Gerilyn Gillespy

I think perseverance has been key to my success. My stepdad, who raised me, passed away when I was young, and I watched my mom, who had been a stay-at-home mom with a degree in accounting, have to go back into the workforce and relearn work skills. I learned resilience alongside her, and it's probably why I'm at Microsoft today. I learned Word and Excel with her and worked to support myself through college while still teaching and staying active. I'm always looking for challenges and I approach everything with optimism. I'm definitely a lifelong learner, always trying to find more in what I'm learning about. In fact, I often tell my own children, who are grown, that I'm still trying to figure out what I want to be when I grow up. That curiosity and drive to keep learning and growing has carried me through nearly 30 years in education.

The best career advice I've received is to always pursue every opportunity. Throughout my career, in all the places I've been, I've always been willing to raise my hand, look in different areas, and take risks to push myself. I may not have gotten every opportunity I pursued, but I was always willing to put myself out there. Things happen for a reason, and when you put yourself in certain situations, you need to take advantage of those situations because you've earned it somewhere along the way. That's something I've tried to share with others when I'm mentoring them. Don't hold back from opportunities, even if you're not sure you'll get them. The act of pursuing them and taking those risks is what helps you grow and advance in your career.

I would suggest that you ask questions, be curious, and believe in yourself. Imposter syndrome is real, but you need to look at yourself and recognize that you deserved this opportunity, you deserved to be here, so take full advantage of it. Don't let self-doubt hold you back. You've earned your place at the table, and it's important to remember that and own it. Curiosity and confidence in yourself will take you far, especially in fields like technology where women are still underrepresented. Keep asking questions, keep learning, and trust that you belong.

I think the biggest challenge, especially around tech, is getting others to understand how it relates to themselves, particularly when it comes to females. There is not a large number of females in technology. Even when I was in high school in the 80s, I think I was the only girl in one of my coding classes, and that was unheard of at the time. But even now, in technology and in leadership roles, when I visit schools and meet with high schools, I see the need to help people understand the different ways that technology crosses across many different types of careers. You can love the arts and still see yourself in a STEM career. I grew up in a first-generation Italian household where girls took care of families and worked, and it was a different generation. My sister and I were the first ones to go to college and finish. The challenge is helping women recognize that you don't have to be perfect, but you have to continue to believe in yourself. That's important right now, especially for women in any kind of leadership role as they move through any career.

My family and the relationships that I have are most important to me. My daughter, who is now grown, shared a TED talk with me when she was in high school about being a wrongologist, about being wrong and always looking to find answers. That concept of reflection has become so important in my own work. I'm always looking at where my own biases are and where I could ask more questions. I've been in leadership a long time, so I know that at the end of the day, a final decision has to be made, but being able to have that reflection and to remember that the relationships and the people around the work and the choices we make are important. Recognizing the human element in leadership and continuing to value those relationships is what matters most to me.