There are two major challenges in implementing technological solutions as part of institutional reform in development project: the alignment issues with bigger – nationwide – agenda and addressing the resistance in – usually – corrupt environment. This paper aim to provide some reflections on the implementation of information technology to reform the Indonesian judiciaries. Lessons learned from past experiences are provided, as well as a proposal to modify the classic IT-business alignment model and the use of agent based approach to determine the information technology implementation roadmap.