Establishing an ongoing two-way conversation with its donors is a crucial part of building a sustainable and passionate base of support for any charity. It enables an organization to learn about their donors’ interests, talents, connections and giving abilities so they may guide their supporters along their philanthropic journey. However, the task of initiating a meaningful and informative conversation can be an awkward and mysterious experience for many charities. In this article we present ten (10) fundamental questions that an organization can ask their donors to kick-start a compelling long-term discussion.