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 high-capacity leaders navigate systemic friction—so you work with impact, not exhaustion.

If a disruption like reorgs, layoffs, or a promotion have blown up your workload – or you’re just stuck in overwhelm – let’s
Untangle Your Next Step in 60 minutes.

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 High-Capacity Leaders while reducing the costly friction that leads to burnout and attrition.

Want the bigger picture?

Untangle Your Next Step is one entry point into my broader Leadership Navigation System for individuals and organizations. We create one breakthrough for you.

This is a strategic partnership rooted in 25+ years of tech and 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 as your thought partner and coach.

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 High-Capacity 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

People often start with a Breakthrough Session to Untangle Your Next Step. Organizations may start with my Strategic Boundaries Workshop or “I Got the Role…. Now What?” for an ERG, team, or Leadership Summit. Below are options for deeper or broader support.

splash of watercolor green

Leadership Navigation System for Cohorts

For organizations ready to retain and empower High-Capacity 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.

splash of watercolor green

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, and strengthen your ability to navigate complexity without burning out.

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

splash of watercolor green

Workshops, Circles, and Speaking

Practical, high-impact experiences for teams and communities. From my 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.”

previous arrow
next arrow

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 and Message Sharpener AIs 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.