Human beings are, by nature, self-aware beings. This capacity lets us know who we are, how we do things, and what we (and others) are doing at any particular moment. In organizations, self-awareness is an essential prerequisite for effective action, decision-making, and learning processes. However, it must be built and maintained by continuous interactions among their members. This chapter lays out the foundations of a comprehensive high-level modeling framework as a means for enhancing organizational self-awareness. The modeling framework encompasses an architecture and ontology, which puts together human, social, and organizational approaches with modeling frameworks coming from the computer sciences and IS/IT fields. The proposed approach is illustrated with two example applications which use the finer-grained concepts of the framework. An analysis of the implications of this approach and issues to be addressed is provided.