The document describes a role-playing exercise conducted at a workshop on digital asset management (DAM). The class was divided into groups, each representing an organization facing a challenge that could be addressed through proper DAM practices. One person in each group acted as the digital asset manager tasked with identifying how roles contributed to a problem and devising a DAM solution. Scenarios involved a greeting card company sued for using an unauthorized image and a publisher needing to reduce budgets while maintaining production. The exercise allowed participants to gain insight into DAM's multi-faceted challenges and how problems can arise without proper asset management.