Leadership Lessons from Prison that Led Me to the Boardroom


Employees who are engaged and invested in their work are getting harder to find. In fact, a recent poll reveals that 1 in 5 Americans actually spend their workdays spreading discontent due to “bosses from hell.” I learned the hard way that true leadership comes from serving others—taking the focus off the bottom line, and focusing instead on investing in human resources.

My unique perspective on the power of serving and caring for team members started when I attempted to embezzle government funds. A subsequent conviction led to five and a half years in military prison. During that sentence, my perspective shifted from selfish to servant, prompting me to live and train as a monk for three years, and finally, to become a social entrepreneur.

Here are 11 tactics I learned along the way to help leaders achieve higher levels of success by consistently serving and inspiring greatness in others:

Focus on developing your influence as a leader.

The qualities that make a great leader are quite different from those that make a good employee. An employee’s worth is judged based on how well she carries out the different tasks in her job description. But, a leader’s worth is judged based on how well she is able to influence the behaviors of those on her team.

The most effective way to build influence with others is to consistently demonstrate that you truly care about them and have their best interests in mind. Herb Kelleher, founder and former chairman of Southwest Airlines, is a great example of how great leaders develop influence. He consistently showed employees how much he cared by doing things like coming in on Thanksgiving Day to help baggage handlers load suitcases onto planes. When he wrote a letter asking employees to find a way to save $5 a day for the second half of a year, he signed it, “Love, Herb,” and employees knew that he meant it. As a result of the influence Herb had built, employees saved much more than $5 a day on average, helping Southwest keep their then-30-year streak of profitability going.

Create a culture of servant leaders.

Can you imagine being able to attract the most talented people in your industry, ensure that they’re fully engaged while they’re at work, and feel confident that they’ll stay on your team for the long haul? What would that do for your organization? A great workplace culture is one of the most important competitive advantages you can possess.

An e-commerce company called Next Jump is a great example of the power of building an organization full of people who are devoted to serving others and serving the greater good. The leaders at Next Jump consistently show how much they care. The company actually does the employees’ laundry for them. But, they also find ways to help employees grow their ability to serve each other and the greater good. The most coveted award at Next Jump is a $30,000 package that goes to the employee who is voted by his or her peers to be the most helpful, selfless person in the company.

A culture like the one at Next Jump produces extraordinary results. In 2012, the company accepted only 35 new hires out of almost 18,000 applicants. That’s a hire rate of 0.2 percent. And, although turnover in the tech space averages around 22 percent, at Next Jump, it’s less than 1 percent. This is despite the fact that highly talented employees there often receive phone calls from other companies offering two to three times the salary they currently receive.

Increase innovation by being more compassionate.

Most leaders are aware of the importance of innovation, but many make the mistake of assuming that creativity and innovation are synonymous. Creativity, which is the ability to generate novel ideas, is not necessary for innovation. Innovation is a function of sticking with and executing ideas—whether new or old—that don’t conform to the status quo. The result is something tangible, useful, and differentiated. So if you want innovation, you need to create an environment where people feel safe to take risks and stick with ideas that deviate from the norm.

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