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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.

He didn't do it.

The cops very clearly planted evidence on him because they had to make an arrest because all eyes were on them and whoever actually did the deed was making them look stupid.

Why would the real killer hero have kept the weapon on his person and traveled two states over while carrying it and a manifesto in his bag, conveniently turning the crime into a federal matter? The same guy whose bag they found in a park, filled with monopoly money? Why did the police turn off their bodycams, take Luigi's stuff, drive a block away, turn their bodycams back on, go back into the restaurant, and then arrest him?

PLAYBOY: Do you ever get tired of talking about your friendship with Matt?

AFFLECK: I understand the questions. Ben Affleck and Matt Damon, they're friends, they're pals, they grew up together, isn't it great and cute? I get all kinds of questions, like, "So how's Matt?" or "What's Matt like?" And I don't know what sort of answers are expected.

Instead of saying Matt's fine and he's doing his thing, I'II be like, "Well, let me tell you about Matt. Matt can give a blow job in a way that's incredible, really special." Most of the time it's like Entertainment Tonight, and they can't air it. But then sometimes you think you're safe, but someone writes it down and it ends up being taken out of context in Out magazine.

PLAYBOY: Does Matt ever get pissed off about that?

AFFLECK: Matt gets it. We have a similar sense of humor, which I think is the main reason we're compatible as friends and in terms of writing. He always thinks it's funny. It's just a question of the rest of them.

PLAYBOY: Let's see if you've learned your lesson: What is Matt Damon really like?

AFFLECK: [Laughs] He gives a really great blow job.

The second reads

PLAYBOY: In his 1999 Playboy Interview, Affleck jokingly said of you, "He gives a really great blow job." Care to return the compliment?

DAMON: I do give great head. I definitely give a better blow job than Ben. I mean, I'm not lucky enough to be able to blow myself, but if I could, I'd never leave the house.

That’s IT.