The Interview Question to Hire for an Entrepreneurial Culture

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Jan 3, 2023

Business articles are replete with admonitions for companies to embrace a more entrepreneurial culture. Move faster, innovate more, and disband hierarchies, they implore. Those articles aren’t wrong, per se.

Research shows that more than a quarter of people desire an entrepreneurial culture. Additionally, workforces with this culture have higher employee engagement scores than any other kind of company culture.

But if you’re going to hire people successfully to fit that culture, you need to know two things: First, do you really have an entrepreneurial culture? And second, what’s the best interview question to use?

An entrepreneurial company culture, also known as an Enterprising culture, is a type of workplace that values and rewards talent and achievement. In this environment, internal competitions that showcase creativity and intelligence are common. Ideas are judged based on their merit, regardless of the status or seniority of the employee who came up with them. This culture is characterized by regular change, and employees are expected to adapt and thrive.

Leaders in this culture foster a sense of adventure and encourage creativity among employees. These leaders may use competition as a way to motivate and drive productivity, and they value merit and performance over personal connections or referent power. One of the more attractive aspects of this type of organization is that it places a high value on innovation, which can make employees feel more fulfilled and satisfied in their jobs.

You can probably see why so many desire this culture; for smart, innovative, and ambitious employees and leaders, it’s a great environment to grow and succeed. But be forewarned, even though entrepreneurial cultures are desirable, they’re not always easy to achieve. 

The recent study “Managers Don’t Love Innovators” revealed that while 20% of people say their company always prefers people who are bold thinkers, 30% say their organization never or rarely wants bold thinkers. 

Assuming you want to hire people to fit this culture, the most effective question to ask candidates is, “Could you tell me about a time you didn’t agree with your boss?”

What you can’t do with this question is add words to the end like, “and how did you resolve that disagreement?” or “and how did you overcome it?” The report “6 Words That Ruin Behavioral Interview Questions” shows that most interview questions nudge candidates to talk about their successes and gloss over their failures. But when you’re hiring for the entrepreneurial culture, with all its change and innovation, there are going to be failures and disagreements. The key to employee success is the extent to which they can first acknowledge and, second, overcome those failures and disagreements.

Let’s look at some real-life responses to the question, “Could you tell me about a time you didn’t agree with your boss?”

Candidate A Response:” My boss and I had lots of disagreements, but he usually won. His ideas about feasible timelines and deadlines were totally unrealistic. He wasn’t the person actually pulling and mining the data, of course, so his ideas on how much time and effort it took to create a good work product weren’t realistic.”

Candidate B Response: ”Disagreements with a boss can happen in any environment. If that were to happen to me, and it was an appropriate setting, I would very tactfully express my point of view.”

Candidate C Response: ”We were preparing a presentation for a potential client, and I didn’t agree with how my boss was messaging what made us better than the competition. I took it upon myself to rework the slides and then gave my presentation to my boss for review. I’ve found that actually showing my boss both versions is helpful in reaching the best decision. And in this case, my boss agreed that my message was more persuasive.”

You can see that Candidate A has a dose of combative negativity that is unlikely to mesh well in a fast-moving entrepreneurial culture. Candidate B’s hypothetical response avoids giving a specific example, which may be masking their discomfort with disagreements or a lack of experience with the situation. Only Candidate C’s response suggests comfort with disagreements and, even better, experience with handling them calmly, quickly, and professionally.

If you really do have an entrepreneurial culture and you’re committed to selecting only those candidates who fit, this simple question will quickly narrow the pool of people with the right attitude.