At a recent workshop presented in partnership with the Virginia Association of Museums and Virginia Humanities, we convened a panel of leaders representing philanthropy and cultural institutions across Virginia to explore a central question:
What distinguishes organizations that consistently inspire philanthropic investment?
The conversation, moderated by The Curtis Group’s CEO and Chairman, Keith Curtis, was candid and grounded in day-to-day experience—from foundation leadership to executive directors to advancement professionals responsible for building and sustaining donor relationships.
Earlier in the day, Keith and Ginny Badgett, Consultant at The Curtis Group, led a session on donor cultivation and stewardship, focusing on where organizations should direct their time and energy and how intentional relationship-building shapes long-term results.
What emerged across both conversations was not a single strategy, but a pattern: The organizations that sustain philanthropy over time are not doing more. They are focused on what matters most—consistently and with clarity.
Stability Is Not Assumed—It Must Be Demonstrated and Communicated
One of the clearest themes was the importance of organizational stability—not just as a reality, but as something donors can see and understand.
That includes consistency in leadership and direction, a clear and credible reputation in the community and a track record of following through on commitments.
But panelists made an important distinction: stability is not simply about tenure or longevity. It is about how effectively an organization communicates its continuity, particularly during moments of transition.
A new executive director does not signal a “new” organization. Donors need to see that the mission, impact and institutional strength remain intact.
At the same time, credibility is reinforced through alignment between message and action. As one panelist noted, credibility depends on whether an organization’s actions consistently reflect what it claims to value. This idea surfaced in a different way earlier in the day: relationships are built—and reinforced—over time. Organizations that demonstrate stability are often those that stay close to their donors, consistently sharing progress and reinforcing impact beyond moments of need.
The Executive Director’s Role Is Strategic and Relational
Across the panel, there was strong alignment around the role of the executive director in fundraising success.
Effective organizations are led by executive directors who are willing to engage externally, who prioritize time for donor relationships and who understand their role in advancing philanthropy—not just overseeing it.
But just as important is how that work is structured.
Several panelists described a coordinated approach between the executive director and development lead. Development leaders identify where the executive director’s voice will carry the most weight and create clear opportunities for engagement. In turn, executive directors are given focused, manageable touchpoints—rather than being expected to own the entire process.
In some cases, executive directors serve as the primary relationship. In others, they are brought in at pivotal moments. In all cases, the partnership is intentional.
That level of coordination reflects a broader discipline: meaningful relationships rarely advance by chance. They are the result of deliberate planning, clear ownership and consistent follow-through.
Board Engagement Requires Structure, Not Just Expectation
The panel reinforced that strong fundraising boards do not happen by chance—they are built through clarity, support and accountability.
Effective organizations secure board alignment around the development plan, define expectations for giving and engagement early and clearly and provide tools that make participation accessible.
One example illustrated this well. In an effort to re-engage lapsed donors, board members were invited to participate in a structured outreach effort. Using a shared document, they selected individuals to contact and were provided with talking points and guidance to support those conversations. The result was not just activity, but meaningful re-engagement—including a number of leadership-level gifts.
What stood out was not just the outcome, but the approach. Board members were not asked to “fundraise” in the abstract. They were given a clear way to contribute—and they responded.
This connects directly to a theme from earlier in the day: when organizations are more intentional about their relationships, it becomes much easier to involve others in ways that are focused and productive.
Cultivation and Stewardship Are Simple—and Require Discipline
When asked about cultivation and stewardship, the advice was notably direct:
Pick up the phone.
Send the message.
Make the connection.
Panelists emphasized that these efforts do not need to be elaborate. A brief text acknowledging a visit or a thoughtful follow-up after an event can be just as meaningful as a formal touchpoint.
What matters is consistency and authenticity.
Earlier in the day, we explored the importance of directing that effort intentionally. Not every relationship can be managed at the same level. The organizations seeing the greatest progress are those that focus on a defined group of relationships and engage them consistently over time.
Underlying all of this is a deeper principle: understanding the donor—how they prefer to be engaged, what they care about and how they define impact.
Engaging the Next Generation Requires Intention—Not Assumption
Looking ahead, one of the most important—and nuanced—conversations centered on the next generation of donors.
Panelists were clear: you cannot assume that philanthropic relationships transfer automatically from one generation to the next.
Even in families with long-standing ties to an organization, children and grandchildren may not share the same connection. Their engagement must be built intentionally.
This is particularly important in the context of the significant transfer of generational wealth already underway.
Organizations that are thinking ahead are beginning that work now—creating opportunities for engagement and inviting participation in ways that reflect the interests of the next generation.
At the same time, panelists noted that planned giving conversations are often closer than organizations realize. In some cases, commitments have already been made—but not yet shared—reinforcing the importance of ongoing, open dialogue.
Culture Shapes Philanthropy More Than Strategy Alone
A final theme that surfaced—subtly but consistently—was the role of internal belief.
Organizations that raise significant philanthropic support tend to operate from a shared understanding that their work is essential.
That belief shapes how staff talk about the mission, influences how leaders engage donors and reinforces why philanthropy matters—not as a supplement, but as a driver of impact.
In moments of challenge, that clarity becomes even more important. When organizations are aligned internally, they are better positioned to build and sustain meaningful relationships over time.
A Closing Reflection
If there is a unifying takeaway, it is this:
Sustainable philanthropy is not built through isolated efforts. It is the result of alignment—across leadership, board engagement, communication and relationships.
And while strategies will continue to evolve, the fundamentals remain consistent.
Be clear about your value.
Follow through on your commitments.
Invest in relationships—with intention and over time.
That is what builds trust. And trust is what sustains philanthropy.
Panel Participants
We are grateful to the leaders who contributed to this conversation and shared their perspectives:
- Amy Nisenson, Executive Director, Mary Morton Parsons Foundation
- Shawn Puller, Director of Development, The Paramount Theater
- Alyson Ramsey, President and CEO, Thomas Jefferson’s Poplar Forest
- Eric Rivers, Director of Advancement, Virginia Humanities
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