It is possible to identify two distinct yet complementary epistemological paths to knowledge development. The first one is holistic and field dependent, and builds on the concept of plausibility, and we associate this path with an entrepreneurial mindset. The second is object-oriented and builds on the concept of probability; this path can be associated with the managerial mindset. We believe that both managerial and knowledge management practices have emphasized the second path at the expense of the first. To restore the balance, knowledge management needs to develop processes and tools – associated with scenarios and real options – that will allow it to operate credibly in possible and plausible worlds, so as to extract value from them. We propose a systems framework for thinking through the nature of such tools.