A major challenge facing teacher educators today is creating a field-based opportunity for pre-service educators in which they are able to connect with K-12 students and differentiate instruction to fit the unique needs, attitudes, and diversity of the classroom. This action-research study addresses this challenge by measuring the effectiveness of incorporating pre-lesson reflection questions as a strategy to consider pre-service undergraduate students’ needs prior to the planning of the lesson. Investigators were successful in utilizing this pre-reflective strategy within three distinct populations of pre-service undergraduate students. The investigators partnered with a group of undergraduate students early in their education program, a group of students just before their student teaching experience, and a group of seniors during their student teaching placements. The investigators and students participated in classroom discussions on information about pre-lesson reflection development, on-campus classroom exercises, and small group feedback conversations about lesson implementation, which enriched the connections between curriculum, classroom learning, and community