Five Tips for Better Cover Letters

A question from a friend for whom I consult on occasional career coaching matters:

What’s your take on cover letters: make ’em short ‘n sweet, or go to town and try to sell yourself there rather than in the resume?

To answer my friend’s question: You should always be trying to sell yourself, both in your resume and in your cover letter. I’ve already had a brief discussion on how to improve your resume. Now here’s the companion piece: some tips to improve your cover letter.

Cover letters are a surprisingly polarizing topic among those who do hiring in technology. Some people find them to be a waste of time and will never read them, instead relying purely on a candidate’s resume. Some companies don’t even make provision for submitting a cover letter in their online application processes.

Naturally, your resume is an important document in the job hunt process. It tells your prospective employer what you’ve done and what you know. Similarly, your portfolio (Github, etc.) shows the hiring manager the how of your career: how do you implement the code or the design or the document?

As for myself, I require cover letters from all applicants and here’s why: I hire people; I don’t hire shopping lists of tech skills. While, yes, your skill set is important to me and I will be scouring your resume for every possible nugget of gold, I’m far more interested in who you are, what you can do for me, and how you interact with others. I can teach anyone how to use our technology. I can’t teach someone how not to be an asshole. Your cover letter is going to tell me who you are and, importantly, why I should care. What problems are you going to help me solve? Without that cover letter I have no insight behind the resume or code sample and little motivation to learn more. You’re just another faceless resume in the stack.

Now for those tips I promised…

Customize!

If your cover letter arrives on my desk and is obviously a cut and pasted template, I’m less likely to follow up on your application. To me, it doesn’t feel like you want this job; you’re just looking for any job.

Which isn’t to say you should necessarily rewrite a cover letter from scratch for every job to which you apply. It’s OK to have some sort of scaffold as a foundation around which you build individual letters.

Each of those letters must be customized for the position to which you’re applying. Do your research about the company and position and incorporate that into the letter. Some examples of what you could include:

  • What problem are they trying to solve? They wouldn’t be hiring if they didn’t have problems to solve, so how can you help them?
  • Who is the hiring manager? Address them directly in the salutation of the letter. Decades of direct marketing research show that personalized messages are more likely to be received favorably. Plus, going this extra mile to address your potential manager reflects well on you.
  • What are the company’s values and mission? If you agree with these things, incorporate them into your letter. Naturally, if you don’t agree with the values and mission you should not apply for the position.

It’s not about you; it’s about me

I, as the hiring manager, have needs. I have deadlines to meet and bugs to fix and code to refactor and rearchitect and people to hire and mentor and meetings upon meetings to attend. How are you, $applicant, going to make my life easier?

What many applicants forget is that as a manager I really want to hire you. I need to get the right person in the door and productive so my team can keep moving forward and hitting deadlines. If your cover letter tells me how you will help us do that? I’m already predisposed to like you.

But, really, it’s about you

Your cover letter is your opportunity to show the hiring manager that you’re going to be an asset to the team. You’re skilled, sure, but you also work well with others. You’re well-spoken. You’re witty. You support the mission of the company. You’re going to join the team and make things better for me and here’s how. Tell me who you are and why I should care.

Predict and elucidate

Sometimes when writing your cover letter you must channel your inner Carnac, answering questions before they’ve even been asked. After reviewing your cover letter and resume, the hiring committee may be left scratching their heads over some subjects. This head scratching implies effort on their part to discover the answers. These people are quite busy. If there are other candidates who initially appear as qualified as you but whose applications do not leave so many question marks hanging in the air, your resume will not be put in the short pile. However, if you predict the most pressing questions of the hiring committee and provide the answers up front in your cover letter, it can make all the difference. Some examples of questions which your new team might have when reviewing your application:

  • You haven’t been working for a while. What have you been doing in the meantime?
  • This job is based in Austin, TX but you’re in Portland, ME. Are you looking to relocate or work remotely?
  • You’ve spent the last ten years as a software engineer. Why are you applying for a position as a tech writer?

Form follows function

Coco Chanel once said, “In order to be irreplaceable one must always be different.” Don’t pay attention to those job hunt books you get from the library. They’re wrong: there is no rulebook for the format for your letter.

Your cover letter should reflect your personal style as well as the style and culture of the organization to which you’re applying. Most often, that will be a basic letter in which the content speaks for itself. However sometimes it may make more sense to stand out more. Perhaps a “letter” written in the form of a stack of calls to the company’s public API. Maybe a link to a website you designed solely for this purpose. Animated cat GIF? Um…OK, but only if that’s what makes sense.

Always remember: Don’t be clever purely for the sake of cleverness. The goal of your cover letter is to show the hiring manager who you are, what you can do for them, and turn heads in the most appropriate way. No one likes a cocky show-off.

Announcing Documentation for the Internet Archive S3 API

Back in 2011 I was hired at Internet Archive to develop a digital archive service for memory institutions. Unfortunately, after six months the project was scrapped (along with my position).

In the last month of the project, while waiting for the go-ahead to keep moving forward, I undertook documenting the Archive’s S3-like API. The project was going to need this API and, to be entirely frank, the existing documentation is laughable (sorry, IA team, but it’s a spade). My API doc was nearing completion about the same time the project was axed, but it was never published and ended up collecting dust in my Dropbox.

Fast forward a couple of years. Now, as a co-organizer for San Francisco Perl Mongers, I stream and record as many of our events as possible. Afterward, I upload them to our SF.pm Collection on Internet Archive because I believe in their mission of “Universal access to all knowledge.”

In the process of that uploading, I found myself referring frequently to that old in-progress API doc. Finally it dawned on me that I should probably share the damn thing so others could benefit as well.

It took a lot of cleanup and editing, but now I present to you:

The Internet Archive S3 API Documentation.

This API will allows for the creation and maintenance of items on Internet Archive. It also allows uploading of files to the item and, if the item has the appropriate metadata values, Internet Archive provides online viewers for this item content. For more information, have a look at the API Summary & FAQ.

It’s my hope that this documentation will allow many more user groups, individuals, and institutions to preserve and share their content via Internet Archive (for free, might I add, but donations are always welcome). I think of it as a grassroots continuation of the stillborn Digital Archive Service I once worked to produce.

NOTA BENE #1: If you have a lot of content to upload to the Archive, please be a good citizen and contact Internet Archive to coordinate with them. The crack IA Collections department will help the process be as smooth as possible.

NOTA BENE #2: This is not an Internet Archive document. They are not responsible for any shortcomings it may have. Please see the support page for more information about that.

If you use this document (and I do hope you will) and do find any shortcomings, please let me know! This doc is in Github specifically because it makes it so easy to collaborate on this sort of thing.