This special issue includes a series of interviews with the past women presidents of the Philosophy of Education Society of Australasia (PESA), including Felicity Haynes, Nesta Devine, Tina Besley, and Liz Jackson. This article sets the stage for reading the interviews, though an extended dialogue between the two authors of this project. In what follows, the authors reflect on insights gleaned from the interviews, and the past and future of women leadership in philosophy of education. Using a dialogical format, it (...) highlights different experiences and similar challenges across generations, questions what has changed versus what has stayed the same over decades, and elaborates on the value of the interviews for readers coming from different academic generations and subject positions. It reflects on the state of the field and its future directions from the perspectives of two women philosophers working and thinking across generations. (shrink)