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 systemic friction—so you lead with impact, not exhaustion.

If reorgs, layoffs, or a promotion have blown up your workload, start with a 90-minute Burnout + Boundaries Reset Sprint.

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

Ready to Move Beyond Friction?

Choose Your Path

I’m an individual leader

You’re dealing with burnout, boundaries, or high-stakes dynamics right now. Start with a fast reset, or continue with ongoing navigation if you need deeper support.

I’m looking for organizational support

You want to retain and empower Keystone Leaders while reducing the costly friction that leads to burnout and attrition.

Want the bigger picture?

The Sprint is one entry point into my broader Leadership Navigation System for individuals and organizations.

This is a strategic partnership rooted in 25+ years of tech leadership experience, designed for navigating complex, high-stakes environments.

I equip leaders and their organizations 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

Ways to Work Together

Most people start with a Reset Sprint, and organizations often choose my Strategic Boundaries Workshop. Below are options for deeper or broader support.

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Leadership Navigation System for Cohorts

For organizations ready to retain and empower Keystone Leaders at scale. A facilitated cohort experience that reduces systemic friction, builds strategic influence, and strengthens leadership capacity in high-stakes environments.

Ideal for leaders navigating reorgs, growth, or chronic overload.

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Individual Leadership Navigation (1:1 Coaching)

Ongoing, confidential support for leaders who need more than a one-time reset. We tackle your next blocker, build decision rules and language over time, and strengthen your ability to navigate complexity without burning out.

Best when the pattern is recurring—or the stakes are high.

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Workshops, Circles, and Speaking

Practical, high-impact experiences for teams and communities. From the Strategic Boundaries Workshop to custom sessions on communication, influence, and navigating friction—designed to create shared language and behavior change.

Great for orgs who want fast, visible shifts.

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.