14 "Job Search Taboos" That Might Actually Land You the Position

We want our job candidates to showcase a willingness to experiment, whether it’s exploring new unproven technologies or teaching themselves a discipline outside of their core skill set. While we occasionally call on specialists to help us design and develop products, we’ve found that our most successful colleagues are the ones who do several things pretty well instead of one thing really well.

Large gaps in employment don’t mean what they used to. First, if the employment gap was voluntary and the applicant did something interesting, it shows that they value learning and can deal with uncertainty. Second, if the gap was involuntary, the applicant knows how to overcome the adversity of not having a job and will value one much more than someone else.

For a long time, the corporate world was all but obsessed with enforcing strict rules on candidate’s resumes and cover letters. To me, these standards are not only worthless, but counterproductive. When I’m looking for candidates, I WANT to see their personality spill out. So long as they are not off the wall, a little bit of weirdness assures me my candidate is genuine and honest, which is key.

While some might consider it clutter to include volunteer work on a resume, I find it to be a useful subject to speak about. More often than not, it shows a candidate’s ability to prioritize, juggle multiple roles, and commit to a cause they believe in. Seeing someone commit to an idea, group, or cause they believe in means that, just like an entrepreneur, they can work with others toward a common goal.

Some would view showing humor in a job application as a negative. It can certainly be seen as unprofessional. However, I like people to be who they are and to take some risks. At a small company, you need people who are willing to make a mistake here and there. Putting yourself out there with a little well-placed humor is a worthwhile risk, and it will often get you an interview.

I like it when potential employees say they work better alone. They know themselves and are not afraid of saying so. I know they will be upfront with me, and I also know how to deal with them going forward.

Many times when we see people who are passionate about fields that are not directly relevant to a job position, we consider that a red flag, but that should not be the case. People who are passionate and have pursued a different profession or area can be more resilient, have more drive, and be more aware of challenges.

I’d rather see a candidate right out of college with a lower GPA but great internships and lots of side passion projects than a candidate with a higher GPA and a double major. I love seeing real-world experience.

When I ask a candidate, ‘What was an area for improvement for you?’ when referring to a previous job, I actually want to hear an answer. Candidates who weasel their way out of providing a concrete example of where they could have improved are very hard to get a read on. I’d rather know for sure what your weakness is (it makes you more human) than to be uncertain of how you’re going to behave.

Many may think that an individual having more than one job means that they are unfocused or simply way too stressed. I see it as a strength, as proof that the candidate can multitask, stay successful and responsible in multiple settings, and wear many hats at once. It shows that they will be able to handle many tasks successfully within my company.

Whether it’s their failed business or a bad GPA during a time of personal hardship, an employment history that contains one failure makes for a great candidate for employment. Having lived through failure and overcome it gives a person perspective and self-confidence. Ideally, it also gives them compassion for others who are experiencing difficulty. These invaluable qualities can't be taught.

I prefer to see a diversity of thought, experience, and achievements. Our business model requires us to think differently about the problems that will (future), are (presently) and have (past) confronted small businesses. Candidates who can draw on lessons learned in other fields of endeavor sometimes provide the most innovative approaches to difficult and persistent problem sets.

Some employers view job hopping as a negative thing. But given the number of jobs I had before I was 27, I can relate to people who have had multiple jobs at a young age. If a person is in this situation, it tells me she is not willing to settle and is trying to discover her true passion. As an entrepreneur, you do not settle until you discover your passion. Then you pursue it with all you have.

I enjoy working with those who love what they do, even if they don’t have a formal education in that, as their passion and capabilities can substitute it. They are more open-minded and easier to adapt to change. If someone has the ‘meraki’ to work on something as amateur or hobbyist and decides to turn it into full-time job, this indicates a strong and capable personality, and it is a huge plus for me.