How to Get Your Ask for a Second Gift Right

Donations are crucial for nonprofits of all sizes. And while it’s always a goal to attract new donors and grow your donor base, it’s equally if not more important to ensure those donors provide a second gift. Adding one new donor to your portfolio costs about five times more than retaining a donor — not to mention the time sunk into acquiring a new donor, according to NonProfitEasy.

“The amount of energy you put into getting a gift from people for the first time, it's just not worth losing them,” said Dalene Neopolitan, director of corporate, foundation and government support at Woods Services, a Langhorne, Pennsylvania-based provider of services for people with intellectual and developmental disabilities. “The more you can hang onto those people, the more committed they're going to become to your organization — if you're stewarding them in the right way.”

With that commitment may come more gifts, and your donors who give a second time may want to join your recurring gift program.

“Repeat donors are the lifeblood of most organizations' fundraising programs, so getting the second gift is moving people from that first donor category into the multi-gift category,” Jessica Bosanko, senior vice president at consulting firm M+R, said. “Once a donor's in that category, their lifetime value to the organization jumps up tremendously, and retention jumps up tremendously.”

Getting those repeat donors is particularly vital, as data continue to show a decline in donor count across the nonprofit sector.

“That means that it's especially important, now more than ever, to develop those relationships with the donors that we do have and encourage them to continue giving and supporting our work,” said Kellianne McClain, development officer at Engineers Without Borders USA, a nonprofit that provides engineering solutions to help fulfill people’s needs around the world.

When to Ask for a Second Gift

One of the first dilemmas a nonprofit has to address when asking for a second donation is precisely that: the when.

“I think that that is a question that a lot of organizations wrestle with for fear of not wanting to upset their new donor, or make them feel like their initial gift wasn't appreciated,” Bosanko said. “That said, we repeatedly find — particularly in the advertising space, I've seen it play out time and again — that donors in their first 30 to 90 days since their last gift are the most responsive actually, so I would say you do not want to wait too long.”

Data from Analytical Ones show that donors who make a second gift within three months have a significantly higher lifetime value (LTV) compared to those who gave further down the line. In fact, the LTV of those who gave again within 90 days was almost twice as high as the LTV of donors who gave within 10 to 12 months.

However, because Woods’ donor base primarily consists of the families of the people it serves and houses, making a second ask within a month of the first donation is something the nonprofit doesn’t typically do.

“In most situations, we haven't felt comfortable doing that,” Neopolitan said. “We have a relatively small pool of people that we solicit.”

“We don't want to badger them, per se,” added Diana Martinelli, director of community engagement and marketing at Woods.

For McClain, something to consider is how big that first donation was when planning to ask for a second gift.

“If we're talking about major donors who give in the thousands — maybe they're giving through a large check or a donor-advised fund — I would typically wait a little bit less than a year before making that ask,” she said. “For instance, a lot of people give in December. If somebody gave a large donation in December, I would probably work on sending them a proposal around late September/early October of the following year, which essentially … allows them some time to sit down to consider the proposal.”

For donors who gave a few hundred dollars or less, McClain said she’ll ask about every six months or so, especially if it’s tied in with a campaign.

Tips for Making Your Ask

When looking to ask for a second gift, Bosanko explained that it’s all about connecting with your community. Since balance is necessary, she said that organizations may lean on communicating through channels such as email and peer-to-peer texting, which have different levels of investment — both of time and money.

However, Bosanko warned, the key is to make sure your messaging is not too generic.

“I think a lot of people are really excited about the potential of automation,” she said. “But if your automated messaging is really generic, it's going to have a pretty low response rate. And it may also be a bit off-putting because it just doesn't sound like you're really making an effort to speak to the person in a way that's connected to why they gave in the first place or at the moment in time at which you're coming back to them.”

Here are three guiding principles for connecting with donors that can help make your bid for a second donation a successful one.

1. Get to Know Your Donors

One way to stave off genericity in your messaging is to truly understand your donors. For example, if you’re able to identify certain donor interests that your organization promotes that resonate with a particular donor, you can add them to a mailing list for that topic.

“We're working to keep track of, for instance, what donors are more interested in our water projects or what donors are more interested in our projects in East Africa or Central America, so that we can send them proposals that have those relevant stories in them,” McClain said, “and we can send them impact reports and impact stories that are also relevant to what they're looking for.”

Other ways to identify donors may be based on the appeals they respond to and data that can be collected through surveys, she said.

2. Thank Your Donors

It’s important to show your donors gratitude when they decide to make a donation, especially the first time around. Not only does it make them feel appreciated, but it may also boost how many of your first-time donors give again.

“One thing that we have been doing with individuals especially is once they make that first gift, once a month I send them a new donor postcard,” Neopolitan said. “It's a little postcard that's strictly a thank-you. … I was just looking at it the other day, because we've only been doing this for a few years, and actually, like 40% of our new donors within that time period have made additional gifts since their first gift.”

3. Show Their Donation’s Impact

Also crucial to getting a second gift is making the donor feel like their first donation progressed your organization’s mission. Like your messages of gratitude, this is something you can include in communications between asks.

“After a new donor [gives], what's the second plan of attack?” Martinelli said. “It really is to keep the communication and to keep the ask, and keep their interest. So, we want to show what your money did, what more money can do, what your impact has been — on a personal scale and on a broad scale.”

When it comes down to it, you can leverage these three strategies to space out your asks while still keeping your mission top of mind for that donor.

“We like to communicate, we like to reinforce, we like to thank, we like to stay connected, we like to show results,” Martinelli said. “They're all winning combinations for repeat gifts.”