This paper presents a diagnostic for exploring IT alignment as a "strategic weapon". During the past three years of consulting and research, we have observed executives who are dissatisfied that their IT alignment facilitates projects with technical and process engineering objectives rather than projects that would leverage enterprise resources and improve competitive positioning. Not all IT can or should be dedicated to strategic enterprise-wide IT-based change. However, prominent IT experts argue that as a result of competitive pressures, CIOs must learn and adapt new approaches to implementing increasingly strategic enterprise-wide initiatives. Three case studies illustrate the benefits of using the diagnostic we propose, which explores and defines an alignment that would support strategic IT-based business outcomes.