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5 female execs reveal the best question they've asked a mentor

Know Your Value spoke to several C-level, female executives who said asking these questions truly helped propel their careers.
Girlboss Rally NYC 2018 - Day 2
Alex Williamson speaks onstage at Girlboss Rally NYC 2018 at Knockdown Center on November 18, 2018 in Maspeth, New York. Janice Yim/Getty Images / (Credit too long, see caption)

If you’ve been lucky enough to have one or several great mentors during your career, you know that you likely wouldn’t be where you are today without them. Mentors support, open doors and help you grow professionally. That’s particularly important for female employees who typically face more obstacles and in turn, have a harder time joining the leadership ranks.

If you have a mentor, it’s up to you to get the most out of the relationship by learning and asking insightful questions. Know Your Value reached out to successful, female executives from different industries to hear about the very best question they’ve ever asked a mentor. These questions led to answers and advice that truly made a difference in their professional development and helped advance their own careers.

“How do we move forward when everyone is telling us that our idea won't work?”

Alex Williamson, chief brand officer at Bumble, an online dating site where women are required to make the first move, asked the question above to her mentor, Whitney Wolfe Herd, founder and CEO of Bumble.

“Early on and always with Bumble, people doubted us and turned down working with us,” said Williamson. “There were moments where the doubt would creep up, and you could temporarily wonder if the haters were right, if this wouldn’t work, if what we were doing would be ripped out from underneath us.”

Herd’s advice to Williamson: “Keep your blinders on like a race horse.” Williamson said this mantra helped her “ignore the negativity and also ignore the praise – just keep moving as fast as you can, with complete faith and belief in what we’re building.”

Because of this, Williamson and her team didn’t stop and stare at what their competitors were doing. Instead, they stayed focused on creating their own unique brand. “We’re still racing,” Williamson said. “We won’t stop…”

“How did you reach your level of success, given the sector’s gender gap, especially among leadership?”

Maelle Gavet, chief operating officer at Compass, a real estate start-up based in New York City said that when it comes to mentors, she has “a board of personal directors who provide a diverse set of perspectives and opinions.” She has asked the same question repeatedly throughout her career.

Maelle Gavet, chief operating officer at Compass, a real estate company.Compass

“I’m always interested in how women in the tech industry have broken boundaries and empowered other women to succeed,” Gavet said. Her favorite answer to the question was from a mentor who advised, “Raise your hand, even when you doubt yourself.”

Gavet said that advice is especially relevant for females, since studies show men apply for a job when they meet only 60 percent of the qualifications, while women apply only if they meet 100 percent of them. “Men are promoted on potential, while women are promoted on results,” Gavet said. “It’s my mission to ensure that the women on my team are given the same shot as men – and feel confident and emboldened enough to ask for the same things.”

“Am I crazy?”

Jessica O. Matthews, CEO and founder of Uncharted Power, an energy and data technology company .Uncharted Power

Jessica O. Matthews, CEO and founder of Uncharted Power, a New York City-based energy and data technology company that develops infrastructure solutions for communities and facilities, finds reassurance when mentors tell her, “No, you are not.”

She explained, “There’s such a wave of relief that occurs, when you can be aware of what others before you have experienced and overcome.” Matthews said that since she works “to be the Beyoncé of renewable energy,” she has also learned over the years and from mentors that making sure she is aware of how she is actively caring for herself is also a must.

“How can I differentiate myself?”

Lisa Rapuano, chief financial officer at Facet Wealth, a Baltimore-based financial life management firm.Facet Wealth

In the beginning of her money management career, Lisa Rapuano, chief financial officer at Facet Wealth, a Baltimore-based financial life management firm, asked a mentor the question above.

Bill Miller, her mentor and boss at Legg Mason, told her to “have a sense of urgency and always follow up.” That advice made an impact on Rapuano, who continues to use that basic principle in all areas of her life, from parenting, how she treats her employees and how she deals with her customers.

“The people you work with feel they’re important because you’re super responsive and accountable, and following up not only increases your visibility but enables you to close the loop in a timely manner,” she said.

“What is your ‘why?’”

This was a common question that Eileen McDonnell, CEO of Horsham, Penn.-based life insurance company Penn Mutual, would often ask mentors when she was in middle management.

Eileen McDonnell, CEO of life insurance company Penn Mutual.Penn Mutual

She said Joe Sargent, former CEO of Guardian Life Insurance, was the mentor who provided her with the best advice. He told her that she needed to be resourceful, should never be afraid to ask for help and that her success needed to be tied to the success of others.

That advice helped give her the confidence to always ask “why?” and to seek the help and input of others. “Early in your career, it’s up to you to produce the work product,” McDonnell said. “But my mentor taught me there comes a point in your career where it’s really not about you, but about how you engage with and empower others.”