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How can a question-based approach to philanthropy enable better learning and deeper evaluation across both sides of the partnership and help make progress towards long-term systemic change? That’s what Siegel Family Endowment (Siegel), a family foundation based in New York City, sought to answer by creating an Inquiry-Driven Grantmaking approach.
While many philanthropies continue to follow traditional practices that focus on achieving a set of strategic objectives, Siegel employs an inquiry-driven approach, which focuses on answering questions that can accelerate insights and iteration across the systems they seek to change. By framing their goal as “learning” rather than an “outcome” or “metric,” they aim to generate knowledge that can be shared across the whole field and unlock impact beyond the work on individual grants.
The Siegel approach centers on co-designing and iteratively refining questions with grantees to address evolving strategic priorities, using rapid iteration and stakeholder engagement to generate insights that inform both grantee efforts and the foundation’s decision-making.
Their approach was piloted in 2020, and refined and operationalized the years that followed. As of 2024, it was applied across the vast majority of their grantmaking portfolio. Laura Maher, Chief of Staff and Director of External Engagement at Siegel Family Endowment, notes: “Before our Inquiry-Driven Grantmaking approach we spent roughly 90% of our time on the grant writing process and 10% checking in with grantees, and now that's balancing out more.”
Image of the Inquiry-Driven Grantmaking Process from the Siegel Family Endowment
Earlier this year, the DATA4Philanthropy team conducted two in-depth discussions with Siegel’s Knowledge and Impact team to discuss their Inquiry-Driven Grantmaking approach and what they learned thus far from applying their new methodology. While the Siegel team notes that there is still much to be learned, there are several takeaways that can be applied to others looking to initiate a questions-led approach.
Below we provide 10 emerging lessons from these discussions.
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1. Curiosity, humility, and openness should be the foundational mindsets of funders and grantees
The Siegel team discussed the importance of having a mindset of curiosity, humility, and openness when implementing a questions-led approach to grantmaking. They explained that the large systemic problems that philanthropies are looking to solve are made up of many complex and interrelated factors. Several actors are influencing these problems and addressing them requires the inclusion of multiple perspectives. Today’s problems are also dynamic in nature and are changing every day. Taking a position of humility has allowed them to reassess what they don’t know and develop a deeper understanding of the issues they are trying to change.
2. A learning-based stance allows deeper evaluation of “so what?” and “now what?” across both sides of the partnership
Rather than evaluating grantees based on specific metrics, Siegel’s approach to monitoring and evaluation is focused on partnership and co-learning with grantees. Prior to Siegel’s Inquiry-Driven Grantmaking, they asked grantees to evaluate their progress in terms of their self-defined outputs and outcomes. However, they found that in this approach they were making too many assumptions and were not fully capturing the learnings from grantees’ work. For example, a grantee might have reported placing “25% more of students in high paying careers,” without being asked to share what they learned about the obstacles students faced getting those jobs.
As part of their Inquiry-Driven approach, the team assesses grantees based on their progress shedding light on their agreed upon questions. At the end of every grant period, they ask what they learned from the partnership (so what?) and how the findings can be applied across the foundation and what needs to happen to broaden the impact of the work (now what?). This approach has helped the team unpack the deeper meaning behind grantees’ work and analyze how their efforts might contribute to long-term systemic change.
3. There’s value in having both “short-term insight” questions and “north star” meta-questions
The Siegel team works with grantees on three types of questions. First, as part of their organizational strategy, they develop meta, portfolio-level questions that relate to the broader systemic change they are seeking to contribute to. For example, “How can we redesign education systems to center students by fostering future-ready learning environments that address the interconnected needs of learners, schools, and communities?” serves as the overarching question for Siegel’s Learning interest area.
Then, they develop strategy-specific questions that can be applied to subsets of grants within the portfolio. For example “How do investments in learner-centered ecosystem field-building help bring together leaders and practitioners and crowd in innovative models to help strengthen the field and its outcomes?” is the question that guides Siegel’s Learner Centered-Ecosystems approach. It is more specific and applies more directly to the work of grantees within the sub-portfolio, but also contributes learning and evidence up towards the main question.
From there, they work with grantees to develop narrow, tactical questions that can be achieved within the allotted grant period and feed into the meta questions. For example, “How might the development and use of a shared taxonomy of Learner-Centered models catalyze alignment, innovation, and investment across education and funding ecosystems?” These tactical questions typically emerge organically through their grantee check-ins and are co-developed with grantees and other team members from across the foundation. This “dual question approach” has helped grantees focus on short-term goals while at the same time remain flexible and aligned with the broader system related to their work.
4. The best questions are co-developed and adapted to the grantee’s place in their theory of change
Siegel’s quest for questions is both iterative and collaborative. The grantee questions tend to emerge organically through their sourcing calls with grantees. The team seeks to formulate questions that both grantees are looking to address and align with Siegel’s organizational agendas. The questions typically go through several rounds of revisions and are reviewed by grantees and individuals from across the foundation.
The Siegel team emphasized that the questions developed at the start of the grant are not intended to be static. Questions are a trial and error process and it is often difficult to tell whether it is the right question until you find the answer. In some cases, grantees have chosen to revise their questions part way through the grant based on what they found. Working with grantees to revise their questions has helped create a more agile environment and maintain their core value of humility.
Kyla Kasharian, Senior Knowledge and Impact Associate at Siegel Family Endowment explains: “Anecdotally, we've heard that it's appreciated that we're giving folks the space to be curious. We recently had a grantee who worked with us really collaboratively on their questions. At our six month check-in, they told us that the questions-based approach made them interrogate their work and realize they need to pivot.”
5. Leadership and board framing deeply influence the culture of inquiry
While a questions-based approach can be developed from almost any part of an organization, leadership and board framing of questions can be valuable in fostering a culture of curiosity. Siegel’s Chairman is a PhD computer scientist, whose belief in the scientific method inspired their practice of stating assumptions, testing hypotheses, and iteration. Siegel’s leadership team is composed of individuals from various sectors including corporate, non-profits, STEM, and humanitarian and development, which orients the team towards multidisciplinary knowledge. Program managers manage grants across all three interest areas, allowing them to learn and transfer learnings across the various domains and sectors. The Siegel team notes that this has helped apply questions at all levels of the foundation and ensure grant decisions reflect the broader organizational strategy.
6. Sustaining a culture of curiosity requires interventions across the foundation
In addition to strong leadership, there are several methods that can be used to sustain a culture of curiosity across a foundation. At Siegel, the team seeks to embed questions–and devalue simple answers–across all organizational activities. For instance, questions are embedded in grantee communications, Siegel’s hiring process, and how employees are evaluated. Questions are also embedded in how the organization is structured. There is a full-time knowledge and impact team focused solely on questions and curiosity work.
Siegel employees are given the space to think about ideas that go beyond their day-to-day work, taking turns to lead biweekly, internal team discussions on topics of their choosing. They are encouraged to participate in external conversations and conferences – to both share what they’ve learned and search for new ideas and ways of thinking about a thorny problem or issue. They also set dedicated time to discuss new ideas and research. Laura notes that “while there is not a lot of time, if you want people to be curious, give them time to be curious.”
7. Having a research team can be helpful in evaluating questions and rapidly gaining subject expertise
Siegel’s research team is deeply involved in their inquiry-driven grantmaking practices. The research team helps grant program managers understand the research landscape and identify areas of opportunity for new partnerships. They also help provide feedback on grantee questions and make progress towards answering those questions. Through their fellowship program, they bring in researchers with backgrounds related to specific lines of inquiry who can provide subject knowledge for both questions and answers. The Siegel team notes that the research team’s involvement in question formulation has been extremely valuable and they hope to expand their collaborations between question formulation and the research team in the future.
8. Some grantees are excited by this work; others need tailored pacing and support
A questions-based approach is not for everyone. The Siegel team explained that having a culture of humility is also understanding when there is misalignment and the grantee is not the right fit. During the sourcing phase, grant program managers look for grantees who would be open to their Inquiry-Driven Grantmaking approach. They assess whether they would be willing to participate in grants that are evaluated by open questions rather than standard metrics. They also recognized that some are willing, but need more support; for example, a partner may not have experience with framing their work in relation to questions. In those cases, the Knowledge and Impact team can support by providing examples of other questions, drafting their own suggestions, and taking the time to collaboratively explore the what and the why of a questions-based approach. While this process is relatively new and there is still much to be learned, the Siegel team notes that grantees have generally been excited about the openness and flexibility of their process.
Amanda Ahern, Senior Research Associate for Knowledge and Impact at the Siegel Family Endowment, states: “We look for grantee partners that have the same curiosity that we do and are willing to work through questions as partners.”
9. A questions-led approach can lead to new solutions
One of the major benefits of a questions-led approach is the opportunity for new solutions. Questions can help expand funders' thinking around different topics. Simply reframing a question can lead to an entirely new set of questions that were not previously considered. This can help increase the diversity of solutions and potential to catalyze long-term systemic change.
For example, if you’re addressing the dearth of local news, you might focus on training and supporting local journalists. But if you frame the questions around "what does a healthy information ecosystem look like?", you open up solutions that might also include online community groups, digital archives, libraries, block captains, and perhaps even novel uses of technology that do not yet exist. This question makes visible more actors in the system, allowing new solutions previously not considered or that seemed out of range to take flight.
10. The questions approach has implications beyond individual grants—it can shift philanthropic practice itself
There is an opportunity to increase coordination and transparency around questions and knowledge sharing across the philanthropic sector. We discussed the value of having shared questions among several funders and grantees and how having multiple actors aligned on big questions could help accelerate impact. The Siegel team is interested in having working groups of philanthropic program officers and impact professionals who could formulate and iterate their questions as a group. They think this could help increase alignment across funders and improve the quality of questions philanthropies ask.
Nonetheless several tactical challenges remain in building a field around questions in philanthropy. First, the sector lacks the technical infrastructure for the sharing of questions among funders. Second, philanthropic questions and strategies often change when there is turnover in the organization and there is no mechanism in place to reflect changing priorities. Third, philanthropies would need to agree what an appropriate level of openness would be and whether grantees are comfortable sharing their questions with other funders. While these are significant challenges, a shared questions approach could be extremely valuable for the long-term systemic change philanthropies are looking to impact.
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Interested in learning more about Siegel’s Inquiry-Driven Grantmaking? More information about the initiative can be found in our DATA4Philanthropy Case Study.
Are you looking to apply a questions-based approach in your work? Learn more by reading our Data Innovation Primer on Participatory Sourcing of Questions.
(Financial Disclaimer: Siegel is a supporter of the DATA4Philanthropy initiative)