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Across philanthropy, there is growing recognition that learning from past projects is as central as funding itself. Yet, many funders and their partners struggle to figure out a structure that allows them to learn across the lifecycle of a project. 

Too often, learning is front-loaded (what is described as due diligence) or back-loaded (what is described as evaluation). Opportunities for mid-course reflection are missed. Critical decisions are made without asking at every phase: Are we asking the right questions at the right time?

Over the last year, The GovLab (through the DATA4Philanthropy initiative) and Siegel Family Endowment have explored how questions can become a core learning capability for philanthropy. 

On April 9th, 2026 we hosted our first “Any Questions?” Salon in New York City to further this effort. The event brought together representatives from the philanthropic community for a roundtable discussion on how philanthropy can use questions as a tool for decision-making and strategy development. 

The event included presentations from Stefaan G. Verhulst (Co-Founder of The GovLab) on why questions matter for philanthropy. This was followed by presentations from Siegel Family Endowment’s Laura Maher (Chief of Staff), Kyla Kasharian (Senior Knowledge and Impact Associate) and Amanda Ahern (Senior Research Associate) on their Inquiry-Driven Grantmaking Approach and learnings from their forthcoming white paper. Throughout these, participants offered their thoughts and reflections and discussed the current state of the philanthropic sector.

In what follows we outline five main takeaways from the event followed by next steps for future discussions. 

Key Takeaways

1. Questions are a powerful device for philanthropy, though are not often implemented in a holistic or systematic way

Philanthropies are already using questions to shape priorities and decisions. Participants throughout the room cited examples of how their organizations are becoming more deliberate and intentional with questions.  They are designing internal processes for asking questions and creating collaboration opportunities around different lines of inquiry. They highlighted that questions can be valuable at the strategic level to make critical decisions about funding. They can also be useful for learning and evaluation and everyday programmatic decision-making—including how they work with and assess partners.

While there was strong resonance with the concept, there was less consensus about how to incorporate questions in practice. Participants had several questions about implementation. A few spoke to their challenges in balancing grantee questions with the foundation’s strategy, as well as how to right-size questions to the purpose it was to serve. 

2. Questions are even more important in the age of AI

The quality of the AI output directly corresponds with the quality of questions being asked. As generative AI becomes ingrained in how societies understand and solve problems, communities and institutions will distinguish themselves based on their ability to ask good questions. In an age where information is “cheap”, understanding the context and underlying dynamics is more important than ever.

Participants emphasized the need to build question fluency as a mechanism to improve foundations’ ability to ask questions. They also noted its value in helping to reduce misinformation that might result from generative AI prompts. 

3. Right-sizing and prioritizing questions remain a challenge

Questions are being asked throughout the grant making process. Participants described the need to differentiate between levels of questions. These can include transformational questions that are long-term, deeply complex, and difficult to answer. It can also include strategic questions that guide program directions and operational questions that can be answered in the short-term. 

Once you have defined the appropriate level of question, the next problem is quantity. Given the volume of questions, prioritization can be very difficult and will be unique to each organization. The stakes of a question can also influence prioritization, where lower-stakes questions may enable experimentation and learning in the short-term, while strategic questions will require lengthier consensus building and complex implementation. 

4. The need to assess the power dynamics of questions

The power dynamics encoded in questions was a central theme of the discussion. Questions are not neutral and those who ask or define the questions hold the most power and influence. 

While funders can pursue lines of inquiry with limited external accountability, grantees may feel pressure to align the framing of their questions with funders’ priorities. Participants are already exploring several modalities to make questioning more inclusive and address power imbalances. They emphasized the importance of humility and of including perspectives in the questioning process that challenge existing assumptions. 

5. The need for a culture shift around questions

Building a culture of inquiry and curiosity remains a challenge across many fields, including philanthropy. As one participant argued, asking questions takes courage. Many organizations and even staff within a philanthropy can be fearful of looking silly for asking the wrong question or for challenging existing processes. 

Participants emphasized the need for skill development, particularly the ability to interrogate what is driving the question and asking “why” before giving answers. They also spoke to the value of board flexibility and the need for non-traditional metrics. 

Forward Looking 

In the coming months, The GovLab and Siegel Family Endowment will continue to explore how philanthropy can accelerate questions-driven strategies. Future salons will focus on:

• Unpacking the motivations and power dynamics behind questions;

• Prioritizing and clustering shared questions across philanthropies; and 

• Building a questions architecture to work within complex systems

Please email us at DATA4Philanthropy@thegovlab.org if you are interested in attending. 

Additionally, Siegel Family Endowment will be launching their white paper on their Inquiry-Driven Grantmaking Approach on May 5th. Interested in joining the launch webinar? Sign up using this link.