The Journey to Strategic Clarity: How Grantmakers Know When to Enter or Change a Funding Strategy


Thursday, October 1, 2026
12:00 PM - 1:15 PM (EDT)
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Category: Learning Labs

The Journey to Strategic Clarity:

How Grantmakers Know When to Enter or Change a Funding Strategy 

Thursday, October 1 | Noon – 1:15 PM ET

How do grantmakers know when an issue is worth pursuing? When have we learned enough to begin investing? And how do we recognize when a strategy that once made sense needs to change or even come to an end?

Grantmaking Strategy and Focus emerged as the most common challenge identified by participants in PCP’s member survey late last year (see the graph below). Strategic plans, theories of change, and other frameworks can help bring structure to a funder’s thinking, but they don’t necessarily answer some of the harder questions grantmakers face along the way: What do we need to understand before making a significant commitment? How do we know where we might contribute? And when does what we are learning suggest that it may be time to change direction?

This Learning Lab will explore that journey. We’ll move beyond simply asking experienced grantmakers, “What is your strategy?” to a question that gets at how that strategy actually took shape: “How did you know?” How did you know where to begin? What did you need to learn before committing significant resources? What assumptions changed along the way? And how did you know when it was time to move in a different direction?

David Hobbet, founder of Yesler Partners, will begin by offering several foundational questions that can help grantmakers think more clearly about strategy and discernment. He’ll help us think through questions such as: What kind of change are we seeking? Where within a larger system might we engage? Who else needs to be involved? And what unique role might we be positioned to play?

We’ll then move from frameworks to experience through two case studies representing very different moments in the life of a grantmaking strategy.

Anne Crossman of PineTops Foundation and Thad Austin of EveryAge Foundation will share their experience of mapping for engagement in a new space and how they sought to understand an unfamiliar landscape, learned from those already working within it, and developed enough clarity to begin investing.

Dana Doll of Micah 6:8 will explore the other side of the journey: knowing when it is time to move away from an existing strategy and toward something new. Dana will share Micah 6:8’s transition toward investing in African-led nonprofits, including what led to the shift, how they brought their board along, and how they navigated the difficult process of stepping away from longstanding funding relationships.

Through these stories and a facilitated conversation, we’ll explore the role of research, listening, relationships, experience, board engagement, and changing assumptions in shaping strategic decisions. Our goal is to help participants ask better questions and strengthen their own capacity to learn, adapt, and make wise decisions when the path forward is not immediately clear.

Whether you are entering a new area of funding, reconsidering an established approach, or simply seeking greater clarity about where your foundation can make its most meaningful contribution, this session will offer practical insight into the learning and discernment that often precede good strategy.

 

Presenters:

David Hobbet
Founder, Yesler Partners

David Hobbet is the founder of Yesler Partners, where he advises philanthropic and nonprofit leaders on strategy, organizational direction, and impact. Previously, David was an Associate Partner in McKinsey & Company’s social sector practice, leading strategy, program design, and organizational change efforts across philanthropy, higher education, and the public sector. He also served as Executive Director of The Veritas Forum, where he led the organization through a period of innovation and growth. David earned his MBA with honors from Northwestern University’s Kellogg School of Management and his bachelor’s degree in Political Science from Duke University.

Anne Crossman
Board Member, PineTops Foundation

Anne Crossman serves on the board of PineTops Foundation, a private foundation focused on identifying innovative approaches to long-term, structural challenges. In that role, she has been deeply involved in the foundation’s work to understand new areas of potential investment and develop thoughtful approaches to engagement. Anne is also the founder of Homeschool Expert and has spent much of her career in education. She attended Stanford and Duke Universities, has taught in public high schools and military barracks, and is the author of four bestselling books on education.

Thad Austin
Vice President, EveryAge Foundation

Rev. Dr. Thad Austin serves as Vice President of the EveryAge Foundation and Executive Director of the Common Table Collaborative. He has spent more than 15 years leading and advising congregations, denominations, and faith-based foundations, bringing experience across both ministry and philanthropy. An ordained pastor, Thad previously served congregations in Kentucky and Tennessee, including as Executive Pastor of a 3,200-member congregation. He earned his Ph.D. from the Lilly Family School of Philanthropy and is the author of Caring for Clergy: Understanding a Disconnected Network of Providers.

Dana Doll
Director, Micah 6:8 Foundation

Dana Doll serves as Director of the Micah 6:8 Foundation, where she oversees the foundation’s philanthropic investments. Her work focuses particularly on building trusted relationships with visionary leaders in East Africa and connecting people across disciplines and borders to strengthen their impact. Prior to joining Micah 6:8, Dana co-founded and served as Executive Director of a nonprofit serving refugee women in West Michigan. Her experience as both a nonprofit leader and funder shapes her approach to philanthropy and her interest in building strong relationships with locally led organizations.

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