5 Tips for Hiring Entrepreneurial People

Feb 3, 2015

Screen Shot 2015-01-26 at 3.34.42 PMHiring entrepreneurial people can do wonders for your company. As a manager, it would be foolish to assume you can do everything and have all the right answers. You can’t be an expert on marketing, product, engineering, sales, business development, etc. The beauty is that if you work with entrepreneurial people, you don’t have to.

Entrepreneurial people are those who can:

  • Work with limited resources
  • Enjoy figuring out a solution without a rulebook
  • Overcome any challenges or setbacks

Entrepreneurial people help make business decisions, strategize, and put it quite simply, “figure it out with you.” It is much more beneficial to have more brains tackling a problem rather than one.

But hiring entrepreneurial people isn’t easy. To do it: 

Determine that you actually need someone entrepreneurial.

In theory, hiring entrepreneurially inclined employees sounds ideal no matter what position you are trying to fill. Who doesn’t want a go-getter with need for little supervision?

However tempting, you must be aware of the type of role that you need. Hiring an entrepreneur for a role that does not necessarily need entrepreneurial tendencies can end in disaster.

If you are an early startup, you want to hire an entrepreneur. If you need to build out a team, you want to hire an entrepreneur. If you need data entry help, you shouldn’t hire an entrepreneur.

If you do this wrong, you’ll waste hours trying to find this person or you’ll get lucky and find someone but he/she will probably leave soon. Either way, you’ll be left at Square 1.

Be visible in the right places.

As a recruiter, you need to know where to go to find the entrepreneurial people in your industry.

In tech, a lot of entrepreneurial people seem to go to AngelList. Also, entrepreneurial people tend to go visit any sites that talks a lot about startups.

Feel free to get very creative with this tip. For example, Stanford frequently offers a free, online Technology Entrepreneurship course offered at In this course, students form teams and attempt to build a business within a couple of months. is not a recruiting spot; it is an educational site. But those who take this class are obviously interested in entrepreneurial roles and tasks. This could be a good starting point to find potential candidates.

I would stay away from more traditional job boards like Monster, Indeed, or SimplyHired. They are great for certain positions, but not this.

Network and reach out.

Entrepreneurial candidates are few, but the demand for them is high. It is difficult to find one that doesn’t already have a job or isn’t wanted by companies. To find the best talent, you are going to have to be proactive.

Go to meetups, be part of an entrepreneurship class, ask your friends for referrals, etc. Seek out what events are meant for entrepreneurs and go there. By being part of various networks, you will increase your visibility and increase your chances at hiring.

Determine that they are, in fact, entrepreneurial.

So let’s say you find someone who could possibly be a good fit. How can you be assured they will meet your expectations?

There are probably thousands of theories on how to determine whether someone is entrepreneurial. There’s no one right answer, but I ask myself three things:

Have they taken initiative in the past?

The best indicator that someone is entrepreneurial is that they have shown some form of initiative in the past. They don’t have to have necessarily founded a startup, but you should see signs that they are self-starters. Did they organize an event that was not in their job description? Did they figure out a new and efficient way to go about their jobs?

How do they overcome challenges?

You hire entrepreneurial people to help you figure out obstacles that few have attempted and succeeded. There are going to be failures and challenges. If that deters them, stay away.

Do they seem confident?

People who can solve problems know that they can solve problems. But don’t mistake confidence for arrogance. They are poison to organizations.

Once you hire them, leave them alone.

In economics, “laissez faire” means you “let them do.” Proponents believe that individuals should have the freedom to choose what is best for them. Less government is better government.

I would argue the same for entrepreneurs. When you finally make an entrepreneurial hire, you may be tempted to give them a set list of responsibilities and a to-do list. This is a mistake. Entrepreneurs thrive best when they are left alone to figure things out. Let them make mistakes, let them come up with their own strategies. This is what you hired them to do and that is the only way you’ll optimize their skills. There is going to be a learning curve, but it is best for the future.

Lastly, hiring these types of people is not easy. It takes effort, perseverance, creativity, and a little bit of luck. I guess you can say, you need to be a little entrepreneurial yourself.

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