Are Entrepreneurial Leaders Born or Made?

Generalist vs. Specialist. Innovator or Manager. Emotional Intelligence vs. Data Analytics.


Philip Rowley

Instead of ‘either/or’ in large organizations, management professionals in the most agile firms are hiring people who can develop into entrepreneurial leaders, who have developed a broad set of soft skills. Specialization will get you only so far. 

But where do entrepreneurial leaders come from?

CEOs get the most name recognition, but this kind of motivation and vision has to be nurtured at every level of the organization. The ability to spot opportunities, act in a multidisciplinary way and share credit with a team is a critical factor for success in the fast-moving corporate environment.

People who can walk in another employee’s shoes or who are open minded to new ideas and experiences often possess the soft skills needed to be great leaders. But these people are hard to identify in the hiring process.

HR managers are good at using quantitative metrics to hire people with increasing levels of responsibility in their specialties. But soft skills are tougher to measure.

Generalists and entrepreneurial leaders often wouldn’t be hired into a large company if they came in through the front door. Their value is frequently overlooked or discounted by the quantitative metrics of the resume. Further, they tend not to apply to normal jobs. Like comic book superheroes or Hollywood stars, they may gravitate toward projects via word of mouth and rely on their extended networks.

How can an executive create a firm that attracts the right people?

The environment is important and, specifically, the values that create the environment. First and foremost, hire people who share the organization’s values. You can teach new skills, but you have a harder time changing personal values.

Corporate culture is created through a firm’s employees. Hire people who don’t share the core values of the firm, and that culture will be dysfunctional. Hire people with the right values, and the culture will be agile and adaptive.

Entrepreneurial leaders are generalists.

Start by looking for people with diverse experience and backgrounds. Find the common thread that joins their various work and personal stories. Then go deeper. Entrepreneurial leaders can be identified by a matrix of qualities, achievements and traits. Maybe you know the CEO challenge of taking a prospect to lunch or dinner to see how he or she interacts with a server in front of a boss. Here are other clues:

1. Open minded, eager for new experience

Look for people who seek out new hobbies and who have expert-level skills and certifications in their personal lives or outside their areas of expertise. The generalist isn’t afraid of new challenges, preferring opportunities to learn, especially in new domains.

2. People person, high level of empathy, natural salesperson

Generalists inspire a team around an idea or project, attracting other people with motivation or sometimes a high level of empathy. These people volunteer to get a buy-in when the company rolls out a new initiative or has to change direction.

3. Creativity in problem solving, leading with humility

Entrepreneurial leaders bring an ownership to work and possess a founder’s mentality. They didn’t join an established club in school—they created one and then recruited members. These ideas and initiatives don’t always pan out, but they demonstrate a creativity of thought and a willingness to approach problems from a new angle. The desire to lead is a key source of fulfillment at work.

4. Not afraid of uncertainty

These individuals are more comfortable with risk than others and work toward alleviating risk as they move projects forward. They don’t let risk prevent them from taking on a project in life or at work.

5. Strong professional and personal networks

The ability to network smoothly, to interact with people across many facets of an organization, is a distinguishing characteristic—reputation and experience joined with empathy, or a knack for seeing multiple competing viewpoints as valid. At senior levels, the best leaders will likely come from within an organization because they already have a sense of the politics of the organization and existing relationships. Even at more junior levels, these skills and connections can be developed and honed, including the skill of spotting or training a peer or successor.


Combining these intangibles makes a generalist capable of guiding and growing an organization under even difficult conditions. Partnered with technical leaders and business mentors, the entrepreneurial leader can navigate uncertainty while providing a sense of security and shared mission.

Philip Rowley is executive director of Berkeley Research Group. This column is part of a May 2017 presentation in Toronto on moving from specialized talent recruiting and toward developing leadership skills.