This chapter asks how people can be assisted in learning from practice, as a basis for informing future action, when configuring information technology (IT) in organizations. It discusses the use of Alexanderian patterns as a means of aiding such learning. Three patterns are presented that have been derived from a longitudinal empirical study that has focussed upon practices surrounding IT configuration. The paper goes on to argue that Alexanderian Patterns offer a valuable means of learning from past experience. It is argued that learning from experience is an important dimension of deciding “what needs to be done” in configuring IT with organizational context. The three patterns outlined are described in some detail, and the implications of each discussed. Although it is argued that patterns per se provide a valuable tool for learning from experience, some potential dangers in seeking to codify experience with a patterns approach are also discussed.