||The library automation environment has undergone drastic changes in the past twenty years. Being a front-line practitioner of systems works in Hong Kong libraries, the author sees numerous waves of technological breakthrough, changing the ways libraries provide services, and in effect, transforming traditional and print-based libraries into digital libraries. This paper highlights some of the landmark events on library automation that the author experienced in the past 20 years. The Hong Kong Library Association is celebrating its 50th Anniversary. It is timely to recollect these Hong Kong library systems activities, reflect on them and identify important lessons learnt. By categorizing the key elements in conducting library systems projects, the author attempts to propose a framework, consisting of four areas: technology, learning, organization and leadership, which will act as a checklist for implementing systems projects.