In the era of digitalization, the working style has drastically changed. Currently, remote work is prevalent in most companies and preferred particularly by the young generation, who values work–life balance. This shift in the working style has raised a question about the effective leadership and communication style that can enhance employees’ motivation and engagement. The leadership communication strategy that is effective in face-to-face context may not have the same level of effectiveness in virtual organizational settings. This chapter delves into digital transformation in the organizational context and aims to identify and suggest an efficacious leadership and communication style tailored to the digital environment. This chapter is based on the literature review and empirical findings. It clarifies that digital leadership and communication skills of digital vision setting, digital literacy, digital communication, and cultural and emotional intelligence are significantly influential in enhancing employees’ leader trust and psychological safety. The findings offer valuable insights into the current discussion regarding leadership and digital transformation. Future studies should develop a comprehensive model of digital leadership and communication skills and their organizational and employee outcomes.