This paper presents an analysis of problems that are faced by software development practitioners. While communication, team management, coding and software documentation are some of the persistent problems, the first and major troubles for software practitioners is to select appropriate software development approach. This approach should allow developers to develop adaptive software products. The role of organizational culture, context, practice and concepts in developing adaptive software products is also discussed. This qualitative research study interviewed seven software development practitioners in South Africa, focusing on software developmental methods that allow the capturing of softer, human elements inherent in organizations and the accompanying problems that inhibit their inclusion in the resultant software products. The research used Grounded Theory Method, to construct a framework of requirements that must be considered when choosing a software development approach that allows the development of adaptive software products. This framework highlights the importance of employing a software development approach that is grounded in the relativistic paradigm, adopting a behavioral systems approach and adopting methods whose communication techniques and tools can capture the humanist elements that are inherent in organizational systems.