A Tale of Two Cold Emails

How early career folks can do cold outreach the right way

Recently, I got asked the biggest mistake I see young people make when they try to make connections with more senior people. My answer to that was pretty simple, not putting yourself out there at all. It is always better to do the cold email, or go to the networking event, than not to. With that said, there is good cold outreach, and bad cold outreach. I’ve gotten both recently, so I figured I’d break down the differences.

 As a young person looking to make connections, your cold outreach is already starting at a large advantage. Execs generally want to help folks just starting off. This can be for moral/personal reasons (e.g. we got a lot of help when we were starting out, and want to continue to pay that forward). It also makes good business sense. The young people taking initiative today will soon be the customer, partner, or employee of tomorrow. It’s also to fun to catch smart people at the beginning of their careers, the sense of opportunity is palpable. 

In an email inbox full of spam, sales pitches, and notifications, it is easy for your email to stand out. You want it to stand out the right way. The below email did not do that, and prompted this post. Read through the below (sender identifying info redacted) and see if you can identify what bothered me so much.

There’s some smaller (albeit important) spelling and grammar stuff like “alma” being misspelled, but one major thing stood out to me. The message is completely unpersonalized (there is no mention of my name or of Healthie) and I am literally bcc’d on the email. This person wrote a generic email, added a bunch of folks in the Healthcare IT space to the BCC list, and then blasted it out. This is something I’d expect out of offshore dev agency spam, not an email asking for a personal favor. An email like this takes away any initial good will, and makes me not want to help.

Ultimately, this email felt lazy. In life, it can be ok to be “lazy” about things. However, shortcuts can be taken only if you’re smart enough to not make the end-result feel like a shortcut. With bulk email, this is actually pretty straight forward. You can use mail merge and a spreadsheet to send out personalized emails to hundreds of people. I never would have known that I was one of many recipients, and honestly, I wouldn’t have cared if I did know. Working efficiently and automating tasks is a feature, not a bug. If you’re not able to automate the task, then it needs to be done manually and correctly, or not at all.

In contrast, here’s a cold email example that I thought was fantastic.

It is personalized, to the point, and has a clear ask. It is ultimately still pretty generic, but that is totally fine. I assume the sender sent similar emails to dozens of other companies. That is in no way a bad thing, and I absolutely would have done the same if I were in their shoes. The level of effort put into this email versus the “bad” email above is likely close to the same, but the output is wildly different. 

You don’t have to be Hemingway to make great connections via cold outreach. You do need to show that you (at least appear to) care. The sender of the “good” email ultimately became Healthie’s first engineering intern since COVID. The sender of the “bad” email did not get a response. Smart work can beat hard work, but both smart and hard work beat sloppy work.