This chapter stems from the evidence of a fact: the largest number of graduates in service design or related disciplines is female, and this also happens in the professional field. An inquiry has been conducted to better understand this issue, combining quantitative and qualitative data: on one side, ten design schools all over the world were asked about their percentage of women among service design students; on the other, five in-depth interviews were done with practitioners coming from different experiences in the consultancy area. Then, four hypotheses about the cause of this fact are proposed, and they provocatively overlap with four widespread gender stereotypes: empathy, as women are considered particularly good at exercising it; multitasking, as women are generally considered better at it; aversion to STEM as women usually stay away from these subjects; social purpose, as women are generally inclined to deal with social issues. Such hypotheses/stereotypes are discussed based on the conversations conducted with the five interviewees and on the connected scientific literature: they are still under discussion, but some of them present interesting elements that would lead to their confirmation. At the end of the chapter, a reflection is presented about women’s leadership in the service design field, and a possible roadmap to grow it is suggested: it is about better valuing some abilities like listening, understanding, facilitating, orchestrating the overall experience and, above all, the ability to ‘stay in the process’ without having immediate results and navigate the contemporary complexity.