This report provides a comprehensive analysis of leadership challenges encountered by Woolworths, a major Australian retailer. It begins by defining leadership and exploring different leadership styles, such as democratic and autocratic approaches. The report then delves into specific challenges faced by Woolworths, including issues related to restructuring, poor innovation, and employee dissatisfaction stemming from fair work commission disputes. These challenges are attributed to a lack of strategic leadership and poor communication. The report further examines the need for changes in leadership approaches to address complex market dynamics, emphasizing the importance of market research and competitive analysis. It suggests recommendations for improving leadership quality, such as fostering innovation, encouraging employee development, and improving communication. The report also highlights the importance of proactive problem-solving, creativity, and goal setting to effectively manage leadership challenges within the organization.