Digital transformations help organizations revitalize business processes and customer relationships. Industry professionals and academicians recognize that leadership skills and technology skills are complementary when managing a digital workplace. Using a classroom exercise administered in multiple semesters, we attempted to capture student perceptions of leadership skills and competencies they deem important in leading a company through a digital transformation. Findings revealed that younger generations recognize digital literacy for corporate leaders as a key skill alongside conventional leadership skills. We address the need to enhance graduate and undergraduate business management curricula to provide students an opportunity to examine and develop leadership skills to confidently lead amidst the complexities of a digital workplace.