This study investigated the mentoring of academics for leadership and management in higher education institutions through the application of contextual intelligence. Experts and professionals generally agree that effective institutional leadership and management mentorship, using contextual knowledge, is crucial for achieving institutional success. The paper aims to illustrate the significance of mentoring institutional leaders and managers using contextual intelligence skills. The dearth of literature on mentoring academics using contextual intelligence in South Africa might be addressed through mentoring, as this practice poses a significant obstacle. The challenges of applying contextual intelligence in mentoring academics are highlighted with a focus on four key areas: mentoring, leadership and management, contextual intelligence, and achieving organisational success. Despite their relatively tiny proportion within the overall framework, these elements exert influence over all aspects of the institution s activities. While tackling each impact individually may result in success, the continuous emergence of new factors makes it unlikely for this method to maintain improvement. The findings illustrate that the perception of improvement is determined by a dynamic and intricate setting. The paper plays a vital role in considering contextual dynamics when mentoring for contextual intelligence. [For the complete Volume 22 proceedings, see ED656158.]