Oct 1, 2018

Why Businesses Should Hire Entrepreneurial Leaders

Are you a founder who is having difficulty taking your company to the next level? Is your growing company ready for a new executive hire? Perhaps a new CEO or COO? Do you know what qualities to seek in your new top executive?

Entrepreneurial Founders

As an entrepreneurial founder of a business, you have a lot going for you. In the words of Jane Weisman writing in, “Entrepreneurial (founders) know who they are and what is meaningful to them. They have a purpose in life, know why they started their companies and why they lead them. They understand how their businesses fit into their industry and their community.”


Looking Ahead

Entrepreneurial founders also look ahead and are willing to make sacrifices to secure a bright, long-term future for their companies. Take, for example, Amazon founder Jeff Bezos, who is notorious for continually reinvesting in the company.



Additionally, many entrepreneurial founders like Jeff Bezos also project self-confidence. As noted, “Confidence will help you win clients, customers, joint ventures, and even investors, because you’ll have an easier time convincing people you’re worth doing business. Plus, there’s objective evidence to suggest that confident people make better entrepreneurs: one study in Applied Psychology found that successful entrepreneurs showed significantly higher levels of confidence than entrepreneurial students and students not interested in business.”


Entrepreneurial Leaders - Going Beyond the Founders

Yet founders should not be the only people in the company with an entrepreneurial mindset and desire to act. Many experts believe that businesses should hire entrepreneurial leaders across the organization.

These leaders are typically:

  • Natural salespeople
  • Comfortable taking calculated risks
  • Hands-on and have a sense of personal responsibility for the organization
  • Customer-focused
  • Optimistic
  • Question how things can be done better


Entrepreneurial CEOs stressed that an entrepreneurial CEO is willing to innovate and take risks, and the fact that the business climate is always changing means that a leader who is flexible and who looks for opportunities to launch a new initiative, will be the one who succeeds.

Elena Botelho and Kim Powell analyzed data of 2,600 top business leaders for the leadership advisory firm ghSmart. They combined the information from many hours of interviews from their firm and reported the results in their new book, co-authored with Tahl Raz, called The CEO Next Door: The Four Behaviors That Transform Ordinary People into World-Class Leaders.

Among the highly prized behaviors that the authors believed made great leaders were:

  • Decisiveness
  • Adaptability
  • Engagement for impact
  • Reliability

The authors noted that good leaders are excellent decision-makers, and entrepreneurs often have had a great deal of practice in making decisions quickly that have large ramifications.

The fact that some leaders are more adaptable than others is important, too, because entrepreneurial executives do not become attached to someone else’s way of doing things, but can pivot, change, and satisfy the market and customer.

By the same token, entrepreneurs are always engaged in the problem they are trying to solve, they take responsibility, and they are creative with solutions.

Regarding creativity, You may be familiar with the story of Brian Chesky and Joe Gebbia, who lived in San Francisco in 2007 when a design conference came to town resulting in all the hotels being sold out. Gebbia pitched Chesky on the idea to rent out space for those who couldn’t find a place to stay. The result: Airbnb.

Since then, Business noted, “Airbnb has expanded to more than 34,000 cities and as of 2016, had been used by more than 60 million guests. The company is currently the second-highest valued startup in the U.S. at $31 billion.”

As Inc. magazine recently reported, “Entrepreneurs have more of what it takes to be great executives than leaders who rose through the corporate ranks. But in one key area they display troubling weakness.” They are often not as reliable as their counterparts who came up through the ranks in a company, Inc. observed.


Entrepreneurial COOs

The key to being a good leader is to deliver on promises. Entrepreneurial Chief Operating Officers can help visionary Founders or CEOs who are constantly chasing shiny objects deliver on what they have already committed to. If an entrepreneurial leader falls short on reliability, assign him a wingman who will make sure that “to cross the t’s and dot the i’s.”

For example, we were hired by the CEO of a growing professional services firm to find a new COO to replace one who was retiring. The CEO is very marketing and sales driven - loves coming up with new marketing strategies to promote the business. His new COO has experience developing high performing organizations, and working with dynamic, idea-driven CEOs.



If you are in a company that is small but has its sights set on growing in the next few years, an entrepreneurial leader will serve you best. A leader who understands the big picture, keeps things simple, is creative and innovative, and one who motivates your team well will be able to set your company on the path to success. Once you make your hire, give the new leader the opportunities, the right challenges, and let her show you the value that being an innovative entrepreneur can bring to your business.

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