What We Learned in a Year of Change

At Headwaters, learning is built into our organizational values. We strive to be willing to try new things, pay attention to what happens, listen to feedback, and make changes when something isn’t working. Since 2020, we have made a habit of looking back on the past year and capturing reflections in an annual Learning Book. This resource is mainly for our staff and board, but we also share it publicly so our partners and peers can see what we’re learning and how we’re responding.

This year, the Learning Book itself is changing. In previous years, it focused on grantmaking data, the outcomes in our theory of change, and broader health indicators. After we rolled out our new 10-year strategic framework in 2025, we realized we needed a clearer way to tell the story. Going forward, the Learning Book will focus on the part we have the most control over: how we work as a foundation. Every three to five years, we also plan to take a deeper look at what’s changing through an Impact Report focused on the outcomes in our theory of change.

2025 gave us plenty to reflect on. We were implementing a new strategy, welcoming new leadership and staff, and changing our grantmaking at the same time nonprofits across Montana were navigating funding cuts, policy changes, and growing demand for their services.

Check out our 2025 Learning Book!

Here are some of our team’s reflections from 2025; what we tried, what we learned, and what we’re carrying forward:

Give big changes the time they need. [→]

One of our biggest learning opportunities came from implementing our new strategic framework and launching the Family Power Fund. The transition to a new strategic framework and new way of making grants happened alongside welcoming a new CEO, CFOO, and four new staff to our team. We communicated the upcoming changes to grant partners early, but we didn’t always have clear answers about what they would mean. Timelines shifted, the new process was still taking shape, and we weren’t able to be specific about funding levels as early as partners needed us to be.

Looking back, we could have given everyone more time. We didn’t need to hold ourselves to an arbitrary timeline; taking a transition year while continuing existing funding could have given partners more certainty and given our team more time to learn, align, and build new processes. We learned that sometimes the best thing you can do during a big transition is slow down and give both your partners and your team the time and clarity they need to navigate it well.

Let your values change how you work. [→]

As part of our strategic planning process, we took a fresh look at Headwaters’ organizational values, revisiting what matters most to us and how we want those values to guide our work. Honoring Tribal sovereignty emerged as one of those values. As we continued developing our strategy, our board proposed creating a long-term partnership with the Confederated Salish and Kootenai Tribes (CSKT), with funding dedicated to priorities identified by Tribal leadership.

We brought the idea to the CSKT Tribal Council and asked how they wanted to work with us. The Council appointed two representatives to work directly with Headwaters on the new CSKT Partnership Fund, helping shape an approach that supports priorities in the Tribe’s strategic plan that align with our shared goals for health.

Being more explicit about Tribal sovereignty as a value pushed us to think differently about our relationships and decisions. It reminded us that values are most useful when they don’t just describe what we believe, but actually influence how we work.

Listen and adapt. [→]

In 2024, Headwaters made pilot grants to 17 organizations working to advance health equity, with plans to hold a gathering in 2025 in lieu of a grant report. By early 2025, federal funding cuts and growing political pressure around equity work had changed the environment considerably. We asked participants what would be most useful now and heard that they needed time to connect, talk honestly about what they were facing, and focus on their wellbeing. We shifted the gathering accordingly and came away with a clearer picture of what organizations needed from funders.

We took a similar approach to capacity building throughout the year, piloting support around scenario planning, communications and narrative change, and emotional resiliency, and learning from partners about what was useful. The takeaway for us was to stay flexible. What we plan at the outset may not be what organizations need, especially when circumstances are changing quickly.

Small, flexible grants can tell you a lot. [→]

Our GO! Grants program turned seven in 2025, and demand was higher than ever. We ran out of funds for the program quicker than in any previous year, and some organizations that had previously grown beyond the program’s eligibility limits qualified again after budget cuts. It was another sign of just how difficult the funding environment had become for Montana nonprofits.

GO! Grants remain an important way for us to build relationships and learn about the work happening across Western Montana. In 2025, nine previous GO! grantees became Family Power Fund partners. Seven years in, we’re seeing more fully how this program helps us understand what communities need, who is working to meet those needs, and where there may be opportunities to deepen our relationships and support over time.

Our voice is stronger when it’s part of a chorus. [→]

The biggest challenges facing Montana communities are too large for any one organization or funder to tackle alone. We saw this in 2025 as federal policy changes threatened nonprofits and the families they serve. In response, we added our voice to broader efforts, including joining with other funders to share research, partner on messaging polling, and contribute to pooled funds to offer deeper support to partners. We don’t always need to lead or create something new to contribute. Sometimes our most useful role is to bring resources, relationships, research, or our voice to work already underway.

A meeting space can become something more. [→]

When we opened Confluence Center, we knew nonprofits needed quality, affordable places to meet. What we’ve learned is that its value goes well beyond meeting rooms. In 2025, 156 nonprofit organizations used the space, and nearly 80 percent had never received a Headwaters grant. Events like our annual Día de los Muertos celebration have also shown us what can happen when the broader community feels welcome in the space. As belonging has become a bigger part of our work, it’s expanded how we think about Confluence: not just as a resource for nonprofits, but as a place for building community.

Carrying the lessons forward [→]

Our Learning Book gives us a chance to reflect honestly on our work. We’ve carried these lessons into 2026 as we continue refining our grantmaking, build a longer-term approach to supporting partners beyond grantmaking, refine how and when we use our public voice, and look for better ways to work alongside the people and organizations we support.

If you work in philanthropy and are wrestling with some of the same questions, or you’re a Headwaters partner with thoughts about how we can better work together, we’d love to hear from you. Reach out anytime!