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Sometimes, not always, when searching for my next position or project, I make an effort to write an interesting cover letter, one intended to convey images and passion, a story. I want it to be a great read. For most mundane jobs, an ordinary letter will do, but for the special cases I want the letter to have zing.

If I hand over a copy to a friend who's not a professional writer, I typically get no constructive feedback. I'm not looking for someone to proofread (though I do need that), or judge it in terms of job search advice or the technical jargon used in the particular industry. I want someone who gets good storytelling, who can recognize where an attempt at painting a vision fell short or the pacing isn't right.

These are not the things that cover letters ordinarily have, but I am not trying to land work on ordinary projects.

How to find someone to provide such a critique? (For money, a beer, ...?)

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we can under these guidelines. The only catch is that it will then be under the SE license, which is creative commons. –  justkt Mar 31 '11 at 12:19
    
I understand the desire and need for a creative cover letter. I'd be happy to take a look and offer a few little suggestions if you want to send it to me offline. –  Lynn Beighley Mar 31 '11 at 13:37
    
+1 for a good question and for "If I hand over a copy to a friend who's not a professional writer, I typically get no constructive feedback." –  msanford Apr 5 '11 at 12:42
    
Good question. However, bulk posting of questions may not be such a good idea. –  Kris Jan 6 '12 at 5:57
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2 Answers

up vote 14 down vote accepted

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:

  1. Lack of third-party buy-in
  2. 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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I've tried to respond in a generic way so that other people will find it useful, too. Everything here has been learned through experimentation: A/B testing resumes and cover letters. Bits and pieces may apply more or less depending on the hiring culture of the company you're interested in, and whether or not you've got a direct line to the hiring manager... –  rianjs Mar 31 '11 at 13:34
    
I disagree, that the cover letter is not the first thing they read. The HR people I know read it first for exactly the thing you mention: filtering. You can glance faster over a cover letter than over a resume. Why care about people who cannot get the cover letter right? +1 for the rest of your post. –  John Smithers Apr 1 '11 at 8:11
    
The bulk of the responses in this LinkedIn discussion thread (by hiring managers and HR people) support my assertion, especially the HR people. Hiring managers tend to be a little more in-depth: linkedin.com/answers/hiring-human-resources/staffing-recruiting/… –  rianjs Apr 1 '11 at 13:33
    
The cover letters I have in mind don't go to HR, but directly to decision-making professionals in my field, for positions not listed on monster.com et al. (HR, ugh!) –  DarenW Apr 1 '11 at 21:59
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And every cover letter is custom-written for each job I'm interested in. - Do this even if you ignore everything else: form letters are really obvious. –  Charles Stewart Apr 4 '11 at 11:20
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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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