Productivity Journey: Cold Emailing

Recently, I’ve been on a bit of a break because I’ve been working on college applications and a book with exclusive content and our major stories. But I wanted to take the time today to write about my approach to cold emailing to land an interview with almost anyone you want.

They teach you a lot of stuff in school – how fast a ball will accelerate when you drop it, who was Franklin Pierce, why Macbeth (maybe) had a mental illness – but one invaluable tool that I acquired through careful experimentation was the art of the cold email. Ask most high schoolers around the United States and only a small percentage will tell you that they attempt to make contact with people at the forefront of their respective fields; investigate this number farther and you’ll see that an even smaller number actually get a response.

Why is this?

I attribute this number to the lack of data surrounding the dreaded “cold email.” With the diaspora of technology across the world, it’s become easier than ever to reach out to people that you find fascinating, but this new advantage also means that these intellectual celebrities probably get millions of messages similar to yours and choose to ignore them. 

Not good.

I made that crucial mistake when I first started cold emailing for Businesses With Stories. Yeah, I didn’t have any credit. Yeah, I had no idea how to write a good email. And yeah, I was way too formal.

This spelled disaster. I had a sub 10% response rate for most of my original emails. 

How did I format them? I introduced the reason why I loved their company and their work, making sure to establish the fact that I had done my research. Then I dove into my qualifications and why BWS would be good for them. The first response I got was from WorldTowning. The second one didn’t even work, so I gulped down my fear, found his number, picked up the phone, crossed my fingers, and dialed. 30 minutes later, I had gotten another interview. But I quickly started realizing my mistakes.

The template I was using clearly wasn’t working. There was almost zero interest on the other side even when I started name dropping some of the people that I had interviewed.

After a long string of rejections, I decided that I need to master the cold email to make any improvements in BWS. For experiments, I would try different ways of following up to see if I could get higher response rates. 

On I went. I tested out over ten different templates and tracked progress across them using Hubspot open rates. Hubspot was the great software that my boss had introduced to me. It allowed me to track who was opening my email, how many times they were doing it, and when they were doing it. If you’re looking to start cold emailing, Hubspot is an indispensable tool.

Hubspot is seriously amazing

When I had hit my 6th or 7th template, I started to realize that the less personal and shorter the email was, the more likely I was to get a response. And when I pestered them with a series of short but more personal followups, the read and response rate jumped to almost 50%. 


Talk about paradigm change. I decided to run an experiment after that. I put two of my top response rate prompts next to each other: one was personal, the other was completely templated. I then shotgunned them to about 20 CEOs each and waited. Again, it seemed that the shorter template with personal templates was winning out.

But I couldn’t ignore the fact that there was another lurking variable that could have been impacting my experiment: the companies and the types of people I was sending emails to. I did a quick breakdown of all the people that I had gotten “yeses” from and realized and even stronger trend. Almost all of them were focused on social justice/responsibility, had kids, and worked in tech. I had discovered a pattern. Combining these two areas of knowledge, I quickly was able to get much more interviews than I had originally expected.

I hadn’t really grasped the important of analytics until it helped me improve my close rate and get more warm responses. What can you do in order to improve your cold emails? It’s not that hard.

  1. Use an email tracker to capture key pieces of data that you can use to analyze to see what works and what doesn’t
  2. Be resistant to rejection. Even the best sales people get rejected. A lot.
  3. Remove the unnecessary. Be ruthless and critical. If it doesn’t contribute directly to the outcome, it’s not worth it.
  4. Think like your reader. You’re going to fail nearly 100% of the time if you’re only thinking about bragging about how great your company/publication is. Figure out what your prospect wants, retrace your steps to see how you can get them there, and then illuminate the way.
  5. Go for soft sells. Don’t scare them away with a super direct email. Contrary to popular belief, if you’re too direct, the client may think you’re trying to trick them or you’re not worth their time. Make it so easy to say yes that they don’t even consider rejecting you.
  6. Research. Sure, it’s easier to use a template, but it definitely pays to be personal. That way, they know you care.
  7. Choose wisely. Figure out which types of people are most likely to reply and spend the majority of your energy their. It’s like the 80/20 rule states: 80% of your results come from 20% of your efforts.