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Olympic Tips from PyeongChang: Sherry Cushman on Women and Success

Janice O’Neill, Global Head of Talent Management and Diversity, and 2018 Chair for Women’s Integrated Network (WIN), recently chatted with Sherry Cushman, Leader of the Legal Sector Advisory Group (LSAG), about her experience with the Olympics and the U.S. Bobsled and Skeleton Federation, and what she learned in PyeongChang about women’s success.

Sherry is also actively involved with WIN, focusing on the recruitment of women into the real estate industry, and is fired up about bringing that “Olympic edge” to women’s careers at Cushman & Wakefield.

You attended the Olympics in PyeongChang and have supported the U.S. Bobsled and Skeleton Federation for years. Tell us about your involvement. 

I didn’t know the first thing about bobsled or skeleton seven years ago, but my husband was asked to sit on the USA Bobsled and Skeleton (USABS) Federation in 2010 and I’ve been involved ever since. People don’t realize that the U.S. is the only government in the world that does not fund our American athletes to support their training, coaches, equipment, expenses, and more, so Federations assist with raising the funds to support the athletes and teams.

About 18 months ago I took a bobsled athlete named Lauren Gibbs under my wing as a mentee. She spoke at a WIN luncheon in Washington, DC last fall, and at the time, she didn’t know if she’d make the Olympic team. Not only did she make the team, but she went on to win the silver medal.

At 30 years old—with degrees from Brown and Pepperdine, and a six-figure job—she decided to leave it all behind and try out for the U.S. Bobsled team as a walk-on. She made the team and every year has travelled the world competing, and was selected over many other athletes to compete in PyeongChang on the Olympic team. The gist of the story is it’s never too late to go after a dream, and at the end of day, you need to be true to yourself and your dream.

What about the games inspires you?

I’m a sports person and in awe of the Olympics. Only one in 8.5 million people is an Olympian, and to win a medal is a 1 in 50 million accomplishment.

When Lauren Gibbs visited us last summer, I saw that everything she did morning, noon, and night—eating, resting, training—was laser-focused on winning an Olympic medal. She didn’t get down when something happened out of her control. Her passion to be the best and work so hard towards it was so inspirational.

I was a total jock as a kid, and in the early 70s, the only girls’ sports were swimming, softball, and field hockey. I was the youngest of three and a competitive swimmer since the age of five, but at 11, I wanted to try out for boys’ sports. My Dad, a Marine, said he didn’t have a problem with that as long as I was good at it. My sister and I became the only two girls who played boys’ baseball; basketball; and punt, pass, and kick. I won a regional punt, pass, and kick competition. I’ve always been inspired by sports, and have completed 19 Olympic ocean triathlons as an adult.

You mentioned that U.S. women outperformed their male counterparts this year, winning more medals. In your opinion, what’s an edge that made these women excel?

Women are just crushing it. In the history of the Olympics, never have U.S. women outperformed men. They’re mentally prepared, focused women. Lauren and her team won the silver because they didn’t let anything else distract them from it.

How does the spirit of going after your dreams translate for women in the corporate world? What does it look like?

Success at CRE is in our DNA—women have a natural ability to multitask, and to foresee what may happen the next day and next month. Women tend to carry a lot more responsibility, we’re listeners, thoughtful, and compassionate people. We add such diversity of thinking and talent to the CRE industry. Statistically, when women get into our industry, we are among the most successful in the business. But we need many, many more women.

Part of business/life success is owning your voice. I see young and adult women who sometimes speak in a voice that’s not theirs. They don’t own it; they’re acting it. My goal with WIN is to build women’s voices.

It took years for me to build mine. I was 35 years old before I felt like my voice was mine. It took me seven years of being a broker before I felt like I could stand up in front of a room and own it.

To hear you say that is powerful to other women. You’re saying we’re all a work in progress, and we can find our voice no matter what age.


I made a career change to Studley Worldwide from a career in architecture and started with a phone and a cube. I worked seven days a week and had sleepless nights. It was an eat what you kill environment, and the only person who didn’t think I was crazy to make the transition was my boyfriend, who later became my husband.

It took me three years to make positive income. However, I was also picked as top rookie broker because I brought in 300,000 square feet of transaction my first year as a broker.

My goal is to make it a bit easier for women entering the industry through all of the great  WIN initiatives at Cushman & Wakefield.

So when you started out, you didn’t make money. Tell us what you found out about the U.S. women’s hockey team and equal pay.

In 2017, the U.S. women’s hockey team was aware that their male counterparts were making significantly more money than were women for playing hockey, even though the women were competing on the same circuit and had the same hours and training. A lot of the athletes live hand-to-mouth.

The women’s hockey team was woefully underpaid and they threatened to sit out the International Ice Hockey Federation World Championship in 2017 unless they received equal treatment. After 15 months of negotiations, the women won equal pay and treatment, and then went on to win the gold medal at the Olympics against the Canadians. An unbelievable accomplishment in so many ways. They stood tall for what they believed in and it paid off.

In PyeongChang, we met the coach who led a team of players who would die for each other. They were more than teammates—they had each other’s backs and supported each other when times were tough. We can carry that lesson over to Cushman & Wakefield—women need to back each other. We also need to hold leadership accountable for making sure we expand diversity and support women in having upward mobility within the company.

How can each of us motivate and unite our friends, colleagues, and communities to think, act, and be gender-inclusive?

A lot of it is bringing people together. Whatever our age, gender, or color of skin, we all have trials and tribulations. Some more than others. We’re all human beings and we feel similar things. Too many times we put a wall between us, but fundamentally everyone wants to be happy, work hard, and have opportunities to learn and grow.

You are a strong, vocal woman. Starting with playing “boy sports,” you weren’t afraid to venture out. How do you handle it when people think you are too strong or too vocal?

First, I accept that not everyone is going to like me and I am not here to win everybody over. All I can do is work very hard, be good at what I do, and service my clients and relationships. I work on nurturing relationships and building trust. I also embrace my clients as friends.

As mentioned before, a lot of success comes from finding your own voice and style. Women are good at reading people. Sometimes you need to be charming and add humor, and at other times you need to be firm and not step down. Knowing when to do either is the key in achieving the desired end-game.

See more about Sherry’s Olympic adventure here.

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