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How to Nudge Reluctant Leaders to Ask for Money

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January 9, 2018 – Many nonprofit executives avoid doing fundraising themselves. Others do it when they must but view it as a necessary evil.

A fourth of nonprofit CEOs believe they lack the skills and knowledge to secure gifts, and a fifth don’t enjoy fundraising, according to a landmark 2013 study by CompassPoint Nonprofit Services and the Evelyn and Walter Haas Jr. Fund.

Whether the cause is anxiety, disinterest, or lack of experience, a leader who is hesitant to ask for money can make a fundraiser’s job much harder. "This is a very common complaint from fundraising people," says Richard Walker, a fundraising consultant with Orr Associates.

But strengthening the relationship between top executives and top fundraisers is of utmost importance, says John Lehr, CEO of the National Parkinson Foundation, who has worked in both roles for various nonprofits.

Here’s what Mr. Walker, Mr. Lehr, and other experts suggest to help fundraisers get their bosses to embrace raising money for their cause.

— Timothy Sandoval

Stress the importance of the leader’s role.

Make it clear to bosses that they are an important part of raising money. Some donors won’t give until they meet a nonprofit’s leader, notes Robert Brennan, vice president for advancement at Mount St. Mary’s University in Western Maryland.

Chief executives who are new to fundraising might even need a lesson in how private donations help the organization grow and expand its services, Mr. Brennan says. Part of a fundraiser’s job is to get leaders excited about what they can do with additional money, he says: "If you can’t get the CEO to buy in to the mission, how are you supposed to get people who have the capacity to give excited?"

Get trustees involved.

Talk to trusted board members about getting the leader to take a fundraising role, says Mr. Walker. Sometimes a board member can help set up donor meetings for the executive director and even come along to the appointments.

Nonprofit leaders are also likely to listen to signals from the board on fundraising, because they are accountable to the trustees, Mr. Walker says.

Help the CEO develop the case for support.

Mr. Lehr recommends that the chief development officer and the chief executive hammer out a pitch together that outlines why the organization is worthy of donations. This can clarify the nonprofit’s selling points for the CEO, who can then try out the refined messaging through speaking engagements and meetings with potential supporters.

Give leaders a role to play.

Let executives know exactly how they can help, says Mr. Walker. He advises setting up a meeting with the chief executive to lay out which donor prospects will be the most important to focus on and key actions to take. These might include calling prospective donors, attending private lunches, or visiting loyal donors at their homes.

Scott Justvig, executive director of development and communications for the Salvation Army Metropolitan Division in Chicago, agrees that it's important to get donor meetings on a leader’s schedule. He says his team works months in advance to ensure that donors can meet with his divisional commander, Lt. Col. Charles Smith.

In Mr. Justvig‘s experience, nonprofit leaders are often too busy to set up meetings on their own. "If I gave any of our divisional commanders a list of five donors to try to schedule appointments with, do you know how many appointments we’d get? Zero," he says. When appointments are made for them, leaders will show up.

Provide coaching and training.

Once a chief executive is ready to meet with donors, role-play before the visits, Mr. Justvig advises.

These exercises can cover some very basic ground. For instance, Mr. Justvig says he’s asked each commander he’s worked with in his 35-year career with the Salvation Army — including Mr. Smith — to practice saying big dollar amounts, like $400,000. Many people are not used to saying numbers that big, he notes.

Provide research on donors.

Earlier in his career, Mr. Smith often went into meetings with prospective donors blind, knowing little about their personal lives or whether the amount he was asking for was appropriate.

With coaching and briefings on donors, Mr. Smith says, he’s become a better fundraiser: He now understands that raising money is about building strong relationships over time. And the more he knows about a donor, the better a meeting goes.

"If I was going in to talk about the Salvation Army, I could do that," Mr. Smith says. "But getting to talk to the donors about their family, their past giving history, those types of things, make it so that it’s not so cut-and-dried."

Get some early, easy wins for leaders.

Don’t give executives who are new to fundraising hard prospects at first, Mr. Lehr says: "Ease them into it a little bit." Start with people you know are likely to give at an initial donor meeting or shortly thereafter, he advises.

The first experience securing a big gift can be a powerful confidence-booster, Mr. Lehr says: "There’s nothing like success."

On those first visits, the executive doesn’t have to be the one asking for the gift, either. He or she can simply describe the charity’s mission and programs and have the fundraiser make the donation request — often the most difficult part of the conversation, Mr. Lehr says.

And when leaders do graduate to soliciting donations directly, start them off with smaller amounts and work up to bigger ones. "Put them in positions where they’re comfortable," says Mr. Brennan, the Mount St. Mary’s fundraiser, "and then slowly but surely ramp it up a little bit and make them more uncomfortable."

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