Befriending Dragons: Transforming Leadership Friction into Impact with Cindy Gross

In this episode of Founders Future, with host Olivia Sammons, we are joined by Cindy Gross, PCC, founder of Befriending Dragons. Cindy shares her powerful journey from a 25-year career at Microsoft, where she faced burnout and systemic friction, to creating a company dedicated to helping others navigate similar challenges. She reveals how her personal experiences as a woman and a citizen of the Delaware Tribe of Indians and Cherokee Nation shaped her mission to help "Keystone Leaders"—often underestimated women and non-binary individuals—show up authentically and powerfully within organizational structures not built for them.Cindy delves into her unique approach, which combines transformational leadership coaching, emotional intelligence, and diversity advocacy to create healthier, more equitable workspaces. She explains her proprietary coaching process, which includes one-on-one deep dives, cohort-based group coaching, and workshops, all designed to create sustainable mindset shifts from the inside out. Cindy also discusses her strategic pivot towards working directly with organizations to create change at scale and shares her invaluable advice for aspiring entrepreneurs: "Don't wait for the emergency... Grab the sparks of hope and move forward now."