Power Women: Microsoft’s Alysa Taylor On How To Successfully Navigate Work, Love and Life As A Powerful Woman

How does a successful, strong woman navigate work, employee relationships, family, and life in a world that still feels uncomfortable for women with power? In this interview series, called “Power Women,” we are talking to accomplished women leaders who share their stories and experiences navigating work, love, and life as powerful women.

As a part of this series, I had the distinct pleasure of interviewing Alysa Taylor.

As Microsoft Corporate Vice President of Azure and Industry Marketing, Alysa leads product marketing and is responsible for working across Microsoft to prioritize when we build and how we bring products to market. The key to this role is understanding the market and deeply understanding our customers’ needs. With these signals in mind, we’re able to successfully innovate and prioritize creating new services that help our customers stay ahead of the curve.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your childhood “backstory”?

I grew up near D.C., on the East Coast of the U.S. and had the opportunity to split my time with my parents and grandparents. My parents were creative types that traveled a lot and my grandparents, particularly my grandfather, served as a strong influence for me. He led a nationwide concrete association and an architectural firm and came home with stories about the problems he needed to solve and shared with me interesting anecdotes from meetings he was in. You could always find me “playing office” as a child and I know a lot of my love for innovation and creative problem solving was inspired by those conversations and watching him do that work.

Can you tell us the story about what led you to this particular career path?

Some people assume I have had a clear plan for my career, based on the different roles I have had. But actually, my career path has been more of a series of unexpected “left turns” that gave me new experiences and opportunities.

I started my career in design. In my first role, the agency I worked for saw my strengths in helping clients solve problems and gave me roles that allowed me to hone these skills. I then moved to management consulting, which allowed me to really engage with clients and help them unlock creative solutions. This is where I really started to find the most joy in my work: understanding the problem and coming up with innovative approaches to set my clients apart from the competition.

Can you share the most interesting story that happened to you since you began your career?

Each and every day is interesting in the tech space, especially right now. I am so fortunate to be involved in this transformative moment and intersection of technology and AI that’s happening now. It’s not every day you get to be part of a massive technology shift. With AI, I get to help Microsoft position itself in new ways as we help our customers explore the potential for AI to tackle big challenges and meet customer needs. The stories I hear from customers about how this technology is equipping their employees to be most productive and garner more joy from their work, are the most inspiring to me.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

There are three traits that I value in people:

• Having a growth mindset. This is so important to me, and it’s a vital part of the Microsoft culture. My kids have also learned this, and it shows up when I ask them about their day at school and they respond, “I’m still learning,” or “I don’t know it all yet.” I love that response. We are all a work in progress, but instilling a learning culture and a growth mindset is truly the catalyst to broadening our perspectives.
• Ability to solve big challenges in a collaborative way. I am often in meetings when the conversations are about challenges that we can not predict. These are the opportunities that make you stop, pause, and really consider the possibilities. I love digging into these kinds of scenarios with others and finding the patterns that emerge. It’s the collective brainpower that allows breakthrough moments for innovation.
• Positivity. I get energy from those with an optimistic outlook and it is how I try to approach every day. I really do believe what Zig Ziglar said, “positive thinking will let you do everything better than negative thinking will do.”

OK, thank you for that. Let’s now jump to the primary focus of our interview. The premise of this series assumes that our society still feels uncomfortable with strong women. Why do you think this is so?

Strength comes in many forms and can show up individually in unique ways. Strength to me represents authenticity, courage, and curiosity. This means having the ability to be authentic in every facet of my life, to be courageous to live life fully and with joy, and being comfortable asking questions. A pivotal moment for me in my career was when I had an inflection point and decided to have the courage to show up more “authentically me,” which meant using my voice to influence, leaning in with curiosity, and even wearing what makes me most comfortable. At Microsoft, we curate a culture where we’re encouraged to show up in a way that represents us best. When you can show up authentically, you do your best work. It’s that simple. I think society and workplaces should focus on building a culture that cultivates inclusivity and where all are welcome. With this, strength then surfaces as a unique and valued trait rather than a negative one.

Without saying any names, can you share a story from your own experience that illustrates this idea?

One that comes to mind is from early on in my career. In order to fit in more with the software developers I worked with, I found that I was not wearing what I was most comfortable in. I was wearing things that were more casual and neutral, but personally I love to dress with more of a feminine touch. My girlfriends called this my “grey sweater era.” After a while I realized I should feel OK about showing up to work as my authentic self, in every sense — even wearing my favorite pink, sparkly heels!

What should a powerful woman do in a context where she feels that people are uneasy around her?

Creating an environment where everyone is comfortable and where all voices can be heard is something that is important to me. Driving a culture where there is energy, clarity, and space for new perspectives is the kind of workplace where the best ideas are sparked. It is important to be able to read the room and recognize when people are uncomfortable. In those moments, I work to bring people into the conversation and ask questions of others, so they have an opportunity to be heard.

What do we need to do as a society to change the unease around powerful women?

At Microsoft, I am seeing more and more women join the ranks of leadership. We are continuing to grow our talent and the career potential of everyone. What I have found is that when we focus on impact, and value unique talents and perspectives, we see more diversity and an inclusive environment for people to thrive. We need powerful women to model the way. It becomes a domino effect: the more women show up as their authentic selves, it gives others the courage to do the same. When women with influence show up unapologetically authentic, it signals to the next generation of women to believe that there is power in doing the same.

In my own experience, I have observed that often women have to endure ridiculous or uncomfortable situations to achieve success that men don’t have to endure. Do you have a story like this from your own experience? Can you share it with us?

Every once in a while, I’ll come across a situation where another person in the workplace says something that is questionable, uncomfortable, but may be unintended. When this happens, I push for my clarity and I ask follow-up questions like “what did you mean,” or “can you explain a bit more about that.” I find that when you probe further and dig a little deeper you can get to the root of the intent. So often we’re unaware of our tone or we’re moving so quickly, we don’t understand the impact of our words. Comments can be unintentionally misconstrued. Creating clarity is a key principle in leadership, and the more we ask the follow up questions, the faster we get to the heart of what was intended.

In your opinion, what are the biggest challenges faced by women leaders that aren’t typically faced by their male counterparts?

It’s broadly recognized that women are often caregivers, whether it’s for young children, aging parents, pets, or otherwise. We saw this clearly during the COVID pandemic when women were taking over caregiving tasks, especially after schools switched to at-home learning. I can remember the boys being home while I was on conference calls and doing the same juggling. This is when I recognized the value of a strong support system whether it be close friends and community or family. I have always valued my friendships and the role they play in every facet of my life, and during the pandemic, we supported one another and got through it literally together. My advice is to continue to invest in the communities that matter most to you, because it’s where you will find the support during challenging times.

As a working parent myself, I’m all too familiar with the juggling required when you have an active family life and a demanding career. But while people often say you can’t have it all at the same time, I believe that by taking an integrated approach across work and family, you can be present where it matters most in the moment.

Let’s now shift our discussion to a slightly different direction. This is a question that nearly everyone with a job has to contend with. Was it difficult to fit your personal and family life into your business and career? For the benefit of our readers, can you articulate precisely what the struggle was?

I’m a mother of two boys, and I strive to show them that I take an integrated approach to our life together. I focus on being present where I’m at — if I’m at the office or in a meeting that’s where my focus is. If I’m at a lacrosse or football game, I will be ever present in that environment. Our lives ebb and flow in various ways, and I find the key to making it work is finding joy in every moment, by being present and focused on that experience. But, sometimes life events tip the balance. One of my sons had a health scare as an infant, and in that moment I knew where I needed to have my focus. I took the time I needed to focus on him, his health, and what he needed most. It’s important to know when to take a step back, when to refocus your energy, and when to pivot. Then, once he was healthy — I was able to step back into the workplace present and fully committed.

What was a tipping point that helped you achieve a greater balance or greater equilibrium between your work life and personal life? What did you do to reach this equilibrium?

The tipping point was that same defining moment. My son was three months old when that happened and he recovered completely, and he’s now a healthy teenager. But that moment forever altered my definition of success and stress. Holding my infant son, I knew then that success meant having a healthy child. I recognized that if my family is healthy and happy, everything else is completely manageable. That was my new baseline from which to operate.

When you’re truly clear on what’s important like that, you can approach your career with a new perspective. This perspective will serve you well in times of stress and chaos, but it also helps you determine your values, goals, and boundaries.

OK, super. Here is the main question of our interview. Based on your opinion and experience, what are the “Five Things You Need To Thrive and Succeed as a Powerful Woman?” (Please share a story or example for each.)

Remember what matters. It’s important to remind yourself every day what really matters. I anchor myself on what matters and build everything else around that. And when I get caught up in day-to-day stress — like we all do — I come back to that and re-ground myself. Your career must support what matters to you, and when you keep that in perspective, other things fall into place.

Know what gives you energy. I use the concept of the “Green Zone,” which is the intersection of two questions: What gives you energy, and what are you good at? It takes some thought, as there are many things most of us are good at that don’t bring us energy. Conversely, some activities give us energy, but we may not be great at them. For example, I have a passion for interior design in particular, which has led me to re-arrange my office and my house multiple times. I love design as a creative outlet and hobby, but not necessarily to make it my professional day-to-day work. What I do love is building businesses, so creating a successful businesses sits in the heart of my Green Zone. I use that knowledge when I have to make decisions about my career.

Maintain your energy. Outside of work, I’ve always used running to lose my mind in music. But while working with my coach, he talked about training for my career like an athletic event and investing in my mind. When I told him I was often waking up in the middle of the night with the worries of the day, he told me I wasn’t giving my mind enough time to clear out. He suggested that I needed silence to think things through and process those thoughts. So, I now run in silence, and it’s helped.

Left turns are okay. I believe left turns can push you in new ways and help you build new strengths and create new opportunities. That’s why I think it’s important to stay open-minded when thinking about career moves. At a minimum, being open to unexpected developments in your career lets you take stock of what you’re doing, what experiences interest you, and what kind of culture you want to help create.

Know yourself. Being true to yourself is probably the hardest and most important thing you can do. Many years ago, I did a leadership assessment. The measurements showed my drive and results scores were high, but my creativity and spirituality scores were near the bottom. I was stunned, as that was not the person that I knew. Like I suspect many others do, I was hiding part of myself because I was afraid of hurting my success if I stood out. But it’s actually the other way around: When you’re true to yourself, you’re bringing your best to the table. So, I’m now committed to bringing my whole self to work every day with the goal of creating an environment where my team can do the same.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

There are several that come to mind, but with Reese Witherspoon I admire so much about her. She is a creative thinker, a performance actor, a producer, a businesswoman, a dedicated mother, and a devoted friend to those around her. I see a lot of similarities between us, and I’ve been impressed with her initiative to create opportunities for herself and with other women. She founded Hello Sunshine, a production company, with a belief in the power of storytelling to broaden perspectives and change the world for women. I’m so impressed by this mission and her ability show-up authentically in all of these different places. It is something that as a female leader I aspire to do as well.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.