Risk vs. reward.  Alas, whether you’re talking about asking somebody out on a date, starting a business, or making a successful financial investment, isn’t this always the eternal teeter-totter that so much of life seems to be balanced upon?

As for the principle’s application in the career marketplace, let’s face it, most job hunters are pretty chicken.  They tend to play it super, super safe.  Whether in their resume presentation or their interviewing banter, they try not to ruffle any feathers or rock the boat in the slightest way lest they alienate a potential recruiter or hiring manager who might be interested in hiring them.  And yet, is this “go along to get along” mindset truly the best strategy?  Do most people actually get good results with this approach — or do we all have it backwards, and we’d experience far better results if we dug deep and found the courage to be more fearless and outspoken in how we go about things?

I bring this up based on a recent exchange that took place in one of my networking events.  In this meeting, one of my guest speakers was asked by someone in the audience about how to answer the ever-popular “what’s your greatest weakness?” question.  His response?  He said “I’d look the interviewer in the eye and tell them that if they tend to focus on peoples’ weaknesses, versus their strengths, I probably wouldn’t want to work there.”

Needless to say, I almost choked on my coffee.

It’s not that I fundamentally disagree with this line of thought, or that it doesn’t make sense in a perfect world, but the very notion of somebody stating something like this an interview is way, way out there in terms of risk-taking behavior.  If I were interviewing somebody myself, and somebody responded in that way, I’m truly not sure how I’d feel about it.  Would I penalize the person for calling me out on my interviewing approach — and corporate culture — or would I respect them for their candor and reward them for not just telling me what I want (or expected) to hear?  How about you?  How would YOU respond to such an answer, if you were the one hiring?

Regardless, the whole exchange got me thinking.  Without question, the vast majority of job hunters play it boringly safe — and the conventional wisdom is that this is the right thing to do.  What would be the likely results, however, if job hunters rolled the dice a little and tried some off-the-beaten path approaches and responses.  Things like…

•  Job hunting with no resume whatsoever; simply using your LinkedIn profile as your sole piece of written collateral
•  Including unorthodox resume sections called “Where I Shine” or “What Sets Me Apart” or “What I Rock At / Suck At”
•  Sharing data on “What You Learned” or “How You Grew” or “What You Overcame” for every job listed on your resume
•  Using humor in a resume; livening your text up with self-deprecating comments, amusing asides, or witty observations
•  Writing a cover letter that attempts to specifically guess and articulate the employer’s exact needs, worries, and/or pain points
•  Trying an more bizarre cover letter approach such as a poem, short story, or link to an online video
•  Practicing the lost art of walking into company in person and handing off a resume to an actual human being, if at all possible
•  Tracking down a company’s facsimile number and faxing them your letter of interest and/or resume
•  Attending networking groups that aren’t intended for you (e.g. man in a women’s group, finance person in an IT group…)
•  Writing ongoing social media posts (LinkedIn, Facebook) that document the ongoing experience(s) of your job search
•  Offering to share some objective feedback about a company’s brand or reputation as part of the interview process
•  Asking an interviewer if you can take the reins and deliver a 5-10 minute formal presentation on why you’d be a great hire
•  Asking hiring managers, politely, to respond to some negative feedback you’ve seen on their Glassdoor reviews
•  Arriving at the interview with a 90-day plan, PowerPoint presentation, or another concrete handout demonstrating your value
•  Sharing a copy of a personality assessment you’ve taken with an interviewer, using it as grounds for deeper discussion
•  Asking an interviewer to describe their management style and explain how they get the best out of their employees
•  Standing up to a bullying recruiter and asking them to sell YOU on why you’d want to work for their organization (I’ve seen this work!)
•  Informing a company that you’d be willing to work for a month, for free, to prove yourself (this actually worked, too, for a client!)
•  Following up on a rejection letter, a week or two later, asking to be given a second chance to prove yourself
•  When asked about salary goals, state “I’m not cheap, I’d be looking for (insert ambitious number) – but I’m worth every penny!”

Don’t get me wrong – I’m certainly not advocating any of these strategies, in particular, merely outlining a series of possible things a job hunter could do that would be somewhat risky and quite different from the norm.  I’m sure we could think of some other ideas, too, if we put our heads together.  Essentially, however, I’m just encouraging people to ponder whether a serious job hunter might reach the point where some of these unorthodox tactics would make sense to try, just to see if they bear fruit.  Or whether there’s room for a typical job seeker to conduct a “controlled experiment” around one or more of these techniques, just to see what results from it.

Again, it all comes down to the risk vs. reward continuum.  Do I think many of the above methods could alienate a given employer or cause somebody to lose out on a promising employment opportunity?  Yes, absolutely.  Do I think that one of these bold moves could possibly impress an employer and snag somebody a job they wouldn’t otherwise land?  I’d have to say yes to that, too.  I think it would all come down to the exact situation, the audience, and how well such a concept is executed — as well as a person’s general worldview about such things and where they stand on the “what do I really have to lose at this point?” scale.

Food for thought, hopefully, at the very least…