August 10, 2026 | Read Time: 8 minutes
As the Gordon School nears the midpoint of a $17.5 million endowment campaign, Alexandra O’Connor is turning to the board for both strategy and the latest scuttlebutt.
Some board members have strong connections to targeted donors, says O’Connor, the Rhode Island school’s director of philanthropic engagement. Others offer insight into life events that might shape a prospect’s capacity and willingness to give, such as the recent sale of a business, a divorce, an inheritance, or a mixed experience at the school.
A private school like Gordon typically draws from a narrow funnel of prospective donors — primarily alumni and parents — and a knowledgeable board member can make all the difference.
“Some of the best work I do is sitting down with somebody who’s connected well to the community,” O’Connor says. “You take it for what it’s worth from each person. But it helps put together the picture as you’re trying to bring a donor in.”
Prospective board members at nearly all charities know they’re going to play a governance role and that they’re going to be expected to give. Just as important is the role board members can play in getting others to financially support the charity. But fundraising isn’t something for which all board members feel prepared.
“Sometimes they’re like deer in the headlights,” says Romona Jackson, founder of the Women’s Advocacy Center, a Memphis nonprofit that supports victims of domestic abuse. “Their eyes get big and they just stare at you, like, ‘I didn’t know I was going to be required to talk to people.’”
The Chronicle spoke to several nonprofit leaders and fundraising consultants about how to find board members who can help raise money — and how to help the reluctant ones grow into the role.
Recruit members with fundraising in mind and put expectations in writing.
When Jackson founded the Women’s Advocacy Center in 2018, she discussed fundraising with prospective board members, but they didn’t all pick up on its importance. Over time, she put those expectations in writing. Each board member at the center was expected to “give or get” $5,000 for the charity every year. For Jackson, who retired in July, that was nonnegotiable; board prospects who balked were invited to support the charity in another way, perhaps through volunteering.
Many nonprofit leaders like having long-tenured board members around, to mentor less-experienced members in duties that include fundraising. But the advocacy center uses short two-year board terms — renewable just one time — to bring in new blood and keep fresh ideas flowing. Although the charity has always hosted an annual fundraiser, a new board member who is chairing the development committee suggested a first for this fall’s gala: a themed event, based on Lewis Carroll’s Through the Looking-Glass.
“I thought it was a good idea,” Jackson says. “When you bring somebody new in, they often have a different perspective.”
Charities often seek out wealthy people for their board. But when it comes to fundraising, as opposed to personal giving, wealth is less important. Sure, a rich person is likely to have affluent friends, but most fundraising is broader than that.
It’s not a confrontation. It’s a meeting of the minds as to what we can do together.
“When you’re raising money through foundations, corporations, or public funds, those are all areas that require connectivity and relationships, not necessarily one wealthy person impressing another,” says Stephen Orr, co-founder of the Orr Group consultancy for nonprofits.
Pay attention to how people interact with the nonprofit before they seek to join the board, says Wayne Olson, president of Winter Haven Hospital Foundation. If you want people willing to contribute to the hard work of fundraising, look for those who go the extra mile — such as helping pick up trash after a picnic, he says.
“I once asked my pastor, how does the church pick deacons?” Olson says. “And he said, ‘Wayne, we don’t pick the deacons. They pick themselves.’”
Provide training at every board meeting.
A passion for the cause is not enough — board members need to have their facts about the charity down cold and some familiarity with the basics of fundraising, the experts say. Olson says he’s “old school” and still provides each board member with a binder with tabs, so that they can read up on the history of the charity, details about its programs, and its mission.
Board members who understand the charity’s goals and can articulate how new funds will help are better able to overcome their fears about asking others for support, says Rochelle Jerry, a fundraising consultant.
“When board members have a clear case for support, and talking points, it becomes less intimidating and more relational,” Jerry says.
Training should be part of every board meeting, says Amy Eisenstein, a fundraising consultant and the co-author of A Board Member’s Guide to Capital Campaign Fundraising. But it can be as simple as having an experienced trustee lead a discussion for 15 to 20 minutes to help others gain fundraising skills and confidence, she says.
It’s important for board members to move beyond the presumption that others won’t want to hear their pitch. “Sometimes a board member will say, ‘She just went through major surgery, or she just lost her husband, I don’t think this is a good time,’” says Claire Axelrad, a longtime consultant and the chief fundraising coach at Bloomerang. “Actually, that’s exactly when they want to hear from you because they want to be connected to people.”
CEOs who complain that their board doesn’t do much typically aren’t giving the board enough guidance, Axelrad says.
Jerry suggests supplying board members with a menu of actions they can take. Introduce the charity to one prospective corporate partner. Write five thank-you letters at the next board meeting. Host a small gathering. Join a cultivation meeting with the organization’s leadership.
Pair board members with staff to close gifts.
Board members help pave the way for gifts but rarely have the skills or knowledge to finalize the deal. For a very large gift, the CEO should be involved, Orr says. For a gift just below the top tier — perhaps $10,000 at a midsize charity — a board member should be assisted by the chief development officer. Even gifts as small as $1,000 should involve lower-level development staff, he says.
“It’s good practice not to expect the board member to go off on their own and fundraise,” Orr says. “Many times they’re asking the wrong questions, and they often don’t have enough intimate knowledge of the organization to know what the money will be spent on.”
The more that people have relationships with the place, the more they’re drawn in.
The most important role board members can play is helping to create a spider web around a donor, says O’Connor of the Gordon School. “You have the donor in the middle, but then they’re surrounded by different relationships that connect them to the organization,” she says. “That could include the head of school, another member of our leadership team, a beloved faculty member, and a board member. The more that people have relationships with the place, the more they’re drawn in.”
Hold board members accountable.
Board roles are volunteer positions for people with busy lives; the promises they make at board meetings may be the first to slide. Even if a board member agrees to hold a porch party, a development officer may need to follow up to get the plan in motion, Axelrad says.
“Call them up and say, ‘Do you want to invite your own friends? We’ve got a list of people. When do you want to do it? Do you want to provide the food? Do you need us to provide the food?’ You have to make it really concrete.”
Even more important is providing annual feedback to board members about how they’re doing, experts say.
Orr, who founded and led the New York charity Youth INC for 20 years, says that every January, he would request one-on-one meetings with each board member to go over how they fared on programmatic, fundraising, and board recruitment goals.
“It’s a really great tactic for a CEO to sit in a board member’s office, look into each other’s eyes, and say, ‘Can we do this? Let’s set some goals,’” Orr says. “And they like it. It’s not a confrontation. It’s a meeting of the minds as to what we can do together.”
Celebrate the wins.
Last year, a large foundation made a six-figure grant to the Women’s Advocacy Center after one of the charity’s board members spent considerable time cultivating the relationship, Jackson says.
“When that happens, you don’t just say, ‘Man, that’s great,’ and move on to the next thing,” Jackson says. “You need to really take the time to celebrate.”
The nonprofit wrote about the achievement in its newsletter, and Jackson asked the board member to describe how she helped secure the gift at a board meeting. Providing that platform not only recognized the trustee’s accomplishment — it also helped other board members realize that they could play a similar role in bringing resources to the charity.
“She’s not a professional fundraiser,” Jackson says. “She’s a person just like them who simply had a conversation after feeling prompted to do so.”
