The Art of the Cold Email

Episode Summary

Full Transcript

HEIDI: Welcome to The Startup Solution and "The Art of the Cold Email." I’m Heidi Roizen from Threshold Ventures.  

Some people are surprised to find out that though I’ve been a tech exec for forty-some years, my undergraduate degree was in Creative Writing. Yeah, there’s a story in that that I’ll save for another day. But suffice it to say that once I got out of college, I came to realize that there were more jobs in tech than in writing the next great American novel.

But lucky for me, all that education still ended up being a good investment. Because it turns out that being able to write well is quite useful, particularly for entrepreneurs. Why? Because a lot of what you have to do as an entrepreneur is to reach out to people that you don’t know, and a lot of that is done in written form. So, the ability to grab someone’s attention and tickle their fancy enough to get them to respond turns out to be a pretty valuable skill.

.  .  .

This skill is so important that there’s even an entire course on it at the Stanford Graduate School of Business, taught by the legendary Glenn Kramon, a Pulitzer-prize-winning former editor of the New York Times.  

And once a quarter, Glenn invites me to come in and teach it with him.

During our joint session, Glenn and I pick apart a handful of emails written by his students, suggesting ways that they could be improved. Sometimes Glenn and I don’t agree, and we end up having lively debates, much to the amusement of everyone in the room. But, after many years of doing this together, Glenn and I have come to agree on a number of ways anyone can give their cold emails a better chance of hitting their targets.   

And since most of you don’t happen to be attending the GSB right now, Glenn agreed to let me share some of our pointers with you here.

Let’s start with one of the basics: length. In 1657, polymath Blaise Pascal said, “I have only made this letter longer because I have not had the time to make it shorter.” And a few hundred years later, Albert Einstein said, “make things as simple as possible, but no simpler.” Both of these are great guidelines for writing the perfect cold email. You’re trying to make a compelling pitch, but you’re inevitably emailing busy people, so the shorter the better. Remember, you’re not trying to carpet bomb someone with everything you’d ever want them to know about you in your first attempt, you’re just trying to get enough of their attention to want to engage with you in a next step. So, you need enough content to do that, but not a bit more.

Now, by definition, you’re writing to someone who doesn’t know you, so you’ll want to make it easy for them to find out more about you. And I think the best way to do that is to make sure your LinkedIn profile is up-to-date and well-written. The first thing most people do when they get a cold email, if they don’t just hit delete, is to figure out who is this person? And for most of us, the go-to initial resource is LinkedIn. You can even add a link to your LinkedIn profile in the signature block of your email to make it easier for the recipient to take that step if they want to. And I can tell you that I appreciate it when someone does that.

As for the content itself, you should think about a cold email as if it were an entry into a competition because that’s what it is. It’s a competition for someone’s time and attention, and your cold email is competing with everything else coming at that person. So, in order to win, you have to stand out. As Glenn Kramon says, you need to be one in a million, not one of a million.  

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I just slogged through a bunch of writing that provided many excellent examples of how not to do this. I was reading applications for our Stanford Fellows program. We had about a hundred entries for twelve spots, so I had a lot of reading to do. One of the essay questions was, “why do you want to be in this program?” And as I read through the answers, I started feeling a sense of deja vu in that many of the answers were eerily similar.  

And then it occurred to me that maybe ChatGPT was to blame. I’m guessing that those applicants took our fellowship description and the essay prompt and asked ChatGPT to write about why a motivated, accomplished tech exec getting their master’s at Stanford would want to be in our program. But guess what – all the applicants were motivated, accomplished tech execs getting their master’s at Stanford. So, a well-written but generic answer was not going to set them apart from the rest of the crowd – and that’s not a good way to edge yourself into a competitive program.

I’m not saying you can’t use ChatGPT to help you improve your writing. In fact, I use it for every podcast episode. After I finish writing the script, I give the whole thing to ChatGPT and ask it what was clear, what was unclear, and did I miss anything. And that feedback has proven to be really valuable to me. 

But when it comes to a competition for someone’s attention, where the winner needs to stand out from the rest, ChatGPT isn’t going to do the job for you. You’re going to have to do that for yourself. So, now let’s talk about how.

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First of all, in order to make a cold email more interesting to someone, you need to know more about the person you’re writing to. Luckily, there are many places to pick that up.

I always start at LinkedIn to get someone’s basics. Some people also put out longer material, either on LinkedIn or on blogs or podcasts, and you might find out more on social media sites like Facebook. You might learn about their views on current topics, what books they’ve recently read, what they’re currently working on, or even their personal hobbies or interests – and all of these things might be useful in crafting connective tissue between you and them in your email.

But again, it’s not time for a carpet bomb. You need to be judicious about what you use and how you use it. Some people start their emails by inundating the recipient with accolades about the recipient’s accomplishments. Sure, it shows you did your homework, but it takes up valuable space and time, and too much of that can even be off-putting.  

Instead, try starting with some connective tissue – something that they and you have in common. Maybe you went to the same school or worked for the same boss. Maybe you both spend time volunteering at animal shelters. Maybe you admire the same author. Or maybe you admire their company that seeks to, say, provide better recovery services for natural disasters – because you yourself survived one. This approach even has a basis in psychology – we humans survive by being part of communities. So, any one of these connection points can initiate a sense of community between you and your recipient.

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Another way to grab someone’s attention is to start with something that builds on what they do know and care about, to tell them about something that they don’t already know. For example, if they are an advocate for the LGBTQ community, perhaps you can tell them about an organization that you are involved with that helps that community. Or write to them about something they wrote about on their social media, to tell them what you learned from it. For example, if you are going to write to me, you’ll definitely grab my attention by telling me something you learned and applied from one of these podcast episodes.

Here’s another tip for creating connective tissue – explain why you are reaching out to that person in particular. I mean, how seriously do you take letters sent to “dear sir”? This is a mistake I see entrepreneurs make all the time when they send their pitch to every single person at every single venture firm they can find. But VC firms are all different, and we VCs are all different, and if we sense that you randomly reached out to dozens, if not hundreds of people, we’re very likely to just hit delete. A sales development leader that I have great respect for, my daughter Marleyna, gave me a tip that you should reread your email and ask yourself if the name of the recipient was cut off, would you still be able to figure out who the intended recipient was? If not, it’s probably too generic.  

And instead of emailing every single investor on every VC website, if you weed out all the people who don’t invest in your sector, stage, or geography, you could then focus more time and effort on reaching out to the ones where there actually is a good fit. And that’s going to provide yet another source of connective tissue by explaining that fit in your email. For example, someone might write to me, “I’m reaching out to you, Heidi, because you serve on the board of Planet Labs, so you understand the importance of geospatial observation – and that’s the focus of my startup." That’s going to get my attention way more than “dear sir.”

But don’t overdo the connective tissue stuff. You should aim instead to keep it brief and have the bulk of what you write support the purpose of your email. It’s fine to put a sentence or two in about your mutual love for rescue dogs, but writing a paragraph about that when what you really want is for them to refer you to their HR department for a job, well, that’s going to make your email even longer and obscure your key message.

Along those lines, you should constrain yourself to that key message – that is, don’t try to cover every single thing in your email; just cover the one or two most compelling points. Remember that an email is your first step towards a relationship, and you won’t go from zero to sixty in one exchange. It isn’t effective to overwhelm a person with data; what works best is just a few compelling points and a clear ask or call to action with an easy next step. You’re just trying to intrigue that person enough to take that next step and answer, not to tie the proverbial knot.  

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Let’s talk more about that call to action. When I get a cold email from someone I don’t know, I usually start by scrolling to the bottom to see what the ask is. For me, the clearer the ask, the better. Are you looking for a job at Threshold or in one of our portfolio companies? Do you want me to speak in your class? Do you want to meet with me for career advice? I think it's amusing when people hide the ask because they’re afraid I’ll say no. I mean, if that’s your concern, maybe you ought to ask yourself why I might say no and then try to fix that problem instead. If the ask will take too much of my time, how about doing more work on your end to make it easier and faster for me to do the part you want me to do.

I’ve talked about this in prior episodes – but when you’re asking a favor, you should be the one making it as easy as possible for the other person to fulfill the favor. So, for example, when asking for someone’s time, ask for the minimal amount possible. And be flexible about when that time can be. You could also give them more than just an in-person meeting as an option. Say, ask for a meeting, but also suggest that if they’d prefer email, you’d be happy to send a few questions to them, and they can reply that way instead. I’ve had many interesting conversations on email with people that I didn’t want to give a half-hour meeting to. And funny enough, some of those resulted in my saying yes to half-hour meetings once I got to know those people better through email.

Another tip for making an email more compelling is to explain how your request can be a win-win for the recipient, too. If I’m writing an email to invite a rising star entrepreneur to speak at my class at Stanford, I might mention some of the prior high-profile speakers I’ve had. Or maybe I point out that their speech will be recorded and posted to Stanford's website, which they might find attractive. Or I could tell them a bit about the audience, like the fact that it’ll include a whole bunch of talented software engineers who will soon be looking for jobs.  

It can also work to offer something in return. For example, if they participate in my survey, I’ll share the results with them when my project is done. This is another element where that initial research about the person might help you figure out the win-win possibilities.

Of course, there isn’t always a quid pro quo, and that’s okay too. As I said, we humans are social creatures wired to be helpful. It’s perfectly fine to say, for instance, “there’s nothing in this for you except paying it forward.” Something like that can often be enough of a reason for someone to say yes.

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I also like to leave the person an “out”. Even if they can’t do what I’m asking, I don’t want them to leave the exchange feeling bad about that. I’d still like to leave the door open for building a relationship in the future. So, I give them an easy way to say no. I might end my ask by saying, "I really appreciate your considering my request, but I know you don’t have a lot of free time these days, so no is a perfectly fine answer."

Offering someone an out might even make it more likely that they’ll say yes. In psychology, there’s a theory that people may feel inclined to do the opposite of what they feel pressured to do. And so, by applying pressure to compel someone to do something, you might actually be hurting your cause. Instead, you can diffuse that bomb, so to speak, by providing that easy out – and ironically, that might make them feel more like saying yes.

Let me throw out a few points on writing style. As I said, I’m seeing a lot of ChatGPT – that is, technically correct, generic writing with no personality, or perhaps a canned personality that you told it to use, which is usually even worse.

Instead, don’t be afraid to show your own humanity and your unique personality. I think humor can be a fantastic tool – though don’t err on the side of being so self-deprecating that you come off sounding like a joker. Funny phrases or interesting words can tickle our brains just enough that we’ll want to read on and think, maybe I do want to know this person.  

And as a professional songwriter once told me, use proper nouns, not just nouns. In the song American Pie, Don McLean didn’t drive his car to the river; he drove his Chevy to the levee. I think song lyrics are a great inspiration for compelling but brief writing because a songwriter has only a couple hundred words at best to tell a whole story. The next time you listen to a song, pay attention to the proper nouns. You might be surprised by how many there are.

Here’s an example of some of these concepts in action. Let me read you two short email intros. Both are trying to convey the same information, but one uses humor and proper nouns to breathe life into the note. 

Number one: Let me tell you a little bit about myself. I’ve worked at a major tech company in a junior engineering role for five years and then transferred into management consulting, which is more intellectually challenging but also requires a lot of travel that I don’t enjoy. 

Number two: About me? After spending five years in the depths of development at Google, I traded up, or at least out, to a consulting role at McKinsey. While it’s stretching my brain, it’s also rapidly earning me 1K status on United – definitely not a life goal of mine.

Doesn’t that second person sound like they’d be more interesting to talk to?

.  .  .

Now, while I want you to let your personality shine, you also need to come across as respectful. This is another reason why the homework I talked about at the beginning is so important because it’ll help you read the virtual room to figure out the right tone, level of formality, or level of directness to use with the recipient. Perhaps a more formal tone would be best when, say, reaching out to a senior executive at the SEC. More casual or even more colorful language works for some environments or cultures, but it can be perceived as disrespectful in others. And if in doubt, you might want to play it a bit safer.

Also, consider your medium. Different forms of writing are appropriate for Slack versus email versus instant messaging. Maybe I’m old school, but I consider email the medium of choice for cold outreach. That said, you don’t want your email to end up in someone’s spam folder. You’ll already be giving your emails an advantage by crafting and sending them one at a time since spam filters try to weed out things sent to a lot of people. But too many attachments, or even too many graphics or fancy formatting, might send you to spam as well. And when I see fancy formatting, the first thing I think is that this must have been sent to a lot of people, which is exactly the opposite of what you want me to think.

Your subject line might also get you flagged as spam. If you want examples of bad subject lines, just go look at your own spam folder. The point of a subject line is to get a person to want to open the email, so aim for the fewest words that have a shot of setting you apart and making that happen.  

.  .  .

Let me add a few final things to avoid. And I’ll start with your ego. Boasting. Bragging. You want to put forth your credentials without pomposity, and that might take a few tries before you strike the right balance of confidence and humility. If you’re concerned that you come across too strong, have a trusted friend read it before you send it. But pick a friend who will be brutally honest – flattery is the last thing you need right now.

Also – and this should be a no-brainer but based on all the cold emails I get, I need to say this – don’t make dumb mistakes. I’ve had my name spelled wrong. I’ve had someone address me as a partner at a different venture firm than the one I work for, and yesterday I got one that said “Hi, Bob.” Once I had someone ask me to make an intro to a well-known executive – whose name they misspelled. Sometimes, job hunters send me emails to forward to our portfolio companies, with attached cover letters and resumes that reference a different company than the one they’ve asked me to forward it to. Talk about a wasted effort.

I’ve also had people apply to jobs where communication skills are critical, and yet their emails were filled with misspellings and grammatical errors. This should be an easy thing to fix with all the great tools out there for correcting grammar and spelling. And last but definitely not least, please read everything over one more time before you hit send.

Cold emails aren’t just words on a screen – they’re you in written form, and they’re going to create someone else’s first impression of you. So, if you want them to be successful, take the time to make them personal, interesting, and efficient for the recipient to read and act on. And hey – if you need practice, feel free to email me. Just make sure you get my name right – because I delete anything addressed to "Bob."  

And that concludes this episode of The Startup Solution. I hope you’ve enjoyed today’s show, and if you have, please share it with someone who you think could use it. I’m Heidi Roizen from Threshold Ventures.

Further Reading

Here are takes on cold email writing from Grammarly and the Harvard Business Review. While I think a lot of the advice is similar to what I talked about, each of these posts provides a few different tips that could be of value.  

Also, I didn’t cover when to send a cold email or how quickly and often to follow up, as the episode was getting long, and these weren’t exactly about writing. But, for those of you who also want my opinion on those topics, here you go.

Another point people should pay attention to is when they send their email. There have been numerous studies done about this, and I’m not surprised to see that in general, open rates are higher for sales outreach emails sent on weekday mornings, though Mondays and Fridays seem to have detractors as well as advocates. But most of the research is done on salesy type emails, and the whole point of this episode is about highly personalized emails. So, you guessed it, the time you should send yours should be highly influenced by who you are sending it to. Interestingly, I’ve found that some super busy, high-level people actually respond better in the evening or on weekends. On the flip side, I generally think it's a bad idea to send emails on common vacation or holiday times, such as the Fourth of July or Christmas, when people’s heads are generally not into work.  

People also ask me how quickly and how often they should follow up. It depends on how important the interaction is to you, how targeted the recipient is, and how time-critical the request is. Again, we’re talking cold emails here. If your boss or your direct report isn’t answering your emails, yeah, I’d follow up right away, and as much as you need to get a reply, those aren’t cold emails. With cold emails, my own rule is I wait at least a few days, maybe up to a week, depending on the topic, and then allow myself one ‘‘bumping this to the top of your inbox in case it got lost in the shuffle” additional try. My sales expert daughter offered a few pro tips as an alternative to bumping the same email up. One is to ‘save some ammo’ that you didn’t use in the first email to lead the bump. For example, “PS, here’s a link to an article Bill Gates wrote about why he thinks nuclear power has a bright future – relevant to this discussion." Or enter their head space a different way than email, for example, by trying to add them on LinkedIn with a note like, “Sent you an email with a bit more context – I look forward to connecting.” But whichever way you choose, I think only one extra outreach is permissible. If I still don’t get a response, I move on to someone else. I know many people disagree with me – and some of those have been rewarded with eventual contact. So don’t let me stop you!

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