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The Good, The Bad and The Ugly: Hiring an Ex-Entrepreneur

In Hiring Strategy — by Dave Anderson

Entrepreneurs are unique. They’re a rare breed who reject the stability and comfort of a conventional career to pursue their own passion and ideas.

However, many of them don’t stay independent forever. Success, failure or other life milestones can motivate an ex-entrepreneur to dust off their resume and start applying for jobs.

If you’re a hiring manager, you’ll have a tough time figuring out what to make of these candidates. On the surface, someone with leadership experience will be a great addition to your company. But as you dig deeper, you might find they lack traditional qualifications, such as advanced degrees and minimum years of experience. And you’ll also wonder how these free spirits will adjust to the rigid structure of being an employee.

Ex-entrepreneurs make great leaders

In the most basic sense, we hire for two types of roles – leaders and contributors. Leaders take on broad problems by creating a detailed strategy. Contributors use specialized skills to carry out the different parts of the strategy.

Ex-entrepreneurs are great fits for leadership roles. They’re skilled at figuring out “hacks” or creative ways to solve the complex problems businesses face. Traditionally-trained managers turn to the same prescribed methods when coming up with a strategy but former entrepreneurs are accustomed to thinking outside the box. If your company strives to be different than its competitors, adding leaders with entrepreneurial backgrounds could be just what it needs.

Ex-entrepreneurs are also experienced at building and managing teams. They know when it’s time to bring a contributor on board and what qualifications the hire will need to have. A strategy is useless without skilled people to execute it and former entrepreneurs know exactly what it takes to accomplish their vision.

If you decide to hire an ex-entrepreneur, let them do what they do best. Give them the freedom to be creative, hire their own people and go against the grain from time to time.

Ex-entrepreneurs make terrible contributors

Ex-entrepreneurs, by their very nature, make for poor contributors. They might have the necessary skills for a fixed role but they’re not used to doing the same thing each day. And expecting them to do so isn’t the best use of their talent.

While you should encourage leaders to think outside the box, you need contributors to follow set processes. This expectation can drive an ex-entrepreneur mad since they’re wired to look for more efficient ways to get things done.

This isn’t to say all former entrepreneurs make for bad contributors. Many of these candidates may have realized they’re not cut out to be a leader and are seeking a more structured role. You’ll figure out their exact motivations as they progress through the hiring process.

Hire smart and hire successfully

Effective hiring starts with defining the objectives for the role you need to fill. You then get to know each candidate and select the person who is most qualified and the best fit.

Unfortunately, making sense of an ex-entrepreneur’s qualifications is tricky. They often lack the common indicators of skill and experience we’re used to relying on, like advanced degrees and experience in supportive roles.

You should forgo hard and fast qualifications when considering an ex-entrepreneur. Let’s say you’re seeking a Head of Business Development and receive an application from the founder of a successful e-commerce site. They probably don’t have the 10 years experience the job description calls for but do know how to build beneficial business relationships. Let them talk about how they grew their business and what ideas they have for business development in your company.

Even if you find a brilliant ex-entrepreneur who is cut out to be a great leader, you’ll question where their heart is at. Will they stick around for the long haul or quit to pursue another endeavor? Determining a candidate’s passion is always difficult, regardless of their work history. Ask them why they left their company and about their future career plans. Look for sincerity and you’ll be able to make an educated assumption on where their passion lies.

Ex-entrepreneurs are not all the same

Sure, most ex-entrepreneurs are smart, creative self-starters who aren’t afraid to take a risk. But at the end of the day, they’re people like you and me. Some make for good employees and others don’t. Trust your hiring process and you’ll find people from all different backgrounds who can move your company forward.

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