This article is based on conversations between a mother and daughter about academic leadership. Both authors served in different time periods and at different career points as heads of departments ("chairs") in Canadian universities. A literature review suggested that women's academic leadership is a contested topic, especially in relation to organizational cultures and associated gendered expectations. New directions were identified, as scholars move towards comparative studies, poststructural theoretical approaches, analysis of neoliberal trends in universities, and awareness of variation among women. We noted that "Canada" was largely missing from most of the literature reviewed and that middle management had received less attention than senior roles. Our method was collaborative autoethnography, a means of sharing thoughts about one's experiences and analyzing them with regard to wider social issues. Quotations are taken from a taped discussion in early 2018 and are organized around similarities and differences in our narratives. The conclusion raises issues about the difficulties associated with performing this particular middle management role; questions around the consequences of chairing for women in different age groups; the implications of increasing reliance on contingent academic labour; apparent differences between the Canadian experience and what has happened elsewhere; and promising directions for future research.