Cindy Gross
Leadership Coach Specializing in DEIB and Women Empowerment, Issaquah, Washington
"Don't find yourself. Make and remake yourself."
Meet Cindy - The Full Human Being
Cindy embodies a unique blend of empathy, resilience, and directness in her coaching approach, making her an invaluable partner for women looking to elevate their leadership and impact. Colleagues and clients alike describe Cindy as someone who creates a safe space where individuals can confront their fears and set their inner power free. She understands the importance of addressing and integrating all parts of oneself, including fears and dreams, to achieve true personal and professional growth. She believes that great leadership and effective workplace cultures are rooted in this genuine human connection.
To Cindy, a loving and human workplace is one where diverse perspectives are not just acknowledged but actively integrated into decision-making processes. She advocates for environments where people feel seen, heard, and respected, believing that this inclusivity leads to both personal fulfillment and organizational success.
Cindy’s dedication to helping her clients reframe challenges and choose empowering actions reflects her commitment to making work a place of growth, empathy, and genuine human connection. If you are ready to embark on a transformative journey with Cindy, reach out to her here.
How Cindy Can Help You Transform Your Organization
Cindy brings a wealth of experience and a heartfelt commitment to transforming organizations into more inclusive and supportive environments. As an Executive Coach, Cindy specializes in helping women and non-binary folks who work in tech or own a business navigate work culture with confidence. She understands the challenges her clients face, whether it's dealing with workplace harassment, overcoming biases, or breaking through glass ceilings. Cindy's professional journey has equipped her with the insights and tools needed to address these issues head-on.
In her coaching, Cindy emphasizes the significance of listening to and honoring each individual’s lived experiences. She affirms the emotional wounds her clients carry, honoring their experiences, and supports them to embody the person they want to be. She believes in the power of authenticity and guides her clients to rediscover their true selves.
Cindy's dedication to helping her clients is evident in her ability to ask insightful questions that lead to impactful outcomes, enabling her clients to develop the leadership skills necessary to thrive in their careers and be recognized and rewarded for their contributions. Want to learn more about Cindy’s professional capacities? Connect with her on LinkedIn.
Cindy’s Story
As a citizen of Cherokee Nation and the Delaware Tribe of Indians, Cindy proudly embraces her heritage with a focus on the Cherokee concept of ᎦᏚᎩ Gadugi - where we come together as one and work towards a shared purpose. She works to amplify voices that are often left out of the mainstream narrative in ways that nurture racially equitable systems.
Born in a small town in southern Kansas, Cindy spent her early years in various regions across the southern United States, including Missouri and the Dallas-Fort Worth metroplex. She earned a business computing degree from the University of Oklahoma, which set the stage for her career in technology.
Cindy's professional journey took her from Texas to Idaho, and she eventually settled in the Seattle area to continue her work at Microsoft. Her experiences in the tech industry, often as the only woman in the room, fueled her passion for advocating for women and non-binary individuals in male-dominated fields. She contributed chapters to two technical books, published a “top 10” SQL Server blog, and has a long catalogue of speaking engagements. She hosts livestreams and posts articles about the tech industry, equitable leadership, and how to combat gendered and racialized work expectations. Her involvement in diversity, equity, and inclusion initiatives, such as the Women of Windows executive board at Microsoft, highlights her commitment to cultural change and allyship. These experiences, coupled with her personal journey of self-discovery and healing, have shaped Cindy into a compassionate and insightful coach.
Cindy's serves on the boards of Leadership Eastside and Wonder Women Tech. She has earned certificates in “Leadership Strategy for Violence & Abuse Prevention” from the University of Pennsylvania, “Racial Equity Adaptive Leadership,” “Executive Insight – Leading Adaptive Leaders,” and “Adaptive Community Leadership” from Leadership Eastside, ICF PCC Level 2 “Certified Generative Coach” from inviteCHANGE, “DEIB in Tech” from the Kapor Center, and “Critical Race Theory Summer School” from the African American Policy Forum. To learn more about Cindy's academic and professional achievements, connect with her on LinkedIn.
Outside of her professional life, Cindy embraces her adventurous spirit. She loves green Thai curry and recently discovered that vanilla oat milk cold brew lattes are fabulous. She spends time with her cuddly orange Flerken cats, the brothers Zeke and Goose, who have been her companions since January 2020. Their playful antics and affectionate nature bring joy and warmth to her life. Cindy enjoys board games - “Space Base” and “Century: Spice Road” are her current favorites. She is passionate about sci-fi and fantasy stories, especially those with dragons and women leading the way. Stories that flip fairy tales around, showcasing powerful women as the center of the story, continue to inspire her imagination.
Cindy’s personal journey is deeply influenced by the relationships she cherishes. She surrounds herself with people who share her values of safety, justice, empathy, and authenticity. These relationships have taught her the importance of creating spaces where people can be themselves, voice their needs, and feel truly heard.
If you ask Cindy for a book recommendation, she will point you towards "The Sugar Jar" by Yasmine Cheyenne, a book about setting boundaries that work for you. Her love for unconventional stories and the lessons she draws from them are central to her coaching philosophy, where she helps clients navigate their own narratives with confidence and clarity.
Everything Else You Wish You Knew About Cindy
“Assuming “whole, capable, resourceful, and creative” can feel like erasure to systemically harmed folks because the system doesn’t allow that freedom for everyone. Coaching can be partnering to help an underserved client see their self more fully and “act as if” they are able to be whole, capable, resourceful, and creative WHEN they have everything they need within their systems.” - Dr. sarahlloyd, PhD | the equity whisperer
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