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In our Harvard Business Review article published on February 28, 2023, “What Makes Leadership Development Programs Succeed,” we unveiled the pivotal factors distinguishing impactful leadership development programs from ineffective ones. The insights we shared in this article built upon our ongoing and published empirical research on the outcomes of leadership development initiatives (Yemiscigil et al., 2022a, 2022b, 2023a). Motivated by this work, the aim of this leadership perspective is to propose a novel lens in establishing effective leadership learning and development through a new understanding of expectations, intentionality, and measurement of outcomes (Born, 2016; Born et al., 2012, 2017, 2019; Enger et al., 2010; Hendrix et al., 2015; Yemiscigil et al., 2022a, 2022b, 2023a).