Literature on educational reforms is rich of cases where changes have been attempted, without however to attain success. Likewise the Greek education system had experienced a lot of reforms, most of which have failed to make the intended changes and they attenuated shortly after their implementation or they ceased at the stage of legislative planning. On the other hand, the traditional research have failed to develop a coherent theoretical perspective and provide satisfactory interpretations of the perpetually unsuccessful reforms. This paper is part of wider project which attempts to address the above issue following the Complex Dynamical Systems (CDS) perspective, that is, by fostering the CDS epistemological assumptions and applying nonlinear methodological approaches. This endeavor focuses on teachers' readiness for change and explores the dimensions of the resistance to change related to the values, attitudes, dysfunction beliefs and planed behaviors of teachers. Given that the project is still ongoing, here, only the outline of the research design and the strategy followed are discussed along with some preliminary findings. At a first stage, the investigation implemented focus-group settings to reveal clues of those dimensions. The recorded data were analyzed via orbital decomposition analysis (ODA), a method designed for categorical time series and discourse analysis. Some of the crucial dimensions of resistance-to-change were subsequently measured via a survey instrument and were used to predict teachers’ position with linear and nonlinear models. Statistical analysis showed that the cusp catastrophe model was superior to the linear alternatives and revealed discontinuities in teachers’ positions, while certain variables proved to be bifurcation factors. The implications of these findings are discussed, while methodological aspects of ODA and catastrophe theory modeling are briefly presented. The present work sets a framework for the application of complexity theory and nonlinear dynamics in organizational theory of educational change.