The complexity with which today’s leadership works, especially in diverse workplaces where multiple cultures, backgrounds, expertise, talents, languages, and values consistently intersect, it is difficult to stick to a single leadership model or theory. The biggest challenge in this regard is the inability to associate a program to a solo culture or group values because contemporary workplaces are amalgamations of diversity, uncertainty, and dynamism. This means that following a particular leadership style, which often presumes that everyone working for the program shares common values, beliefs, and objectives, has become unfeasible. This situation calls for revisiting leadership practices in a globalized world, exploring how such situations are emerging and addressed in different disciplines, and what can be done to contribute to a renewed understanding of leadership that is compatible with global forces and also reflective of the local community. This paper begins with a literature review of Teaching English to Speakers of Other Languages (TESOL) leadership and provides an overview of the multilayered challenges leaders deal with in this profession. It discusses how TESOL leaders could create a balance between global developments in the field of education and TESOL, and the language-based needs of local and non-local students and program requirements. Drawing upon four prepositions, this paper argues that there is the need for leaders to adopt a paradigmatic shift when leading complex educational institutions. It proposes that TESOL leaders could take a global-contextual approach that focuses on the local contexts while drawing upon the global practices when addressing the challenges in a TESOL program.