Increasing digitization of everyday leadership and increasingly demanded agile working methods constantly pose new challenges to leaders, e.g., in terms of the use of digital applications or leading at a distance. Leaders can be supported in everyday life, on the one hand, through individual accompaniment and advice, e.g., through coaching, on the other hand, through specially developed tools and checklists. Both approaches are combined in a so-called “Leadership Toolbox” with the aim of relieving everyday leadership in the age of digitization. The toolbox including the associated tools was piloted in four workshops with 20–25 leaders from various companies and industries. Feedback from practice suggests that especially for younger, still rather inexperienced leaders, the concept of a modular, digital toolbox is useful. An exemplary motivation to participate in the development of the Leadership Toolbox is illustrated using the example of the Bremen IT company affinis AG. Finally, concrete recommendations for action from the toolbox, such as the use of checklists, instructions in the form of “tips and tricks,” and a self-assessment for reflective location determination, as well as online coaching as a further measure provide an insight into the implementation.