Dear Hiring Manager

It's Tuesday night and I'm headed back from Ottawa. I was bored on the train. That is, until I saw this posting on Craiglist:

Small downtown Toronto freelance writing and research agency requires a very organized, detail-oriented Office Manager 5 days a week who will feel comfortable in a high paced bohemian-intellectual setting. . . If you think you can work with a bunch of quirky, eccentric writer types and an office full of often cranky and demanding clients, send in your resume. . . To apply please e-mail us your original and winsome cover letter and resume.

A part-time job working for a freelance writing and research agency? It sounds like a good fit. The only thing that threw me off was the demand for an "original and winsome" cover letter. I worked for three years as a resume advisor, so it really goes against the grain of my very being to write anything beyond "I worked at this place for 10 years, where I developed skills doing exactly what you're looking for."

In short, it was a challenge and I love a good challenge.

Here's what I wrote. (Some information has been removed for privacy's sake.)

February 1, 2011

Dear Hiring Manager:

I’ll admit that it goes against every grain of my being to write a “winsome” cover letter (it’s not that I’m the conventional sort, necessarily—I just strongly believe in old-fashioned professionalism), but I’m going to make a valiant effort. So, to start, here’s the two most important things you should know: I’m a Ryerson University journalism graduate who currently works as a freelance fact-checker and writer.

After completing my degree, I went on to join [a non-profit] (a charitable youth development organization) as the Office Manager. At [acronym], apart from writing fundraising materials and copy-editing government grant proposals, I was also responsible for listening to my eccentric co-workers’ tales of misadventures with neti pots, as well as dealing with the cranky helicopter parents of twenty-somethings. (I have a feeling that your demanding clients have nothing on the parent of a 24-year-old who doesn’t know how to do laundry, yet suddenly has decided that they’re capable of facilitating sexual reproductive health workshops in a developing country for eight weeks.)

Apart from my ability to defy convention by writing an original and winsome cover letter, I also have a number of other practical skills related to your Craigslist job posting. In my undergraduate years, I spent my summers working as an administrative assistant and for [the government], which allowed me to further develop my skills as a generalist. In my attached resume, you’ll find a bit more straight-forward information about how my experience matches the qualities you stated in your posting. But just in case my administrative, writing and customer service experience doesn’t sell you, here are two more fun facts to seal the deal:

1. I was a recent participant in the Miss Universe Canada GTA pageant. I entered because I thought it would be funny. And it was. * (Oh and I somehow managed to win the People’s Choice Award while I was at it. True story.)

2. I host bimonthly trivia nights. I know very important things like that China technically only has one time zone and the most expensive spice in the world is saffron.** (Invaluable knowledge to any workplace, really.)

I’m available for an interview at your convenience and can be reached at [this email address] or [this phone number]. I look forward to hearing from you.

Sincerely,

Jess

* Although this is seemingly random and maybe even an overshare for a cover letter, this fact demonstrates to the reader that I have an excellent, albeit slightly askew, sense of humour. Although this does not make me inherently employable, it does make me a bit more likeable.

** Read: I’m good planning events, researching, fact-checking and public speaking.

(And yes, dear blog readers. I have three years of experience editing resumes. If you'd like me to critique your cover letters or resumes, I will do so for a very small negotiable fee or service exchange. And while we're on the subject, I also do baking and cleaning. Might as well be a generalist to the max, right?)