Cindy Gross, Systems Expert

Befriending Dragons was born from navigating systems that failed me.

I faced burnout, illness, and a lifetime of being underestimated. I realized I had spent years making myself small just to survive. Now, I help others reclaim their voice. I encourage them to breathe fire into their purpose. Together, we navigate the systems that weren’t built for us. I built this System to mitigate the massive 1X-2X cost to replace indispensable talent.

Cindy Gross, a white woman with short brown hair, green eyes, and green glasses, smiling.

What Ignites Me: From Systems Expert to Strategic Partner

I founded Befriending Dragons to help indispensable leaders embrace their full selves – not just the parts that play well when you’re “the other.” My ICF PCC coaching combines with my 25-year systems mastery in the tech industry to deliver strategic results. True leadership comes when you reclaim your voice, nurture boundaries, and show up authentically.

I guide individuals through the complexities of leadership, helping them navigate challenging environments with integrity, influence, and measurable impact. When you lead authentically, you spark ripples of change that stabilize teams and extend far beyond the room.

At the heart of our work is a commitment to empathy, integrity, and deep respect for each person’s lived experiences. Together, we forge a path toward leadership that is real, personal, and powerful.

The System’s Origins: How Crisis Forged the Leadership Navigation System

Years ago, I got a call that changed everything. I was heading out on a bike ride when I learned I had cancer. Suddenly, all the fear I’d buried after losing my mom to the same disease came rushing back. That moment cracked something open. I realized I’d been shrinking myself for years just to survive in systems that weren’t made for me.

But survival isn’t the same as thriving.

We all carry dragons – our fears, hopes, dreams, instincts, and the relentless voice of our inner critic. For too long, I fought my dragons, wasting time and energy trying to silence or outrun them. But when we fight our dragons, we lose sight of what truly matters – knowing and embracing our identity so we can act from our most authentic selves.

In my career, I’ve been the woman who reported harassment and paid the price. I’ve been the leader people turned to when culture needed to change. And I’ve also been burned out, silenced, and unsure of what voice was even mine anymore.

I’ve learned to face the hard stuff, to listen instead of battle, to let more parts of myself exist fully. Befriending Dragons was born from this unraveling—a methodology to transform personal pain into strategic clarity and systemic resilience.

When I let fear surface, when I stopped resisting the truths inside me, I learned from my dragons instead of fighting them. And in that, I found freedom.

I set my dragon wings free. Now, I am guided by my hopes, instincts, and dreams. I help others – including you – step into that same freedom. Learning to embrace, not fight, our dragons, so we can lead from our truest identity.

Certifications

PCC, Professional Certified Coach, ICF
seal: Washington Native American Chamber of Commerce, member since 2024
logo - washington state office of minority & women's business enterprises
Adaptive leadership, leadership eastside 2019
DEIB in Tech, Kapor Center 2023
Gracious Space, Pat Hughes, 2021
Leadership Strategies for violence and abuse prevention, university of Pennsylvania executive program 2020
Racial Equity Adaptive Leadership Leadership Eastside Certification 250x250

What Makes Befriending Dragons Different?

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Corporate Tech Experience

I spent 25 years navigating complex, male-dominated work cultures. I honed my expertise, driving impact and earning industry-wide recognition. This experience is the data-driven foundation of the Leadership Navigation System.

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Systemic Intelligence & Equity

I blend PCC coaching with Adaptive Leadership, emotional intelligence, cultural agility, diversity, equity, and inclusion, and inner development to diagnose and address systemic friction that undermines Keystone Leaders and drags down performance.

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Data-Driven Clarity

I explore with you, affirming your lived experience, and asking powerful questions that cut through the noise to map strategic leverage points. Together we see the system so YOU can influence it more clearly.

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Dragons are more than metaphor. They help us reimagine what’s possible, fly above the noise, and trust our instincts. The Dragon Playbook blends adaptive leadership, emotional intelligence, and mythic perspective to help you lead with vision and vitality — especially when the path ahead is unclear.

At the HEART of My Work

The values that shape how I show up and who I show up for.

Authenticity

You’re not broken. You get to lead as your full self.

Race + Gender Equity & Cultural Competence

We name what’s real—power, systems, and how identity shapes experience.

Curiosity

Insight starts with more useful questions, not quick answers.

Thrival

You’re not here just to get through it, you’re here to grow, lead, and spark change.

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Your Next Step: Strategy Alignment

This is your invitation to be real. Let’s explore what’s hard, what’s changing, and what measurable impact is possible. I’m the strategic partner who helps you stabilize your teams and radiate influence.

Book your strategic diagnostic call today.