Given the predominance of men among elites, it is remarkable how little scholarship there is on the challenges of qualitative empirical work on elite men, especially work that interrogates the intersection of gender and class. We have both sought to include elite men as subjects, noting that the gender of our subjects, their social power, and our own gender performance have played a central role in defining our efficacy as researchers. Darren has researched top French corporate boards (e.g., Rosenblum and Roithmayr 2015). Janet has researched male dominance in the politics of Iceland and Russia (e.g., Johnson 2016; Johnson, Einarsdóttir, and Pétursdóttir 2013). This essay elaborates the challenges in researching elite men and explores the tactics we developed in response to the dynamic gender performances in the interviews, bringing Darren's insights as a legal scholar looking at economic elites to questions about male overrepresentation in politics.