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This paper explores when and how female chief executives can transform institutions in ways that alter gender norms and expectations that traditionally privilege men. The lengthy era of German Chancellor Angela Merkel provides several examples of a flexible female leader able to adjust to fluctuating gender-specific challenges in ways that could engender enduring institutional change. Using Germany as a case study, this paper teases out of Merkel’s experience three specific lessons for understanding how women in general might overcome masculine privilege embedded in executive offices. It also invites feminist institutional scholars to consider the potential for positive evolution of the gendered environment of chief executives in other multi-party and/or federal systems.