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Advice from female entrepreneurs who hired their former bosses

From those who say it made their company stronger to those who regretted the decision, here’s what these professionals learned.

Advice from female entrepreneurs who hired their former bosses
[Photo: littlestocker/iStock]

For many people, there comes a point when the people you admired at the start of your career become your peers. That person who hired you becomes a colleague you have lunch with, brainstorm solutions with, or—in some cases—are in the position to hire yourself.

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Many female entrepreneurs have had this full-circle experience—for better and for worse. From those who happily welcomed their former leader to their company to those who regretted the decision later, here’s what these professionals learned from hiring their former boss:

“Never abuse authority—in either direction.”

While she was building her marketing career, Sara Brooks found a sweet spot in wellness consumer packaged goods. As she learned more, she realized the sector was set to explode. Seeing an opportunity to capitalize on this expansive niche, she started her own agency, Covet PR, in 2014.

It was her first gig in New York, managing beauty and fashion accounts, that introduced her to the boss she’d eventually hire, Jen Yu. Brooks says Yu was always working on budgets and conquering anything that required a high level of Excel or PowerPoint genius.

Since Brooks was more of a big-idea person, she knew Yu was the right fit when her company took off faster than she could keep up. “I needed high-level, senior support, ideally from someone who I trusted, but [who] brought a totally different skill set and point of view to the company. That person was Jen,” she says.

At first, she was hesitant, especially since she wasn’t sure Yu would go for the offer. Or how it would play out if she did. “While I was okay with hiring someone with more PR experience, I didn’t know how she would feel working for someone with less,” she says. “It at times can be a delicate situation because, unlike the majority of people you hire, you not only knew this person, but at one point reported to this person, so both people need to be comfortable with the changing dynamics.”

More than two years later, Brooks say they’ve made it work effectively by exercising healthy levels of respect. “She has never pulled the ‘I used to be your boss card, so you should listen to me,’ and likewise, I haven’t pulled rank, either,” says Brooks. “The most important quality both people need to have to make this work is mutual respect. We often challenge each other—as all leaders should—but always value and respect the opinion of the other.”

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“Hire based on skills.”

Plenty of entrepreneurs will echo Megan Driscoll’s feelings about opening up her own company last year. It was really scary—even five years later—she says, and yet, launching EvolveMKD is the best decision she’s ever made. To be successful, she says bravery is a requirement, not only in the initial plunge, but every time you make an investment in the hiring process.

Since starting her business, she’s hired two former bosses in a freelance capacity, largely due to her faith in their skill sets. Since Driscoll used to manage operations, staff, and strategic advisement for more than 30 clients, she was already quite senior before she set off on her own. So those former leaders to whom she reported? They were senior, too—and it was their wisdom that make them ideal additions to her team.

While she was worried about role-reversal issues, jumping right into the chaos of growing a company with trust already in place made it seamless. That and making sure they were on the same page before making an offer.

“You have to be really realistic about what skills they bring to the table, and ensuring they match what you are asking them to do,” she says. “Sometimes, people cling to what they knew about the person when they originally met them and haven’t evolved their perception of that individual’s skill sets—good and bad—in several years.”

In order to be successful working with a former boss, she says you must be very clear about your expectations. “Be very clear about their lane that they own,” she says.

“Take off your rose-colored glasses.”

Before Dorothy Crenshaw, now the CEO of Crenshaw Communications, started her own agency, she had a gig at Edelman. During her time there, she worked with a leader who helped her navigate cutthroat politics and became an ally in a competitive environment. She valued him and felt that he had her best interest at heart.

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Later, when she ran into an issue at her company, after a large consumer electronics company at the core of her business left, she felt it made sense to bring him onboard. However, it didn’t work out quite as well as she would have hoped: He stayed for two years, which was a year longer than justified, she says, since he never brought in any business.

“Looking back, his contacts were at very traditional companies unlikely to bring on a smaller agency like mine. And he wasn’t comfortable with tech trends like the app economy, IoT, SaaS, and other aspects of the tech clients and programs that were the bulk of my business,” she says. “Later I realized I was a little blinded by my gratitude from our prior working experience.”

Though it was a tough lesson to learn, she says the experience has helped her be smarter about who she brings on the team. “Don’t make hiring decisions when you’re on the ropes and thinking that a single person can save your business,” she says. “In matters like business development, decide how much you’re willing to invest. Don’t throw good money after bad. If it’s not working, cut the cord.”

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