This year-long action research (AR) study, conducted in the context of a physical education teacher education (PETE) program in Portugal, explored how critical reflection among preservice teachers (PSTs) developed in response to tailored questioning by an external facilitator (EF). Participants were six PSTs and the first author, who assumed the dual role of EF and researcher. Four AR cycles, each involving a self-reflection analysis, intervention, and the development of the PSTs' reflections were completed. During each AR cycle, the EF examined the PSTs' teaching-learning practices and views and generated tailored questions to support critical reflection. Data were collected through focus group interviews and written reflective journals. The EF also made participant observations to contextualize each PST's teaching-learning process, resulting in field notes. Using various question types (e.g. leading, probing, and procedural next-step questions) designed to address individual needs, PSTs progressed from a basic reflection level to thinking critically about their teaching-learning practices. The questions were helpful for PSTs in interpreting daily issues faced in teaching-learning and understanding the relevance of self-analysis and attention to learners' needs in fostering critical reflection. Given these results, we recommend that PETE programs incorporate a component or module explicitly promoting reflection on and analysis of PSTs' pedagogical practices.