In the Two Islands Activity, students are given a fictitious prompt to examine and reflect on how their positionality influences their perceptions regarding their assumptions about gender and sexuality in interpersonal workplace interactions. Through the active process of perception checking, students examine how gender and sexuality stereotypes may influence their perception of a situation and their potential implications on business relationships. The activity is framed around the interpersonal Communication Theory of Identity as it relates to positionality, or how multiple identities (i.e., race, ethnicity, gender, class, sexuality, ability, age, and political ideology) in social and political contexts shape gender and sexuality roles and stereotypes within the workplace. Perception checking is an active, reflective process of asking questions and seeking alternative viewpoints to account for disentangling these perceptions. This activity encourages students to reflectively examine their identities, experiences, and stereotypes concerning cultural norms and ideologies of gender and sexuality.