Befriending Dragons

Turn Challenges into Strength,
One Bold Step at a Time

You have the strength. Now, let’s give you the strategy. I help indispensable Keystone Leaders master the real challenges—the systemic friction—so you lead with impact, not exhaustion. For organizations, this strategic shift mitigates the massive 1X-2X cost to replace critical talent.

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

Ready to Move Beyond Friction?

Introducing The Leadership Navigation System: A 12-month strategic partnership rooted in 25+ years of tech leadership experience, designed for organizations committed to retaining and empowering their indispensable Keystone Leaders.

We equip your leaders with sophisticated tools and a structured methodology to diagnose systemic friction, build strategic influence, and drive measurable ROI—transforming organizational chaos into a competitive advantage.

What if fear wasn’t a roadblock, but the spark of something legendary?

Whether you’re navigating a new leadership role, shifting team dynamics, or the weight of being “the only one,ˮ Cindy is here to walk beside you.

This work is personal, real, and powerful. It’s not about fixing you – it’s about reframing your narrative so you can release old patterns and expectations to forge the authentic person and leader you aspire to be.

Why Dragons?

In organizations, the ‘dragons’ are often the systemic friction and invisible battles that drain your best leaders. Befriending these dragons isn’t about eliminating challenge; it’s about giving your Keystone Leaders the strategic tools to see that friction clearly, navigate it with influence, and transform it from a source of burnout into a catalyst for impact and resilience.

A woman in a black suit gently touches the head of a detailed green dragon, showcasing a close interaction between them.

The Leadership Navigation System is for:

Strategic Solutions for Navigating Leadership Friction

Let’s Work Together

Discover strategic solutions designed to help leaders navigate systemic friction, clarify their path, and drive meaningful impact. From organizational programs to personalized coaching and group circles, each offering provides the tools for sustainable growth.

audience with question marks floating above their raised hands

Leadership Navigation System for Cohorts

Invest in retaining and empowering your most indispensable Keystone Leaders. Our flagship 12-month cohort program (5-10 leaders) delivers a proprietary system to diagnose Leadership Friction, build strategic influence, and drive measurable ROI. We also offer focused 6-month Pilot Programs.

Two women walking with their dragons on a mountain path

Individual Leadership Navigation (1:1 Coaching)

Deeply personalized support for your unique leadership journey. Navigate systemic friction, calibrate your internal compass, and build strategic influence through confidential 1:1 coaching. Engagements available for 3, 6, or 12 months, whether you’re investing in yourself or seeking organizational sponsorship (including our premium 12-month Individual Deep Dive).

4 women at a table laughing as they discover their colorful dragons

Workshops, Circles, and Speaking

Foster collective growth and address specific team needs. Join Leadership Circles for peer support and shared learning. Bring customized Workshops to your team to tackle friction points like boundaries or communication. Engage audiences with strategic Keynotes on navigating complexity and retaining talent.

What My Clients Say

sarahlloyd
dr sarahlloyd

dr. sarahlloyd

deputy director @
Washington State Charter School Commission
small business owner

“Cindy has a way of sifting through the noise of logistics and emotions, to get at the heart of an issue. She invests heavily in the experience, and success, of her clients — and her investment is obvious through the entire coaching experience. She is a powerful coach, and she has the ability to not only ask critical questions at the right time, but to model the questions you will need to ask yourself moving forward on a sustainable path to thriving.”

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Just Curious? You’re in the Right Place.

Catlike watercolor green dragon sleeping on top of a journal labeled "Burnout and boundaries" with a manicured hand reaching out to pet her
What feelings and thoughts will you befriend today?

Feeling the pressure of ‘environmental exhaustion’? The first step to reclaiming your strategic focus is building clear boundaries. Use my free, interactive Dragonfire Boundaries GPT to design your first line of defense in under 5 minutes.

Ready to Befriend Your Dragons?

Let’s get curious, together. Book a call to explore what our work can mean for you, your team, or your leadership journey. Let’s Talk.