The cold email—an email to someone you don’t know—is one of the most essential tools in an entrepreneur’s toolkit. A great cold email can connect you to journalists, investors, mentors, partners, sales leads, the list goes on and on.
In fact, when Foundr first got started, it was a cold email from our founder Nathan to Richard Branson that helped the magazine really take off.
Even if you’re not contacting multi-billionaires, in the business world, sending cold emails is inevitable. It’s also one of the trickiest types of emails to write. But when you pull it off, it can open up doors and opportunities that would otherwise be locked. Luckily, the same basic guidelines apply no matter who you’re cold emailing, so to some extent, it can be distilled into one powerful formula. We’ve done exactly that in the following post.
Before we get started, it’s important to know the first rule of cold emailing: try your hardest to avoid cold emailing. It’s really best as a last resort. The alternative? Find a mutual connection and ask them to introduce the two of you.
This is best done by scouring connections on LinkedIn, or Facebook if you get desperate. But, sometimes the cold email is unavoidable. Sometimes we just don’t have the network to find a connection, and that’s okay. Because cold emails do work, just at a lower rate than warm emails, so that means you’ll have to send more of them.
In other words, it’s a numbers game. But that doesn’t mean that the “spray and pray” method works for cold emailing, because it doesn’t.
Not an effective method of cold emailing
Think about it—you’re emailing a stranger out of the blue, and they probably get tons of emails just like yours. So they aren’t gonna pay attention unless it’s short, direct, and they understand what you want from them. Let’s go through what that looks like in practice.
Be Direct and Concise
Whether your aim is to make a sale, pitch to a journalist, or simply connect with someone interesting, the basic structure of a cold email is essentially the same:
It’s short and direct. And it hits the following points:
1. Who you are
2. What is the point of the email
3. Why you’re emailing them
4. How and when the recipient can take action (and leave an out)
5. And last but not least, a little gratitude goes a long way
There are many ways to present all of this info. For now, focus on the brunt of what you want to say, and what you need the email to accomplish. It seems simple, and it is, but it’s a step that, unfortunately, a lot of people skip. Have you ever gotten a cold email that made you go, “So….what does this person want from me?” I bet you have. And I bet you ignored it.
A cold email is placing a burden on someone, a stranger, to take time out of their day to listen to you. Your responsibility in this tacit social agreement is to make it as easy as possible for them to read and take action.
The strongest cold emails are short and sweet. And I mean really short. Boomerang, a Gmail extension that helps you schedule emails, found that “the sweet spot for email length is between 50-125 words, all of which yielded response rates above 50%.” Three to five sentences is the ideal length. This paragraph is about 80 words, for reference. It doesn’t matter if it’s perfect, because if it’s too long, it won’t be read at all—maybe skimmed, if you’re lucky.
Really, what it all comes down to is constantly putting yourself in the recipient’s shoes. Would you open that email? Would you read that email? Would you respond to that email? Would you think that person is crazy or would you want to know more? Throughout the process, keep asking yourself those questions and it’ll be a guide to your decisions on the content and presentation of the email.
Remember, this person doesn’t know you. They don’t care about you, they care about their own problems. So ask yourself, why should they care about you and your company? What’s in it for them? The focus of a successful cold email is not about you, the sender. It’s about the recipient, and what’s in it for them. This is where so many cold emails fail: by not making clear why they should care. Keep the focus on their needs and their wants, and they will listen to what you have to say.
Do Your Research
Before doing anything, you need to research the hell out of every person you plan on contacting. You want to know what projects and problems they’re working on, their work history, their successes, what makes them tick, what makes them happy, what drives them crazy, and what you have in common.
An accurate visual representation of the research stage
Most importantly, you need to know how they can help you. This is another common mistake I see all the time, an offshoot of the dreaded “spray and pray” technique. If you don’t know why you’re emailing someone, how are they going to know? And how in the world are they supposed to help you? Don’t put that work on them, because nine times out of 10, they’ll just move on with their life.
The goals of this step will vary slightly depending on what kind of email you’re sending (PR, advice, coffee request, etc), but there are a few goals that are always the same:
1. Find things in common. The more obscure it is, the better. There’s a great post by Adam Grant where he writes, “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.”
2. Understand exactly what you want from them and what you want your email to accomplish.
3. Get a feel for them as a person, so you can make your email sound like it’s from a real human.
4. Have proof-of-work to mention in your email. Greg Brockman of Stripe, in an article on cold outreach for recruiters says, “Make sure your emails include something that proves you’ve done some work investigating the person and understanding them. Make an intelligent comment about one of their talks, or include a suggestion for one of their projects.”
Search them on Google, adding their company or industry as a keyword if they have a common name. Open up their social media profiles, website and/or blog. I go tab-crazy here, so that I can absorb all the information in one go.
For an example, let’s say I want to cold email Nathan, the head honcho here at Foundr. I’d search him, and add “foundr” since Nathan Chan is fairly common, and there’s a musician with the same name.
Open allllll the tabs!
Start with the LinkedIn profile. Look at:
- Any common connections (highest priority, because you should be getting a warm intro if you can)
- What companies they’ve worked for
- Keywords that align with your interests, to reference in your email
- Hobbies, education, and all of the random stuff listed at the bottom of the profiles. Most people never look at this part, but you can learn a lot about a person from what they choose to write here.
I see that Nathan and I have four mutual connections, which is a great opportunity to reach out to those people and see if they will introduce me to him—or in this case, since they are high-profile people, perhaps just mention in my cold email that we have these connections in common, as a form of social proof.
Next visit their Twitter profile, and other social media accounts, where you should see a different side of their personality. What do they spend their time thinking about? What are they passionate about? What do they find funny, annoying, painful? Depending on how important this cold email is, dig deep until you understand them enough to engage on a personal level.
Nathan’s Twitter page is largely sharing content from Foundr (surprise, surprise!). So to get a bit more insight on what he values, I head over to his “Likes” tab (previously “Favorites”), where I can see tweets by other people that he’s liked. Sometimes this can offer fantastic insight into a person’s interests and personality.
The last step is their website and, if you’re lucky, any articles or blog posts they’ve written. What are they interested in? What kind of language do they use, casual, formal, or somewhere in between? What’s the tone of their writing, their conversations? In other words, what’s their brand? If you speak their language, so to speak, it really levels out the playing field and ups the odds of them a) being interested in and b) replying to your email.
Have a Specific Ask
After doing your research, you should know exactly what you want from the recipient. Think about it from the receiving end—you get an email that says, “Hey, this is my company, it does this. Thanks!” This is part of being direct and concise: Your email should have a thesis, one line that tells the recipient at a glance what you want.
Take a look at a cold email I sent to Sean Ellis, asking him to come speak (for free) about growth marketing at a program I was in. He knew the program, but he didn’t know me at all.
He responded within a day. And looking at my email, you can see that I presented all of the relevant information fairly succinctly. I mentioned who I was, why I was emailing him (and more importantly, why I was emailing him, specifically), what I wanted from him, and I set him up so that taking action on the email would be very easy, by offering all the information up front, including specific times that would work.
In the email above, my ask was clear: come speak with a group of growth marketers for an hour. For additional context, I used the words “brief chat” to indicate that it’s a casual offer, not a presentation or anything he has to prepare for. I was also specific about the topic of conversation.
Using a minimal amount of space, I was able to clearly communicate what I wanted from him, while also providing context so he’d know exactly what he was getting into. Because I did my research, I knew that he knew what the program was and where it was located, and I also knew he lived in Southern California, but he traveled to San Francisco regularly, so I didn’t bother specifying the location or wasting his time describing the program.
Because I’d done my research, I knew exactly where to meet him halfway (or most of the way), exactly what I needed from him in this minute (which was to express interest in speaking with us and/or pick a time), and as a result, the email is short and to the point.
With super busy people, you want to eliminate as much of the back and forth as possible by being specific and giving them easy next steps. Drive the conversation forward with details.
You’ll note that I also made it super easy for him to take the next step by going ahead and offering some times that would work. This is another common mistake: people often send emails ending with things like, “I’d like to buy you coffee sometime” or “We should talk.” And let’s not forget the kiss of death on any email: “Thoughts?”
Like, could that be more vague? Your emails must invite a distinct response. Not being specific and upfront is just putting the burden back on the recipient, and remember, the key to cold emails is to make it as easy as possible for them to respond.
Being upfront and offering times that you’re available is a great way to show that you’re a professional and that you respect their time. I usually will say something like, “I’d love to chat next week. I’m available M, T, W from 11-3 PST. You can reach me at this number.” I somewhat arbitrarily assign times so that it’s easy to lay out, instead of saying something like, “I’m available Monday from 11-3, Tuesday from 12-2, and Wednesday afternoon.”
Don’t leave anything open to uncertainty. Simplify, simplify, simplify every last piece of the email, until it’s lean and mean.
Make it Personal
Cold emails should always be highly targeted and personal, otherwise you’re just wasting your time. You want the recipient to feel like they have been singled out for a specific reason, rather than being a name on a spreadsheet. As Adam Grant put it:
“On the receiving end, I was surprised by the number of readers who wrote asking for help without explaining why I was the right person to help them. We know from research on social loafing that when people feel they have no unique contribution to make, they feel little responsibility to step up. Good emails overcome this barrier by highlighting what drew you to this person and the distinctive value that he or she can add.”
This is crucial because it’ll answer an important question for the recipient: “Why am I getting this email?” And at the same time, it’ll show the recipient that you did your due diligence, and that you know exactly how they can help you, and that they are more than just a name or number on an outreach list.
In addition to highlighting how the recipient can help you, another key aspect of a great cold email is a compliment. People love to be flattered. Compliments have been shown to activate the same part of the brain as receiving money—making compliments is truly the poor man’s currency.
Interestingly, one study found that flattery works even when the person knows that you have an ulterior motive. In the study, the researchers refer to flattery as insincere if you have an ulterior motive. But life has shades of grey beyond research studies, and I think we all know that you can sincerely compliment someone while also having an ulterior motive.
It’s not that hard to find something you genuinely admire about a person. (Hell, even Hillary Clinton had an answer when asked what she admired about Donald Trump—she said he raised good children. LOL).
Luckily, you most likely won’t have to dig that deep to find a sincere compliment for someone you’re reaching out to. If you’re honest, they can tell, and they appreciate it. A lot of people don’t get much recognition for their work in the business world, so they will appreciate the compliment.
In my example email above, I complimented the recipient on his writing about growth marketing and startups. I started the email by saying:
“First off, I wanted to thank you—I stumbled upon your blog a few years ago and it helped me understand what I wanted to do with my career. It’s always great to find someone who approaches things so deliberately and writes so clearly.”
It’s a little long, and if I was doing it today, I’d shorten it a bit. But it worked, so it was good enough. You’ll note that I offered a very specific comment, instead of saying something like “Omg I love your blog!” By being specific, you’re putting more effort into it, revealing that you’ve done your research on the person, and increasing the likelihood of the recipient believing you.
Send it off
So, you’ve written the email. Now it’s time to send it. The first step is to find an email address for your recipient. Maybe you already have one, or you know that the person’s entire company uses firstname.lastname@example.org. But if you don’t, here are a few ways to hunt down that information.
First off all, you want a tool like Rapportive, FullContact, or Discoverly, which are email add-ons that provide information about your contacts. I used to use Rapportive a lot, but it has been a bit neutered since it was bought by LinkedIn, so try a few apps out and see which one you like best.
Once you have one of these apps installed, and you enter email@example.com in a new email, the app will tell you whether that’s a real email address or not. Generally, I’ll try a few simple variations of an email before getting into more advanced methods. If it doesn’t fit the above formula, people are often firstname.lastname@example.org, email@example.com, or firstname.lastname@example.org.
When I get the right email address, Rapportive will show the person’s profile
If you still can’t find an email address, the next step is to try an email permutator tool, like this one. There are a bunch of these tools floating around but they all do a similar thing: You just enter your contact’s information, and it’ll spit out a ton of possible email addresses. Then you can paste them in an email draft, and Rapportive (or your tool of preference) will tell you which one is active.
There’s also tools like MailTester, which will tell you if an email address is active or not. Hunter.io is an all-in-one tool for finding email addresses—I haven’t used it, but I’ve heard good things. If you’re still searching for that email, here’s a super thorough post from Zapier about additional techniques and tools that you can try.
And last but definitely not least, you need to nail the subject line. After all, all the work you did on the email isn’t going to matter at all if the person doesn’t even open your email. I saved this part for last, because in my experience, it’s much easier to decide on a subject line after the email has been written.
The first goal of a subject line is to avoid the spam filters. The main trick to this is to just make sure you sound human, like a real person. Hopefully, you are human, so it shouldn’t be too difficult. Here is a big fat list of words that often get caught in spam filters, so put these words on your blacklist.
The second goal of a subject line is to get the email opened—nothing else matters at this point. The actual pitch is in the email, so for now, the subject line just needs to be intriguing enough for the recipient to click on it and read your pitch. One way to do this is to evoke the curiosity gap, which has been proven to increase open rates:
“Participants wanted to open messages when they had moderate levels of uncertainty about the contents. They were ‘curious’ what the messages were about. This occurred when they knew who the email was from but were not sure of its content.”
You probably know of this concept from seeing clickbait headlines splashed across your Facebook feed. It’s been overused and abused, for sure, but it’s still a useful concept to follow. You don’t need take it to the extreme, like Upworthy does: “You’ll never guess what happened after this man got coffee!!” All you need to do is make the recipient curious enough about the content of your email to open it. That’s the gap.
The third goal of the subject line is to convey the subject of the email. You want to, briefly, make it clear what you’re asking for. When in doubt, keep it simple. I really hate writing subject lines, so I tend to just go the straightforward, simple route, and it seems to work. There’s a tradeoff between vague and specific. If you go a little vague, you’ll naturally evoke the curiosity gap. Too vague and it can be frustrating or sound clickbaity. A few examples of subject lines that have worked for me:
“Hi , ?”
“Reaching out about ”
“Can I help with ?”
You’ll notice that these are all super simple. And that’s okay, because they work. The key to nailing the subject line is to, again, put yourself in the recipient’s shoes. Would you open an email with that subject line? Why, or why not? Be brutally honest with yourself, like a stranger would. Make sure you get it right, because you’ve only got one chance to get their attention.
At the same time, don’t agonize too much. Be decisive. Hit send.
So, you’ve sent the email. Good job! If it’s an important one, you’re probably compulsively checking your email for a reply every five minutes. If you’re lucky, you’ll get a response in a day or two. If you’re less lucky, you might not get a response. That means it’s time to follow up.
Following up is absolutely crucial for successful cold emailing. Most people just won’t reply to your first email—they are busy after all, and they don’t know you, so they aren’t invested in helping you (yet).
A great follow-up email has the following elements:
- It’s a reply to the original email, so the recipient has all the information in one place.
- It’s short
- It provides brief context (“Following up re: coffee meeting”)
- It contains your original ask (“Do you have time to talk Monday or Tuesday?”)
Another key aspect of follow-ups is the timing. Most people have different preferences with this, but generally, I like to follow up around four to seven days later, at a different day and time than the original email. Fridays and weekends are off limits—you’re decreasing the odds that they’ll even see your email. (Think back, I bet you can recall a time when you totally missed a Friday afternoon email.)
People are often reluctant to follow up because they are afraid of being annoying. But really, any busy person will actually appreciate a respectful follow-up. It’s a gentle reminder. Because you have to realize, and remember, that most likely, the person isn’t ignoring your email for any specific reason. Most likely, they didn’t see it, or they forgot about it, or they haven’t had a chance to respond yet. So by following up, you’re giving them a gentle nudge, and greatly increasing the odds that they will respond.
Back to the example of my cold email above, it wasn’t necessary to follow up in this case. But if I had, it would have looked something like this:
Wanted to follow up here. Let me know if you’d like to come in and speak to us, and/or if any of the times noted above work for you. I understand if you’re too busy, no pressure. 🙂
It’s short and to the point, because all the information he needs is already in the initial email, in the same email thread. It’s casual and friendly—there’s no expectation or guilt or pressure, no emotional manipulation, just a straightforward, gentle nudge.
There are a few great tools that can help you in this area: Boomerang, for scheduling follow-up emails, and Streak CRM, for seeing how people interact with your email (you can see if they opened it, clicked any links, how many times they opened it, etc. Makes you a little paranoid, right?).
The cold email is a delicate and tricky endeavor. But it’s also highly effective, and for the most part, an inevitability. So getting the art of a cold email down will have a positive effect on your business.
What are your techniques and tools for writing great cold emails? Any success stories? Share in the comments below.