Seven Interviewing Tips to Identify Entrepreneurism in Job Candidates

Don Tennant
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5 Ways to Kick-Start Employee Energy

It’s graduation season, which means it’s also job candidate interviewing season for IT professionals. One of the qualities I’m increasingly hearing IT pros say they’re looking for in new hires is an entrepreneurial spirit, because such a spirit is indicative of self-confidence, adaptability, and devotion to an end goal. So how do you go about spotting that quality in prospective employees?

Michael Houlihan and Bonnie Harvey, coauthors of “The Entrepreneurial Culture: 23 Ways to Engage and Empower Your People,” have come up with a list of seven tips to help answer that question. Here they are, in no particular order:

Ask them if they're willing to bet on themselves. Entrepreneurs don't have any income unless they are constantly satisfying their customers, and they're constantly looking for ways to increase their income, profits and growth. In other words, they bet tomorrow's paycheck on today's ideas and effort. Ask candidates if they want to get paid on attendance — that is, receive a salary — or if they're willing to bet a portion of their compensation on their own performance. Seek out individuals with self-confidence and demonstrable self-reliance, who know they can add significant value. Of course, this means you'll need to implement some kind of profit-sharing plan if your company doesn't have one already.


Pay attention to body language. Watch how each candidate moves. You can do this unobtrusively by asking them to get a file from the next office or a cup of water from a nearby table. Do they lumber aimlessly, take their time, shuffle back slowly, flop down into the chair, and lean on their elbows? Is their posture like a question mark? Or do they move with hustle, determination, and purpose? Keep in mind that when people sit erect and lean slightly forward, they're indicating engagement and interest.

Talk about their mistakes. Ask candidates to describe the biggest mistake they ever made professionally, and more importantly, what they did about it. In particular, discover whether they took responsibility, fixed the mistake quickly, and went on with their project, or if they blamed others and were "victimized." Successful entrepreneurs know that blame is disempowering, while doing what can be done to prevent reoccurrence is staying in control. Ask follow-up questions to see how well each candidate analyzed what happened, and whether they took steps to prevent the same thing from happening again. Entrepreneurs can't afford to make the same mistake twice. They build their successes on the backs of their mistakes.

Look for evidence of resourcefulness. Ask job seekers how they solved a professional problem when they lacked the time, support, or funds they needed. Listen for evidence of how they used their imagination, asked for help, and thought outside the box. Specifically, figure out if they identified, repurposed, and used unlikely resources to achieve their goals in spite of the obstacles. Take note of how they rephrased the problem, saw the bigger picture, and enlisted the help of strategic allies who would also benefit from the solution. See if their solution solved more than one problem. Entrepreneurs know that the ball is always in their court.

Gauge their preparedness. Does the candidate expect you to ask all the questions? Do they just react to your initiatives? Do they wait for you to tell them about your company, its goals, its successes, and its challenges? Or do they ask you questions? Candidates with entrepreneurial DNA will treat you like a prospect for their services. They think of everyone as a customer for them, their service, or their product. They know that the best sales pitch is, “I can help you sell your product,” and they can't do that unless they have thoroughly researched your company in preparation for the interview. Entrepreneurial candidates will be familiar with your products, your challenges, and your history. They'll come to the interview with a pen and notepad and a list of questions.

Figure out how they work on a team. Contrary to popular opinion, entrepreneurs are not loners. Realistically, they know that they must build, depend on, and be an essential part of a team. This requires respect for how each player contributes to the overall success of the company. Look for candidates who show an interest in understanding all the jobs, procedures, outsourced services, and suppliers that keep the customer loyal. Ask them how their last job fit into their company's big picture. Ask them how they worked with their teammates and improved communication both inside and outside their previous company.

Test their attentiveness and organization, and see how they perform under pressure. During the final portion of the interview process, tell the candidate more about what the job entails, who they will be working with and why, how the job supports the customer experience, how your company is organized, and what performance expectations are. Be sure to include how the funds get from the ultimate consumer to the company to cover their paycheck. If this sounds like a large chunk of information to convey, well, that's the point. After your explanation is finished, ask the candidate to write a one-page summary of your company, the money trail, how they will be working with their teammates, and why they qualify for the job. Then, tell them it's due by 5 p.m. the next day. This summary will tell you volumes about the candidate's comprehension, organization, communication, and ability to hit a deadline. These are all attributes of an entrepreneur.

A contributing writer on IT management and career topics with IT Business Edge since 2009, Don Tennant began his technology journalism career in 1990 in Hong Kong, where he served as editor of the Hong Kong edition of Computerworld. After returning to the U.S. in 2000, he became Editor in Chief of the U.S. edition of Computerworld, and later assumed the editorial directorship of Computerworld and InfoWorld. Don was presented with the 2007 Timothy White Award for Editorial Integrity by American Business Media, and he is a recipient of the Jesse H. Neal National Business Journalism Award for editorial excellence in news coverage. Follow him on Twitter @dontennant.



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