Classification schemes are embedded into everyday life and people often expect that each category is fixed and stands alone from one another (Bowker & Star, 2000). In terms of gender, this is evident when people focus on gender as either male or female. With the increasing presence of people who are openly transgendered in the workplace (Taranowski, 2008), people’s expectations about gender as something ‘that just is’ are questioned. There is an emerging research literature focusing on people who transition in their work environments, but comparatively little on their coworkers. This research focuses on the experiences of the coworkers’ to examine how they interpret the meaning of gender after their colleague transitioned from being a “man” to being a “woman”. By analyzing and interpreting people’s behaviours in the context of a workplace where an individual reconstructs what it means to embody a specific gender identity, the feelings and behaviours that arise when expectations about gender are contradicted can be examined.