Small and medium-sized enterprises (SMEs) contribute to the stability and growth of economies by creating employment in rural and urban areas. More than 60% of SMEs do not survive for longer than 5 years; a lack of leadership skills is among the key problems. The purpose of this multiple case study was to explore the leadership skills owners-managers used to sustain their businesses for longer than 5 years. Research participants were 4 owners-managers of SMEs from the manufacturing industry in Trinidad and Tobago that sustained their businesses for at least 5 years. The contingency leadership model and the skill-based leadership model formed the conceptual lens for this study. Data were collected using semistructured interviews and direct observations. Data were analyzed using Miles and Huberman's analytical strategies and Morse's cognitive process of coding, pattern matching, interpreting, and summarizing the data. Five themes emerged from the data analysis: leadership skills, leadership values, development of leadership skills, leadership challenges, and improvement in leadership skills. The findings from this study could influence positive social change by providing insights on leadership skills SME leaders could use to sustain their operations for the longer term, resulting in reduced failure of SMEs. A decrease in the failure rate of SMEs might contribute to improved economic conditions, leading to the reduction of poverty in families and communities.