Generally, Caribbean teachers seem to have limited engagement with applying observation of young learners' language in the classroom setting. For this chapter, a sample of 40 Grade 1 to 3 teachers from six Caribbean countries provided information to examine teachers' use of observation of learners' oral discourse to inform instructional pedagogy in English Language teaching. Based on primarily qualitative methods, a standardized structured-interview guide, focus group discussion, and classroom observation guide were used to collect data on teachers' classroom instruction. The findings revealed that while teachers declared knowledge of the merits of applying observation for evaluating learners' real language, the evidence of application of this assessment strategy was missing. In addition, results which showed that some teachers appeared to lack awareness of utilizing information about learners' home language use to cater to their individual language needs, warranted attention to transformative pedagogical perspectives in English Language instruction.