How can an owner, potential buyer, developer, or investor know if a vacant office building is suitable for conversion to housing and to what extent this is functionally, technically, and financially feasible? This is an important question, especially in a time of high vacancy rates and a strong demand for housing. This chapter discusses the so-called transformation meter, also called a conversion potential assessment tool: a checklist that helps determine which characteristics of the market, location, building, and involved parties are favourable or unfavourable for a successful transformation, potential risks, and how these risks can be mitigated. The transformation meter is phased from a “quick and dirty” general assessment to a more detailed analysis. Additionally, the role of this tool in the decision-making process regarding a go/no-go decision—whether to proceed with further planning or to stop investigating feasibility—is discussed. The chapter concludes with a brief discussion of other tools available for assessing the opportunities, obstacles, and risks associated with repurposing buildings.