The initial assertion of this paper is that information systems development (ISD) failures can best be addressed through a systems approach. Such an approach is characterised by Linstone’s Multiple Viewpoints or Checkland’s Soft System Methodology (SSM), both of which are supported by Singerian inquiring systems. The paper notes that these approaches are both forms of action research and therefore examines the support given to other forms of action research by Singerian inquiring systems. Organisations which recognise that they are not perfect when it comes to ISD and wish to do something about it can be considered as Learning Organisations. Senge’s approach to Learning Organisations is seen as being generic. In the context of ISD, it is contrasted with SSM. In particular, the support required by these approaches from the classical inquiring systems is being considered. Further, the implications of what any resolution might mean for ISD is also considered. The final focus is to consider the framework of ISD as a social construct and examine the benefits of a non-classical inquiring system, based on the philosophy of Rorty.