Questions you need to ask when hiring entrepreneurs


In the hiring community, there is a common perception that entrepreneurs are difficult to retain as these free spirits are unable to remain loyal to the rigid structure of an organisation. An entrepreneur is often seen as an individual who is not a fan of a conventional career path; some merely use it as a stepping stone to realise their very own pet projects.

However, according to Harvard Business Review contributor, Chris Smith, there is a difference between hiring an entrepreneur and an entrepreneurial spirit. The fact is, every organisation requires an employee who is a self-starter, one who is actively seeking out for original and creative solutions to make better decisions for the company. In other words, every employer needs an entrepreneurial spirit on their team.

As a hiring manager, you’ll have a harder time not just deciding if you should hire an ex-entrepreneur but how to spot one with a true entrepreneurial spirit. To make things easier for you, we have listed 3 ways that can help you hire wisely and recognise these entrepreneurial spirits:

  1. Discover the motivational factor and the level of patience

Entrepreneurial-spirited individuals are people who are motivated to constantly stay one step ahead, people who are eager to learn, experiment, apply and share. They are the ones focused on the bigger picture, the ones who understand the goals of the company in every aspect and the ones who strive to make the company a better place.

Pro: Having such an entrepreneurial-spirited employee is an asset to any company as the employee will always find ways to create improvements for the company because they care about the visions that the company stands for.

How to identify one: During the interview, ask direct questions such as “What motivates you?” A typical entrepreneur’s answer will usually have a focus on personal achievement and lacks the desire to contribute to the company’s mission; whereas an entrepreneurial-spirited employee will provide answers as to how they will find success and motivation through their role in growing the business of the company.

Con: Entrepreneurs sometimes have a huge appetite to make decisions far too quickly and at times, this creates frustration when things don’t go as fast and as smoothly as they have imagined due to certain rigorous structure that exists in a typical organisation.

How to identify one: Assess the candidates with a situational interview question where you can find out how they would handle a potentially slow-moving execution of their ideas. The perfect entrepreneurial-spirited candidate should be realistic, well-balanced between their ideals and the real world and possess a strong sense of understanding in the way things are handled in a bureaucratic order.

  1. Assess the bold risks and what lies within it

Entrepreneurs in general, are seen as people who love taking risks. This is not entirely true as they don’t just blindly dive in; their ultimate goal is actually to minimise risk at every new attempt they make. That being said, if the need requires them to, they are not afraid of running an experiment with the objective to succeed and discover new solutions, and in doing so, grants them the reputation of being risk-takers.

Pros: Entrepreneurial-spirited employees believe that “with great risk comes even greater potential reward.” Due to their unconventional school of thought and the ability to see risks with optimism, entrepreneurial-spirited employees are the ones who might come up with a breakthrough innovative idea for your company.

How to identify one: A situational interview question can help you gauge if the candidate is not just a risk-taker but a problem solver and is able to create new solutions to tackle difficult issues in the workplace for the benefit of the company.

Cons: At times, entrepreneurs tend to hold strongly onto their ideas and if their ideas are deemed risky to others, this may cause some conflict in the workplace. What’s worse is, if these are ideas that are driven mainly by self-interest or the need to be recognised.

How to identify one: Use behavioural interview question or this; ask the candidate to give an example of the time when the candidate faced a problem in the past and how the problem was solved. From here, you can assess to see if the actions/steps taken were measured and conducted with fair consideration of others and in the interest of the company. The ideal candidate does not blindly execute a mission for personal-gain without considering the risks it brings to his or her colleagues and the company.

  1. Check for work passion and ownership

Entrepreneurial-spirited individuals do not crave for power, or a title or a position. Instead, they are driven by a need to own an initiative, a new idea or the launch of a new product. Their definition of power is different than one who seeks for an authoritative position in a company. They want to be seen as the driving force behind a new invention, not as a dictator.

Pros: The need for an entrepreneurial-spirited employee to create something significant will mean proactive innovation and constant useful contributions being given to your company without the need to even push for it.

How to identify one: To find out if your candidate has the qualities you seek, ask if they have created something significant in their previous company or a founder of an initiative. Such entrepreneurial spirit will never shy away from telling you his or her success stories.

Cons: Sometimes, arrogance and greed could get into the minds of an inventor. In this sense, the entrepreneur may start to think too highly of himself or herself, and start to look down on others, or have difficulty working as a team. In a more severe scenario, autonomy may even be a requisite that the entrepreneur needs to lead the new venture.

How to identify one: Ask questions such as, “What do you take pride in?” or “How would you describe yourself as a team player?” The answer can determine if your candidate is the entrepreneurial-spirited employee that you are looking for or merely a self-centred typical entrepreneur.

It is important to distinguish the difference between hiring a typical entrepreneur and an entrepreneurial spirit. As articulated here, the ability to tell the difference between the two types of entrepreneurs will ultimately bring positive impact to your corporate strategies and add immense value to your organisation as a whole.


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