In this downright weird economy it can be hard to find the humor in a career search, but it turns out humor is a great teacher.  Here’s a story about a square peg and a round hole – and what can be learned from finding a way to make a square-peg prospect’s personality fit with the round culture of the hiring company.

I was heading a retingency search for a VP-Technology for a cloud services start up with 45 people. In developing a search strategy to guide the selection, I worked with the CEO to define the position: skills, educational profile, past experience, management style, all the many attributes of ‘culture fit’. After a long meeting where we crafted a job description and a better sense of their authentic employer brand – and in which I privately thought, “I hope Jesus Christ is looking for a job,” I headed off to my favorite coffee shop to regroup.

As usual clusters of animated people gathered around power outlets debating the benefits of various technologies. One man, sitting off in a corner, was watching the nearest group with a smug smile on his face. I sat with a latte to simply watch the fun (I love to people watch).

Midway through a heated discussion of security in the cloud, the lone guy – dressed like a hard-core software ninja in ponytail, Birkenstocks and shorts – leaned towards the group and launched into an explanation of cloud-based spam, phishing and virus protection approaches. I realized, as I watched him work the small crowd, that I had found our candidate. My 3-D vision told me he had the technical chops; although he was wardrobe challenged, he mesmerized the group he addressed; and he had self-confidence and a touch of arrogance – all attributes we were looking for. I picked up my latte and asked to join him.

In an interesting hour’s discussion I extracted more information: Jake had a wry sense of humor, was looking for a job, spent a lot of time alone developing software, and needed a brush-up on his social skills. The next task was to convince my CEO that we had our VP-Technology.

After looking at dozens of resumes and enduring interviews with people who were well qualified on paper but lacked the certain spark of the guy in the coffee shop, the CEO agreed to interview him.

Of course Jake showed up for the interview in sneakers, jeans and someone else’s logo polo shirt. He asked challenging questions and displayed impatience when he didn’t get the straight answer. He bluntly told the CEO what he thought about the company’s website, its product claims, and then offered three areas where he thought he could make a difference. In meetings later that day with the start-up’s technical staff he was greeted with suspicion which quickly warmed to acceptance as it became apparent he not only knew his stuff, but was advocating for positions the staff thought were right but hadn’t been able to socialize with the senior team.

It took a bit to convince the CEO – we still conducted a selective search using all the ‘right’ methods, including job advertising on the internet, new media, contacts in my private network and more – but nowhere did we find the flash of brilliance + something unique this guy had. I was able to convince the CEO that Jake’s lack of ability to dress well and his challenging interview style were actually pluses – because he had the right technical skills, a certain edgy charm, and credibility with the technical team.

It turns out that every career search demands that we challenge our assumptions and remain open to possibilities. Hiring processes are essential but creativity and that 3-D sense I mentioned are just as important. Each search comes down to people hiring people. The ability to see the various angles and gifts of each candidate – while keeping a sense of humor, and looking beyond the square hole/round peg trap – can mean the difference between the right hire and a long-term staffing retention issue.

Tell us how your intuition or spidey-sense has helped in a job search – and let us know your thoughts on humor!

Guest Blogger: Meghan M. Biro, founder of TalentCulture, is a globally-recognized expert in talent acquisition, creative personal and corporate branding and new media strategies that accelerate talent acquisition.

Photo Credit, R’eyes