This research examined the role of middle management in executing strategic plans in two colleges in a South African higher education institution (HEI). Strategy execution is a complex operational process. Flawed sense-making of the strategy could lead to strategy breakdown, and challenges may occur concerning understanding and executing the strategic plans. Therefore, the main aim of this study was to examine how middle management in the two colleges at the HEI engaged in the sense-making of the strategic plan. The study set out to: examine how middle management participated in the sense-making of the two colleges' strategic goals; determine how middle management communicated the strategy to employees at the two colleges, and identify the challenges middle management faced with strategy execution at the two colleges. The research employed a qualitative research approach. Interviews were conducted with a purposive non-probability sample of ten middle managers in the two colleges at the HEI. Primary data were collected through semi-structured interviews. Data were analysed using thematic analysis. The interviews were conducted at the middle management’s offices and lasted between 20-45 minutes. The study findings revealed that each college engaged in the sense-making processes differently and that there are different understandings of the role of middle management in executing strategic plans. The study highlights the need for middle management in the two colleges in the HEI to engage in training in executing strategic plans. The findings may help us understand how middle management in the two colleges executes strategy and how sense-making occurs. In addition, it could assist with role clarification of university service units in implementing the strategic initiatives, as most literature focuses on strategy formulation rather than execution.