As Vice President of Microsoft's U.S. Small-and-Midsized Business group, Cindy Bates leads the company's efforts to help SMBs realize their full potential through the use of technology. Raised in a family of entrepreneurs, Cindy holds a strong personal interest in entrepreneurialism and a passion for serving the small business community. She has spent much of her career addressing the needs of SMBs in some capacity. Today, she is a recognized thought leader in the SMB space, is widely quoted by SMB press, and is a contributing columnist to Entrepreneur.com.
How has your life experience made you the leader you are today?
I was fortunate to grow up in a very supportive family where I was encouraged to try new things. My mother talked about viewing experiences as "chapters in my book" and even when the experience was challenging, if I viewed it through that lens, it emboldened me to take risks. I could fail and it could still make for an interesting chapter. That early support gave me a sense of confidence, and helped shape my approach to leadership, which I'd characterize as very people centered, setting inspirational goals, taking risks, all based on a culture of strong collaboration and teamwork. It also fostered my sense of curiosity and a desire to seek a diversity of viewpoints, which has helped me to build strong teams and successfully address challenges where the solution was not clear cut.
How has your previous employment experience aided your position as the VP of Microsoft SMB Group?
Throughout my career, I've been focused on helping businesses to be successful. Early on in my career, I delivered business strategy and marketing expertise to Fortune 200 companies. I then advised major retail companies on their financial and e-commerce strategies while at Merrill Lynch. And when I joined Microsoft nearly 15 years ago, I was managing director of the company's Corporate Development and Strategy group, where I focused on mergers, acquisitions, investments and joint ventures in the SMB applications market. For the last four years, as head of the US Small and Midsized Business group, my focus remains helping businesses to be successful by educating them on how technology can help them start, grow and thrive. Working with SMBs, which are the lifeblood of the economy and employ half of America's workforce, is incredibly gratifying.
How do you maintain a work/life balance?
I include a healthy work-life balance among the key factors that define what success looks like for me. I feel like I'm striking the right balance when I am 100% present in whatever situation I find myself in; when I'm at work, my head, heart and soul are at work. When I'm outside of work, my focus is on my family, friends, and activities I enjoy. It's about making time to relax and regenerate, whether that's truly powering down over the weekend, or blocking out my vacation time in the beginning of the year including two weeks in August where I always plan something I really look forward to (a recent trip to Peru with my Mom being one example), and multiple long weekends. Making sure to carve out time away from work makes me that much more effective at work. Prioritization and learning how to say no to meetings or projects that I don't need to be involved in or should delegate to someone else are also key.
What have the highlights and challenges been during your tenure at Microsoft?
The highlights all have to do with the people I've met along the way, both inside and outside the company. At Microsoft, I work with some of the smartest and most passionate people I've ever encountered. Together, we've tackled a lot of challenges. Educating a largely non-tech audience about new technology is one such challenge, and it's exciting to introduce them to game-changers like cloud technology, such as Microsoft's cloud productivity suite Office 365. When SMBs embrace the cloud, they can keep the focus on their business and maximize IT value with low overhead and low complexity.
What advice can you offer women seeking a career in technology?
First, make it a point to look for ways to add value. In practical terms, that might mean understanding the objectives of your peers and your manager so you can orient yourself around doing things that matter and that add the most value. People notice who adds value. By making it a priority to do so, you'll earn a reputation for it, and opportunity will come knocking on your door.
Second, look at every interaction and new connection as an opportunity. It's about making meaningful connections with people in all aspects of your life who might introduce you to new opportunities.
And third be bold. If an opportunity is at least a bit outside your comfort zone, it most likely presents an opportunity for growth and professional development. My team knows well my favorite quote: "Whatever you can do or dream you can do, begin it. Boldness has genius, magic and power in it!"
What do you think is the biggest issue for women in the workplace?
I think it can be challenging for any professional to feel that their experiences and worldview might contrast with most others around them. Women have different perspectives to bring, particularly to STEM fields, and they are perspectives the industry needs. Innovation is integral to delivering products and services that the marketplace wants. And by definition, innovation is fueled by fresh thinking and new ways of problem solving.
What are your thoughts on Sheryl Sandberg's Lean In book and movement?
I think Sandberg's book offers a valuable perspective. Everyone needs to make choices in their lives and careers. Sometimes the choices are not easy. Women who hold specific career aspirations can find valuable insights and encouragement in Sandberg's point of view. Whether a woman should be more assertive in her professional life is an intensely personal decision, and depends upon her unique personal and career circumstances.
How has mentorship made a difference in your professional and personal life?
My mentors have been instrumental to my success. Having the encouragement of someone who has navigated similar situations, be it at home or at work, can be extremely empowering and provide added confidence just when you need it. I've also found it helpful to assemble a personal advisory board, even informally, of people I trust who can provide different perspectives when I'm facing big decisions or just need a sounding board. Surrounding myself with people from different industries, geographies and backgrounds has enabled me to lead with creativity, empathy and a well-rounded perspective.
Which other female leaders do you admire and why?
I admire women who are authentically themselves and pursue their dreams with confidence. One leader who comes to mind is Sara Blakely, the founder of Spanx, who started the company with just $5000 and created an entirely new category. Now she's the first woman to join the Giving Pledge, a challenge Bill Gates and Warren Buffett have posited to the world's billionaires to give at least half their wealth to charity.
What are your hopes for the future of Microsoft SMB?
Microsoft's mission is to enable people and businesses to reach their full potential. It's a mission I take very much to heart, and one that I feel comes alive in the SMB space as we deliver technology that helps millions of entrepreneurs and business owners to grow their businesses and pursue their dreams. In particular, cloud technology offers new and powerful capabilities to SMBs at an affordable cost. I am inspired every day by the stories of businesses that have been transformed by cloud-based technology like Microsoft Office 365. My hope is that more and more SMBs come to recognize the value of technology in enabling their growth and success, and that Microsoft can play a role in that journey.