Key Lessons from Our 2024 Learning Book

At Headwaters, we regularly pause to reflect on what we’re learning – about the work we fund, the challenges our partners face, and the changing conditions that shape health and well-being in Western Montana. We do this because learning is essential to staying responsive, refining our approach, and building stronger partnerships rooted in the real experiences of the communities we serve.

Our annual Evaluation & Learning Data Book pulls together insights from staff reflections, grantee reports, data trends, and conversations in the field. We recently wrapped up our 2024 edition; here are ten lessons that stood out:

1. Collaboration Requires Structure and Support

We see stronger outcomes when organizations collaborate, and partners are increasingly reaching beyond their own walls to share learnings and build capacity across their fields. This takes coordination, facilitation, and the right support to make it work. Philanthropy can help by funding coalitions and coordinator roles, offering flexible resources, and creating space – like convenings or shared venues – for connection and planning. One example is our Narrative Change Action Lab, where we invite grantees to bring their partners for a deep dive into strategic storytelling.

2. Structural Change Takes Time, and Staff Retention is Key

Long-term change doesn’t happen overnight, and it can be slowed by staff burnout, turnover, and unstable funding. Many organizations are relying more on part-time and contract positions, which can make it harder to sustain progress. More than ever, we’re looking at ways to support leadership development, staff retention, and organizational stability, and we continue to take a long view. Our current strategic framework spans 10 years because meaningful change takes time, and foundations need to plan, and fund, accordingly.

3. Listening to Community Shapes Better Practices

Listening to grantees, community members, and lived experts continues to shape how we work. When partners help set direction and share feedback, trust grows, and community health improves. In 2024, we hosted our first grantee input session to hear directly from partners about their priorities and how they want to engage with us. Grantees are also centering community voice – such as by adapting health needs assessments to reflect early childhood priorities and using messaging surveys to guide advocacy around Medicaid. These practices are helping make strategies more responsive and effective.

4. Belonging is the Foundation for Leadership and Engagement

When people feel seen, included, and connected, they’re more likely to step into leadership and advocacy roles. Grantees are laying that foundation in many ways – through schools that engage families beyond the classroom, coalitions hosting substance-free community events, and a unique theater tour that sparks public conversations about mental health. These efforts build trust and resilience, creating the conditions needed for long-term systems change.

5. Public Funding Is Uncertain and Our Response Matters

The winding down of COVID-era funding, and more recently, the creation of the Department of Government Efficiency (DOGE) are creating uncertainties around public funding. We’ve heard that the flexibility of Headwaters’ funding has helped grantees bridge gaps caused by cuts and delays. To meet the moment, we’re also increasing our grantmaking, exploring tools like a revolving loan fund, and participating in funder coalitions to elevate Montana’s needs and help attract new funding to the state.

6. Confluence Center Is More Than a Venue

Last year, Confluence Center saved nonprofits over $100,000 in rental fees while offering an inclusive space for mission-driven work. Since opening two years ago, this home for nonprofit events has become a hub for connection, helping us engage with grantees and spark new partnerships. With demand rising, we’ve staffed up and created new tools to support event hosts. Now we’re asking: could other communities in our service area benefit from a space like this?

7. Storytelling and Data Drive Change

In 2024, our report Supporting Our Neighbors helped debunk myths and shift narratives around public assistance in Montana. More broadly, we’ve seen that combining clear data with real stories strengthens advocacy and shapes public understanding of the issues communities face. Health policy reporting brings attention to overlooked issues and is sometimes cited directly by lawmakers. Funders can support by partnering with researchers and journalists to help share what’s happening on the ground and investing in efforts that link research to real-world solutions.

8. Youth and Family Leadership Drives Systems Change

Partners are creating meaningful opportunities for youth and families to lead – from serving on boards to influencing policy. Native youth participated in legislative training and were recognized on the House floor. Parents and caregivers organized in their communities and testified at the legislature. These efforts don’t just build individual power – they help shift who has a voice in shaping decisions that affect community health and wellbeing.

9. Familiar Challenges, New Solutions

Some challenges – like stretched resources and staffing – show up year after year. But we’re also seeing new solutions. Rural organizations in particular are finding creative ways to meet the unique needs of their communities. One organization, for example, worked with food access and child development partners to share space, lowering administrative costs and making it easier for families to access multiple supports in one place.

10. Trust-Based Philanthropy Is Still the Right Fit

General operating support, flexible funding, and conversation-based reporting remain central to our approach, and grantees tell us they matter now more than ever. Our willingness to adjust expectations based on context, such as stepping back during election years and legislative sessions, also strengthens trust and makes space for partners to lead. At the 2024 Philanthropy Northwest conference, partners shared how our trust-based approach has worked for them.

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As we look ahead to a new chapter under our 2025-2034 Strategic Framework, these lessons will help guide our way. We remain committed to being flexible, staying grounded in community, and continuing to learn alongside our partners.

Check out our 2024 Evaluation & Learning Data Book here!

Interested in discussing our learning work? Reach out to Steph Schilling at stephs@headwatersmt.org.