Edward Jones CEO discusses the path to successful leadership (2:48)

Many people, during the course of their careers, will find themselves wondering whether they are truly spending their time doing what they want.

Edward Jones managing partner (the firm’s official term for its CEO) Penny Pennington recently explained how she grappled with that question during her own professional growth.

Related: Why you should speak to your financial advisor when markets are volatile

Pennington stopped by the New York Stock Exchange to discuss her thoughts on the subject in an exclusive interview with TheStreet’s Editor-in-Chief Sara Silverstein. (The video appears at the top of this page.)

“I’d like to hear a little bit about your journey to CEO, and mostly when in your career did you realize that CEO was an attainable goal for you?” Silverstein asked.

Pennington provided some background on her career path and then likened her experience to an iconic scene from a 1939 film.

“I’ve been in financial services since 1985, so I’m coming up on a 40-year career,” Pennington said. “I was in commercial banking for 14 years and I found Edward Jones in 1999. I don’t know if your viewers have seen the old version of The Wizard of Oz, but when it goes from black-and-white to Technicolor, that’s what happened in my life.”

“When I came to Edward Jones, I was a practicing financial advisor for six years, as were all of my predecessors,” she continued. “Our previous managing partners all started as financial advisors. What that means is we know what it feels like to be in the seat to build trust with families and to build a practice.”

Taking risks outside your comfort zone

Pennington discussed the number of positions she has held at the financial services company and explained why she believes that is meaningful.

“I’m on my fifth role since I came in, in 2006,” she said. “The reason that I say that is I think it’s very important for all of us as professionals to be what Satya Nadella (the Microsoft CEO) called ‘learn-it-alls,’ not ‘know-it-alls.’ To take what feels like a risk, to step outside maybe your area of technical expertise or a particular comfort zone and to go into a place where you’re going to learn.”

“And the world that we live in today, learning adaptability, dealing in ambiguity, building teams, making decisions with incomplete information — that’s what leadership is,” Pennington explained. “And then rallying a team through purpose to be able to really make it make a big difference.”

Pennington then circled back to the original question Silverstein had posed.

“And so you asked, you know, when did I know, quote-unquote, that this might be an attainable goal,” she said. “We call Edward Jones an opportunity factory. We create opportunities for our clients. As a result, we have opportunities as talented professionals.”

Edward Jones Managing Partner Penny Pennington talks with TheStreet at the New York Stock Exchange.

TheStreet

A key to success is getting ‘comfortable being uncomfortable’

The Edward Jones managing partner emphasized how she learned to embrace risk.

“As I was moving through our organization and learning new things, I realized about 15 years ago that my success was going to be dependent on my ability to take those risks and move into new places,” Pennington said. “So what I say to people is get comfortable being uncomfortable and raise your hand, especially for the things that your gut says, ‘I want to say no to this!'”

Pennington said she believes that these are precisely the challenges it is important to take on.

“Raise your hand for those things,” she said. “I was raising my hand to say, put me in places where I can take that risk and be supported by my organization and my teammates so that I can learn and grow. And as far as I can go in doing that, that’s what fires me up.”

“That’s a good day for me, is when I’m feeling uncomfortable.”

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