Executives are increasingly facing various challenges associated with digitalisation, especially the simultaneous handling of many topics, loads of information flushing in via digital channels, rapid changes, and finding the right balance between the old and the new. Building on a growing body of research suggesting and systematising leadership skills, we conduct an online-survey with executives to investigate the connection between selected skills and the ability to cope with specific challenges. We find that a strong ability to think and act entrepreneurially, (self-)organisation and IT skills, a profound ability to motivate others, and a high degree of flexibility, commitment, and creativity are positively linked to the ability to cope with several digitalisation-related challenges. Surprisingly, being a strong team player does not seem to be necessarily advantageous. Moreover, many executives desire more calmness, which suggests that being able to decelerate is important in the digital age.