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Donors are people. And people want to be seen. Sometimes, simply being present for donors can return major dividends. 

That was the case with Jimmy. Let me tell you about him.

And fair warning here: this blog post is vulnerably honest. 

Jimmy and I met randomly at a gala after I was just a few months into a new fundraising job. We shared a table, and I learned about his impressive background. 

Jimmy was retired, a trained therapist and scholar, and an accomplished businessman. Back in the 1970s, he had published a book that took an especially creative approach to his field. It did well. And when we met, the book was already in its 10th edition. Jimmy was also a sought-after business consultant and real estate investor. And he believed in the mission of our organization.

He was an excellent major gift prospect.

Jimmy also had this uncanny ability to find Charitable Gift Annuities (CGAs) that gave amazing returns. For those who don’t know, a Charitable Gift Annuity is an agreement between a donor and a nonprofit. The donor gives a lump sum at the beginning of the agreement, usually pretty hefty, and receives a series of payments in return based on a calculated percentage of the total gift – either for a set number of years or until the donor’s passing.

It’s a good way for an organization to acquire capital, and it allows the donor to remain connected to the organization over a number of years. And of course for organizations that manage their annuities well, the goal is to cultivate a long-term relationship with the donor.

Several decades before my work with Jimmy, he had been offered a pretty generous interest rate for his annuity and had outlived the value of the original donation.

I learned about this little issue one afternoon when my supervisor came into my office and said, “Bill, we need you to call Jimmy.” 

It was my unenviable job to explain the situation to Jimmy and ask him to even things out. 

Fun, huh?

Well, I diligently reached out to Jimmy, doing my best to set the stage for a productive, nonconfrontational conversation.

I found a nice restaurant. Made reservations. Arrived early. Made sure we sat at a preferred table. Gave Jimmy an update from the org. Shared greetings from leadership. Thanked him for his generous support.

And initially, the meeting went well. Jimmy was having a good time. He reminisced about his history with the org, told me about his latest business venture, ordered an appetizer and dessert. 

He was having a good time. 

Then came the news.

I told Jimmy that his annuity was under water.

And Jimmy’s mood changed.

Dramatically.

He raised his voice, rolled his eyes, even gave a pound on the table.

So here I was, a brand new gift officer, no more than a few months into my position, and I was stuck having to explain to an appropriately upset donor why he “owed” my organization money.

Little did I know, there was a backstory to Jimmy’s resentment. 

And this is, unfortunately, often the case.

Jimmy had felt neglected for a long time. Here he was, a trained businessman and accomplished writer, who deeply believed in the mission of our organization. He was smart. He had good ideas. And he was willing to help. 

But Jimmy had been neglected for years. His existence – much less his generosity – had not been acknowledged. So the last thing he wanted to do was dig the organization out of a hole it had created.

So Jimmy left in a huff.

And I was bummed.

But I also thought to myself – maybe, if I listen to Jimmy, if I make sure he feels heard, and if I let him know that someone at the organization cares enough to “see” him, he may just come around.

So I stayed in touch with Jimmy. Sending him notes and cards and emails every few months. Inviting him to gatherings and asking him questions about his travel and investments. I sent the periodic email and shared reports on a program Jimmy was particularly fond of. 

Jimmy didn’t respond to my request that he balance out his CGA. But I let that question simmer, figuring I’d attend to the relationship for a while and let Jimmy respond when he was ready.

In the meantime, I did more research. I spoke with others who knew Jimmy. And I learned what made him tick.

Then finally, I invited Jimmy to join me for a Chardonnay along the Chicago River. I found a place not too far from his home that was quaint and had a nice view. It would be a great spot to begin repairing the relationship that seemed broken.

Well, things didn’t start out so great. I made a handful of rookie mistakes. (I told you this post would be vulnerably honest.)

First, it was around 90 degrees on this summer Chicago afternoon, and the location where we planned to meet was only accessible by multiple flights of stairs. 

Did I mention Jimmy was in his 80s? He was in great shape, don’t get me wrong. But anybody – at any age really – who had to walk a bunch of stairs on a hot afternoon would be in a bad mood by the time they got there. And Jimmy was. Strike one.

Second, the place wasn’t really a good place to have a meaningful conversation. There were indeed a few tables randomly situated out front, right along the river. But there were no umbrellas, no shelter from the sun, and the wine selection was skimpy. Strike two.

Third, we had to find a different place to enjoy a beverage. So I embarked on a quick and desperate search on my terribly outdated cell phone and found a decent place within walking distance. But to get there, we had to go back up all the stairs, walk a couple blocks, and hope to God that it was a decent place to buy drinks. Strike three.

We eventually made our way to the new location and were able to breathe a sigh of relief in the comfortably air-conditioned building. We ambled into a lovely little seating area, found a table, and were immediately visited by a cheerful server who helped get our minds off the bad start to our visit. 

Jimmy ordered a chilled chardonnay. I followed suit. And we both gulped down a glass of ice water. Things were starting to loosen up.

Then one more fiasco. 

About twenty minutes in, after Jimmy had made a good dent in his wine, he was gesticulating dramatically. I can’t recall the exact topic, but it was something Jimmy was especially excited about. 

And he ended up knocking over his glass of wine! 

Smacked it right off the table. And made a lovely mess in the process.

I immediately called the server, told Jimmy multiple times that it wasn’t a big deal, and made sure he knew that out of all the people in the world who would be upset by an accident like this – I was certainly not one of them. 

We eventually laughed, got Jimmy a replacement drink, continued our conversation, and both left feeling good about the relationship and the possibility that a future donation might take place.

Score one for the good guys. 

But still, no gift. 

Over the course of the next several months, I stayed in touch with Jimmy about every six to eight weeks – dropping him a line, providing updates, responding to his reading suggestions, and always staying optimistic. 

I used the phone, email, handwritten notes, marketing brochures, and WhatsApp when Jimmy was traveling internationally.

And sure enough, about a year-and-a-half after our first visit – the one where he pounded the table in frustration – Jimmy agreed to donate one of his Chicago properties to our organization. 

It was a nice condominium, fully paid off, in a downtown building, and it was valued at about $300,000. 

We sold it immediately and put the cash in the bank. Jimmy’s annuity was back in the black, and the organization’s mission was advanced.

Whew.

But getting there was no walk in the park. 

It was a lengthy process, fraught with multiple twists and turns. 

But I did my best to maintain a listening ear and an attentive attitude. I let Jimmy know that I saw him, that I cared about his opinions, and that he was a valued part of our organization. 

And that long-term strategy paid off.

I tell you that convoluted, somewhat embarrassing story to demonstrate a few ideas about fundraising.

1 – Donors are people. They want to be seen and heard. And even if you manage to bungle things dramatically, simply being present can pay big dividends. Literally.

2 – The road to successful fundraising is rarely straightforward. I have yet to experience a large gift that is without a few twists and turns. So if you are a fundraiser hoping to close a big gift, buckle up. And anticipate a bumpy ride.

3 – Major gift fundraising success – any fundraising success really – takes time. Don’t anticipate that just because you have hired a major gift officer – or even if you have spent a few months trying to close major gifts – the gifts will come in. The average amount of time required to close a major gift is eighteen months. And really big gifts will take years, sometimes decades. 

4 – But that doesn’t mean you make an ask and then sit on your hands and wait. While you are waiting for a donor to respond, continue cultivating them, stewarding them, inviting them into the life of your nonprofit. And use that space to continue building your pipeline. Cast a wide net. Invite others to coffee. Build momentum by having multiple conversations with multiple donors about multiple giving opportunities. Eventually something will stick.

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