As the field of Information Systems (IS) continues to advance, organizations will constantly be facing the challenge of paradigm shifts. This paper extends prior work on IS personnel training by emphasizing the retraining of IS professionals during a paradigm shift. The application of the Osgood (1949) transfer surface to the software development domain is proposed. A model is developed that defines the concepts of positive, negative and no skill transfer within the software development domain. This model demonstrates that the similarity of the stimuli and responses of the software development projects can predict the direction of the skill transfer. Anecdotal evidence of critical points in the model is provided to support applicability to the software development domain. This paper provides a theoretical beginning for work on paradigm shifts in the software development domain and highlights the importance of knowledge transfer in the face of technological change.