Cover Letters



Updated August 24, 2022
Technical Recruiting and Hiring

You’re reading an excerpt of The Holloway Guide to Technical Recruiting and Hiring, a book by Osman (Ozzie) Osman and over 45 other contributors. It is the most authoritative resource on growing software engineering teams effectively, written by and for hiring managers, recruiters, interviewers, and candidates. Purchase the book to support the author and the ad-free Holloway reading experience. You get instant digital access, over 800 links and references, commentary and future updates, and a high-quality PDF download.

Cover letters (and whether to include them when you’re a candidate or consider them when you’re an employer) have historically been a bit of a contentious topic, mostly because of the purported time they take reviewers to read. As a recruiter or hiring manager, you’ll be able to tell quickly if it’s a generic, copy-pasted form letter. If it is, the letter can’t tell you much. But if it’s not, then it’s absolutely worth reading—the candidate just gave you a huge window into who they are and how they communicate, in a way that a resume cannot. If the letter reads like a thoughtful, passionate human wrote it, then wise hiring teams will seriously consider talking to the candidate. This holds true even if you’d be on the fence just judging from their resume alone.

The converse doesn’t always hold true, however. If a candidate looks competent but isn’t over the moon about your company yet and hasn’t gone out of their way to show their enthusiasm, that’s not a reason to reject them. If you feel strongly that they’d be great in the position, it’s best to let them know you want to talk—you’ll have plenty of chances to sell them later.

Selling vs. Gate-Keeping

Despite changes to technical hiring practices, related hiring practices have been slow to catch up—especially when it comes to filtering candidates through the top of the funnel. Companies typically set up hiring processes to gate-keep rather than sell. But the demands of the market dictate that technical hiring be more about selling than filtering. The difficult part for companies isn’t sorting through a sea of candidates to figure out who’s “the best” or who’s worth engaging with.* Rather, technical hiring is a sourcing problem. A successful effort begins with getting candidates interested enough to talk to you in the first place and remain engaged as they go through the hiring process.

At a high level, selling is no different in the context of recruiting than it is in more traditional sales of goods and services. You talk to your customer (the candidate), ask questions, listen closely, and learn about their past, what their pain points are, and their hopes and dreams—and then you weave a carefully crafted narrative about how working at your company can actually deliver on those things.

Selling starts with writing great job descriptions that focus on how the role will improve the candidate’s life. This may include learning new things, gaining more responsibility, helping to fix problems in the world that matter to them, and so on. Selling ends with compelling offers tailored to the candidate’s needs. And in between, a good process will treat every candidate like a unique individual, never taking for granted that they have plenty of other options.

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