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6 Things I Wish I'd Known About Cover Letters

Updated on January 26, 2011

Cover letters are probably one of the hardest things to write when it comes to applying for jobs. It's hard to strike that perfect balance that makes you sound confident but not arrogant, competent but not overqualified, original and creative but not totally wacko. So having written several over the past months and reading everything from articles on the Harvard Business Review to blogs written by people like myself, I thought I'd compile a list of things I've learned so far.

1. Never, ever write "To whom it may concern."

If you can (and there is usually a way), find out the name of the person who is going to be reading the cover letters/resumes. Sometimes it's a collective of various people in Human Resources. If that's the case, then it is ALWAYS better to address your cover letter with "Dear Hiring Manager."

2. Do NOT use a generic cover letter for every employer.

This may seem like a given, but it's worth mentioning nonetheless. Sure, you have certain information that will almost always be in there: your exceptional verbal/written communication skills, your attention to detail, your task-management skills. What I've found is that the more specific you are to the job, the better. I know it can be a lot of work to write a brand new cover letter for every employer, but if you're sincerely interested in the job, it's worth the extra effort. Use specific words from their job description/requirements and explain why YOU are the best person to handle all of those things. Show a genuine interest in the company and convey that you know more than the average person about their goals and their overall approach.

3. Be direct and concise.

Don't start listing and explaining all the things you've done recently, hoping that one will jump out and catch the hiring manager's eye. Instead, go into detail about jobs and responsibilities that have given you the valuable skills you are now offering your prospective employers. Say precisely what you can offer him or her and what you hope to achieve.

4. It's okay to change your tone depending on the organization.

There are a lot of cool places to work these days, like start-up internet communities and blogging sites. Many of these are run by younger entrepreneurs who don't mind some degree of familiarity in a cover letter. You don't want to be overly familiar, of course. But it's better to stand out as someone who is comfortable talking about themselves than as someone who is trying too hard. I recently read an interview with someone who began their cover letter to the online site Meetup with "Hello Meetup people!" He works there now. The recruiter noted that his greeting stood out and made her smile, which was refreshing amidst a pile of letters addressed to "Dear Sir/Madam."

5. Get a second pair of eyes to read it over before hitting 'send.'

I always ask my mom, who is a great writer, to read something before I send it along. Even if I've read it six times and think everything is perfect, she always finds one or two things to tweak that sound the slightest bit better or more professional. Instead of saying "I know I would make a great addition to your team," say, "I would love the opportunity to become a member of your team." That shows grace and appreciation as opposed to what could be perceived as arrogance.

6. No one wants to see on your cover letter.

This obviously goes for resumes as well. I am of course exaggerating with the "beach baby" thing, but even your first and middle name with a number on the end will strike recruiters as unprofessional. I recommend getting an address like so: I've heard hotmail addresses, specifically, end up in the spam folder. It's quick and easy to get a second email address where you keep track of all your job-related matters.

In closing, I hope I haven't been too much of a Debbie Downer in this post, but I myself have made a few of the above mistakes and have come to regret it. All we can do is learn and not repeat the same mistakes though, right? This might go without saying too, but always sincerely thank the person for their time and consideration in reading your cover letter. If you're really bold, tell them precisely when you will be checking back on the status of your application. Hope this was at least somewhat helpful!


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