Organizations apply information security risk assessment (ISRA) methodologies to systematically and comprehensively identify information assets and related security risks. We review the ISRA literature and identify three key deficiencies in current methodologies that stem from their traditional accountancy-based perspective and a limited view of organizational “assets”. In response, we propose a novel rich description method (RDM) that adopts a less formal and more holistic view of information and knowledge assets that exist in modern work environments. We report on an in-depth case study to explore the potential for improved asset identification enabled by the RDM compared to traditional ISRAs. The comparison shows how the RDM addresses the three key deficiencies of current ISRAs by providing: 1) a finer level of granularity for identifying assets, 2) a broader coverage of assets that reflects the informal aspects of business practices, and 3) the identification of critical knowledge assets.