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Cover me: Why writing a cover letter is harder than it looks

Applying for a job today hardly mirrors what it was 10 or 15 years ago. In fact, it's not even close.
The idea of walking into a business, filling out an application or leaving with actual talking to a person and finishing with a firm hand shake is no more.
The application process consists of a cover letter, resume, uploaded to a web site where most likely a computer system or, potentially, an actual person weeds through the potential clients and aren't interested in anything other than finding a few key buzz words in order to determine if you're qualified.
What is missing from the equation is the face to face contact that typically wins over potential interviewers or you can actually get that sense of how someone is, their attitude and work ethic just with a face to face interaction, how they answer questions or their overall demeanor as a person.
That, however, is not reality when it comes to applying for a job.

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In reality, the cover letter is going to get you noticed; that is the job interview per say for the moment, as you'll be quite unlikely to get in front of an actual person right away. So in order to get that all important interview, you have to score a cover letter that isn't going to push you out of the running.
The cover letter must be concise, smartly written and focus on what you've done but without being too overly complimentary of yourself. You should make it a point to stick to the facts, and opt away from opinion or speaking in terms of what you attempted to do and almost did.
One key element is how you address the letter, mostly to actual "Dear" aspect. You want to avoid the to whom it may concern or something informal like hello and really make the letter specific. Do some research and find out who you're actually sending it to; a name, their title, all of which can be found on the company web site most likely or even if you aren't sure who to address it to, remember that thing called a phone and phone number. Call the company directly, inquire about the job and find out who's getting these resumes and cover letters.
Covering your bases starts with the aptly titled cover letter, and looking at this document as a snapshot that addresses the hiring manager directly will send you down a path to get that one on one interaction that could seal the deal with a handshake, and new job.

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