The development of competencies known as 21st-century skills are garnering increasing attention as a means of improving teacher instructional quality. However, a key challenge in bringing about desired improvements lies in the lack of context-specific understanding of teaching practices and meaningful ways of supporting teacher professional development. This paper focuses on the need to measure the social quality of teaching processes in a contextualized manner. We do so by highlighting the efforts made to develop and measure teacher practices and classroom processes using the Teacher Instructional Practices and Processes System© (TIPPS) in three different contexts: Uganda (secondary), India (primary), and Ghana (pre-school). By examining how such a tool can be used for teacher feedback, reflective practice, and continuous improvement, the hope is to pave the way toward enhanced 21st-century teacher skills and, in turn, 21st-century learners.