Projects involving technology are notoriously dogged with difficulties and a number of lessons can be learned. Rather than detail examples from particular TEL projects, the author offers an approach based on the empirical study of such projects over a number of years. The key factor in holding back technological developments in the HE sector is the lack of a robust, mature and positive approach to assessing and managing risk. The Sliding Planning window approach provides a more flexible framework in which to respond to the unexpected. The sector and beyond is on the brink of a major shift in the nature of TEL projects brought about by the so-called Web 2.0 phenomenon - a new project paradigm is therefore needed. The CAMEL model is explored as a way of harnessing the culture of reflective practice in the FE/HE sectors through sharing ideas in communities of practice.