How to Cold-Email a CEO

Updated 01/31/18
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Writing an email to a powerful person can be pretty intimidating, especially when you're an unknown entrepreneur. But instead of letting the fear control your destiny, ask yourself this one question: What do you possibly have to lose? If you ever want to achieve your dreams, then you need mentors and advice from people who have been there and done that. After all, they might be so inspired by your bold approach and write back.

A well-written email to the right person can open up incredible opportunities for growth and learning. In fact, that's exactly what happened to 21-year-old social entrepreneur Daniel L. Jacobs, who told Business Insider he wrote to the "busiest people on the planet," including presidents and C-level executives of Fortune 500 companies, asking if he could learn from them, and "the unthinkable happened." Jacobs actually received an email back, followed by another, and another. This opened up some exceptional opportunities and mentorships with some of the industry's top CEOs.

So are you ready to find out how? It's time to boost your confidence and write a cold email for a job that could change everything. But before you hit send, scroll down for a few tips on how to pen a powerful email that would compel any CEO to open it.

cold email for a job
We the People

Ask for Advice

At their core, humans are wired to help others. When you think about it, all of those CEOs you hold in high esteem had to start somewhere, so who helped them get there? It's very likely they too had mentors along the way and possibly someone who gave them advice early on, which led to their big break. Once they've reached the top, they usually want to impart that knowledge. Asking for advice in his cold emails is how Jacobs earned a reply and consequent mentorship from the president of NBC. In a board meeting years later, he said, "Do you know why I decided to meet with you, Daniel?

Because in 20 years in this business, every single person who reached out to me cold wanted something. They wanted money, a job, something. You were the first person who asked—only—for advice."

Asking for advice was key to Brian Wong's cold email success too. In a LinkedIn post, the founder and CEO of Kiip shared some wise words that changed his career: "If you ask for money, you get advice. If you ask for advice, you get money." This sentence changed his perspective on cold emails, and every time he "asked those I admired for advice, they actually gave me money." Now he always cold-emails executives. "People usually feel too intimidated to reach out, so executives don't expect it," he wrote.

"You have the unique opportunity to capture their attention." And it worked. When Wong launched Kiip at 18, he became one of the youngest CEOs to ever receive venture capital.

Convey Your Passion

If you have a genuine interest in the industry or company, show it. There is nothing more exciting than reading an email from someone who's so passionate that it reinspires your passion. The person reading it will ultimately feel obligated to return the same level of interest. Your enthusiasm will also showcase a confidence and drive, thereby elevating your pitch and showing you deserve to be working with them.

Get to the Point

Your message should be short and to the point. High-level executives don't have time to read long-winded emails, so brevity is key. Get to the point quickly and grab their attention within the first two sentences with something that compels them to read more. To increase your chances of getting read, Forbes says your email shouldn't be more than three or four sentences, or "short enough for someone to read and respond to in under a minute." If you need further instruction, follow the magazine's sentence-by-sentence template.

Make It Personal

Before your finger hits the keyboard, remind yourself that the person you're emailing knows nothing (or very little) about you, so make sure they do by the time they've finished reading. When Fast Company sent 1000 emails to busy execs to see what works and what doesn't, it found that the usual advice given to "optimize cold email is all moot without one thing—personalization."

So how do you make an email to a stranger personal without launching into a monologue about yourself or writing out your entire life story? First, don't write one standard email and send it out to everyone on your contact list; CEOs can sniff out a generic email a mile away, and it stinks. Second, making it personal means making it about the other person. According to a Forbes article, if you want "their time, expertise and guidance," then swap out the "I" and "me" with more "you" and "your." Always take the time to add their name so they feel like they are the only one receiving it.

You can't possibly win someone's trust without following this step—which brings us to our next tip.

Do Your Homework

If you decide to hit send with a blanket email that isn't personalized toward your reader and offers no indication of your knowledge about the person or company, then don't expect a reply. In the Fast Company cold-email experiment, the team found that the "best way to form relationships over email—to be a giver when approaching someone cold—is to show that you've done such homework." Taking time to research your subject beforehand will pay off in dividends and, more importantly, result in a reply.

Not only does it show your enthusiasm, but it can also highlight common interests between you and the CEO and a chance to pique their curiosity with something interesting. In the same way that a first impression counts when meeting face-to-face, make sure your email leaves them thinking about you—in a good way.

Remember Timing Is Everything

When it comes to busy executives, timing is everything. Given executives' weekdays are usually spent ticking off a massive to-do list, Harvard Business Review says the weekends are the best time to send a cold email since they "typically have more time to read something on a computer screen, rather than a device." And you might be surprised at how many of them actually do read all their emails, especially the interesting personalized ones.

Just remember that even when you do follow all the best advice and write an incredible email, Peter Sims told the Harvard Business Review you should still "expect a 50-90% failure rate the first time you cold-email someone—i.e., no response. If you don't get a reply, don't worry—it's hardly as bad as calling someone cold and having them hang up on you." So push aside your fear, write that cold email, and see what happens. Or as Sims wrote, "Just ask: What's the worst thing that can happen? And: What's the best thing?"

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This story was originally published on January 25, 2016, and has since been updated.

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