Befriending Dragons

Is it Me or the System?

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

Ready to Turn Friction into Fuel?

Choose Your Path
Not sure which fits? Start with a free Clarity Call.

✅ 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 caoching 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.

Start with one real situation

Is it Me or the System? is a single session on one real situation: what belongs to the system, what belongs to other people, and what’s yours. It’s also the entry point to my Leadership Navigation System for individuals and organizations.

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

I help leaders and their organizations see friction clearly, build influence, and turn that friction into fuel instead of burnout.

What if friction 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,” 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 friction and invisible battles that drain the best leaders. Befriending these dragons isn’t about eliminating challenge; it’s about giving the leaders everyone depends on the strategic tools to see that friction clearly, navigate it with influence, and transform it from a source of burnout into fuel 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:

Ways to Work Together

Individuals often start with an Is It Me or the System? session. Organizations may start with my “Strategic Boundaries” talk, “Is it Me or the System” workshop or “I Got the Role… Now What?” talk for an ERG, team, or Leadership Summit. Below are options for deeper or broader support.

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.

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.

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.”

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Just Curious? You’re in the Right Place.

Book cover: Empowering Women in STEM: Building a Culture of Resilience, edited by Sanya Mathura.
Chapter 23, out now.

Start with my chapter, “Befriending Dragons: From Burnout to Confidence,” from Empowering Women in STEM: Building a Culture of Resilience.

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.