When people hear the words “major gifts,” it can feel intimidating.
You know the gifts are bigger. You know there’s more riding on the relationship. But the actual how-of-it can feel unclear.
I remember feeling that way early in my career too. One of the biggest shifts for me was realizing this: Major Gifts is a system, not a mystery.
There’s a structure to the work. And once you understand the structure, you stop feeling like you’re guessing all the time.
At its core, major gift fundraising follows a cycle: identification, discovery, cultivation, solicitation, stewardship, and then, repeat.
Most fundraisers understand the beginning and the end of that cycle. The part that tends to feel the fuzziest is cultivation.
I’ll hear things like, “Okay, I know I’m supposed to be cultivating this donor… but what does that actually mean?”
And honestly, that’s a fair question.
Cultivation is the longest part of the process, and it rarely looks exactly the same from donor to donor.
Sometimes it’s inviting someone to see a program firsthand or sending an article connected to an issue they care about. Sometimes it’s remembering things they mentioned, like their daughter was graduating this spring. And sometimes it’s simply knowing not to ask too soon.
Good cultivation is thoughtful. It’s intentional. And it usually happens over time.
That’s why major gift fundraising requires more planning than people often realize.
At any given time, you may be managing relationships with 100 people or more, all at different stages of the cycle. You’re tracking interests, conversations, family details, timing, capacity, and next steps, while also trying to build genuine trust. That’s a lot to carry in your head.
Which is why the best major gift fundraisers don’t just rely on instinct, they build systems.
They make plans. They practise conversations before they have them. They learn how to ask better questions. They get comfortable talking about money out loud.
Because reading about major gifts and actually doing major gifts are two very different things.
And if you’ve ever felt unsure after a donor meeting, wondered whether you asked for the right amount, or spent months moving a relationship forward only to feel stuck, you’re not alone. Every major gift fundraiser has been there.
It’s one of the (many) reasons communities like AFP and AHP matter so much. We grow faster when they have space to learn alongside people who understand the work.
And it’s also why we’ve been quietly building something behind the scenes at Kittiwake. If you’ve seen any of our team at conferences or events lately, you may have already heard a few hints.
We’re excited to share more soon!
Until then,
Sarah
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