The inherit complexity of an educational system further complicates the challenge of introducing technology-based educational initiatives into a school environment. Once introduced, the initiative has the potential to become self-sustaining or to cease once the term is over. Such uncertainty makes the use of expensive information technology (IT) in schools “risky business,” which requires school leaders go above and beyond their current routine to extend the system's capacity to sustain the innovation. A discretionary behavior of school leaders and teachers is one of key factors that contribute to or prevent the sustainability of an innovation. A lack of understanding of what encourages an individual's discretionary behavior and how discretion is fostered in school practices contribute to the challenge of innovation's sustainability. If the individuals’ discretion is required to sustain a technology-based educational program within a school, do their actions dwell outside or inside of the school environment? More importantly, how does a discretionary chain of command operate and can it be aligned? In this chapter we use an “ecological model” approach to describe the influential factors, which affect project's sustainability by transforming effective discretionary approaches of school leaders and teachers from policy to practice. We draw our description of the model on the results of the empirical study of Hong Kong schools involved in the design and strategic IT implementation of the e-Leadership Enhancement Project (eLEP).

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