Hearsay Social CEO Clara Shih: 5 ways for female tech entrepreneurs to get ahead

October 19, 2015, 4:30 PM UTC
Key Speakers At 2014 WIRED BizCon
Clara Shih, founder & chief executive officer of Hearsay Social and Board Director of Starbucks, speaks at the 2014 Wired Business Conference in New York, on Tuesday, May 13, 2014. Photographer: Peter Foley/Bloomberg *** Local Caption ***
Photograph by Peter Foley—Bloomberg via Getty Images

“Can you grab me a glass of water?” “Which way is the men’s room?” “Where’s my badge?”

Hearsay Social founder and CEO Clara Shih fielded all three of these questions (and more) as she stood in the registration line for a chichi, invite-only event for technology startup founders several years ago. The elation she felt upon her arrival deflated as she realized many of the roughly 200 other attendees, all men, didn’t realize she was also an entrepreneur.

“I remember being flooded with emotion,” Shih recalled during a speech last at the Grace Hopper Celebration conference, attended by more 12,000 woman in technology careers. “I realized that the college version of me would have cried and called my mother. The early 20’s version would have been confrontational.”

Instead, Shih covered her embarrassment through commiseration. She acknowledged that she, too, would love some refreshments, a bio break, and a quicker check-in process. Then, she set those exchanges aside and focused on interacting during everything single session where it made sense for her to offer an educated opinion. Eventually, every single man who caught her off-guard that first day found her and apologized. There were seven in all, and many are now her allies.

“We need not overreact,” Shih advised the standing-room-only Grace Hopper crowd.

When Shih attended her first Grace Hopper conference as a Google employee in 2004, there were just 800 attendees. After several years working at Salesforce, she co-founded her social media management company in 2009, raising $51 million in backing to date. While she marveled at this year’s record Grace Hopper attendance, Shih acknowledged it will be many years before female technologists and executives will find themselves on equal footing with their male counterparts.

Here are five ways they can cope in the interim:

Listen carefully. When Shih moved with her family to Akron, Ohio, during elementary school, the Chinese immigrant didn’t speak a word of English. She’s used to being interrupted and ignored. She seeks out those who aren’t contributing to conversations and asks deep probing questions. “I need to speak up, but I can do so most confidently when I listen first,” Shih said.

Be OK with being different. When Shih worked at Microsoft (prior to her Google stint), one of her co-workers advised her to stop trying so hard to be one of the guys. Her behavior wasn’t perceived as genuine, which was doing more damage than good. “The more you reflect on and own what makes you unique, the more accepted you will feel,” Shih said.

Invest in two-way friendships. Shih, like the large majority of women at the Grace Hopper conference last week, believes women across the tech industry need to do a much better job rallying to each other’s cause. This is something she learned from her self-declared mentor, Facebook chief operating officer Sheryl Sandberg. But she also warned women from becoming too insular, from excluding men from this conversation. “Invest in one meaningful conversation at every event you attend,” Shih said.

There is no failure, only learning. Being a perfectionist can work against women in a startup environment. She encouraged the Grace Hopper crowd to take more risks and to embrace every mistake they make. “It’s not failure, it’s data,” Shih joked.

Lift another woman. To get around persistent gender gaps, especially among the ranks of technical employees, women in the field need to encourage interest. That could mean giving someone the training necessary to move from customer support into engineering. Or contributing time to organizations such as Code.org or Techovation, which offer bootcamps and education in everything from software coding to finding startup funds. “If each one of us chose to mentor just one woman or girl, it would have a huge impact,” Shih challenged the Grace Hopper crowd.

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