This article explored how employees with transgender experience manage openness regarding their gender identity and transgender experience in the workplace; and to identify the motives underlying these strategies as shaped through the interplay of individual experiences, workplace interactions, expectations of gender performance/doing gender, and cisnormative structures. In this qualitative study, 105 study participants with transgender experience shared their experiences working in Sweden; 20 participated with in-depth interviews and 85 answered a survey. Thematic analysis was performed with an abductive approach, using the lenses of cisnormativity and gender performativity. The analysis first identified different a range of strategies for managing openness; however, the main contribution of the study lies in understanding the motives underlying these strategies. Four motives were identified for the management strategies: (1) Being a role model, (2) A drive to be accepted, (3) Fear of discrimination and microaggressions, and (4) Organizational and social facilitating conditions. Respondent experiences highlight that working life and social inclusion interplay with individual factors when it comes to well-being and openness. Findings suggest development of workplace interventions to reduce fear of discrimination and improve other preconditions to support employees' preferences for managing openness. These include, for example, respecting employees' preferred level of openness/privacy, openness-sensitive leadership, organizational support for gender diversity through policy and organizational structures, along with training focused on everyday interactional competence that reduces the burden on employees with trans experience to educate others, and acknowledging transgender experience as an asset to the organization.