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4 Leadership Lessons from Self-made Billionaire CEO Sara Blakely

Don't be intimidated by what you don't know. That can be your greatest strength and ensure that you do things differently from everyone else.

–– Sara Blakely, CEO, Spanx


When we think of the most senior business leaders, we often conjure mental pictures of stodgy chief executives spewing numbers and corporate speak.
 
It’s unfortunate because leaders like these do not connect with their most important stakeholders -- employees, investors, partners, and others. By hiding behind the veneer of business babble, they deny people what they want the most from their leaders: authenticity.
 
This is why one of my primary missions in working with CEOs and other senior leaders on their presentations is to help them find and share their truth – their authentic selves.
 
Admittedly, there are many paths to success in business, but the best journeys are authentic.
 
It’s not an easy path. It takes determination and courage to push past the fear of being so real, but those few who are willing to do so become truly great leaders.

Spanx CEO Sara Blakely
A great example of this is Sara Blakely, who grew up wanting to be a lawyer like her father but was unable to obtain a high score on the LSAT. After trying her hand at stand-up comedy, she sold fax machines door-to-door before starting her company, Spanx.

(If you are not familiar with Spanx, the company says it sells “the largest selection of slimming intimates, body shapers, hosiery, apparel, and the latest innovations in shapewear for men and women.”)

Blakely is America’s youngest self-made female billionaire, according to a 2014 Forbes profile, which estimated her privately held company earned "over $250 million in annual revenues and net profit margins estimated at 20 percent.”
 
The origin story of Spanx is that Blakely was going to a party and didn’t want panty lines to show through her white pants, so she cut the feet off pantyhose and later patented the idea. While she possessed little knowledge about fashion or retail, in 2000 Blakely, at age twenty-seven, began her shapewear and legging company, investing her life savings of $5,000.
 
In 2013, Blakely became the first female billionaire to join The Giving Pledge, the campaign founded by Melinda and Bill Gates and Warren Buffett, which has the mega-wealthy pledge to donate the majority of their wealth to philanthropy.
 
Today, this mother of four young children continues to be an advocate for women through her Sara Blakely Foundation, which supports women in education and entrepreneurship.

Blakely’s path and approach offer unique leadership lessons:
 
1) Embrace failure
One of Blakely’s biggest lessons is to embrace failure, a lesson she learned as a child. In an interview with Entrepreneur, she talked about how her father helped shift her mindset:
 
My dad encouraged us to fail. Growing up, he would ask us what we failed at that week. If we didn't have something, he would be disappointed. It changed my mindset at an early age that failure is not the outcome, failure is not trying. Don't be afraid to fail.
 
Most of us don’t enjoy failing, even go to great lengths to avoid it. But the real failure lies in not trying. Instead of seeing failure as an outcome, try to view failure as evidence that you tried. As Thomas Edison said, “I have not failed. I’ve just found ten thousand ways that won’t work.”
 
One of the ways Blakely leads her employees is through sharing her mistakes and encouraging her employees to do the same. Employees share their mishaps and blunders during these “oops meetings,” which routinely end up turning into humor-filled anecdotes.
 
While speaking at the Stanford School of Business, she noted: “If you can create a culture where [your employees] are not terrified to fail or make a mistake, then they’re going to be highly productive and more innovative.”
 
Blakely is especially curious about how the fear of embarrassment can hold power over us. If we intentionally acknowledge our mistakes and find humor in them, the fear loses power.
 
2) Don’t take yourself too seriously
New employees at Spanx are required to do standup comedy as part of a training boot camp. It encourages them to feel less intimidated and to let go while embracing fun as part of the Spanx experience. “I don’t subscribe to the fact that you have to act serious to be taken seriously,” Blakely said.
 
In honor of that playfulness, when Blakely first started Spanx, the packaging said, “Don’t worry. We’ve got your butt covered.” She has continued to keep her company – and its products – lighthearted and fun.
 
Blakely advocates using humor to capture a potential client’s interest. She has noted that even the name of her company makes people laugh.
 
Her previous experience as a saleswoman came in handy when she was growing Spanx. “When I cold-called to sell fax machines door-to-door,” she said, “I learned very quickly that if I could make somebody laugh or smile I’d get another thirty seconds before they’d slam the door in my face.”
 
While you may not be cold-calling in your day-to-day life, using humor can break the ice in most conversations. It helps to put people at ease and bring down their defenses.
 
Humor can also be a powerful leadership strategy, according to new research from Harvard and Wharton. People attribute confidence to those who are brave enough to tell a joke.
 
3) Be relentless
Sara spent two years trying to convince manufacturers to take a chance on her before a mill owner in North Carolina agreed to help her. He had been convinced by his daughters to take on this invention, which they told him would be a “goldmine.”
 
“I must have heard the word ‘no’ a thousand times,” she said. “If you believe in your idea 100 percent, don’t let anyone stop you! Not being afraid to fail is a key part of the success of Spanx.”
 
Blakely didn’t let the word “no” deter her from pursuing her vision. She continued to push forward until she heard “yes.”
 
4) Break the rules
While speaking to Stanford students, she recalled how she used a rogue tactic to get noticed at Neiman Marcus. Her products were in the back of the store, where few customers frequented. She bought envelope dividers and put Spanx around the registers, promoting greater visibility.
 
After management realized they hadn’t approved this tactic, the head of Neiman’s allowed her to keep doing it because it was so successful. From turning the undergarment industry on its head to trailblazing new paths for women, Blakely has remained innovative and forward thinking.
 
How about you?
 
What’s your view of “failure”?
 
Do you encourage risk taking with your team?
 
How could you take yourself less seriously?
 
Do you have an “oops” moment that you might share with others?

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