Major one-time donations and planned gifts tend to come from contacts that have a good long-term relationship with your organization or key individuals in it, a strong alignment with your mission or some part of it, trust that your organization will successfully deliver on commitments, and resources that enable them to make a major gift. Custom fields in CiviCRM can be used to track specific interests and demographic information related to ability to give. During the cultivation of the relationship, personal face-to-face relationships developed through CiviEvent and board activities can be important. Tracking of relationships among high net worth individuals, or cross-linked board memberships of other organizations can be important in identifying prospects for major donor campaigns and the best person to contact for the request. Once the ask has been made it can be useful to track meetings and phone calls regarding the negotiations about the terms of the gift, tax implications, and so on. These can be stored in generic Activities, or a more structured workflow can be created using CiviCase.