Special thanks to Rachel Burstein, for conducting these interviews, analyzing the feedback, and prompting us with rich discussion about our areas of growth
We believe feedback is essential to continuous improvement. Philanthropy operates within inherent power imbalances, making it all the more important to create structured opportunities for grantees to share honest perspectives about what’s working and what isn’t. We believe feedback serves a dual purpose: it strengthens our relationships with grantee organizations by demonstrating that their voices genuinely shape our practice, and they provide us with the critical feedback we need to evolve our approach.
As in previous years, we commissioned a set of confidential interviews with nine grantee organizations, conducted by an independent researcher and writer during the 2025 calendar year (see methodology for details). Our independent researcher provided findings, which we discussed extensively as a staff team. Below, we share what we heard—the commendations and the critiques—alongside how we’re responding. This transparency is itself a practice we’re committed to: being as honest about our areas for growth as we are about what we’re doing well.
But First, Some Context on the Philanthropic Sector Overall
Uncertainty around federal funding and the tense political environment served as backdrop to this year’s interviews, even as interviewees experienced these realities in different ways. All saw philanthropy as uniquely positioned to help nonprofit organizations weather the storm, though none viewed philanthropy alone as a panacea. Interviewees stressed the importance of philanthropic investments that were geared toward long-term change and ecosystems, rather than stopgap measures to cover lost governmental funding or support for popular flavor-of-the-month programs or approaches.
The current moment is unique, but grantees stressed that philanthropy need not adopt exceptional approaches to meet the moment. Instead, funders ought to double-down on building deeper relationships and engaging in co-learning with grantees—practices that grantees value regardless of the political environment.
In contrast to past years, interviewees spent little time discussing the day-to-day mechanics of effective philanthropic partners (e.g., the need for multiyear commitments, the importance of reducing meaningless paperwork, etc.); these were considered table stakes. Instead, interviewees pointed to a need for intentional collaboration and deep courage from philanthropy.
Summary of Key Findings
1. The Current Moment Demands Flexibility and Adaptability—But That Can Create Ambiguity
Interviewees emphasized the importance of trust, honesty, and open communication between funders and nonprofit organizations, especially at the current moment when the funding and political landscape remains uncertain. Grantees felt that this honesty ultimately led to better outcomes and greater contributions to the field.
Still, interviewees acknowledged that it can sometimes be difficult to forge such deep and open relationships from the outset. “It gets easier as the relationship develops and there’s a track record of success,” one reflected. Another explained, it is “heartbreaking to write a grant and get absolutely no feedback.” Grantees shared that funders could better resource nonprofits during this period by supporting pilot projects and offering clearer guidance on the amount and timing of anticipated future funding—steps that can help sustain organizations during the relationship-building phase and reinforce the value of investing in those relationships.
Interviewees appreciated the ease of their relationship with Siegel Family Endowment, but often pointed to a negative flipside: ambiguity in processes. As one interviewee explained, “The process with Siegel was reasonable; nothing was straining. But it was somewhat ambiguous.” It wasn’t always clear to the grantee how the grant process worked, what materials needed to be submitted, what the timeline was for grants, and which Siegel staff members they should direct questions to.
While several grantees noted that they were uncertain about Siegel’s processes early on in their relationship, they also noted that they felt more comfortable inquiring about what was required as their relationship deepened. However, the uncertainty didn’t vanish entirely. Grantees stressed the importance of clear structures and timelines for check-ins, evaluation, renewal, shared learning, and other processes, even as informality dictated their relationship with foundation staff.
In some cases in philanthropy, foundation staff conduct informal oral check-ins and aren’t clear about what concrete goals need to be met or what formal reporting needs to be submitted by a grantee in order to pass muster with a foundation’s board. “It’s not always clear if you’re doing a good job or meeting the mark,” one grantee explained. Another explained that their organization wasn’t always sure what level of detail was needed for renewal requests or communication with a foundation’s board.
While both felt comfortable raising the issue with foundation staff, they sometimes struggled to get clear feedback from program officers with whom they had close, candid relationships and who conveyed that performance was strong. At times, this assessment was not shared by senior staff or board members—creating awkward moments at best and, at worst, jeopardizing funding.
How We’re Responding
We recognize that prospective grantees invest considerable time building relationships with funders, which makes transparency and open communication essential from the very first conversation. We’re committed to communicating funding decisions and “no” earlier in our process rather than leading organizations through lengthy discussions that won’t result in funding. While we named this commitment last year, it took time to fully integrate into our culture and pipeline; we now feel confident we can do this consistently.
We hear the frustration about developing materials that receive inadequate responses, and ask very little of prospective grantees during initial conversations–encouraging them to send existing materials, and share drafts and bullet points rather than polished documents.
To better manage expectations, we have launched a new section on our website detailing what and how we fund. We also now estimate a 12-month runway from initial conversation to grant approval for new partnerships, and once we decide to pursue a grant, we provide transparent timelines at every stage.
As noted above, ambiguity also exists after a grant has been made. We also understand that our myriad of reporting and engagement options can feel unclear, so we’re working to be more explicit about what’s optional versus required, and what different touchpoints accomplish.
We’re also clarifying our learning and evaluation approach: while we don’t track traditional metrics or programmatic outputs in the same way other funders might, we are evaluating rigorously; our emphasis is on the shared question and hypothesis we’re exploring together, and the quality of learning we’re generating. We recognize this is an adjustment for many partners accustomed to different reporting structures.
We acknowledge a difficult reality: sometimes grants both generate great learnings and may later become misaligned as our questions evolve. When this happens, we commit to transparent communication about why priorities are shifting and welcome honest conversations, while recognizing the wider dynamics of difficult choices and resource allocation that go on in a grantmaking institution.
2. Funders can flatten entrenched hierarchies—and encourage better outcomes—by engaging in co-learning with grantees.
All of the interviewees agreed that relationships between funders and nonprofits are inherently asymmetrical. This power dynamic can be uncomfortable for nonprofit personnel and even have devastating consequences for nonprofits’ programs.
One interviewee explained that their organization sometimes encounters funders who “move the sector toward a predetermined solution that isn’t necessarily the right one and forces nonprofits to either fit that or disappear.” Such rigidity further magnifies inherent power dynamics between nonprofits and funders and dissuades experimentation with new models that may lead to better outcomes.
Our inquiry-driven approach doesn’t eliminate these power dynamics, but grantees felt it significantly shifts the relationship by prioritizing what we’ll learn together over what we expect them to accomplish. Grantees mentioned Siegel’s collaborative grant proposals, investigations of shared questions, and joint funder-grantee attendance at convenings and conferences as examples of collaborative endeavors that can flatten hierarchies and lead to better outcomes. Several grantees shared that Siegel was supportive when they pivoted their strategies or desired outcomes based on learning—a rarity in funding relationships.
One grantee commented that a shared learning agenda allows us “to look at the humanness of the work that is sometimes lost when you’re talking about KPIs.” Another reflected that beginning with questions rather than solutions allows the funder to “own the fact that they might not be asking the right question.” All agreed that shared learning and shared processes between funders and nonprofits helped improve outcomes and energized grantees about the work.
How We’re Responding
We’ve refined our inquiry-driven grantmaking approach to strengthen collaborative learning while maintaining the flexibility grantees value. Previously, each grant carried its own standalone learning question. Now, we’ve elevated core inquiry questions to the sub-portfolio level, creating shared questions that multiple grantees explore together from different angles.
This shift enables us to work with each grantee to articulate a clear hypothesis for how their work contributes to answering these broader questions—positioning them as co-investigators rather than isolated implementers. We’re placing greater emphasis on identifying patterns and insights that emerge across our portfolios, synthesizing what we learn from formal and informal check-ins to build collective understanding that no single grant could generate alone (for example, read a summary of insights from a consultation with rural partners).
Importantly, this approach has sharpened our sourcing criteria. We actively seek partners who are interested in collaborative learning—organizations curious about exploring questions alongside us. When grantees share our commitment to inquiry, the power dynamics don’t disappear, but we hope they will shift: we become partners in generating knowledge that advances the field, rather than funder and recipient in a transactional relationship.
3. Philanthropy can play a critical role by investing in, advocating for, and demonstrating the importance of underlying infrastructure that often flies under the radar.
Unprompted, a significant number of interviewees cited the important role that philanthropy can play in elevating the profile of critical areas of need that are often overlooked in public discourse and funding. One grantee put it this way: “[Philanthropy can] pay attention to the things that are not the bright and shiny things, but at the end of the day make a huge difference.”
Many interviewees expressed frustration with funders who seemed to jump on the bandwagon of each new trend, looking for a silver bullet solution to challenges that were complicated and deeply entrenched. For example, one interviewee in the education sector said that funders often pushed their organization to investigate new uses for GenAI, without regard for what schools actually needed. “We’re missing out on a lot of the real need that we’re seeing in communities,” the interviewee said, citing the importance of focusing on school funding, the physical and digital infrastructure of schools, and keeping immigrant communities safe at school, among other things.
Interviewees pointed out that such overlooked topics often cut across standard programmatic areas. The absence of significant funding for these areas made some nonprofits think twice about pursuing projects that weren’t focused on “bright and shiny objects.” Others voiced frustration that the structures of philanthropy didn’t always have a place for programs that aimed to address systems change or that cut across multiple areas. One grantee said, “A lot of funders don’t know what to do with us because we’re crossing disciplines [and traditional program areas].” Another grantee explained, “I would love to see philanthropy invest ecosystematically versus programmatically… You end up with very siloed interventions, rather than organizations coming together to support a shared vision that could collectively have a big impact.”
Grantees recognized that such an approach was easier said than done, but cited two practices that could help funders move closer to an ecosystem approach. First, interviewees valued reflecting on cross-sector macro trends with funders and other nonprofits. Such reflection might occur in a convening of nonprofits working on similar issues, joint attendance at a conference where the sector is learning together, or simple check-in sessions devoted to reflections on learnings across the field. Second, interviewees challenged funders to focus on the needs of populations and communities that are typically left out of the conversation, giving them a chance to share what interventions and programs they feel are most important.
How We’re Responding
A core belief at our foundation is technopragmatism: starting with the problem you’re trying to solve and asking whether technology—AI or otherwise—can help. Often, the answer is no.
While we acknowledge that AI is changing how we accomplish our goals, we don’t give preference to proposals that feature emerging technology. Rather, we believe that AI is simply the latest iteration of technology, and our responsibility is to ensure that whatever comes next is designed for and used appropriately by the communities we serve. We’re doubling down on how techno-pragmatism is integrated throughout our grantmaking and making it a central theme in all our communications and narrative work.
Techno-pragmatism means we deliberately fund “unsexy” work—backend infrastructure, research that informs better decision-making, governance structures that ensure accountability, solutions that may not generate headlines but solve real problems. We want to send a clear message to our community: bring us your boring ideas. The unglamorous, foundational, and collaborative work that makes systems function has more lasting impact than the bright and shiny innovations that capture headlines.
Beyond technology, our team structure is explicitly designed to work cross-cutting. Our questions span multiple grantees and interest areas, preventing programmatic silos. This year, we’re organizing our work around a framework for understanding the underlying infrastructure needed for progress—conditions, incentives, and evidence—that apply across all portfolios. By using common analytical lenses, we’re better positioned to identify systems-level patterns, fund infrastructure that serves multiple communities, and connect work happening in seemingly different domains.
4. Philanthropy has an opportunity to extend the value of its financial investments by creating new, more equitable networks through intentional convening and more transparent giving.
The uncertainty of the current funding environment is wreaking havoc on the nonprofit sector. Even organizations that have not suffered lost funding themselves are worried about what the future may hold and are struggling to figure out what funding pitches—to both private philanthropy and government agencies—will resonate in the current environment.
All stressed the importance of diverse funding pipelines and hoped for more collaboration and coalition-building across the philanthropic sector. Interviewees named a number of other ways that funders could extend the value of their giving beyond the dollar amount of their check. Many interviewees cited philanthropy’s unique role in convening and introducing grantees and funders, and its ability to support professional growth for nonprofit staff. Another interviewee described how a funder had convened grantees working in similar areas, leading to organic relationships and future programmatic collaborations that wouldn’t have been possible without the intentional creation of a community of practice.
How We’re Responding
We’re making convening more intentional in 2026, organizing gatherings around cross-cutting themes such as “co-design” and “rural opportunity.” This builds networks across disciplines, connecting organizations that share underlying questions but might not otherwise meet. We’re curating focused communities of practice where participants develop sustained relationships and drive action.
We also plan to host events to take advantage of partners gathered at major conferences. To maximize relevance, we’re asking grantees to update us about which conferences they’ll be attending throughout the year so we can facilitate introductions in spaces they’re already attending. (Note: this is a question on our grantee intake form, but can quickly become outdated.) When aligned, we can reach out to other funders if they’re willing to connect.
5. Grantees Noted Our Culture of Curiosity, Learning, and Listening – But Felt We Could Go Further
In contrast to previous years, grantees consistently called out Siegel’s uniqueness among foundations, describing our inquiry-driven approach as radically different from their experience with most funders. “Siegel is an exemplar when it comes to leaning into the belief that there’s a different kind of narrative to elevate,” one grantee said. All interviewees cited our commitment to ongoing learning as distinctive, noting that while many organizations want to learn, few develop processes that actually elevate it. At least two stated that Siegel “walks the walk.” Grantees pointed to specific practices that embody this culture: collaborative learning agendas, joint conference attendance and panels, and what one described as the K&I team’s “authentic excitement about getting to learn alongside an organization.” A majority cited staff members’ willingness to genuinely listen—respecting grantee expertise and taking their perspectives fully into account when making decisions—as a hallmark of our approach.
While some grantees felt Siegel already has strong visibility in the philanthropic community (Ex. “It’s exciting to see that Siegel is on the national stage trying to move the philanthropic sector forward”) others wondered if we could go further. Unprompted, a majority encouraged us to share our approach more broadly to help the philanthropic sector evolve toward more collaborative, learning-based processes. “I wonder if Siegel could push the field toward this approach,” one said. “What would a more aggressive push look like together?” Grantees envisioned us banding together with other funders to promote co-design processes with communities and socializing our inquiry-driven methods.
How We’re Responding
We’re committed to making our inquiry-driven approach more visible and accessible to the field. In the coming months, we’ll publish a whitepaper documenting our inquiry-driven approach, its connection to the emerging “science of questions,” and its application to philanthropic practice. This whitepaper, alongside role-specific guidance for foundation staff at every level, represents our effort to share our philosophy and practical frameworks for those interested in learning more. Together with our ongoing efforts to publish what we’re learning from grantees across the portfolio, our goal is to contribute to collective field knowledge—not simply report on our own activities.
Finally, over the past few years, we’ve made meaningful headway in both informal and formal partnerships with peer philanthropies, and in contributing to broader field-wide mobilization. Notable milestones include our now-annual Tech Together convening, which brings more than 200 funders in technology-related fields together for a one-day intensive, and the recent launch of Humanity + AI, an initiative with more than 10 leading philanthropies.
We see two clear opportunities to go further: first, by continuing to solicit grantee feedback on how and why these collaborations should exist—and how they can translate into more direct benefits for grantees; and second, by increasing transparency across our website and other channels so partners can more easily track these efforts and their progress.
Acknowledgement and Grantee Appreciation
We are deeply grateful to our grantee partners for taking the time to share thoughtful and candid insights that will inform and strengthen our grantmaking in 2026 and beyond. We value this feedback not because it is uniformly positive, but because it reflects the trust and openness of the relationships we have built together. Your perspectives help us learn, adapt, and do better. Please know that you never need to wait for a formal interview or survey to share your thoughts—our door is always open.
