The Ask Guessing Game
Gut Feel & Good Fortune are Not Enough
Set the scene: A gift officer has a solid relationship with a major donor and thinks they are prepared to make an Ask. Extensive research has been collected on the donor, including their philanthropic capacity estimate and whatever else could be found on the web. They gathered notes from their conversations, street research from people who know the donor, and the donor’s giving history to the organization.
Now it’s time to come up with an Ask amount for their gift conversation.
Despite all of the gift officer’s research, there is an uneasy feeling that whatever Ask amount they use, it will, at best, be a guess. Prior experience suggests that the donor information they collected, including the philanthropic capacity estimate, may not represent reality. Our gift officer experiences anxiety about being too cautious or aggressive with their Ask, which might leave money on the table — something they’re loathe to do. They walk into the gift discussion uncertain and tell themselves that making the Ask is about intuition, thinking fast on their feet, and divine good fortune.
This scenario is quite common but rarely discussed in professional advancement circles. As gift officers privately describe it, coming up with the Ask is like “shooting from the hip.” Simply put, most fundraisers rely on gut feel and instinct to determine an Ask amount.