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LUMINARIES Podcast: Leadership Lessons From Shirl Penney

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Many financial advisors who aspire to become leaders of their own firms are undoubtedly born, not made. But that doesn’t mean they have the know-how to be great leaders.

“Most advisors need help around leadership to become a CEO,” Shirl Penney, founder, president and CEO of Dynasty Financial Partners, argues in a podcast interview with ThinkAdvisor.

“A lot of people got into the business because they were passionate about serving clients and being an advisor. Others are excited about being able to operate their own business and to transition from advisor to CEO,” says Penney, a finalist for a 2022 ThinkAdvisor LUMINARIES recognition award in the Executive Leadership category.

What’s the top requirement for being an excellent executive leader? Penney says it’s “having empathy for clients and your team, and [having] a sound vision and ability to communicate that clearly and easily to your team.”

In the interview, he also explores other leadership essentials, such as being an outstanding strategic thinker. “That’s very valuable when,” he says, “you have to make longer term investment decisions. Those become even more critical as the business scales and grows and you have to make even bigger bets.”

“At Dynasty,” Penney continues, “we play a little more chess than checkers: You have to think in- depth. But you have to be dynamic in your management style as well.” Delegating is “an actual skill,” he points out.

“To really accomplish significant things, you have to empower the team and [have everyone] buy into the collective vision and understand their role. [Leaders] who are still trying to do too much on their own are [limited] in getting things done.”

As a teen, Penney was “fascinated by Wall Street” and loved math, he recalls. He picked up information about the financial world by reading magazines that tourists brought with them when they summered in Eastern Maine, where he grew up.

So motivated was he to work in the industry that he bought a suit for $13 from the Salvation Army — Penney was from modest means — hopped a bus to New York City and showed up at Salomon Smith Barney.

Interviewed by the firm, he told them: “I’ll outwork anyone here. Just give me an opportunity.” They did; and he stayed – in a number of leadership roles — for six years and another three at Citigroup.

In April 2008, he left to start his own business   focused on helping independent advisors. Dynasty officially launched two years later and is now based in St. Petersburg, Florida.

“Starting a business in the middle of the financial crisis,” as he puts it, has indeed been Penney’s biggest professional challenge.

What’s the main challenge in the financial services business today? “The industry is facing a talent shortage issue. Whether you are in the brokerage environment, a bank, an independent broker-dealer or in the RIA space, there isn’t anyone doing a tremendous, positive job of attracting talent,” he says.

“That’s an issue we’re all going to have to work together on. As an industry, we have to do a better job to attract more people and diverse talent into the space,” he adds.

As a LUMINARIES award finalist, Penny says: “No leader stands alone with any type of recognition like this.  “[For me], it’s the validation of the incredible work that the great team at Dynasty, our clients, our resource partners and our investors in the business are doing.”

To hear Penney discuss his leadership philosophy and a mix of industry issues, please listen to this insightful podcast.


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