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Want to build leadership confidence? Fire your workplace villain

After a punch-to-the-gut setback, a high-flying C-Suite executive learned some big lessons in the consistent confidence it takes to be a standout leader. Now she shares her secrets with other leaders.

  • By Mark Gordon
  • | 6:00 a.m. February 26, 2021
  • | 2 Free Articles Remaining!
Courtesy. Heather Monahan says confidence in leadership can come from failing — but then trying again and never giving up.
Courtesy. Heather Monahan says confidence in leadership can come from failing — but then trying again and never giving up.
  • Leadership
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Motivational speaker, podcaster and best-selling author Heather Monahan has developed a niche in teaching entrepreneurs and executives — leaders — how to build and maintain something that can be elusive and fleeting: confidence.

To get there, Monahan, a former C-Suite level executive with Naples-based Beasley Media Group, will often talk about failures — and the power a setback has to redefine your mindset and mental strength. An example of how to practice that ideal? Monahan cites Spanx Founder Sara Blakely.

Monahan interviewed Blakely in October 2019 on her podcast, "Creating Confidence with Heather Monahan." Blakely, who famously went from selling fax machines door to door, cold-calling people around the Clearwater area for seven years, to founding what’s now a billon-dollar apparel brand, says failure was fuel while growing up. Her dad made it so, by asking her and her siblings what they failed at during the week. They talked about what they learned from the failure, teaching Blakely that failure isn’t in the outcome — but in not trying. Now Spanx holds Oops meetings, where individual employees and executives share failures or oops moments.

Monahan, too, says the best way to look at failure is “as a light to finding a new way of thinking about” a situation. In addition to her podcast, Monahan founded Boss in Heels, where she works with Fortune 500 companies and pro sports teams to develop confidence in the workplace and on the court. Based in Miami, Monahan also recently added Harvard guest professor to her resume.

Mark Gordon
Mark Gordon

Although Monahan, in a recent phone interview, shared several of her own failures, her path to where she is now started with not necessarily a failure but a shove. That was when she was fired from her position as chief revenue officer at Beasley. It was a position she held from 2015 to 2017 after working her way up through other sales posts at the company.

Her career with Beasley came to an end, Monahan recounts in a 2019 Ted Talk, when CEO Caroline Beasley called her into her office. (Monahan doesn’t specifically name Caroline Beasley in the Ted Talk, only saying the CEO who beckoned her is the daughter of the previous CEO. That CEO, George Beasley, promoted Monahan three times in 14 years. But his daughter, Monahan says, was her villain — and overcoming her was the thesis of her presentation. A Beasley Media spokesperson, in response to accusations Monahan makes in her Ted Talk, says “we do not comment on employee matters.”)   

Courtesy. Heather Monahan says confidence in leadership can come from failing — but then trying again and never giving up.
Courtesy. Heather Monahan says confidence in leadership can come from failing — but then trying again and never giving up.

“She said ‘I have no need for a chief revenue officer; therefore I don’t need you,’” Monahan says Caroline Beasley said that day in 2017. “‘You can choose which memo you’d like to sign,’ and she pushed two pieces of paper in front of me.” The first memo, Monahan recalls, simply stated she was fired. The second described Monahan in eloquent terms and said she was leaving the firm to chase new career goals.

Monahan said to get the second memo, the one that looked nice to the public, she would have to sign a lengthy release — what she called a deal with devil. “I looked down at the memos, I fought back my tears, I looked back at her, and I knew what I needed to do,” Monahan says on her Ted Talk. “I pushed those memos right back and said, ‘I didn’t write either one of these, so I won’t be signing either, and if there’s nothing else to say to me, I will be on my way.’”

“In that moment I was petrified. I was petrified not knowing how I would pay my bills. I was petrified not knowing the next time I’d get a paycheck or what I would do for a living,” Monahan says. “But in that moment I chose me. I chose to create confidence within me. And while that woman thought she had fired me that day, I had just fired my villain. And when you fire your villain, you set yourself up to take off.”

Get back up

With more than 30,000 views and now available in six languages, Monahan is asked often about her Ted Talk — so much so that it will be the topic of her second book, "Overcome Your Villain," scheduled to be published in November by HarperCollins Leadership. Monahan’s first book, "Confidence Creator," debuted at No. 1 on Amazon’s Business Biographies and Business Motivation lists in May 2018.

Monahan exudes confidence on her podcasts and during her Ted Talk and other presentations. Even in our recent phone conversation, she’s direct and pointed, with a high B.S. detection meter, while also friendly and engaging. Asked to talk about the failures she’s overcome to create her confidence, Monahan laughs and says “there are too many to mention.”

She then rattles off several: Soon after she left Beasley, Monahan signed a partnership deal with Rafaella, a division of Perry Ellis International, to provide social media commentary and speaking engagements. After nine months, that partnership never came together. She later had a partnership with HSN that fizzled. Another fail, she says, was “me chasing Reese Witherspoon for a year and a half to get her to write and do a movie on my book.”

Just like she does often in her inspirational social media posts, on LinkedIn and Instagram, Monahan always attempts to turn failures into leadership lessons. “There are so many examples of my failures,” she says, “but I just keep getting back up and taking another swing.”


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