In this empirical study, the researchers argue that immediate attention is required to ensure that principals successfully implement Coaching Leadership Style (CLS) to enhance the sustainability of learning experience learner success. The problem underpinning this study is that the principals face difficulties in implementing CLS. The study is based on in Instructional Coaching Leadership Theory. The major assumption of this theory is that Instructional Coaching Leadership Theory is viewed as a method of providing sustained and personalized support to the principals and emphasizes the fundamental role of active learning, reflection, and feedback in the learning process. The purpose of this study is to evaluate the challenges facing principals in successfully implementing CSL and how principals can mitigate these challenges. This study used qualitative methodology to gather data from three secondary and two primary school principals in Bloemfontein through structured interviews. The findings of the study revealed that principals lamented the lack of training to implement CLS. In the discussion with the participants, the researchers concluded that necessary steps should be taken to empower the principals on CLS. Recommendations for further research and implications for principalship and training programs are provided. This empirical study contributes to the body of knowledge by exploring how can principals practice CLS to achieve the objectives of the study of successfully implementing CLS to enhance learner success and of devising means of mitigating challenges experienced by the principals. Keywords: Implementation, Coaching Leadership Style, Instructional Coaching Leadership Theory, learner success.