How to Email a Hiring Manager the WRONG way

I get emails from job seekers wanting to work for us sometimes. I occasionally share them with Crash users on the Slack channel to highlight the good and bad, and help them see the way the typical seeker comes across and how they can do better.

Isaac Morehouse
Isaac Morehouse

Here’s an example email (slightly edited for privacy) and my thoughts on it, recently shared with the Career Hackers community.

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Hey Career Hackers, here’s an email I got today:

“I am XXXXX a tech entrepreneur while reading about Career Hackers I felt connected which prompted me to drop you a short note to represent my sincere interest in Career Hackers if I can help you with software development.

Previously, Founded 2 startups XXXXX & XXXXX which got more than 50M downloads and served billions of ad-request months and won multiple prestigious awards like XXXX, XXXX, XXXX, XXXX & many more. Being a single founder has seen various verticals of business like tech, product, business, and analytics. Among these, I always enjoy doing the coding. Hence looking for long term opportunities in s/w development. I have strong fundamentals in OOPS, Java, complex algorithms, if required I’ll be very keen to learn new technologies.

If it sounds interesting & you feel I will be able to help Career Hackers with software development, please feel comfortable to reach out over email, call/WhatsApp on the following number.

Looking forward to hearing from you.”

Notice:

  • This is probably a very talented person, but I don’t feel excited to talk to them…why?
  • There is zero indication they even know what Career Hackers is, or browsed the site (if they did maybe they would’ve sent a video pitch!)
  • No talk about our mission, our needs, or passion for Career Hackers
  • All but the word “Career Hackers” would easily be copy and pasted to every single other company, and feels like it was
  • A giant paragraph of accolades and data points that feels sorta like a massive overload of “I’m so great”
  • The whole thing puts all the work on me to figure out whether and how this person might be valuable to us. They make no effort to connect their skills to our product/needs.
  • It feels presumptuous, like, “Hey, let me spend 5 minutes telling you how great I am. Call me.”

In short, there is nothing tailored here, nothing hard to fake, no “proof of work” that signals deep passion for Career Hackers, no paying attention to our needs, and a wall of generic work experience and accolades I’m supposed to be impressed by.

It’s like going up to a guy/girl you want to date, not taking any time to learn anything about them, and being like, “Hey, I’m pretty amazing. I win every fantasy football league and am the king of mini golf. Text me.” to a guy/girl who hates sports.

It shows when you don’t care about them!

Nothing against this seeker. Everyone has been coached to use resume/cover letter in this generic way. But I’m telling you, as hard as it is to win an interview signaling real interest, it’s 100x harder without it.

Career Hackers is not hiring right now anyway. But we’d have to be pretty desperate to respond to this kind of email!

This email is a much better way to email a hiring manager:


“Hey Isaac,

I’ve been following Career Hackers and am in love with what you’re doing to help job seekers. Your guide to engineering careers was spot on, and the kind of stuff I wish I’d known sooner. I made something for you, check it out here: (link to kick-ass pitch, ideally with custom project coding up something relevant to Career Hackers)

Would love a few minutes to learn your growth plans and if you need any help with engineering, I’m your guy! Even if contract/side project, would love to be a part of what you’re building.

You up for a 15 minute chat?”

That’s something I would have a very hard time saying no to, if for no other reason than to reciprocate all the work he put in and learn more. . I’d think, “Damn. He loves Career Hackers! Maybe good to learn more and maybe keep him on the “farm team” for when we do need to hire.

Don’t brag. Don’t copy and paste. Don’t be generic. Don’t send a resume. Take the time to be interested and create value. Learn how to email the hiring manager the right way.

Good luck!

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Isaac Morehouse Twitter

Isaac Morehouse is the the founder of Praxis, Crash, and Career Hackers. He is dedicated to the relentless pursuit of freedom and is a lifelong advocate of self-directed living and learning.