I would be certifiably nuts to send this to a real prospective employer. But, as a creative writing device, it worked to bring my voice to the forefront and make me sound like a real human being. This kind of in-your-face audacity is probably a touch too harsh, but I can’t imagine having a little backbone as a bad thing. What do you think?
Hi there.
You don’t know me, so let me introduce myself to you. I’m the potential employee that was recently laid off from a technical analyst position for a large multinational company. I want to write you in such a way that will captivate your attention and make you think that I’m a witty and intelligent person. This, of course, may or may not be true — I could be a total coward with some tech skills — but, I guess you really won’t be able to find that out until we sit down and talk face-to-face.
I noticed your ad in/on the paper/web that you were looking for someone with my abilities to help propel your organization to reach its goals. I think it was wise for you to advertise the need for such a person — that is, rather than look for someone to bring your organization to its knees. Sorry; that was just a small joke, but the irony is hard to avoid. I mean, we’re all looking for kind of the same thing, aren’t we: a chance to bring people together and get ahead, and maybe, just maybe to put together a great group of people and doing something really HUGE in life. The fact that we feel the need to state and restate the obvious is just a bit funny, don’t you agree? And that leads me to the purpose for which I write you today.
The purpose of my writing you is not simply to give you a good laugh at my frankness and cleverness, although I hope there’s that. Rather, I’m writing you to let you know that I think I have the skills you’re looking for to do the job you’ve outlined in your ad. But, moreover, I think I have the personality, the experience, and — let’s face it — the sheer determination that your organization needs to do great things. You and I both know that it’s the little things in people that make the big differences in an organization. That attention to detail. That enthusiasm that seems to come out of nowhere. That sense of ownership. I’d like to submit to you that I believe I have those little things that will help you succeed in your own aspirations.
I understand your needs as a team leader to have great people because I’ve had to put together my own project team in the classroom to build great software (ask me about that sometime). I have a sense of the weight of your responsibility to drive success because I spent seven years working for a disciplined, results-driven organization. I understand how our product will need to be positioned for customers — both from a marketing and a technology point of view — because I eat, sleep and breathe the web. I even have ideas about how your product will need to change in the next five years because I spend my free time reading the books, articles and blogs by the people who are building this stuff on the cutting edge.
So, here. Attached is my résumé — take a look and see if you agree that I just might have something to offer. If you like what you see, give me a call and we’ll chat. Meantime, thanks for your attention; I’m looking forward to a mutually profitable relationship in the near future.
Sincerely,
Ken
I don’t know Kenny, it’s a bit long for a cover letter. Remember, brevity is the soul of wit.
Tom: of /course/ it is. The first pass at any creative writing excercise is certainly not going to yield Shakespearian sonnets.

Perhaps the likes of Palahniuk and Gibson can capture sharp, incisive wit on paper in the span of a few minutes, but brevity for me is an iterative process. My first pass (at anything, really) is to shotgun-spray my thoughts onto the screen first. Only after that do I start to trim and prune and weed out the passage, saturating the remaining words with meaning in the process. This version is pretty much that first draft, with some minor edits so I could post it in public without totally embarrasing myself.
That said, I’m really more interested to hear thoughts on the content: Is it trying to sound too brazen? Am I hitting the points that hiring managers really want to hear? Is there any usable content at all, or should I just throw this version away?
It’s too informal. It’s also got a very strange mix of confidence and reservation about it. For example, you clearly want to say “I have the skills you need” – but you end up saying “I think I have the skills you need.” I realize the intent is to say “hey, I think I fit. Lets sit down and find out” – you are trying for a face to face interview. That’s the wrong target. By the time they call you in, you want them to expect you to be the one they want. Aim for the job, not the interview.
Keep it short, and respectful. Be very forward about yourself – this isn’t the time to be reserved about your abilities.
As a side note, don’t use the word “chat” – I have never had someone ask to “chat” where it didn’t come off sounding as though they were angry at me, or otherwise negative. Dunno why. I’d much rather get together and talk.
I’m sure I’ll think of more, but I think I’ll wait and see what draft 2 looks like
SHORT!
no more than a page. but that may even be too much. The cover letter is to give your resume and application some personality. But, follow all of the advise ryan gave you. Strong and determined … but don’t come off as cocky or arrogant.
The cover letter is the only thing that sets you apart from all the other applicants that know 10 programming langauges, mysql, any other number of skills, and good references. Character is important … but you have to do it in a paragraph or 2, not a page or 2.
Don’t say anything that might be construed as ‘cheesy’ or ‘inappropriate’ or ‘cute’ by some someone. But witty is good. There is a fine line there.
Guys, thanks for the info. I’m doing the redux this afternoon, and I’ll try to condense this into three short paragraphs. Just a quick question: “Hi there?” I mean, aren’t you supposed to start formal letters “To Whom This May Concern?”
If you aren’t comfortable with Hi There, change it. It’s definately informal. But “To whom it may concern” is awfully stodgy too.
Dear Sir or Madam?
Yo, Ken Walker Rocks?
This Concerns You, so listen up?
Oh, Hi… sorry… I didn’t see you there. You see, I’m so busy kicking ass as the perfect candidate for your job, that I just didn’t notice you start reading?
Ok. All of those except maybe the Dear Sir… one sucked.
LOL–thanks.
I actually just posted up for my first job. It’s with a local bank here in the Ironbound, whose web presence could use some help. Just first in a series of many, but I actually did use content from this letter, including the “hi there.”
But if I’d noticed your “Oh, Hi… sorry… I didn’t see you there. You see, I’m so busy kicking ass as the perfect candidate for your job, that I just didn’t notice you start reading?” I definitely would have used it.
—
Ken,
I was on AOL today and came across this:
http://findajob.aol.com/findajob/articles/article.adp?id=698
Most of, if not all, is common knowledge but I figured I’d post it.
Talk to you soon,
Chris
Ken,
Let me begin by saying, I truly enjoy the way your write! It’s funny, I can hear your voice in my head as I’m reading your words (they say that’s what makes a good writer)
However, for a cover letter….I have to agree with Ryan…it’s too wordy and too informal. A cover letter should really be no longer than 3-4 BREIF paragraphs. That being said, you don’t have a lot of time to tell the employer a lot about yourself, but you do want to get across to them what’s important. For someone who’s reading your resume means answering: can you do the job, what skills do you have, what education do you have, what experience you have, how it all applies to the position your going for, why you want to work for their organization, and most importantly why you’re the best man for the job. I know, I know….a lot of that information is on your resume….but take a look at this website, (http://www.soyouwanna.com/site/syws/coverletter/coverletter3.html) it will help you format your cover letter.
I understand your desire to be creative with your cover, and that you want your personality to shine through, however, I think you can do that AND adhere to a more professional format. Like Mike said, “witty is good”, but you still want to come across as professional as possible.
Remember, a lot of resumes and cover letters are not read by humans first. They are run through computers that are looking for those “key words”. It’s important to include them when you write your cover.
Good luck brother! XOXOX!