Okay, I’m dating myself here, but how many of you out there happen to remember the words to the theme song of Underdog, one of the best cartoons in human history?  If not, here’s a refresher:

when criminals in this world appear
and break the laws that they should fear
and frighten all who see or hear
the cry goes up both far and near
for Underdog! Underdog! Underdog! Underdog!

This isn’t a pop culture blog, however, so I’ll spare you further nostalgia and get to my point.  While it surprises me how often I have to point this out to people, there’s a fundamental tenet of the job hunting process a lot of candidates need to heed more.  Here it is:

The more of an “underdog” you happen to be for a given job opportunity, the more bold and unconventional your strategy will likely need to be to achieve success.

In other words, if you’re a typical professional in transition, you’re bound to come across NUMEROUS job openings that greatly appeal to you, but where you can also tell you’re severely underqualified — and where you’ll feel like a “square peg” trying to wedge yourself into a sea of “round hole” requirements.  This is the rule today, not the exception.  Employers have inflated their requirements for jobs so severely that almost nobody qualifies perfectly for anything anymore.  Myself included.  For example, if I decided to submit my resume for a career counseling position at a college, I’d fully expect to get passed over despite 20 years of highly successful experience in the field, simply because I have neither a Masters Degree in counseling nor any direct previous experience working in an academic setting.

All is not lost, however.  In those cases where you know you’re an underdog, qualification-wise, the smart strategy is to try and offset this liability with a much bolder, smarter, and more audacious strategy designed to get the hiring manager’s attention.  While the “shoe-in” candidates with perfect resumes can get by with a generic submission, you’ll need to think outside the box and come up with something innovative and imaginative to set yourself apart.  You’ll need to pepper your cover letter (or your interview strategy, if you’re able to sneak in as a dark horse candidate) with bold statements.  Brilliant ideas.  Glowing testimonials.  Action plans.  Humor.  Work samples and portfolio pieces.  Or anything else you can think of that might change the game and provide ammunition for the employer to take you seriously, since you know you’re going to get creamed if it comes down to an apples-to-apples resume comparison.

Want examples of this technique in action?  One recent story that’s gone viral in the last week is the article you’ll find here, where a top executive at FourSquare talks about how he got his big break by submitting an in-your-face e-mail to the company’s two founders.  A similar “wow, that’s creative!” job hunting story came out a year or two ago, here.  Or you could even review a past blog article of mine here, where I talk about how one might potentially use humor to spice up a job search application.

Granted, some of these examples are a bit extreme and much more “out there” than most people probably need to be, but my point is that there’s a correlation between your resume credentials and the degree of risk you should be taking in how you pitch yourself.  If it’s clear you don’t quite have the resume horsepower to carry the day — in terms of a given opportunity — don’t play it safe.  Break away from the pack and try something more creative, distinctive, or unconventional to compensate for the qualifications shortfall.  Even just expressing a strong point-of-view in a cover letter, or some humor, or a quick breakdown of some specific ideas about how you’d perform the job in question might be enough to give you a shot.

Long story short, the more “unconventional” of a candidate you are, the more you need to accept that a “conventional” strategy isn’t likely to work for you.  Agree?  Disagree?