This chapter explores approaches to schools’ implementation of character education, focusing on the strategies employed in assessing character change in the student. Using the “7 E’s” (Explain it, Examine it, Exhibit it, Expect it, Experience it, Encourage it, and Evaluate it), a framework of teaching character trait introduced by Thomas Lickona (2004), the study analyses the differences, similarities, as well as affordances and limitations of each approach as practiced by six primary and secondary schools in Jakarta, Indonesia. Qualitative data were based on focus group discussions with select groups of teachers and principals captured. The main finding of this study emphasises the importance of a clear and effective assessment guide for teachers to observe character changes in students. The assessment guide includes the behavioural indicators of each trait fostered in school, based on understandings of the developmental stages of children and adolescents. Implications of this study include the need for more studies to examine various other frameworks to guide the development of assessment models for the implementation of character education in Indonesia.