The purpose of this study is to implement and evaluate a teacher training program based on the framework of situated learning. Adapting from the situated learning approaches, the author implemented two in-service teacher training programs based on cognitive apprenticeship and community of practices respectively. Each training program was adopted in a different campus of a private kindergarten. During the six-month training, researcher conducted a qualitative research to evaluate the effectiveness of the training program. To investigate how teachers improved their professional skills in constructive instruction, the researcher invited four supervisors and 10 kindergarten teachers to participate in the training program. The qualitative data included classroom observation, focus group, interviews, and teachers’ reflection notes. The results suggest that both programs may aid learning of engaging in constructivist instruction by providing external supports such as model instruction plans, mentoring, cooperating to solve problems. Nevertheless, the relationship or power hierarchy between mentors and learners is important in cultivating mentees’ capabilities. Practices sharing in community of practices approach, rather than supervisors’ expertise and diagnosis, will help the mentees to enhance their capabilities of solving problems.