In this chapter, the journey of a school administrator in initiating a curriculum reform to cater to the diverse special learning needs of students in a working class school in Hong Kong is presented. Poon, a senior teacher for 9 years before being appointed the administrator in charge of academic changes in 2006, provides an insider’s account. Lin, a university professor and Poon’s mentor, provides additional theoretical analyses to conceptualize the importance of the school changes presented for other contexts. Before 2006, HKRSS was a traditional secondary school in Hong Kong where teachers taught a standardized curriculum in isolation from each other, with little understanding of students’ individual learning needs. Today, teachers engage in a process of collaboration and a collective discovery of the importance of differentiated instruction and assessment for all students. Constant sharing and collaboration among teachers regarding curriculum adaptations, pedagogical innovations as well as task and assessment differentiation have formed the new school culture. This new philosophy is the result of a comprehensive restructuring of curriculum, learning materials, instructional practices and assessment methods. This chapter provides an account of this difficult journey, the ups and downs experienced, and the lessons learned in the process.