Conducting effective fundraising strategy meetings can be tough, especially if you’re driving the planning, preparation and coordination largely on your own. Prospect development professionals are often tapped to lead or participate in fundraising strategy meetings, for good reason — our data insights and research findings can be crucial to developing effective strategies. But that perspective by itself won’t lead you to the best strategy, just as lacking the prospect development perspective won’t lead you there either.

The best strategies are borne of a collaborative process — partnering with others to innovate and create new ways of conducting business when “we’ve always done it this way” grows stale. Here at the Colonial Williamsburg Foundation, we’ve learned to strike the right balance between the prospect development perspective and the fundraiser perspective by partnering to redesign and leverage the most out of our principal gift strategy meetings.

When I started my new role as director of prospect development in early 2023, leadership tasked me with organizing the monthly principal gift strategy meetings. I was to prompt the fundraisers for prospects to discuss and to bring new prospects for review, leveraging a more data-driven perspective. That sounded very straightforward, even easy.

The pain points became clear after a few months of coordinating these strategy sessions:

• Getting prospect names from the fundraisers to discuss could be challenging — they were often traveling, so I’d have to prompt multiple times (provided I remembered to send multiple reminders). Usually, the same fundraisers provided names each time, thus…
• We often discussed the same prospects in multiple meetings. Over time, the discussions got shorter and not everyone around the table seemed engaged.
• New prospects discussed didn’t always move into a discovery assignment for qualification. With new principal gift prospects, we wanted to explore opportunities to connect via our networks rather than cold calling, but these follow-up action items often fell through the cracks.
• To fill the agenda, I reviewed overdue principal gift proposals to add to the discussion. This was seldom productive — the proposals weren’t actually stuck, they usually just needed some data clean up. Plus, we were already addressing overdue proposals in other meetings.
• The fundraisers had to manually prepare a prospect strategy worksheet using a Word Document template — this was time-consuming, static and usually didn’t make it back into the database.
• I, or my staff, would conduct hours of research only to learn that they already knew about the biographical information; what they really, specifically needed was a deep dive into relationship mapping or an exhaustive analysis of their external philanthropy. Research was not always what the fundraisers lacked for strategy development, but what they did need help with was…
• Getting senior leadership and/or the president involved in the cultivation strategy. Sometimes the smaller follow-up action items needed, like getting the president to draft a hand-written note, fell through the cracks.

Also, during these months, Colonial Williamsburg underwent a database conversion, a public campaign launch and senior leadership changes. Eventually, I was not only organizing the meeting but directing most of the agenda and driving the discussions as well.

While bandwidth was certainly an issue for me, my main concern is that we weren’t having the most productive or effective strategy discussions. To get the most out of these strategy sessions, I needed help to better design the meetings and clearly define what we wanted to accomplish in them. So, I turned to the associate vice president (AVP) for development who oversees the principal gifts fundraising program to help revamp our strategy sessions.

Over the course of a few conversations, some of which also included asking the principal gift officers for their ideas and input, we worked to clarify several aspects of the principal gift strategy meetings:

• Scope: What do we want to focus on in this meeting? What are the expected outcomes of this meeting?
• Roles and responsibilities: Who owns the meeting, and who decides on the content?
• Research needs: What information is needed to best facilitate these discussions?
• Tools: What tools can we use or create to help us work more efficiently and productively?

Scope

The scope for these meetings will be limited to deeper, thoughtful and timely strategy discussions around our principal gift or transformational donors. We may bring in additional stakeholders, like our senior leaders and directors of programming and historical sites, for their insight and assistance. The expectation is to address any roadblocks or challenges, discuss engagement opportunities and decide on concrete next steps.

Roles and Responsibilities

While I will continue to provide research and new prospect leads, I’m no longer responsible for prompting the fundraisers for discussion names, or for driving the meeting entirely. The AVP now decides on the content for discussion, as she has more insight into senior leadership’s top-of-mind priorities. Her administrative assistant now handles the logistical tasks of compiling the agenda, collecting prospect names for discussion, etc.

Research Needs

As most prospect names discussed are known donors, we decided research will focus more on relationship mapping and deeper dives into external philanthropy. For new prospect names, usual research takes place, but we focus heavily on relationship mapping to illuminate a path of connection. Proactively, we are focused on relationship mapping with our Board of Trustees and Top 100 prospects to identify new prospect leads.

Tools

We were thankfully able to invest in relationship mapping software to enhance our research efforts for this meeting. Leveraging this tool allows us to focus on prospects with whom members of our board or our president has a connection, and therefore a more natural introduction.

The existing prospect strategy worksheet is still in use as a Word document; however, we are actively working on a custom report to replace it. With a custom report, the fundraisers can document their work in the database as usual — their strategies, pending steps, proposals, etc. — and can generate a strategy worksheet on demand. This alleviates the fundraisers’ manual efforts to document the data twice — once in the Word document strategy sheet and then again in the database.

 Additionally, I created an action item tracker with a standard Excel template. This is an especially useful tool to maintain the action items that need to be completed by others who may not be in the room for that discussion. We document the prospect name, what action is needed, the context for the action, who is responsible for completing the action or responsible for prompting senior leadership to complete an action and when the action needs to be completed. We review the pending items on this tracker in every meeting, which keeps us all accountable for timely follow-up. The tracker is maintained in a Teams group and is accessible to key players at any time. In the future, the plan is to create a custom report to utilize the database to keep track of this for us, but for now, the manual action item tracker sheet keeps us on top of items that used to get buried in the agenda notes.

Enacting these changes together has already begun to shift the tenor and outcomes of each strategy discussion. We’re discussing more new prospects every time and the discussions are more focused on our top prospects and top priorities. We’re closing the loop on follow-up action items faster and we’re not losing track of the more minor actions. What was a heavy lift for me just a few months ago is now a much more productive, collaborative meeting and we’re getting more out of the strategy sessions than ever before. I only wish I’d asked to partner sooner!

Lindsay Rogillio
Director of Prospect Development and Analytics, Colonial Williamsburg Foundation

Lindsay Rogillio is the director of prospect development and analytics at the Colonial Williamsburg Foundation, leading the prospect management, prospect research and prospect data analytics efforts. Prior to her current position, Rogillio spent nearly 10 years in higher education prospect development offices at the University of South Carolina and Virginia Commonwealth University. She has volunteered with aasp's Membership Engagement Committee and Best Practices in Prospect Development Committee. She holds a master's in library and information science from the University of South Carolina, and is completing a master's in decision analytics from Virginia Commonwealth University. Rogillio loves traveling, salsa dancing and enjoying every food festival she can make it to.