And Now What? The Key Question in Major Gifts Fundraising


Simple or complex?  Basic or advanced?  Checkers or chess? Which approach best describes your fundraising?

Driving between meetings recently with my dear friend and client Peter*, we talked about the evolution of a major gift his organization secured and the twisted seven year path his team navigated from a “no thank you” in 2019 to a gift of $2.5M in 2022.

It sounded like he was describing a series of well-calculated chess moves. While the details of the journey are fascinating and worthy of a chapter in a book on prospect engagement, he reduced the approach to always asking one simple question: And now what?

Following a kind rejection for capital support from a local company (and while others mourned the loss), Peter, the Chief Development Officer and his CEO Rick took a beat, licked their wounds and asked “And now what?”

  1. Keep the door open, ask permission to stay in touch.
    And now what?
  2. Encourage the company by getting a organization board member to make connections to others in the company.
    And now what?
  3. Listen and learn about the needs of the company’s leaders and local employees.
    And now what?
  4. Work with company staff team to bring the first cricket pitch to the area (fully funded by the company).
    And now what?
  5. Host a ribbon cutting (with press) of the new cricket pitch inviting the company owners (making them the heroes of the story).
    And now what?
  6. Invite top leadership to attend an organization event to learn about the mission and be inspired.
    And then what…?

Following 3+ years of relationship building, partnership, staff engagement and community service opportunities, the organization again visited with top leadership at the company to discuss how, together, they could continue to meet the needs of staff, their families and the community at large. You know the rest.

As the staff and volunteers celebrated the largest single gift in the organization’s long history, Peter and Rick smiled, took a beat and thought to themselves: “…And now what?”

Ready to replace your checkerboard and play some chess? Ask yourself: and now what?


* Thanks to the Metrowest YMCA for sharing their story with us. They created the cricket field on YMCA property and invited company leaders to the YMCA’s annual Marathon Breakfast for a morning of learning and inspiration.


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Posted by Jon Simons
Jon Simons

Written by Jon Simons

In his role as Executive Vice President, Jon has oversight over product development and training for DBD Group. He, along with the rest of the leadership team, provides strategic direction and insight for the company. He plays a key role in welcoming new consultants and ensuring that they offer the same quality service and tools as the rest of the DBD team.

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