As Adam Grant points out, “Similarities matter most when they’re rare. We bond when we share uncommon commonalities, which allow us to feel that we fit in and stand out at the same time.” The point is, you want to find a way to go from “stranger” to part of the recipient’s group. 3. Alleviate your audience’s pain or give them something they want. Why should the recipient care about your email? Why should this busy person take time to respond to it? What’s in it for them? Remember that people will go much further to avoid pain than to acquire pleasure. If you’ve done your research and found a major pain point for the recipient, and you can offer relief, highlight that. Consider this example: A VC friend of mine once complained on Twitter about how his car was constantly getting tickets because the street signs were misleading. An entrepreneur looking to pitch his start-up started his cold email with a link to a robo-calling service that took care of parking tickets. The VC used the service and was so thankful that he not only took a pitch meeting but also connected the entrepreneur to several other VCs, two of whom ended up investing. If you can’t solve a problem, give people something they want. Offer to connect them with someone they’d like to meet — that stands out, since almost no one gives before they ask. But your gift needs to feel appropriate, from one stranger to another. An Amazon gift card would be super awkward and weird. I know, because someone sent one to me once. 4. Keep it short, easy, and actionable. The opportunity to help someone is very enjoyable for a lot of people — it may even qualify as a “want.” By asking for help, you are giving them the chance to feel good about themselves. But make it easy for them. You probably know this, but short emails are more likely to be read than long ones. And emails that request clear, specific action get a much higher response rate. Long-winded, rambling cold emails suck. One of the best ways to keep things short and direct is to write the way you’d talk. If you met this person at a cocktail party, you wouldn’t just walk up and start pitching them. You’d introduce yourself, say something nice, connect with them over a shared friend or interest, and then make a request that makes sense. I would recommend reading your email out loud before you send it. If it sounds natural, then it will read well. This is how I edit my own writing. To make your “ask” easy and actionable, do as much work for your audience as you can. “Let me know if you want to meet up” is terrible. This forces someone to exert mental energy to make a decision for both of you, and it puts the onus on them to sort out the details. It’s short, but not easy or actionable. Compare that with this: “I can meet on Monday or Tuesday between 8 a.m. and 11 a.m. at Compass Coffee on 8th. If that doesn’t work, tell me what does, and I’ll make it happen.” That gives them a clear, easy action to take, with specific bounded options. But there’s more to a good “ask” than just telling people what you want. How you tell them matters a lot. 5. Be appreciative — and a little vulnerable. I would even go so far as to say you should be slightly submissive. I’m not saying to grovel before your audience like they’re a feudal lord. You are asking someone who does not know you for a favor. By expressing gratitude and some vulnerability, you give them the feeling that they are a good person if they choose to help. You also give them a little rush of power and status, because you’re approaching them. This gets results. Even just saying “Thank you so much! I am really grateful” to a request doubles response rates. And tell people it’s fine if they are too busy. Giving them a way out actually makes them more likely to help you. All this may sound obvious, but again, very few people do it. I’d say about half the people who have cold emailed me expressed no appreciation beyond a perfunctory “thanks.” And the other half either sounded brusque or entitled. Really — strangers asking for huge favors say things like “Lemme know how quickly I can expect you to get this done.” Clearly, they don’t feel like waiting around. But that tone has repercussions: I don’t feel like helping them. Finally, don’t use a template. If you Google “cold email template” you will find a LOT of them. I looked through dozens, and though some were very good for mass email and sales, I could not find a good template for a personalized cold email. Which makes sense. By definition, if something is personalized, it doesn’t come from a template. That’s why this article lays out principles but has no scripts. I did find some good examples of cold emails (this one, for instance, and this one), with breakdowns of how and why they worked. You’ll notice they each used almost every principle here.

A Guide to Cold Emailing

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