Digitalization is a global megatrend that changes companies’ internal and external value-creation activities. The introduction of digital technologies requires organizations to adapt their internal operations and external product and service offerings to remain competitive. Leaders must possess specific skills and characteristics to guide their organization successfully through digitalization. We conducted a literature review to research which leadership skills are required for successful digitalization regarding companies’ internal and external dimensions. We employed an inductive analysis that identified 92 articles from 2011 to 2021, which allowed us to structure the results into nine main themes. We revealed that leaders for successful digitalization must be visionary and customer-centered while embracing change. Supporting properties for successful leadership in digitalization are flat hierarchies, empowering employees, possessing digital savviness, and engaging in partnerships and ecosystems. In conclusion, digitalization requires true leadership, not mere management, to embrace risk-taking and promote teamwork and collaboration. This includes continuous awareness of diversity and cultural differences, which must be actively managed.