By Stefaan G. Verhulst, Co-Founder of The GovLab, and Kyla Kasharian, Senior Knowledge and Impact Associate at Siegel Family Endowment
If we want better outcomes in education, we need to start with better questions. That was the premise of a deep dive we led at the Grantmakers for Education 2026 Annual Conference.
Questions are fundamental to learning, curiosity, and critical thinking. Yet education systems often prioritize answering questions over developing the capacity to ask them. In an age when AI makes answers increasingly accessible, the ability to formulate meaningful questions may be more important than ever.
But questioning is also about power and agency. Whose questions shape educational or funding priorities? Whose perspectives are missing? Addressing this question inequity matters not only for learners and educators, but also for funders whose questions determine what gets supported, measured, and valued.
Drawing on the new Q-Lab initiative, Stefaan introduced the case for advancing a Science of Questions, while Kyla shared Siegel Family Endowment’s inquiry-driven approach to grantmaking.
Together with participants, we explored how to strengthen question literacy across education systems and philanthropy—moving from questions as an occasional starting point to questioning as a deliberate, inclusive, and rigorous practice.
What followed was a rich discussion that challenged some of our assumptions and surfaced practical opportunities. Below, we share some of the key insights, ideas, and provocations that emerged from the participants.
Building question literacy in education
Start where there’s already flexibility. Summer programs, project-based learning, and the International Baccalaureate already run on questions. But adults usually write those questions. A simple reframe is to ask students first: is this the right question?
Vocabulary matters. “Question literacy” may not land with district and state systems. “Critical thinking” may. Meeting systems in their own language is part of the work.
Power shapes who gets to ask. Classroom dynamics often keep learners from voicing their questions. Participants suggested teachers and leaders model their own questions, rather than positioning themselves as the arbiters of answers.
Readiness is the prior question. Does the system actually want to change? If not, the first step may be building the case for change, before introducing question literacy at all.
The Portrait of the Graduate came up as a live example. Its questions are the right ones, participants said, but who gets to fully embody them is still unresolved. And systems built on inequitable foundations have no built-in incentive to change.
Building question literacy in philanthropy
Influence is not power. Philanthropy has influence, but it does not hold power over the systems it funds. Staying clear on that distinction matters. Boards have to accept that they are not the experts and may be wrong about what communities need. A willingness to cede control is the prerequisite for real question culture in our field.
Trust-based philanthropy and inquiry can coexist. The goal is not more questions. It’s fewer, better ones.
Inquiry has limits. Co-funders may impose their own requirements, which caps how far a question-based approach can go. And in responsive grantmaking, inquiry can get in the way: in a crisis, just give the money.
Zoom out on service delivery. Even when a grant simply keeps clinicians funded, inquiry still belongs at the strategic level. That means thinking in 3-, 5-, and 10-year horizons rather than single grant cycles, and asking questions at every stage of the grant lifecycle, not only at impact measurement.
Normalize failure. “Fail fests,” where funders openly share what went wrong, came up as an underused way to build a culture of questioning.
Build shared evidence for hard questions. On divisive “why did this happen” questions, such as school segregation, philanthropy can’t compel belief. But it can collect and elevate evidence. Participants pointed to climate science, where international consensus panels create shared ground. Education, like healthcare, lacks an equivalent mechanism, and that gap keeps blocking progress.
Where we go from here
The session left us with a clearer sense of both the promise and the limits of a question-first approach. Questions won’t replace funding in a crisis, and they won’t move a system that doesn’t want to change. But where there is room to reflect, better questions help funders align, surface the gaps no one is addressing, and learn faster together.
A few things any funder can try this year:
- Ask grantees what questions they’re holding, after the grant is committed.
- Share one thing that didn’t work with peer funders.
- Before your next strategy refresh, map the problem space with the communities you serve before deciding what to ask.
Thanks to everyone who joined us in the room and pushed our thinking.
