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How Microsoft U.S. President Deb Cupp Levels the Playing Field for Women in the Workplace

Gender diversity continues to be a thorn in the side of social progress in America's labor force. But some experts say narrowing the gender gap and transforming workplace culture are both attainable if more women are hired, promoted, and elevated to leadership roles. 
For Deb Cupp, president of Microsoft U.S., accountability is the start to building a more cohesive workplace for all employees. Culture and gender discrimination are often cited as reasons for the lack of gender diversity in companies, but at Microsoft, Cupp said the company is being intentional about meeting equity goals.
"Holding ourselves accountable to our commitments — understand where we are making progress and what we have to do more of. Even though the D&I report is only a moment in time, we're practicing, learning, and growing every day at Microsoft," she told Cheddar.
Cupp started at Microsoft just over four years ago as corporate vice president of strategy and programs and quickly rose through the ranks to head up the tech giant's U.S. business. Her rise to leadership, especially in such a short span of time, is rare. 
A workplace study by consulting firm McKinsey & Company and LeanIn.org found that just 28 percent of women filled senior corporate management roles in early 2020. 
While her rapid ascent was atypical for women in management, Cupp laid out three main principles that helped her navigate the still male-dominated tech industry:

Ground Yourself on Impact

For Cupp, having a plan in place and being decisive about the next career move was essential. She said she typically makes career decisions based on how impactful she believes she can be in the role and whether the position was a priority for the company.
"I focused on delivering value in the role that I was in, focused on learning as much as I could, challenging myself, and building my internal network," she said.

Rely on a Personal 'Board of Directors'

Cupp admits she doesn't always have a master plan and sometimes the next career move isn't always clear. In those instances, she pointed out that it's important to have people in your corner that you can reflect with, ask questions, and seek guidance through. 
"I have an amazing network of folks, men and women, who I can call or text anytime for support, advice, or mentorship. People who I can trust, get feedback from, are honest, have clarity on what is important to me, and help me make decisions…and sometimes, just there when I need a friendly ear. I really value these relationships, and they've had a strong impact on my career and life," Cupp told Cheddar.

Be an Ally

When growing your career, maintaining and building relationships is key. Cupp said even small reassurances and gestures can go a long way in allyship.
"A simple example, when I am on Teams call, and I know there is a woman on that call that has great insight, but they're nervous to speak up, I will message them individually and tell them, 'You know this better than any person talking right now. You've got something to say. I'm here. I got you. Jump in!' It's those little gestures that can really help women have the confidence to be heard," she said.
While women were forced to leave the workforce in droves amid the pandemic to care for family, Cupp said Microsoft is focusing on flexibility. The company wants to afford women the opportunity to grow their careers and care for families simultaneously. Implementing hybrid work options and incorporating consistent training on unconscious bias, non-inclusive language, and covering can all create more equitable workplaces.
Cupp also noted the importance of empowering employees to help create a more sound work environment as it has been linked to a boost in performance, improved job satisfaction, and stronger connections to the company. She said Microsoft's position on empowering employees is one of the reasons she remains at the company. 
"It's important to set guardrails, but I want to foster an environment where people feel like they have permission to just go and do things they feel are right. This is where innovation can happen when we create a mindset of 'If you try something and it fails, brush yourself off, learn from the experience and move on to the next thing," Cupp told Cheddar.
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