My first ask was for $100,000 and I completely botched it — but I knew I’d fallen in love with fundraising.
After working for a couple years in the college’s admissions office, I realized I wouldn’t be able to move up. Everyone seemed to be there for life. So I started exploring a lateral move to the development office.
After multiple interviews — all of them over meals with every other question being a version of “How do you feel about asking for money?” — I accepted a development associate position. I guess I convinced the hiring managers that I wouldn’t embarrass the college while eating and that I knew asking for money was central to this position. (I am still shocked by how many people accept a fundraising position but seem surprised that it requires them to actually raise funds.)
After a few weeks at my new job, I still hadn’t been able to go on an ask with anyone. Tired of waiting, I created my own. Even though that was almost two decades ago, I remember it like it was yesterday.
I planned well. I had laid out a compelling case for why my prospect’s values would perfectly coincide with one of the projects in our capital campaign. A $100,000 project.
But I messed up in two big ways.
First, I didn’t tell the potential donor I was coming to talk giving. I wimped out and said, “I’m going to be in your area and would love to stop by.” Because of that, I wasn’t really able to concentrate on him at all. I spent most of the visit trying to find a hook—a phrase, some way to manipulate the conversation to talk about the capital campaign.
Somehow, I did it. We talked about the college, his family’s interests, and aspects of the campaign. Then I made the ask, which was a bit complicated. You see, the potential donor’s wife had died in a tragic accident, and my ask involved his asking the company of his deceased wife to make a $100,000 naming gift in her memory.
I really believed that the values lined up and that this would be a meaningful way to commemorate her life. He was kind but said he wouldn’t feel comfortable doing that since the company had already done so much in her memory. I drove the two hours back to my office.
That’s when I realized the second big mistake: I’d asked him on the one-year anniversary of his wife’s fatal accident.
When I realized this, I was mortified. But apparently I’d been so sincere in seeing his family values line up with college projects that the prospect didn’t flinch. And he never let on. We continued to have a good relationship while I was working at the college.
Despite the mistakes, this ask was a turning point for me. I was completely hooked. I’d been infected by the fundraising bug. I was convinced that, if asked well, a donor would thank me for letting him give to the cause.
Fundraising is like a complicated chess game, but instead of winning by defeating your opponent, you win by helping people invest in what they value.