Critical reflection is pivotal for enhancing practice in peer observation of teaching (POT). Our analysis of educators' reflections in a developmental POT program revealed a deficiency in the level of critical reflection. In this paper, we reflect on the reasons behind this shortfall and changes made to enhance the scaffolding of critical reflection. Adjustments include addressing emotional challenges, introducing guided stages, and incorporating reflective prompts that encourage educators to ponder the 'why' rather than the 'what' in their teaching practices and decisions. The reflections presented hold promise for bridging the gap in effectively scaffolding reflection in the POT literature.