Why Hello!

I was trained in the dark arts of the cover letter by my mother, who is a hiring manager. And her training has paid off: I've been consistently told my cover letters are excellent. Let me pass on the wisdom.

The job of a cover letter is to give a prospective employer strictly more information than is on the resume. This is where you take the resume contents and put them into context. You look at the job requirements (you are looking at the job requirements before applying, right?) and look at your resume and ask the question (in your head) "why would a person think this candidate would be good for this job?" and your cover letter is the answer to that question. If you don't answer that question, the hiring manager is going to have to do it themselves, and you have way more information to work with than they do.

This is especially important if you're moving from one industry to another, because then the relevant connections aren't obvious. It's also very important if you're overqualified, because then you can use the letter to say "I know it looks like this job would be too entry-level for me, but I'm interested to pursue it for reasons x, y, and z". You can also use this space to explain away something that might otherwise be disqualifying, like job-hopping or a long break in employment. The tone to strike here is always matter-of-fact and constrained to topic - don't go into detail about health stuff or personal tragedy, just tell them what they need to hear: that this period of your resume was affected by [bad thing] but that it's now in the past and you're looking forward to the next chapter. Remember, one of the things they're trying to learn is whether you'd be content in this role, or whether you'd be miserable and leave after 2 months, which would force them to do all the work of hiring again. You're trying to establish that you will fit right in and not cause problems. Knowing what drew you to this job in particular (and don't just say 'money', that's true for everyone) helps with that.

Cover letters are your elevator pitch. Why you, over anyone else with the same qualifications? What things can you advertise yourself with that can’t go on a resume? It’s literally self-advertising. Tell an employer a persuasive narrative about yourself that will make them want to interview you.

For a quick example: this blog led to me getting my first fact-checking gig, which has become my Real JobTM.

My resume shows the blog, that first client (which I still work for, eight years in!), and subsequent professional advancement. It’s not a bad resume these days.

Every cover letter I send tells the story of how I tried to do education on the internet and got so frustrated by incorrect/contradictory/unsourced information that I taught myself how to fact-check to find some dang correct facts. That I’ve dug so deep looking for accurate answers that my work has been published in peer-reviewed journals, cited in law articles and other academic literature, and influenced the trajectory of legislation. And that I still love it! A decade later, it is a joy every single day to dig my teeth into the newest topic and make sure everything is right. This, I say, is what I will do for them.

That’s the story my resume could never convey.

I have a trick for this! It's called ask someone else.

No, really. Someone in your friends / family / favorite colleagues from that last job is going to be your biggest supporter, so make use of that!

Ask them how they'd pitch you to someone else. Insert theoretical scenario of them somehow socially encountering someone hiring for the perfect job for you - what would they say to make that person interested? What about your work history do they think would be compelling? What skills do they think you should promote?

It is really hard to figure out how to market yourself. Especially these days when there's a more performative aspect to job applications than just having the right skills. Make use of the people who love you want to see you do well.

I think this sort of thing used to be easier when written letters of recommendation were more common, honestly, because those were literally someone else advertising you to someone else.

Another thing you can do - which will feel so awkward but is worth it - is to ask friends, colleagues from previous jobs (maybe not your current one), or past/current clients to give you a blurb! If you have a professional website, those are a great thing to use to flesh them out to prove you are a real person with real skills. If not, you can keep them to look at when you need inspiration or can't remember to save your life what you're good at and why someone should hire you.

My best suggestion if you're like uh, no, I cannot write something cogent is... don't. Barf everything vaguely relevant onto a sheet of paper. Do a free-writing exercise with no constraints. Write down all the silly, ridiculous, egotistic shit you'd like to tell an employer about why they should hire you. Get it all out on paper without censoring yourself so you can get any of it on paper - and this this important, do not send it. Read it back, and draw from it to make your actual cover letter. If you're struggling, show it to someone else and ask them what they think is important/interesting/marketable.

Drafting things like cover letters and even your resume with the support of your community will seriously make them so much better. You get eyes on for spellchecking and grammar, but also to help make sure it flows and that you're not using jargon or technical language a hiring manager might not understand. It can be hard to ask and I totally get that. It's something where I think it's worthwhile to sit with the discomfort. Applying for jobs successfully really isn't a skill that's taught these days! So we succeed best when we support each other.

I practice what I preach here. This is hard for me too - I am successful because I lean on community. I don't remember the last time I wrote a cover letter without having someone else preview it, even though I have a solid template I've worked from for years. I literally just asked @kaijutegu to help me cobble together a bio for a client that wanted to include me on their website (aaaaaaaa). I read and give feedback on cover letters for my friends as well, because it's got to be a two way street.