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How HR Leaders Can Become More Entrepreneurial

You don't have to be part of a tech startup to take professional risks.

A business woman standing next to a light bulb.
​​Illustration by James Smallwood for HR Magazine.

​Entrepreneurship is lionized in our culture now. Everywhere you turn, you see headlines about tech firms that turned from someone’s solo vision into a global success story seemingly overnight. But the common tendency to equate entrepreneurship with startups or Silicon Valley does us all a disservice. 

In fact, every HR leader can benefit from embracing entrepreneurial thinking. It’s not about raising venture capital or creating a hot new app. It’s about pushing ourselves to take risks and think innovatively. Here are five key lessons to keep in mind to raise the bar and move your organization forward. 

Don’t stay in your lane. The best HR leaders “lean in on the business holistically, not just the ‘people’ side,” says Mark Legestee, vice president of global talent and organization development for Yum! Brands Inc. based in Louisville, Ky., which operates Taco Bell, Pizza Hut and KFC restaurants worldwide. “I think it’s critical for HR leaders to demonstrate deep know-how of the business, show initiative to drive the business and have courage.” 

When HR leaders understand the overall business context, they can relate better to their colleagues in other departments and gain respect and influence. You can amp up your knowledge by asking people across the organization about the issues they’re facing, networking through professional societies and social media, reading widely on business and leadership, and getting information on the ground from clients and customers. 

For example, Legestee recently spent time in Dubai and India, where he visited business leaders across all operational functions from the three brands and met team members in restaurants. Even if you’re not in a position to globe-trot, take the initiative to meet people who extend beyond your day-to-day circle, both within and outside the HR community.

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Embrace constraints. If you’re like many HR leaders—particularly solo practitioners—you likely don’t have the time, budget or staff you’d prefer at your disposal. While that can be frustrating, it can also spur innovative and entrepreneurial thinking. Research shows that when people’s resources are limited, they tend to come up with more creative options for solving problems than they would otherwise.

That certainly rings true for Joy Brand-Richardson, vice president of professional development for the JCC Association, which runs Jewish Community Centers across North America. She notes that in smaller JCCs, it’s not uncommon for the HR function to be performed by an office manager or executive administrator. 

“In those cases,” Brand-Richardson says, “people need to be extremely entrepreneurial by setting up processes and programs for staff to follow and imagining how they might incorporate some of what is done in larger organizations into their smaller shops.” This prompts staffers to learn from colleagues in other organizations and to explore partnership possibilities and new ways of leveraging vendor and volunteer help. 

Ask the hard questions. Entrepreneurial leaders must be willing to face facts and ask uncomfortable questions of both themselves and others. “We specifically talk about courage,” Legestee says. “What courageous actions should you take to impact the business? What should we do that we’ve never done but always wanted to?” 

Sometimes pursuing a promising new direction means abandoning a long-cherished program that’s no longer a strategic priority, and that can be politically fraught. In the moment, the trade-offs might not seem worth it. But focusing on the future can help you to get in the right long-term frame of mind to make tough decisions.

“Annually, we meet to plan the following year,” Legestee says. “In that meeting, we usually start by imagining what the business may be like in five to 10 years, and then we push ourselves to implement ideas that get us there faster.”

Reward entrepreneurial employees. The concept of “thinking entrepreneurially” often gets lip service, but, in practice, some executives and managers still disapprove of employees who pursue side ventures. The best leaders, though, see things differently. Consider the case of Lenny Achan, a nurse at Mount Sinai Hospital in New York City who ultimately became head of communications for the entire hospital system after following a very nontraditional career path. How did he do it? He became fascinated with smartphone apps and decided he’d learn how to develop them on his own time. He ultimately built and launched two. 

The concept of “thinking entrepreneurially” often gets lip service, but, in practice, some executives and managers still disapprove of employees who pursue side ventures.

His boss found out and asked to meet with him. Achan was terrified because he thought he might have inadvertently violated a policy that he didn’t know about. Instead, his boss told him, “We need someone to run social media for the hospital. I think it should be you.” He recognized that Achan’s entrepreneurial instincts weren’t a sign of disinterest in his job—rather, they signaled his ambition and leadership potential. Achan did such a good job running his organization’s social networks that ultimately he was promoted  to run the entire communications program. 

Great leaders understand that entrepreneurial thinking is a skill that, once honed, can be applied very successfully in one’s day job. It’s a way for employees to seek out their own professional development—and your company is the beneficiary. If the executives in your organization don’t see it that way, take the initiative to make the case to them. 

Don’t wait for change—lead it. The workplace is rapidly changing, and successful HR leaders know they can’t wait for change to come to them. When you aggressively pursue opportunities, you shape how the future unfolds. At the JCC, for example, Brand-Richardson recognized that more than half of JCC executives would retire in the next six to 10 years, creating a clear talent development need. 

“I am continuously inventing new ways of providing professional development opportunities for our staff around the U.S. and Canada,” she says. “Our talent management program is an example of how we took a need and created the pipeline for engaging and advancing staff through a training program that values strengths and helps people accomplish goals to grow their professional toolbox.” 

By getting in front of change, her team transformed a potential crisis into an opportunity. You can do the same. 

Dorie Clark is the author of the new book Entrepreneurial You (Harvard Business Review Press, 2017). Her past books include Reinventing You (Harvard Business Review Press, 2013) and Stand Out (Portfolio, 2015), which was named the #1 Leadership Book of 2015 by Inc. magazine. She teaches at Duke University’s Fuqua School of Business.


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