The challenges facing educators in institutes of higher learning are intensifying as they need to adapt curricula and assessment methods to better align with industry demands and offer practical hands-on experiences for students. This effort is especially critical when educators strive to implement work-integrated education (WIE) programmes aimed at enhancing student work-readiness. Through semi-structured interviews with 41 educators across three polytechnic institutions, the study sought to understand the myriad challenges inherent in orchestrating effective work-integrated curricula. These educators’ experiences, drawn from approximately 40 hours of recorded interviews and analysed thematically, shed light on the pressing difficulties and the resultant opportunities for professional development. The analysis unearthed four predominant challenges encountered by educators in managing student engagement, mediating expectations between various stakeholders, ambiguity of their role in the workplace, and ensuring quality placements for students. To address these challenges, educators enacted strategies based on their intent of the programme which led to their professional development. The findings posit that through engaging in collaborative problem-solving and negotiation, educators can enhance their pedagogical and curricular strategies, thereby potentially transforming their teaching practices within the realm of work-integrated learning. This research underscores the transformative potential of WIE programmes, not only in advancing student readiness but also in fostering significant professional growth for educators.