While calling for the need to continue engaging in conversation with differing understandings of leadership effectiveness, the author demonstrates what this could look like in practice by conversing with three leadership authors, Hannah Arendt, from the field of Political Theory, James McGregor Burns from the disciplines of Political Science and American History, and Joseph C Rost, from the field of Education Administration/Leadership. In this article, the author seeks to understand differing and contradictory notions of leadership effectiveness as they are proposed by Burns and Rost. Following Arendt, the author (a) distinguishes the nature of action as understood by Burns (acting as making) and Rost (acting as initiating), (b) outlines the dominant influence of ‘acting as making’ or homo-faber image of leadership within the discipline of leadership studies, and (c) considers the implications of including ‘acting as initiating’ for leadership learning and education.