by Betsy Steward

As a fundraising consultant, one of the most common questions I get from my nonprofit clients — both staff and board members — is about how soon you can ask a major donor for a significant gift. In my experience, there’s no formulaic answer. Every situation, like every donor, is unique.

“When” to ask requires careful consideration in each case. It’s best if every donor meeting includes an ask: for a connection, for advice, for continued conversation, for another meeting, and in some cases, for a gift. But don’t rush to solicit because your numbers would be better if that donor would just hurry up and GIVE! Timing is everything, in life and in fundraising.

Calculating the timing of your ask based on the number of meetings is not a good way to approach this challenge. Of course, to manage your time effectively, you must spend some time on analysis, including keeping track of just how many meetings you have with each donor. But if your attention is fully on numbers — the size of gifts, the number of gifts, the number of meetings — instead of the quality of your donor relationships, you can miss out on more, bigger, and future gifts.

Cultivation: 90% of a fundraiser’s time.

The bulk of our time as major gift fundraisers is best spent in donor cultivation: educating, explaining, and engaging.  Fast-tracking your donors because you’re thinking transactionally will result in fewer and smaller gifts.  

An illuminating cultivation success story in my experience happened when I was Director of Development at Westchester Children’s Association (WCA), a century-old child advocacy organization in the NYC metropolitan area. WCA had a donor I’ll call Arlene, whose first donation was made in 1996, eleven years before I was hired in 2007. That first donation was $50. The following year, she donated $300.  In the eleven years before the organization decided to invest in a development professional, she gave varying annual gifts between $25 and $2,500. For a few of those years, she served as a member of WCA’s board, and, after completing her term and stepping down, she continued to serve on various committees.

When I was first hired, I noticed that WCA’s board members didn’t seem to interact very much before and after board meetings. Nobody hung around to ask how another board member’s kid was doing with college applications or how their spouse was liking the new job. A county-wide organization like ours meant that board members didn’t go to the same grocery store, their kids didn’t go to the same high school, and they didn’t attend the same house of worship, even though they may have been of the same faith.

Donors form concentric circles around your nonprofit.

I thought that growing the relationships between board members would benefit WCA, because I see the relationships of donors to the nonprofit as a series of concentric circles, beginning with those donors closest to the organization — the board — and extending out in widening circles to include all donors. Moving donors closer and closer to the inner circles starts with strengthening the relationships between individual board members.

With that in mind, I suggested to the Executive Director that we ask one of our board members to host an informal cocktail party for board members and their partners/spouses. Although the guest list was limited to current members, I made an exception in the case of Arlene. She had continued to serve on committees long after completing her board service, so I suggested we include her and her husband.

My suggestion was based on my instincts, not my fundraising numbers. I had no idea that Arlene had the capacity to give a major gift. My attention at that early point in my tenure was on organizing the entire fundraising effort for WCA — installing a new database, creating the case for support, and establishing the annual fundraising calendar as well as gift acceptance and acknowledgement policies — so I wasn’t spending much time on individual donor research. It just felt right to invite her.

Focus on the relationship and the numbers will follow.

Arlene was so thrilled to have been included that she reached out to me many times in the months following the party. We met for lunch, for coffee, and for phone chats, sometimes with the ED, and we got to know each other. We were both passionate about WCA’s mission, and we discovered a lot of other shared interests, too. In my first year at WCA, her donation grew to $3,000. The second year, she gave over $5,000.

At that point, the ED and I looked at each other and said, “What if we ASKED her for more???” So we asked her for $10,000, and she gave it.

The year after that, we asked her for $25,000, which she gave.

The following year, we launched a capital campaign. By this time, we had done enough research to know that Arlene had the capacity to give at a much higher level. We asked her to consider being a lead donor to our campaign with a $250,000 gift. She gave it.

Don’t offend your donor by asking too early.

I believe Arlene had had the resources to give $250,000 in 1996 if she had been properly cultivated and solicited. But for eleven years, no one from WCA talked much with Arlene. No one explored her personal reasons for being involved. Once she left the board, no one asked her for her opinions on our approaches to the problems WCA was addressing. And certainly, no one asked her to give more.

Knowing Arlene as I now do, I believe she would have been offended if she had been solicited without having been cultivated. People give to people they know and trust, and until the board member cocktail party, no one had gotten to know Arlene very well. 

Build your donor’s trust, and then trust your donor.

The invaluable lesson I learned from that experience was the critical importance of spending time cultivating donors, and of focusing on the relationship rather than the money. I call it “transactional thinking” when I see my clients completely focused on the numbers. I advise them to trust that the money will follow if they genuinely explore their donors’ interests and then find connections between those interests and the nonprofit’s work.

 Of course, I’m not suggesting that you ignore the numbers… but putting them first in your thinking is putting the cart before the horse. As you build your donor’s trust in you and your organization, you can also build your own ability to trust that the donor will come through.

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Betsy Steward is an independent fundraising consultant. She advises clients on major donor solicitation, cultivation, and stewardship, as well as fundraising best practices, back-office organization, board presentations and writing to donors (appeal letters, emails, proposal letters, thank-you notes, etc.). She can be reached at BetsyVSteward@gmail.com.