Imagine some of the dumbest, most ineffective pick-up lines you’ve heard or (gasp!) used on someone while at a local nightclub or gathering spot. Chances are the worst ones were either:

  1. So over-the-top cheesy, they invoked an immediate grimace or slap
  2. So boring and overused, they were barely noticed by anyone within earshot
  3. And, in all likelihood, none of these wretched one-liners led to success for the picker-upper. Because first impressions matter. They matter a lot.

    Now let’s talk about your cover letter.

    As a recruiter and career strategist, I see this “horrible pick-up line syndrome” play itself out again and again at the front end of cover letters. In fact, the vast majority of cover letters I review are terrible. (There, I said it.)

    They’re cheesy, generic, or completely redundant to the person’s resume. They tell me more about what you want than what you can do for me (or for the hiring manager).

    Sounds grim, until you realize that you can totally turn this reality into a massive advantage—if you play things right.

    Construct a conversational, memorable, and directly relevant cover letter, add a strong and conversational lead, and then send it to an actual contact within your targeted organization—and you’ve just set yourself miles ahead of the pack. Remember, most of your competition is creating cover letters with loser lead-ins that make reviewers cringe, snooze, or (in extreme cases) want to slap them.

    Allow me to illustrate: Imagine you are a talented field engineer who needs to find a new job due to a family relocation to Texas. You’re targeting a large company that makes and installs wind turbines. Which cover letter intro do you think is more likely to command the reviewer’s attention?

    Cover Letter A

    Dear Sir or Madam,

    Please consider me as a candidate for the Wind Turbine Technician position. I want to work for a thriving company in the field of alternative energy that will allow career growth. I feel I am a good match.

    Cover Letter B

    Dear Mr. James,

    I recently relocated my family to Texas. As we neared our new home, I noticed with intrigue the many wind turbines dotting the landscape. Suddenly, it hit me: “This is the career for me.” After unloading the moving van, I promptly researched companies in this sector that may benefit most from a skilled field engineer with expert electromechanical skills. That’s when I found you.

    Did you pick B? Awesome. Tells a story, speaks directly to what this company is seeking, and is addressed to a real person.

    Let’s go another round.

    You’re now an all-star IT professional living in Seattle. You’re dying to work for Starbucks, but you imagine that the competition will be fierce. So how are you going to kick off your cover letter?

    Cover Letter A

    To Whom it May Concern:

    I am writing to express my interest in the IT help desk position you have advertised on I am looking to work for a major company in Seattle that provides a positive work environment and a vision for the future. I think Starbucks is perfect for me.

    Cover Letter B

    Dear Ms. Sheridan:

    A group of us IT folks were sitting around talking about our favorite Pacific Northwest companies this morning (coincidentally, over coffee). As you might figure, Starbucks was among the first names that came up. What makes you such a standout among Seattle-based corporations? Here’s the list we compiled:

    [Insert a few key things about Starbucks that illustrate that you know exactly what Starbucks is all about, and what they’re up to]

    Did you pick B again? Outstanding. Do you see the difference?

    Cover Letter A begins with a generic, cliché salutation. It says little and focuses heavily on what the job seeker wants out of the deal. Cover Letter B, on the other hand, shows personality and style, and showcases that the author has done her homework on Starbucks.

    Here’s the thing, folks. People like reading interesting, engaging stuff. They like stuff that paints a picture, tells a story, and maybe even makes them smile. People like it when you’re human, genuine and memorable.

    And you know what people love? In both bars and board rooms, people adore an excellent, compelling, and memorable pick-up line.

    Love Job Jenny's advice? So do we. Check out Job Jenny's Ridiculously Awesome Resume Kit, new this week! Learn how to craft your own ridiculously awesome resume, and get more inside tips on finding a job from Job Jenny.

    Photo of men and women in bar courtesy of Shutterstock.