This paper discusses the important design and implementation challenges that must be addressed in a decentralization reform, reviews how countries have attempted to resolve those challenges, and distills key lessons that could apply to the Philippines. A key lesson from the many countries that have decentralized is that a big-bang reform is likely to face tremendous implementation challenges, such as confusion about the functions and powers that are being transferred, political pushback, inadequate planning, and costly reversals. In contrast, this paper argues for a phased, selective, and iterative reform process, with adequate time allotted for preparation, consultation, and implementation. It suggests the development of a readiness index to guide the process, specifically, the choice of subnational governments that will be more quickly able to take advantage of the devolution of authority and responsibility to contribute to national education goals. It also calls for a combination of incentives and guardrails that encourage responsible decision-making by subnational governments, while thwarting political capture by local rent-seeking interests.