4 Things Recruiters Should Know About Hiring Entrepreneurs

September 23, 2014

There’s a debate in the hiring community about whether entrepreneurs make good hires.

These leaders look great on paper but can have trouble adapting to larger organizations. First and foremost, entrepreneurs are difficult to retain because they’ll likely want to start another company. Second, there’s a perception that entrepreneurs aren’t trustworthy – that they’re more likely to spend more time chasing their own business ideas than furthering their employers’ objectives.

These concerns are valid but they’re far from universal truths. Entrepreneurs make great hires for roles that involve risk and ambiguity. Their experiences can help established organizations explore new opportunities, challenge outdated assumptions, and most importantly -- avoid failure. In other words, entrepreneurs have the potential to be your best hires but you need to make sure that you’re matching them to the right roles.

Here are 4 things that recruiters should know about hiring entrepreneurs:

1. Entrepreneurs are mission and vision-driven

What This Means: Entrepreneurs tend to care very little about titles, daily responsibilities, and ‘on-paper’ job descriptions when choosing their roles. They’re more interested in the ‘why’ of a job, as well as the ability to make the biggest possible impact. They’re interested in how their employer’s values align with their own, and they’re constantly looking at an organization’s ‘big picture’ of how finance, operations, sales, marketing, and engineering come together.

Pro: Entrepreneurs will constantly look for ways to improve your company’s processes based on past successes and future opportunities. They have the potential to help their employers avoid major mistakes and will ‘do whatever it takes’ to achieve results for one reason alone -- because they care about the values that an organization represents.

Con: Because entrepreneurs are so mission-driven and vision-oriented, they’ll often become frustrated with the corporate processes and rigorous structure that large, high-growth companies need to succeed.

What recruiters can do: Gauge your candidates’ patience levels. Ask entrepreneurs how, in the past, they have handled a potentially slow-moving or bureaucratic process. Learn about the tradeoffs that they have had to make between their teams’ day-to-day activities and ‘the big picture.’ Top candidates will be self-aware enough to recognize how important it is to keep their personal ideologies balanced with the steps they need to take to finish a product.

2. Entrepreneurs like ambiguity

What This Means: Entrepreneurs thrive on the opportunity to launch new initiatives in environments of extreme uncertainty. They enjoy the process of bringing a new product to market or testing out a new idea. They enjoy forging their own paths and will constantly seek out new challenges.

Pro: Entrepreneurs most likely will focus on forging their own path within your organization and also proactively seize opportunities to make meaningful contributions without being asked.

Con: Some entrepreneurs who thrive on ambiguity will absolutely hate structure -- which means that they won’t find success in highly-regimented team environments.

What Recruiters Can Do: Screen for ‘workflow fit.’ When recruiting entrepreneurs, it’s important to see whether they are the right fit with your team’s culture in terms of information-sharing, approvals queues, and process creation. All companies have different levels of structure, and it’s important to assess whether the entrepreneur’s core strengths -- the ability to navigate ambiguity -- align with your existing team’s existing processes.

3. Entrepreneurs are risk-takers

What This Means: Entrepreneurs thrive on the opportunity to run experiments and explore new business opportunities. They’re not afraid to jump into an initiative that might fail -- because they’ve already done this multiple times. They know that trying is the first step to success. They aren’t afraid to fall down.

Pro: Since entrepreneurs are optimists who see risks as opportunities, they will be open to running experiments and testing businesses hypotheses that others in your company might be afraid to try. They’ll roll up their sleeves, get their hands dirty, and dive into any challenging task -- head first.

Con: Entrepreneurs may clash with cautious or risk averse teams that aren’t open to experimentation -- they need the support, encouragement, and infrastructure of an innovative environment to succeed. Not to mention, drastic risks often aren’t worth taking -- it’s entirely possible that an entrepreneur will make an irreparable mistake.

What Recruiters Can Do: Talk to candidates about their decision-making processes. Key hires will demonstrate an ability to balance risk with caution. Ask for situational examples that illustrate an ability to complement an existing team.

4. Entrepreneurs sometimes move faster than your company can keep up

What This Means: Entrepreneurs are fascinated by exciting new opportunities, product ideas and solutions. They have a hunger to make decisions and execute quickly.

Pro: Entrepreneurs have a talent for getting things done and will circumvent any barriers in their way. They are relentless in their pursuit of their goals and can help your company move faster.

Con: Entrepreneurs can be very intense people who move too fast for your organization. The process of waiting -- for development resources, for instance, will only frustrate them. They may be unwilling to slowdown or have unrealistic expectations about the needs of a larger organization -- to operate at a steady pace and pursue growth slowly.

What Recruiters Can Do: Screen for tempo and the ability to adapt. Ask situational questions that illustrate whether the entrepreneur will be happy with the speed of existing operations.

Final Thoughts

The process of recruiting entrepreneurs is far from black and white. These individuals can add immense value to existing organizations and teams -- but they can also be a total mismatch with existing processes and workflows. For the rewards of hiring an entrepreneur to outweigh the potential risk, recruiters must evaluate the importance of innovation within their organizations.

To thrive and to add maximum value, entrepreneurs need to be able to create new solutions and processes -- to challenge existing processes to forge new paths. In other words, your company needs the right environment -- one that embraces risk and experimentation --  for entrepreneurs to succeed.

* image by Lifehack.org

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