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Get Your Major Donors on the Path to Big Giving at Year-End

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July 28, 2025 | Read Time: 10 minutes

The summer is an ideal time to deepen ties with donors and craft a cultivation plan for the rest of the year, major-gifts experts advise.

Savvy major-gifts fundraisers know now is a great time to strengthen ties with donors and make a cultivation plan for the rest of the year — setting up their organizations for big gifts at year-end, say veteran fundraisers and consultants.

Whether your organization is just starting a major-donor program after cuts in government funding or it’s been seeking major gifts for a long time, you can take steps now to build strong relationships with donors that will yield results during the critical year-end push. The Chronicle talked to major-gifts experts who shared their best advice for getting it done.

“We can have this panic in December of, ‘Oh my gosh, I’ve got to talk to all of these people about their year-end gifts,’” says Marcy Heim, a longtime fundraiser who now runs the consultancy the Artful Asker. “I think the most important thing in this time of year is to think about what conversations do we need to have now that help us be sure that we’re both ready to have that conversation about a major gift as the year progresses.”

Identify prospects, and assess their ability to give.

The key to a well-functioning major-gifts program is to understand who your prospects are and where they are on their giving journey with your nonprofit. If you’re just beginning a major-gifts program, you’ll need to do a deep dive into your donor database to understand who the best prospects are, says Jack Alotto, a long-time fundraiser who now works as a consultant.

All of the major donors are already in your database, and you need to really work your database.

“All of the major donors are already in your database, and you need to really work your database,” he says. The best prospects have a history of consistent giving, often multiple times a year. It helps, he says, to do a wealth screening to see who has the capacity to make a major gift. The dollar amounts differ depending on the organization. For some groups, a major gift may be anything more than $10,000, while $500,000 may be the starting point at other nonprofits.

If your organization can’t afford wealth screening, try to dig around on Google to find information on potential prospects, says Ashley Dittmar, chief development officer at the Adventure Project. She recommends focusing on the “top 15 to 20 donors in your database to be that major-gift portfolio.” Dittmar, who has worked at both small and large nonprofits, says that’s a manageable number of people to meet with and spend time cultivating regardless of organization size — even if you’re also shepherding the midlevel and annual-fund portfolios.

For established programs, many prospects will already be identified and in the pipeline, says Pearl Hoeglund, director of the Fundraising Academy at National University. Those donors will be in various stages of cultivation, along with new prospects who will be in the introduction phase.

Summer is a great time to go through the portfolio and assess where people are in their journey, Hoeglund says. Figure out how many touches someone has had with the nonprofit this year and what the notes say about where each person is to craft your plan for interacting with them for the remainder of the year. “You really need to do that data dive,” Hoeglund says.

Meet with donors.

Once you understand who the major-gift prospects are and when your organization last contacted them, it’s a good idea to schedule a meeting with any prospects you haven’t personally interacted with. That way you can get to know what motivates them.

The best way to learn about donors is learning directly about them from them.

“The best way to learn about donors is learning directly about them from them,” says Jarrod Williams, a major-gifts fundraiser who’s worked at many nonprofits, most recently as development director for the Urban League of Greater Pittsburgh. Williams encourages fundraisers to hold introductory meetings and find out where the donor’s interests lie.

“Say, ‘Hey, I know it’s summertime. I know you’re busy, but I’m new to the organization,’ or ‘This is a new program, and I just want to introduce myself to you so you know who I am, and I would love to learn more about who you are,’” he says.

Figuring out what the donor cares about is key to devising a smart cultivation plan, Alotto says. “Let’s say I think that a donor’s main interest is in women’s health, and in the course of my conversations with her, I learn her real interest is cardiology because her dad had a heart attack. I have to build on that,” he says. Then he’ll need to think through ways he can put that donor in touch with areas of cardiology that will be meaningful to her.

Craft a cultivation plan.

Once you know how many touches a donor has had and what their interests are, you can craft a plan for cultivating them throughout the year. There is no magic rule of thumb about how many interactions you need to have with a donor to get a major gift, fundraisers say, but it’s not going to be one lunch and then a big donation.

It’s all about relationship building and building and strengthening that relationship, making them feel, not like ATM machines, but investors.

“It’s all about relationship building and building and strengthening that relationship, making them feel, not like ATM machines but investors — investors that are bringing some social change and advancing the mission,” Alotto says. “You have to have a plan and a focus to meet with them regularly.”

These calls and meetings build the relationship that will allow you to ask for that major gift down the line. “Touch points, in my opinion, are your opportunity as a fundraiser to express kindness and caring to the donors,” says Pamela Perkins Dwyer, director of major gifts at the Los Angeles Master Chorale. During the summer, she loves to reach out to donors to inquire how their summer is going or dash off a handwritten note saying she’s looking forward to seeing them at a fall event.

Any plan you craft should be designed to help the donor feel cared for, understand the organization’s mission, and get a close-up view of the programs and initiatives they’re most interested in and could advance with a gift.

“Say I’m going to meet with this major-gift donor the first time and show her the behavioral health section of the hospital,” Alotto says. “Then we’re going to take her to the ER in June. In July, we’re going to have coffee. In August, I’m going to have her meet a physician, or whatever it is. But it’s a plan with a timeline and activities and a budget to do them.”

If fundraisers keep up-to-date with donors, they should have some sense of whether the organization will reach fundraising goals with major donors.

Back when he worked as a major-gifts fundraiser, Alotto had a donor he thought would be willing to give $500,000 to support the hospital. But after he took the donor on a tour of the facility, the donor met with a neonatology doctor and was moved to give more.

“We went from a half-a-million dollar gift to an $800,000 gift, specifically because that physician was able to articulate way better than I could as a fundraiser the value and the importance of neonatal intensive care,” Alotto says.

Make adjustments and update goals.

The best laid plans often go awry, says Perkins Dwyer, of the Los Angeles Master Chorale. Many things can influence whether someone wants to give, and often they’ll share their reasons with the gift officer. For example, Perkins Dwyer says earlier this year some donors told her they were giving to the L.A. fire funds rather than their typical donation to the chorale. That made total sense given the magnitude of the fires, but it meant that fundraisers needed to include that information in calculations about whether the organization would reach the goals it had set.

Many donors are also affected by the stock market, and they may express concerns about moving forward with a gift if the markets are down. Or a donor’s personal life may take a turn that makes them inaccessible to the organization for a time. All these things need to go into the notes in the database, and you may need to adjust your strategy or the organization’s overall major-gifts goal, Williams says.

If you start in the summer, I would say if you if you are stewarding it correctly … why wouldn’t you have a gift by September?

If fundraisers keep up-to-date with major donors, they should have some sense of whether the organization will reach those fundraising goals. “Hopefully on a regular basis, whether it’s quarterly or whatever makes sense for your organization, you’re assessing where things stand,” Hoeglund says. “It’s not a surprise at the end of the year, if you’re already checking in and communicating.”

Share impact — and ask when ready.

Because major donors usually have already made gifts to your organization, it’s really important to share the impact of previous gifts with them, says Perkins Dwyer.

“You want to be making them feel like they have done exactly what they thought they were going to do with their money,” she says. “Let them know what has happened so they can see the results.”

Heim at the Artful Asker adds, “When they’ve been thanked and that gift has had the impact they wanted it to have, then they’re open to talking about what’s next.”

While talking about what’s next, it will be important to get their view on what a big impact looks like, so you can create a shared vision for impact, Hoeglund says. “You can say, what does ‘transformational’ look like to you with your gift?”

Seeking major gifts is typically a long-term project, and it can often take 18 months to get a donation, says Alotto, the fundraising consultant. However, if your donor has strong ties to the organization and the fundraiser is having meaningful contact with the donor, the timeline can be quicker.

“If you start in the summer, I would say if you are stewarding it correctly and actually working and building that relationship with the donor, why wouldn’t you have a gift by September?” Perkins Dwyer says, arguing that you never know until you ask. “It may not be a million dollars — and then it may be a million dollars.”

She points to an example of a gift that came about quickly after meeting with the donors but resulted from an untapped long-term relationship. While looking through her database, Perkins Dwyer found a couple who had given $2,500 annually to the Los Angeles Master Chorale for 10 years, but no one from the organization had ever met with them. She invited the couple to lunch and “had the best conversation” — and she learned the gentleman was an heir to a multibillion dollar company.

“When I asked for a gift, he said, ‘Well, of course, I’ll give you this amount of money. Nobody ever asked me. I didn’t know that you could use this kind of money for a concert,’” Perkins Dwyer says. She was able to explain how much the concerts costs to put on, and with that, “he turned into a million-dollar donor.”

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About the Author

Contributor

Rasheeda Childress is the senior editor for fundraising at the Chronicle of Philanthropy, where she helps guide coverage of the field.Before joining the Chronicle, she covered financial and business news about nonprofit associations at Associations Now. Childress is a longtime journalist who has written and edited a variety of publications, including the Kansas City Star, Higher Education Technology News, and Campus Crime. She holds a bachelor’s degree from Howard University in Washington, D.C.

Contact: rasheeda.childress@philanthropy.com