Befriending Dragons

Befriending Dragons is a coaching and leadership development practice for women and underestimated leaders in tech and mission-driven spaces. We help people build what we call the Dragon Playbook — a leadership clarity system rooted in identity, values, boundaries, and bold decision-making. Or, in tech terms, your Operating System of Me. Our approach is grounded in self-trust, not self-optimization. You won’t find hustle culture or performative leadership here. Instead, we help you reclaim your voice, protect your energy, and navigate change without losing yourself. Founder Cindy Gross draws on 25+ years in corporate tech and her lived experience as an Indigenous woman to create spaces where truth, transformation, and strategy can coexist. Cindy is a coach, speaker, facilitator, and culture shifter — known for her clarity, candor, and dragonfire warmth. We believe: Leadership is not about perfection. It's about clarity. Boundaries are a form of love and self-respect. Fears and instincts aren’t distractions — they’re data. You don’t need to slay your dragons. You need to listen to them. Explore free resources, book a talk or team workshop, or join a coaching container designed to help you lead from your truest self. Ready to befriend your dragons? Start here: https://befriendingdragons.com