How Better Questions Can Transform Grantmaking Practice

This event is part of the PEAK2026 Second Set Series.

Philanthropy is often rich in answers—but what if the path to greatest impact lies in asking better questions? In this interactive workshop, Siegel Family Endowment will introduce inquiry-driven grantmaking: a practical, iterative approach that centers curiosity and draws on the emerging “Science of Questions” as a foundation for effective and equitable philanthropy.

Participants will explore how re-centering the grantmaking process around inquiry instead of outcomes strengthens learning, evaluation, and authentic collaboration with grantee partners. Drawing on Siegel’s process—including portfolio-level learning questions, grantee-developed hypotheses, tactics for mapping insights across strategies and portfolios, and reflective frameworks (e.g. “What / So What / Now What”)—attendees will learn how to embed inquiry throughout the grant cycle.

Through guided exercises and small-group discussions, participants will practice reframing common challenges into learning questions that surface deeper insights, accountability, and adaptability. This session will model how shifting from compliance-based reporting to partnership-based learning can transform traditional metrics into meaning.

By the end, attendees will leave with actionable tools, templates, and reflection practices to integrate inquiry into daily grantmaking, building stronger trust with partners, and advancing more equitable results.

Participants will:

• Understand the principles of inquiry-driven grantmaking.
• Practice incorporating learning questions into grantmaking priorities.
• Gain practical tools (templates, case studies, whitepaper) to embed inquiry across the grant cycle.
• Learn approaches for collaboratively pursuing learning questions and metrics with grantees to advance equity and shared learning.

Speaker

Kyla Kasharian, Siegel Family Endowment

What To Expect

This session is 90 minutes and will be recorded. Registrants will have access to the recorded session for one month post-event.

Registration

Cost per person for each session:

• Organization Members: $50 per session
• Consultant Members: $50 per session
• Individual Members: $75 per session
• Nonmembers: $75 per session