The objective of this article is to investigate obstacles that hinder the assessment of return on investment (ROI) for academic staff development initiatives in public universities in South Africa. The primary objective of this study is to address the following research inquiry: What are the obstacles hindering the assessment of return on investment (ROI) for training and development interventions offered to academics within the higher education landscape of South Africa? The study employed a qualitative research methodology, which was based on an interpretive philosophical standpoint. The researchers employed purposive sampling to carefully select a total of fourteen participants who were selected to represent a range of cases or institutions. These included six universities and government institutions, namely the Department of Higher Education and Training (DHET), the Department of Science and Innovation (DSI), and the Education, Training, and Development Practices Sector Education and Training Authority (ETDPSETA). The interview data was subjected to thematic analysis using ATLAS.ti. The factors that hinder the measurement of ROI include the intricacy of the process, insufficient capacity, time lag between training and improved performance, lack of motivation, financial limitations, absence of processes, fragmentation of training and development interventions, interventions producing non-financial advantages, and insufficient data. The study enhanced the existing information on human resource development and practice by identifying the obstacles to measuring return on investment (ROI). Additionally, it offered practical advice and suggestions for future research.