In the world of fundraising, few moments carry as much weight as “The Ask”—that pivotal point where you invite someone to invest in your cause. Too soon, and you risk catching your prospect off-guard, undermining trust. Too late, and the window of opportunity may close, with enthusiasm waning or circumstances changing. Understanding when to make “The Ask” is as much an art as a science and results from the work of relationship building and strategic planning with your program and fundraising team.
Engagement
Meaningful engagement takes many forms and includes program staff who do the actual work of your organization, or an invested board member or top executive staff. Engagement must be prospect-specific and may include invitations to small group events followed by personal meetings that demonstrate and give witness to your organization’s impact. The goal is to inspire and involve the potential donor in the risk, the journey and the success of the mission in a way that connects to the prospect’s own concerns and interests. This is best done by asking questions and listening to your prospect’s dreams and past investments, to help reveal how their aspirations intersect with your organization.
Recognizing Readiness – Two Unique Case Studies
Watch for certain signs that indicate a donor is ready for “The Ask.” Some of these include:
- Active Engagement: The donor shares an emotional draw or investment in the cause
- Personal Connection: The donor articulates ways in which your mission resonates with their personal experience and a motivation to continue to invest
- Positive Feedback: They express appreciation for the impact your organization has made and indicate an interest in being part of future successes
In my first case study, the donor was a known philanthropist who had generously supported his church and church-sponsored universities, as well as community organizations. He had also supported conservation efforts devoted expressly to ducks, hunting and landscapes that support them. The donor was personally involved in bringing together like-minded duck hunters and ranchers, both old and new friends, to join him at his ranch to hunt together in the mornings and enjoy evening dinners and conversations.
Two of these hunters were also fellow program staff who had joined the group in the last few years. Our organization had just begun a new program to protect the larger flyway that ducks, waterbirds and other birds use along the Pacific coast and adjacent interior of the US, and we were seeking funding for this exciting and sweeping new vision. Program staff and I met often to plan how to introduce the donor and his friends to our new program in their evening conversations during these duck hunting “camps.” Although not a part of these camps, the fundraising team and I continued to provide support to our program staff throughout the key cultivation period.
Following the completion of several cultivation steps, we contacted our prospective donor to request a meeting to provide a detailed presentation of the new flyway program and to seek his support. He agreed to the conversation and invited us to his office. We soon met and had a promising start with cordial greetings and exchanges of recent duck hunting stories and events he and the program staff attended together.
When it was my turn, I described the depth of the new program and the commitment pledged by our board of directors. I then described how we were seeking a lead gift from a donor who would signal his leadership support and encourage his peers to follow his example to anchor the new program’s success. I asked him to become that lead donor. I then asked him to consider a $1 million matching gift, and to encourage his fellow duck hunters to match his support by making six or seven-figure match gifts to protect the Pacific Flyway and our beloved birds that use it.
The room became noticeably quiet, with time seeming to almost stand still. Then, suddenly, in a burst of emotion and joy that warmed us all, the donor said yes! The room filled with a special energy that I can only describe as a kind of spiritual connection, one that comes from such moments and the incredible generosity, love and devotion for nature that the donor shared with us.
My second case study profiles a new board member of a conservation group focused on policy and wilderness protection. He previously worked with a much larger organization that utilized land purchase and easements to protect land, a simpler method he preferred. While he valued his new board’s impressive history, strength and diversity, he was less comfortable with the organization’s advocacy mission, resulting in his more modest giving.
He owned an international software firm and traveled often. After his beloved family, his passion was wilderness. He spent his time off hiking and climbing, summitting countless peaks and always encouraging others to join him. He kept lively conversations going on the trail, typically outpacing his companions and often presenting complex story problems as a bonus.
My responsibility was to guide the new board member’s integration into the organization by introducing him to staff and fellow board members. The goal was to deepen his understanding of our advocacy strategies and foster greater engagement. This approach led to a steady increase in interactions between staff, board members and donors, enhancing both participation and financial contributions.
We implemented the plan by creating more opportunities for engagement in wilderness settings, where staff, board members, and donors participated together in activities such as hiking, climbing, rafting, and other outdoor pursuits. These trips often incorporated discussions on current projects and organizational issues. Over a nine-year period, these experiences not only solidified the new board member’s commitment but also encouraged him to play a more active leadership role. Notably, he made his first seven-figure donation and inspired others to give and assume leadership positions on the board.
His impact on the organization exceeded all expectations. He advocated for a targeted campaign to expand access to the wilderness, motivating numerous new individuals to participate in outdoor activities and support the preservation of wilderness areas.
