: How to obtain a thoughtful critique of a job application cover letter? Sometimes, not always, when searching for my next position or project, I make an effort to write an interesting cover letter,

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I think you're in a bit of a bind here. I think you'll have an easy time getting "does this work for you?" feedback, which is crucial. However, I think you'll find it very difficult to find constructive, "here is how you can make your letter awesome" feedback. Let me explain.

You're trying to be attention-grabbing and evocative. Notice that this is basically a self-marketing strategy that you yourself are selecting; you could choose a different one (as rianjs wrote), but this strategy could be good for you. Attention-grabbing is what you want, right? Well, yes - but it's also a strategy that could misfire pretty horribly. Because if the recruiter doesn't fall for your letter hook, line, and sinker, he's very likely to reject it outright for being unprofessional, gimmicky, and/or inappropriate. It's basically an all-or-nothing gamble, and potentially a very risky one. Here's an article about absurdly inappropriate manuscript submissions; it's fun reading on its own, but I'm linking it here to illustrate that a lot of peoples' idea of "unusual" and "creative" can be a major turn-off for the person at the other end. Not only that, the weirdos are so weird and unprofessional, they often make the recruiter allergic to any sign of mold-breaking "creativity." "Just FOLLOW THE INSTRUCTIONS," they are muttering to themselves, "don't be like the guy who sent his submission in inside a pizza box. Don't be anything like him." That can be a lot to get past.

So, you're looking for two things. You're looking for a reliable indicator of whether or not something you wrote is absolute dynamite. And if it isn't, then you want someone who will turn it into dynamite.

The first is easy. Ask a bunch of friends. People whose opinions you trust and respect; people with different tastes and sense of humor; people who won't be afraid to tell you if your letter isn't as awesome as you want it to be. You don't need professional writers - you need friendly dynamite-detectors, and your friends are fine for that. If they don't really like it, you can rest assured that the recruiter is likely to be far, far harsher than your friends.

The second is near-impossible. There's nobody who really does what you're looking for as an occupation or a hobby, except maybe advertising executives... And you're trying to create something really unique, that has to be as near to 100% effective as possible. Even if someone does give you constructive advice, you need to make sure that advice really really works. And frankly... if there were somebody out there who could spin up unique application cover letters from not-so-great into pure dynamite... well, I don't know about you, but I know I couldn't afford him. :P

I might be misunderstanding just what it is you're trying to do with your letter; maybe it falls into some category of writing that has an established community of practitioners. If my above comments didn't hit home for you, then consider the following question: what categories of fiction, non-fiction, or marketing might fall closest to what you're trying to do with your letter?

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Cover letters are tricky, because if you're writing a CL for a traditional job you're probably competing with somewhere between 50 and 300 other applicants. This means HR has to find a fast way of filtering the wheat from the chaff. Your resume is generally the first thing an HR person looks at. If you make it past the first screening, your cover letter may have a chance of getting read. Unlike its name implies, the cover letter isn't the first thing to be read anymore. (Was it ever?) Some places only look at the cover letter if they're feeling strongly about a few candidates, and need a tie-breaker.

In any case, you've got two fundamental problems you need to overcome when angling for a job:

Lack of third-party buy-in
Attention scarcity

You have somewhere between 5 and 25 seconds to get someone's attention; to get them to see you as a human being rather than text on a page wasting their time.

People don't read monologues (even clever ones!) because they're being bombarded by messages every day, and they have other things competing for their attention. If they want to read long-form content, they're gonna read a book or a magazine, or you better be solving an acute problem that they need help with right now. Don't believe me? When was the last time you wrote a long-form business email to someone you already knew, and it was obvious that they didn't read it the next time you interacted with them? And this is someone who knows you and has some investment in the relationship already.

In terms of cover letters, I've learned to love brevity and whitespace, no matter how badly I want to write an amazing essay explaining why I'm perfect for their company and their opening. Generally that means 2-3 sentences, 2-4 short bullets, and 2-3 sentences to close, and that's it. (And every cover letter is custom-written for each job I'm interested in.) This is an information-dense format, and the use of bullets breaks up the look and the flow of the cover letter. Bullets are better than a wall of text because they tell the reader that there's a discrete piece of information here, instead of needing to start at the beginning which is the subconscious message of a wall of text.

I used to do the long-form thing. My response rate was less than 10%. Now my response rate is damn near 50%, which very, very good. As with all non-fiction writing, it's about understanding who your audience is, and the context in which they're likely to be reading what you've written. Your message is pointless if it never gets heard.

Remember: You're not trying to seal the deal with your cover letter. You're just trying to get them to pick up the phone and call you.

(And if this sounds like marketing/copywriting advice, that's because it is. When you write a cover letter, you're absolutely marketing yourself.)

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