The purpose of this article is twofold. First, it sheds light on an intergenerational leadership process experienced by two African American women. This piece is a leadership story situated within a School of Education in higher education that describes the challenges faced by a Dean with many over 10 years in the role and a newly minted Associate Dean. The influence and impact of intergenerational dialogues is described as a meaningful and necessary process to better understand leadership in institutions of higher education.