English language proficiency is a significant aspect of education in many multilingual and formerly colonial societies. In these contexts, English often acts as a medium of instruction in schools and in societal communication. In the West African country of Ghana, specifically, some students experience challenges in comprehending and communicating effectively in English, which impacts their overall academic performance. This article uses a critical constructivist lens to examine lived experiences of two former students of English-medium schools. Using narrative research and semi-structured interviews, the study identifies educational practices and language expectations that the participants suggest negatively impacted their learning and also their social interaction in school. Findings of the study highlight the crucial role of linguistic ability in English in promoting students’ social and academic performance and the need to address strict linguistic expectations. The study suggests that educational leaders can do more to promote inclusive school environments that value diverse linguistic skills and foster equal learning opportunities for all individuals. By enabling a supportive and inclusive language environment, schools can enhance student-teacher relationships and promote academic success for all students.