The purpose of this study was to identify leadership styles that impacted the digital transformation of an organization. Six information technology leaders from healthcare organizations were chosen to lead and participate in a digital transformation effort across several organizations in the Midwest (USA). The information collected was transcribed for clarity and to identify patterns in leadership styles that were evident. A qualitative research design using semi-structured interviews was established to determine this impact and how leadership style influenced an organization’s direction regarding its digital transformation. Specific research literature in this area was addressed and provided a framework for this issue, including the types of leadership styles which were commonly used. These styles influenced large-scale decisions within an organization. In addition, the success of this transformation was evaluated in the context of leadership styles occurring naturally within an organization. The research findings indicated that leadership style was highly impactful in transforming organizations and employee-based involvement and input played a critical role in the success of the change effort. In addition, organizational leaders lacked some of the technical knowledge required to lead this project. Leadership styles are influential in organizations and can implement norms, expectations, and desirable outcomes during large-scale transformative projects.