Across organizations, most leadership development programs share a similar formalized and centralized structure. This similarity reflects a neglect of the specific contexts in which leadership development programs are implemented. The objective of this article is to understand the insensitivity to organizational contexts that is inherent in the structure of such programs. To do so, we monitored the implementation of a leadership development program in a multinational company from the construction industry. Over a period of 18 months, we collected material from four countries across four continents, with 41 semi-structured interviews, participant observations, and multiple documents. Our analysis builds on Pettigrew’s contextualist framework, combining power and contexts to understand the program structure. We suggest the insensitivity of leadership development programs to contexts lies in power dynamics: the legitimization strategies of the program designers are mostly decisive in shaping the structures of these programs. Contexts are not absent, however. They are present and valued in the legitimization strategies but only as long as they justify the structure of the program as designed by these actors; if contexts call for alternative structures, legitimization strategies neglect or bias contexts. In other words, power strategies instrumentalize contexts in the implementation of a leadership development program. Overall, our research calls for re-embedding the study and practice of leadership development programs into organizations, with a recommendation to those involved in their implementation to broaden the scope of their programs in terms of structures, contexts and power for enhanced program effectiveness.