This article presents an overview perspective on the potential benefits of applying multimedia technology to redesign and invigorate the career-long performance assessment and professional learning of school leaders. Funded design and development efforts of one multimedia project - the Administrator Case Simulation (ACS) Multimedia Library - focusing on the professional assessment and development of school principals involved in collaborative school leadership are highlighted. Project research teams at the ACS Multimedia Lab have focused in the past seven years on using available multimedia technologies to develop school leadership assessment and organizational learning case simulation resources for school principals and other school leaders. This article provides an overview of the multimedia case simulation concept, describes collaborative R&D project efforts involving regional and state school leaders, highlights multimedia case design features, and discusses implications of technology-integrated case designs for informing personnel assessment and evaluation programs and for enhancing the reflective thinking, decision making, and professional learning of school leaders. Finally, recommendations are offered for engaging in further research and development efforts using the integrated systems professional learning approach presented, and for creatively expanding technology-integrated case simulation designs to develop similar professional assessment and learning resources for all school leaders.