Cindy Gross Is Redefining Leadership for the Leaders No One Sees

Please share a brief introduction and your business:

I'm Cindy Gross, founder of Befriending Dragons, a Native Woman-owned leadership company. My expertise is built on 25 years in tech, including 18 years at Microsoft. I leveraged that deep corporate knowledge to create The Leadership Navigation System, a strategic, long-term B2B coaching program. My business equips indispensable Keystone Leaders—senior, often women and non-binary professionals—to conquer organizational complexity, directly reversing the Capacity Erosion that results from unaddressed Leadership Friction.

Did you always know you wanted to be an entrepreneur?

No, my path was a progression from an indispensable corporate leader to a strategic founder, driven by purpose, not just profit. For decades, I was deeply committed to the corporate structure, often focusing my advocacy externally—fighting for DEIB and LGBTQIA+ rights—because fighting for myself felt unacceptable. The realization that my unique blend of technical mastery and systemic coaching was the precise, high-value intervention the tech industry needed to retain critical talent forced the transition to entrepreneurship.

Take us back to when you launched? What was your marketing strategy?

My initial marketing strategy was organic, trust-based, and expertise-driven. I focused heavily on speaking engagements and professional networking, generating interest by offering valuable free resources like playbooks and specialized webinars. This approach built immediate trust and successfully converted clients, but it wasn't scalable. I struggled with hours spent changing messaging and spent too much time chasing "shiny objects" and routine tech distractions instead of executing my strategy. The good news is that I've since won a grant that allowed me to secure the AI Sales Accelerator from the Laurens, providing a custom AI coach that helps me stay on track with a focused brand voice, clear offer, and sustainable strategy.

What accomplishments are you the most proud of to date in your business?

I am most proud of codifying my 25 years of systemic wisdom into the practical, measurable methodology of The Leadership Navigation System. This program successfully takes the complex, invisible battles that once caused my burnout and transforms them into tangible, repeatable frameworks—like the System Map and the Boundary Blueprint—that are now the foundation for our clients' sustained success and measurable organizational ROI.

What is one thing you wish you had known when you started your Entreprenista journey?

I wish I had fully realized that my pricing is a strategic intervention and an act of leadership, not a reflection of personal worth. For women and marginalized business owners, charging our true value creates permission for others to do the same. Understanding this earlier would have dramatically reduced the energy I spent on constant second-guessing and price anxiety, even though I still have to be intentional about holding that boundary.

When hiring, what is your go-to interview question?

My go-to interview question is: "Tell me about a time you tried to bridge a major divide between two different teams or departments where their goals seemed completely opposed."

This question reveals:

• Systemic Intelligence: Do they recognize the complexity of organizational friction (like silos and opposing goals)?

• Communication Mastery: Can they show how they translate objectives and build trust across different organizational cultures?

Influence Without Authority: Can they demonstrate success in getting disparate groups to collaborate for a shared outcome?

What did you go before starting your own business?

My background is rooted in deep technical expertise and organizational strategy within the US tech industry. I spent 25 years in tech, including 18 at Microsoft, where I was the indispensable professional holding complex projects together. I was known for communicating fluidly across all organizational layers —from drilling down into the technical details with front-line implementers to articulating the high-level business strategy to a CEO. My value was in translating complex technical expertise into tangible business value. This experience taught me how power, identity, and systems interact, which is the foundation of my coaching methodology.

What made you take the leap to start your own business?

The leap was driven by a crisis of conscience and burnout. Despite doing outstanding work, I faced bias, reported harassment, and carried the weight of unrewarded "glue work," all while managing intense personal challenges. I realized the friction wasn't a personal failing; it was a systemic business problem. My core purpose became clear: I wanted to be the safe, strategic partner I desperately needed but couldn't find. I developed The Leadership Navigation System to give other underestimated leaders the methodology to lead with authentic, sustainable impact, transforming their pain into lasting systemic change.

Do you have any recent wins?

Yes, we’ve achieved key strategic milestones to scale our impact:

• Strategic Validation: I secured a key grant from the Washington Native American Chamber of Commerce that validated our business model and helped fund the necessary infrastructure to scale our impact and equity mission.

• Methodology Refinement: I invested in the Leadership Circle Profile 360 certification and advanced sales training to sharpen our proprietary frameworks and ability to articulate our B2B value.

Infrastructure Build-Out: I successfully built the digital ecosystem—including a new community platform, CRM, and coaching tools—required to move beyond my individual capacity and prepare for a sustainable cohort model.

What's one app on your phone that you cannot live without?

My calendar app. It is my most crucial tool for setting and maintaining boundaries and leading with intention.

Who are your customers?

We serve two key clients:

The Underestimated Keystone Leader: These are the essential, senior leaders (managers, directors, VPs, or top individual contributors) in the US tech industry who are carrying critical responsibility and facing a "stay or go" crossroads. They are deeply ambitious and seek a proven, practical path to sustainable influence.

Tech Organizations: Our paying customers are mid-to-large tech companies and IT departments that recognize the high risk of losing critical, high-impact talent. We partner directly with executive sponsors (CTOs, VPs of People/HR) who need a measurable, strategic intervention to reduce costly turnover, stabilize teams, and accelerate key initiatives.

What's your top productivity tip?

My top productivity tip is to make your invisible system visible. Start by deeply understanding your own authentic values, strengths, skills, and sources of joy. This self-awareness is part of designing your intentional 'Operating System of Me' and helps you map your unique internal system. When you're clear on these internal anchors, you dramatically improve how you see yourself and communicate your value to others.

Next, use a tool like the System Map to diagnose the external environment, transforming your long to-do list from a source of anxiety into a manageable, strategic project. Once you map the Leadership Friction , you can stop wasting energy on the low-leverage tasks causing drag and strategically focus on what creates maximum impact.

What's your favorite business tool?

My favorite business solution is The Leadership Circle Profile (LCP) 360 Assessment. It's a cornerstone diagnostic tool for my methodology. It provides an objective, data-driven mirror that immediately validates for leaders that their struggle is often due to systemic friction, not personal failing, and provides a clear path forward.

What's your approach to work-life balance?

My approach is intentional work-life alignment, not passive balance. I use my Personal Leadership Vision to guide where I apply effort, ensuring my career trajectory aligns with my deepest values and desired legacy. This is achieved by creating strategic, enforceable boundaries to protect my time and focus. When my professional life is intentionally aligned with my authentic self, I lead with greater impact and sustainable energy.

How do you avoid burn-out?

I avoid burnout by viewing it as an ongoing practice of self-awareness, not a fixed achievement. I constantly work to implement what I call Calibrate the Compass for myself. This means regularly defining and protecting strategic boundaries using my Boundary Blueprint, which is always a work in progress. It's about recognizing that burnout is a symptom of systemic Leadership Friction, and my job is to interrupt those chaotic reactive patterns and make conscious, creative choices about where I invest my finite energy.

What advice do you have for aspiring Entreprenistas?

My best advice is to stop waiting for things to settle down before you make your big strategic move. The most valuable work happens precisely when the system is in flux. Use your current environment—the chaos, the challenges, the "friction"—as the data set for your next strategic move. Focus on mastering your internal "Operating System of Me" and applying practical tools to convert external friction into leverage, ensuring you're building a business that creates sustainable impact and not just survival.

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