“Prudence in a maze of metaphors” follows a fictional day in the life of a woman to explore a variety of challenges individuals commonly face in their professional environments. Prudence’s story uses metaphors such as Sticky Floor, Glass Ceiling, Double Bind and Motherhood Penalty to illustrate her experiences. Although these metaphors are associated with gender-related barriers, the case could also be extended beyond gender to address broader systemic challenges related to race, socioeconomic background, disability and other factors that influence professional life. Prudence’s journey could become a representation of the invisible barriers faced by various groups, including issues of privilege, societal expectations and structural inequalities. We hope that this compelling compact case and teaching note will support instructors in navigating and unpacking powerful discussions about diversity and inclusion issues – a must-have conversation. The case provides a comprehensive framework for exploring complex topics, facilitates peer learning through shared experiences and encourages self-reflection on personal biases and structural barriers. Instructors have multiple options to navigate the “maze” of issues involved in creating inclusive cultures, which enables them to adapt the content to their own audiences. Crucially, this approach allows executives to develop and practice the skills needed to navigate difficult conversations constructively. The case also provides space to explore and address the perception some men may have of feeling “stuck” or challenged in advancing their careers, offering a chance to discuss how different groups experience and interpret barriers in the workplace. The insights gained from this discussion underscore the nuanced ways that gender dynamics affect both men and women, revealing how workplace barriers are experienced differently yet still have overlapping challenges that can be addressed through inclusive strategies.