The goal of being able to build quality in software products from the get-go is something that many organizations are trying to achieve. However, the very definition of software quality is somewhat elusive which makes it difficult to agree upon the perceived level of quality in software products. Moreover, working with legacy systems poses its own set of challenges as uncertainty of preserving overall quality in the legacy product seems to be an everyday struggle for many teams. This talk builds on a multi-perspective definition suggested by Gojko Adzic in his blogpost “Redefining Software Quality” some years ago. For each perspective a series of well-defined questions will be presented that help teams challenge its own assumptions about quality in the end-product. The talk is based on practical applications of Gojko’s definition as embraced by the teams working on a legacy enterprise software in healthcare domain.