This book explores the meaning, perceptions, historical and current cultural and psychological roots of gender stereotypes and patriarchy in the workplace. It provides a comprehensive analysis of the types of stereotypes, their origins, and theoretical underpinnings as well as a comparison of the different paradigms across cultures. As the narrative progresses, the book then provides a conceptual model of impact of gender stereotyping on female expatriates and provides evidence of women experiences at work and in the society from across different countries. It also shows mindsets across different generations and examines the possible impact of generative AI tools. This all reveals how this phenomenon still exists despite the increased number of women in workforce and how these stereotypes perpetuate harmful norms that limit individual potential, reinforce inequality, and enhance discrimination. Relevant for scholars, researchers, students, practitioners, and policy makers, this book encourages readers to self-reflect on their own internalized beliefs and biases, paving the way for personal growth and societal transformation.