Against the backdrop of an unprecedented increase in the number of older adults in Singapore, the escalating pace of change which necessitates continuous learning, and a dearth of empirical research related to instructional design for older adults, this study sought to fill this gap by investigating the strategies utilized by successful instructors to deal with older adults within the classroom context, from their perspectives. Conceptualized within the interpretivist research paradigm, it adopted symbolic interactionism as its theoretical framework, applying a constructivist grounded theory strategy, within the qualitative research method, to generate the theory. The primary sources of data were in-depth semi-structured interviews and non-participant classroom observations, of nine instructors from diverse backgrounds. The progressive empowerment of learners emerged as the central proposition of the theory generated through the study. Comprising the three phases of empathizing, engaging and empowering, the developed theory provides a systematic, process-oriented instructional model, to guide current and prospective practitioners teaching classes that consist of learners conforming to such a profile. To date, such a model, from an Asian perspective, does not appear to exist.