Editors’ note: This article, first published in print during Nov/Dec 2004, has been republished for Nonprofit Quarterly with minor updates.

For more than fifteen years I’ve worked as a professional fundraiser. Although I’ve been on the receiving end of direct mail pieces, friends’ requests to sponsor them for whatever-a-thons, and school children waving candy bars, I had never been on the other side of the table with someone about to ask me for a major gift until this year. This article recounts that experience and the insights it gave me into asking and being asked for major gifts. These lessons can help us understand what works in making major donor solicitations — and what doesn’t.


A few months back, I received an invitation to lunch with the new director of an educational program that I had attended (names and details have been concealed to protect the squeamish). I was interested, yet more than a little puzzled by the invitation. I had been a nominal donor since graduating, and a not particularly involved alumna.

A meeting with someone from the program wasn’t unprecedented. Last year I’d had lunch with a member of the development staff. She had surprised me with an e-mail saying she was visiting my area and asking if we could schedule a visit. Since this invitation came with just a few days’ notice for a trip that probably was in the works for some time, I assumed I was a “filler” visit, and rightly so. With my giving history and profession of fundraiser known to the school, no smart development officer would consider me a high priority for a major gift. I agreed to meet her. In addition to the possibility of my making a larger gift, I thought it would be illuminating for my own work to analyze how I felt throughout the process, from receiving the first contact, to the meeting itself, and any follow up afterward.

I thought it would be illuminating for my own work to analyze how I felt throughout the process, from receiving the first contact, to the meeting itself, and any follow up afterward.

Lesson 1: Never Ignore Donor Communication — No Matter How “Insignificant”

Direct mail had prompted my occasional gifts of $100– $200 to the program before. I did not give more for two reasons; generally amateurish copy and the continued use of “Miss Susan” in the salutation. Of course, I was probably a tougher audience than most, even though I’ve sent my share of poorly written letters and misspelled the recipients’ names.

It wasn’t the quality of the program’s letters or the original salutation that really bothered me; it was the program’s failure to correct the latter mistake. Despite my returning corrected address labels, I still got pieces addressed to Miss Susan. Every time I saw the old name on the reply envelope, it did not inspire confidence that this was a well-run organization worthy of further investment. My own bias defined “well-run” as adequate money and attention paid to fundraising.

Most important, the lack of correction made me feel that no one had listened. I’d given up on sending in more labels because I tired of the effort and figured there were multiple databases involved and the correction would only make it into one at a time. This feeling of vague disgruntlement confirmed for me how critical it is to listen to someone when they go to the trouble to make contact, even on a seemingly small thing like use of an old name (although identity is really a big thing to most everyone). If the program had promptly made the correction, I doubt I would remember anything about it.

When I analyzed further my lackadaisical giving to the program, I realized I had been looking for reasons either to give more, less, or not at all, and the letters had primarily supported the latter two actions. And, like most people, I would not give a major gift solely based on a mail appeal. Which brings me back to my lunch with the development officer.

Lesson 2: Dig a Little Deeper

She was a good listener and picked up on my signs of interest as I recounted various memories about the program. She introduced news of current events at the program and either expanded on them or dropped them according to my response. We talked about some of my interests (opera, among them) and my husband’s profession (also a fundraiser), and the fact that we have no children. If she was trying to get a sense of our financial assets, the meeting revealed us to be urban DINK’s (Dual-Income, No Kids), a middle-class couple with well-paying professions for the not-for-profit sector, but living in one of the most expensive areas in the country.

Family money is always a possibility in such situations, of course, but only just a possibility. Our Bay Area locale and connections might have set us up for a dot.com stock market windfall (and/or downfall), but again, only just a possibility. A few discreet questions would have explored either (and might have provided some clues for the program’s research staff to follow up on), but she did not ask them.

This feeling of vague disgruntlement confirmed for me how critical it was to listen to someone when they go to the trouble to make contact, even on a seemingly small thing like use of an old name.

Lesson 3: Competition Works

She did talk about the program’s upcoming fundraising campaign and left me with a case statement and a strong example of a very recent graduate who now worked for the program and who was so enthusiastic about his education that he had already pledged $5,000. I had a good idea of his likely income and was frankly amazed. In addition to feeling shocked, I found myself wrestling silently with comparisons between us, starting first by denying we had anything in common. For example, I imagined somewhat agitatedly, “He still lives near the program’s vicinity and is much more attached to it, he might have felt pressure from others at work, he probably has wealthy parents, or fewer obligations,” and the like. I was familiar with this kind of distancing rationalization, because I’d heard variations of it dozens of times from prospects I had solicited.

Lesson 4: Peer Competition Works Even Better

It was only after leaving the restaurant that I began to think about what I had in common with this graduate. Peer competition came into play. I thought, somewhat belligerently, “We both came out of the same program, but he’s even younger than I am and presumably has fewer resources he’s made on his own. My giving needs to reflect the fact that I’ve had more years to make money. I received a good education there. And I feel strongly about giving back. I see myself as a generous person.” The whole thought process included the question, what would my friends be giving to the program? I realized I did not want to give too little (cheap, unsuccessful, ingrate), but also did not want to give too much (sucker, show-off). I’d never thought of myself as the typical herd animal, but that’s probably typical herd-animal thinking.

I mentioned the whole experience to a fundraising colleague whose financial picture was similar to mine. He laughed and said off-handedly, “If it’s a gift over five years, you could just pledge $10,000.” I realized that a peer was probably giving at higher amounts than I ever considered, and felt ashamed. I’d always thought that choosing to work in the nonprofit sector was a donation of sorts. However, whenever I heard people respond to a solicitation by saying they gave their time and that should be plenty, I always groaned inside.

Lesson 5: The Prospect Does (At Least) 50 Percent of the Work

So from this lunch I was left to ponder and prepare for the solicitation I assumed would come once the campaign was underway. During the lunch we had talked briefly about people with whom I was still in touch, and I wondered if it would be one of them or staff who would solicit me, and how that might affect my final decision. As far as I knew, the friends I had retained from the program weren’t that magic combination of eager volunteer, gifted fundraiser and generous donor. I didn’t think I needed someone to apply direct peer pressure. Just hearing about the gift of someone else I considered an equal in situation would be persuasive enough for me.

During my calculations, the case statement the development officer had handed me didn’t influence me in the slightest. I don’t even remember reading it, which pains me to realize because of hours, days and weeks I’ve spent painstakingly crafting annual reports and brochures for various organizations. I’d like to think that it was my alumna status that made the written description less important, because I do read most publications for other organizations. When it came to my decision about supporting this program, it was my memory of it that was the strongest motivation, not its current activities or plans.


A year after that first lunch, I was surprised to get another e-mail from the development officer asking me to have lunch with the new director of the program. I had assumed that she and I might meet again, but doubted I rated a visit with the director. I wondered why they were spending their undoubtedly limited time on me. Given the implied reciprocity, it also made me a little uneasy. In accepting the invitation, I was accepting the possibility, if not confirming my intention, of greater support.

Lesson 6: Make the Meeting Count

The director met me in the lobby of my office building and we went to a restaurant where I had made a reservation. It was a nice change to have someone offer to come to me, at a time ideal to my schedule, since work as a fundraiser almost always consists of meeting at someone else’s convenience. We had a friendly little chat as we walked and I liked him well enough. I could see how a lunch or meeting with an attentive, intelligent person — focused totally on you — would be a nice way to spend time (I might feel different if I had negative feelings about the program).

Once we were seated at the restaurant, the talk turned to the program. He gave me an update and talked about various new developments. He hardly asked me any questions, which was definitely a handicap, since he was presumably there to get to know me better. After he described some aspect of the program, I would respond with questions or reminiscences, and while he answered the questions, he then returned to his train of thought. The only question he asked me directly was something the development officer should have already told him: “What did my husband do?” Perhaps he had forgotten or felt awkward revealing that he already knew personal information about me.

It was enjoyable to discuss the program and I was upfront about my fondest memories. Several of these were about the chapel, the site of the welcoming ceremony for new students, various celebrations and graduation. He agreed it was a special place and told me of his plans for renovation and improvements. He also told me some of the prices for air conditioning ($500,000 or so) and a new organ ($950,000). He was especially enthused about the new organ until I confessed, I disliked organ music, which seemed to surprise him (I would have been more surprised if someone actually liked organ music). But he did stop talking about the organ once I said that.

Lesson 7: Step Through an Open Door

Here we go, I thought, Money (although the six-figure prices he quoted made me sit up a little straighter in surprise and almost deterred me from pursuing the topic). But I plunged in, “As the new director, how do you like the fundraising part of your duties?” I remembered the many times I’d gone to solicit business-like people and made nervous small talk until they rescued me by saying, “How can I help you?” I figured I owed him a nice softball of a question for all those kind prospects that had helped me out in the past. He responded, somewhat anxiously it seemed, “I’m really enjoying fundraising,” then recounted a story of a visit he had made to an alumni group in another state. At the end of his talk there, someone said to him, “Of course, you are going to ask us for money, aren’t you?” He assured her, “No,” and went on to tell her how he just wanted to get to know them better and gather their opinions about the program’s future or some such nonsense.

Once I removed my jaw from my salad plate, I told him that I usually responded to that common question by simply replying, “Yes, I am, and let me tell you why,” then launching into the case for support or, if appropriate, saying, “I’m not going to ask you for money today, but someday, yes, I will probably do so, and let me tell you why (see above).” I explained that I’d found that people appreciate a direct response. Given his blank look I decided it would be rude to launch into a primer on fundraising so I shut up and drank some more iced tea.

Lesson 8: Don’t Mention Exclusive Groups

He mentioned that the group he had been addressing was a volunteer Alumni Council. I perked up, thinking, hey, that would be interesting. I assumed with the campaign coming up, at least part of its duties would involve fundraising, and there I could certainly help. Suddenly one reason for the lunch seemed clearer — he was looking for recruits. I realized quickly that a title and group activity would definitely tie me into a campaign effort. But when I asked him if the Council was responsible for regional fundraising, he replied “Somewhat,” but then expounded only on their efforts encouraging admissions, providing internships and forming career networks for new graduates. I began to wonder if I needed to remind him what I did for a living. After I asked one more question about the Council, I dropped the topic, as I felt like I’d signaled my receptiveness enough and began to feel a little rebuffed. Clearly, recruitment was not the goal of the lunch.

We both ordered coffee and our conversation wound down, with me growing increasingly perplexed. Maybe my lack of enthusiastic response to $500,000 and $950,000 quotes was all the information he sought and it was clear that I was not going to be the lead donor and hence, lead volunteer. Even if I had that kind of money, however, I can’t imagine saying, “Let me write you a check for that,” without being asked directly. Nonetheless, he seemed relieved that the money topic was over as he sat back with his cappuccino and asked about worthwhile museum exhibitions currently in town. There was the obligatory wrestle for the check, which he won. He had invited me, but I wanted to say (at least once in my life), “Hey, you’re with the not-for-profit here.” We parted ways cordially, with nothing said about the campaign or fundraising that I had not initiated.

I remembered the many times I’d gone to solicit business-like people and made nervous small talk until they rescued me by saying, “How can I help you?”

Lesson 9: Thank the Prospect — and Use the Thank You Strategically

I did not receive a thank you note, which might have explained the situation, from the director or the development officer. I always consider the thank you note an opportunity to reiterate (or clarify, if necessary) the primary points of the meeting and outline the next steps. Even after a relationship is long established, the institution, or the entity being funded (or being considered for funding) is always somewhere in the picture. Fundraising is never a purely social occasion. I even began to wonder, since he insisted on paying for the meal, perhaps I should have sent him a thank you note.


This experience was interesting to me as both a fundraiser and as a prospect. I was happy to see that a few of my lessons were axioms I’d been telling anxious and skeptical volunteers all along. These included Lesson 3: Competition Works, and Lesson 4: Peer Competition Works Even Better. From the prospect’s point of view, I now understand why. And these lessons caused me to rethink who I imagined to be the ideal prospect for these tactics. In the past, I primarily used them with groups consisting of men, financiers, lawyers or athletes (I plead guilty to stereotyping): say, a man working at Bear Stearns with a law degree on his wall and a football helmet in his closet. No more. These guys just responded immediately and unmistakably; but so did I, confirming these strategies to be universally applicable.

Another surprise lesson to me was how pleased I felt to be approached. I felt flattered and included.
Though I had often encouraged nervous volunteers to make their calls by telling them that prospects were excited to be asked (and hurt if they weren’t), I must have harbored some secret doubt that was dispelled by this experience. I guess I had absorbed too many bad vibes from prospects who took out their negative feelings about a program, guilt over not giving previously,
discomfort with even thinking about money, or crabbiness about the weather on any fundraiser who happened to cross their path. I realized I had unconsciously blamed the negativity on some failed technique of my own even though I didn’t take credit for a positive response. I usually chalked the latter up to belief in a cause or fond feelings about an institution, not something I had done right. Again, no more.

Of course, the idea of taking too much credit for a positive or negative response was dispelled by confirmation of Lesson 5 — The Prospect Does (At Least) 50 Percent of the Work. This is a variation on something I had always used to reassure staff who did everything perfectly, only to be refused. I would say, “You only control your own efforts, the other person is a big part of the equation.” Until I was the prospect agonizing over the decision — in this case, without much guidance from the institution — I did not realize just how much my own factors affected my potential gift and its timing.

It was helpful for me to see the solicitation process from the other side of the table and to be pushed beyond my own giving comfort zone into considering a commitment to the program that would probably be the largest philanthropic gift I had ever made. I felt excited and ready to make that commitment but the opportunity was lost, as Lesson 6, Make the Meeting Count, was something the Director had yet to learn. Perhaps the greatest lesson of all was a reminder of what all good fundraisers know: opportunity is the most valuable thing we have to offer.