A colleague asked me today, “what different strategies would you use to ask someone for $250,000 as opposed to $50,000?”
The first thing to clarify is whether you’re asking the same person for these different amounts of money. Put another way, are you asking “how do I get someone to shift from making a donation that’s not a big decision to making a donation that is a big decision?” Or are you asking, “how do I get up the nerve to look someone in the eye and ask them for a quarter of a million dollars (or more!)?”
Regardless of which of these questions you’re really asking, in each case you need the same basic elements. You need a story that is real, compelling, that has emotional content. A story that you believe in, that you think is important. A story that is true for you, for your organization, for its beneficiaries. A narrative that resonates with and reinforces the world view of the donor. A narrative that the donor can be a part of – can place themselves in and, in the best of cases, can help write themselves.
The size of the donation (the “ask”)? It has to come out of this narrative and this truth – you can’t bolt it on afterwards and have any hope of success.
So, going back to the two questions, if someone is giving much less than then can, then the story is not holding true for them on some level.
If you are asking for much less than you should, then the story is not holding true for you on some level.
Which one is it?

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