What Happens When Leaders Choose to Lead Together?

Reflections from the Hawaiʻi Women Rise Leadership Intensive

There are moments in leadership when you know something important is about to happen before you can explain exactly what it is. I knew it in my na’au (deepest part of myself) before we began the two-day Women Rise Hawaiʻi Leadership Intensive. It began with asking for permission to speak into their lives.

What may seem like a small thing, I believe it is one of the most important acts of respect we can offer one another as leaders. Leadership is deeply personal. Our decisions affect families, communities, organizations, and generations. We should not allow just anyone to shape how we think, lead, or view ourselves. Influence is a privilege, not a right.

When they said yes, they weren't simply agreeing to participate in a workshop, they were agreeing to be challenged. What followed was one of the most meaningful leadership experiences of my career.

A Room Full of Extraordinary Women

Each woman arrived carrying significant responsibility and wearing many hats–executive directors, community leaders, advocates and visionaries.

Most had spent years navigating complex systems while carrying the hopes of the communities they serve. Yet beneath their accomplishments was something many nonprofit leaders understand all too well—leadership can be incredibly isolating.

That isolation is amplified in Hawaiʻi. The physical distance from the mainland creates real barriers to accessing professional networks, technical assistance, and peer learning. But an even greater challenge has emerged through the way much of philanthropy and nonprofit funding has evolved. Too often, organizations serving the same communities find themselves competing against one another for limited resources, even when the problems facing those communities demand collaboration.

No one organization can solve housing. Or education. Or behavioral health. Or food insecurity. Or the widening economic divide. Or the community safety net. 

Yet we continue to build systems that unintentionally reward working apart instead of working together. The women in this cohort knew that reality intimately.

Innovation Born from Necessity

One thing became abundantly clear over the two days. Hawaiʻi has never waited for perfect conditions. Its leaders innovate because they must. It is part of the DNA of the islands. 

Resource limitations, geographic isolation, cultural complexity, and economic pressures have required nonprofit leaders to become some of the most creative systems thinkers in the country. Ironically, many of these same conditions are emerging in Idaho.

Although separated by nearly 3,000 miles, Idaho and Hawaiʻi are experiencing strikingly similar trends.

• Income inequality continues to widen.

• Housing affordability has become one of the defining issues of our generation.

• Communities are growing more diverse while public resources struggle to keep pace.

• The nonprofit sector is being asked to solve increasingly complex problems with finite resources.

Perhaps most importantly, neither place can afford fragmented solutions. Both require greater cross-sector collaboration.

From Individual Leadership to Collective Leadership

One of the goals of the 2-day intensive hosted by the Patsy Mink Center for Business and Leadership and Central Pacific Bank was not simply to develop stronger individual leaders. It was to help create a community of leaders capable of solving the challenges they are all experiencing–together rather than alone.

Throughout the workshop we explored governance, organizational life cycles, strategic partnerships, future-ready boards, organizational capacity, leadership resilience, ecosystem mapping, and new models for collaboration. We did a leadership reset, which is critical for all of us who are leading nonprofit organizations. 

The conversations gradually shifted. Instead of asking, "How do I strengthen my organization?" The questions became: "What can we accomplish together?" "What business model might we explore to best serve our communities?" "What services should remain independent and what could be shared?" "How do we educate our boards to think differently?"

These are entirely different questions. They move leadership beyond organizational success toward ecosystem success. By the end of the workshop, these women were no longer simply exchanging ideas. They were beginning the hard work of designing new ways to work together. That is where real systems change begins.

Preparing Boards for the Future

One lesson surfaced repeatedly. The future will require boards of directors to think differently than they have in the past. Governance can no longer focus solely on fiduciary oversight.

Boards must understand: 

• Changing demographics.

• Economic trends.

• Technology.

• Partnership models.

• Shared services.

• Collaborative governance.

• Regional solutions.

Future-ready boards will need the courage to ask not only whether their own organization is healthy, but whether the entire ecosystem serving their communities is healthy. This requires new tools as well as new frameworks. And often, difficult conversations.

Our work moving forward is to help boards understand those realities while giving them practical ways to evaluate what organizational structure or combination of structures will best serve their communities.

Sometimes that will mean remaining independent. Sometimes it will mean partnering more intentionally. Sometimes it may involve shared services, fiscal sponsorships, joint ventures, mergers, or entirely new models that haven't yet been imagined.

The goal is never organizational preservation for its own sake, rather it is stronger outcomes for the people we serve.

Women Leading Through Complexity

Another conversation surfaced repeatedly throughout the two days. Many participants spoke candidly about leading within environments where women continue to navigate unequal expectations, which requires extraordinary resilience.

At the same time, many leaders continue to carry the weight of historical disenfranchisement while working to preserve culture, strengthen communities, and create opportunities for future generations.

These realities cannot be separated from leadership. They shape how trust is built. How decisions are made. How partnerships are formed. How communities heal.

Acknowledging those truths allowed deeper conversations to emerge—conversations rooted in both honesty and hope.

Something New Was Born

As the workshop concluded, I sensed that we had reached the moment I had hoped for. Not because every problem in the room had been solved. But, because something had shifted. The women were no longer thinking as isolated nonprofit leaders. They were beginning to think as architects of a new ecosystem.

One participant later wrote: "Those two days of learning with you were amazing. I felt rejuvenated and ready to take on complex societal issues with you and the rest of the amazing cohort."

That single sentence captured what I had witnessed. Not exhaustion but renewal. Not competition but community. Not simply leadership development but collective leadership.

The Beginning, Not the End

The Women Rise Hawaiʻi Leadership Intensive was never intended to be a standalone training. It is the beginning of building technical expertise that helps leaders strengthen governance, educate boards, evaluate organizational models, and create stronger cross-sector partnerships capable of addressing Hawaiʻi's (and Idaho’s) most pressing challenges.

The same lessons apply in Idaho. While we might have a different geography and different history we have remarkably similar challenges.

Communities thrive when organizations stop asking, "How do we protect what is ours?" and begin asking, "What is possible when we build something together?"

That question may ultimately become the defining leadership challenge of our generation. And after spending two days with these remarkable women, I believe these leaders in Hawaiʻi are ready to help answer it.