This will sound familiar. A fundraiser has a good relationship with a donor and wants to prepare to make a major gift ask. Extensive research has been collected about the donor. It includes a philanthropic capacity estimate from services like iwave and DonorSearch, and whatever else could be found online. Notes from conversations, street research from people who know the donor, and the donor’s giving history to her organization are also gathered. Despite all of the research, the fundraiser has an uneasy feeling that whatever ask amount is settled upon, it will, at best, be a guess.