Organizational learning typically focuses on implicit adaptation in the firm's internal environment. This paper discusses organizational learning in the extended enterprise: consisting of the turbulent competitive/political environment of threats and opportunities, and the organization's internal environment - traditionally consisting of people and their institutions - extended to include the information technology platform. Here, internal and external policies need to be modeled for an effective adaptation of the enterprise. Artificial intelligence and machine learning methods are applied to organizational design in monitoring and analyzing decisions based on the impact and structure of the organization - monitoring changes as part of the learning and adaptation cycle.