Leveraging Technology for Trust-Based Evaluation

by Steph Schilling, Evaluation and Operations Associate

My advice to fellow philanthropy professionals is this: Don’t let the limitations of a grants management system stifle your values. Start with your values and build your processes and systems from there. 

At Headwaters Foundation, we are committed to embodying Trust-Based Philanthropy in every aspect of our work. More than providing multi-year, general operating grants, this approach is rooted in building mutually accountable relationships and dismantling the power dynamics prevalent in conventional philanthropy.  

Central to this commitment is our belief that true impact comes from collaborative partnerships and community-driven solutions. This belief permeates our organization, from our conversational grant reporting to our internal policies and culture. One question we often receive about our trust-based approach is, “what does your learning and evaluation look like?”  

In this blog, we share our methodology and highlight the role of SmartSimple, a powerful grants management tool that empowers us to think expansively and focus on relationships while tracking progress.  

Why Evaluate? 

In conventional philanthropy, the foundation sets the metrics of success and nonprofits are compelled to conform. We do things differently. We collaborated with the community to co-create a theory of change which serves as the foundation for our learning and evaluation framework. Our evaluation serves three purposes: 

• Accountability: We hold ourselves accountable to the community, our partners, and our mission, and aim to ensure alignment between our commitments and our actions. 
• Tracking Progress: We use evaluation to gauge progress toward the outcomes defined in our theory of change, and to help us learn as we go. 
• Long-Term Health Metrics: We monitor population-level data to see if the strategies we invest in are contributing to positive trends.  

Each year, we compile our findings into a Learning and Evaluation Data Book, which we share with our Board and partners for transparency and collaborative learning. See the latest here. 

Harnessing Technology 

We use the power of technology, specifically SmartSimple software, to streamline our learning and evaluation processes. I recently teamed up with them for a webinar on this very topic. If you’re eager to dive deeper into any of the following examples, check out the recording. 

• Tracking Outcomes: We track progress toward outcomes defined in our theory of change. Because we’re focused on systems-level change rather than direct service delivery, we collect qualitative and narrative data, mainly through conversations with partners, which our team inputs and links to related outcomes.  
• Beyond-the-Check Support: We are committed to supporting partners beyond grantmaking. We track various forms of assistance provided to grantees, from hosting trainings and convenings to offering thought partnership. 
• Events Management: Recognizing a need in our community, last year, we opened Confluence Center, a free event space for nonprofits. We automated scheduling and post-event surveys and integrated a booking page into our website to make it efficient for us and our partners. We also use SmartSimple to help us track the impact of the space.  

Join the Conversation 

While we are proud of our commitment to Trust-Based Philanthropy, we acknowledge that we are a work-in-progress; we are constantly learning and iterating. My advice to fellow philanthropy professionals is this: Don’t let the limitations of a grants management system stifle your values. Start with your values and build your processes and systems from there. 

I invite you to connect with me to explore how you can operationalize Trust-Based Philanthropy in your learning and evaluation work. There is also a Slack channel for SmartSimple users, great for getting questions answered or simply finding camaraderie with other users. Reach out to me at [email protected] to join the dialogue.