Cindy Gross | Befriending Dragons

Adaptive Leadership

Adaptive Challenges

Adaptive Leadership addresses stubborn systemic Adaptive Challenges where we are collectively stuck around our shared purpose. There’s an underlying conflict of values and no known win-win option or playbook. There’s no authority or expert to close the gap. The values currently prioritized don’t work for the collective to achieve our shared purpose.

Adaptive challenges don’t just exist at the organizational level—they show up in the day-to-day decisions of leaders at every level. In complex workplaces, individuals must learn to work within established structures while also questioning outdated norms and advocating for meaningful change. Adaptive leadership empowers you to recognize patterns, engage stakeholders, and experiment with new approaches—all while managing resistance and uncertainty. It’s about leading with both courage and strategic awareness, ensuring that innovation happens within the realities of your environment.

Adaptive Leaders

Adaptive Leaders put people and relationships first. We work towards collective impact through shared purpose. Our goal is to change entire systems, often by changing the hearts of a few pivotal people. We keep a values focus as we work together differently to achieve the shared purpose we decided on with EVERYONE who is impacted. The change and the process we use to create the change enable thrival.

I learned Adaptive Community Leadership through Leadership Eastside in the Seattle area, and it changed my life. I’m now on the Leadership Eastside board, I coach campaign teams, and I co-facilitate leader days with the cohorts.

Thrival

We develop habits, patterns, and routines in how we talk about ourselves, our systems, and each other. In many places the dialogue centers the status quo. It assumes the norms of current and past power structures are the best or even only way to be. In that system we fight for survival in scarcity.

Thrival isn’t just about surviving—it’s about leading with purpose in an ever-changing world. Adaptive Leadership challenges leaders to thrive by engaging with complexity, questioning ingrained assumptions, and embracing discomfort as a catalyst for growth. Cindy’s approach helps leaders step beyond survival mode, equipping them with the confidence to adapt, inspire, and drive meaningful transformation within their organizations.

Reframe Your Narrative

Leadership is an ongoing process, not a fixed position. Adaptive Leadership helps you navigate complexity, challenge assumptions, and engage others in meaningful change. It’s about recognizing when old ways no longer serve you—and having the courage to experiment, learn, and adjust.

Cindy helps leaders break free from limiting beliefs, embrace uncertainty, and build the skills to lead effectively in dynamic systems. With the right mindset, tools, and support, you can shift your narrative and step into the leadership role you were meant for.

Resources