Megatrends, such as digitalization, globalization, and demographic shifts, are creating an organizational environment that is more volatile, uncertain, complex, and ambiguous than ever before (Stiehm & Townsend, 2002). In addition to geopolitical changes, the technological innovations of digitalization promote the speed of industrial change and introduced the digital age (Kremer, 1993). The resulting digital technologies, such as AI, Big Data, or Robotics, as well as their economical applications, are crucial for the innovativeness and future viability of organizations. They are revolutionizing the way of working in almost any discipline and across most industries. For example, digital connectivity alone can lead to process adaptations through increased data variety, a focus on customer relationships, independence of time and place, the blurring of hierarchy, and incremental production automation. Despite the manifold opportunities created by the adaptation of new technologies, it is an intensive, long-term process, especially for industrial companies which produce mainly material goods and whose business models predate the digital age (Mertens et al., 2017; van der Schaft et al., 2020; Voigt, 2008). As a result of comparing the existing and ideal levels of digitization within companies, adaptations vary from process optimization and strengthening of business models to the redefinition of products or complete restructuring of organizations (Wessel et al., 2021). Especially for traditional companies, this results in a highly scaled, multidimensional transformation process that extends over several years and to many areas of the company, such as strategy, products, processes, employees, culture, and collaboration (Fenlon & McEneaney, 2018; Porfirio et al., 2020). The study by LaClair and Rao (2002) analyzes the success rate of such holistic organizational initiatives. They compare the change initiatives of 40 organizations in different industries and show that 58% of organizations failed to achieve their goals and another 20% only partially achieved their goals. A review of the common success factors of organizations with high levels of goal achievement showed the constant involvement of leaders at all levels (LaClair & Rao, 2002). Leadership theory was able to deduce decades ago that the involvement and capability of leaders are decisive components of the success of transformation projects. Independent studies, such as the by Hambrick and Mason (1984), who introduced macro-organizational theory, or by change luminary Peter Drucker (1999), created the basis for further analyses and recommendations on conducive leadership behaviors, styles, and characteristics (Schoemaker & Day, 2021; Gilley et al., 2009). If we examine the specific change process of digital transformation, a survey from 2015 illustrates that 90% of CEOs consider digitalization have a significant impact on their industry, although only 25% surveyed are prepared for the changes as part of an implementation concept (Taylor, 2015). This is also reflected in the academic community, which reached a consensus on the coherence between the effectiveness of digital transformation and the influence of leaders. However, few academically based analyses on the influences of specific characteristics exist, such as leadership behavior or leadership style, and their practical implications (Porfirio et al., 2021). Given this background, it is of entrepreneurial relevance to resolve the uncertainties and identify the potentials of successful leadership in the digital age, which may stand for the continued existence of companies, especially traditional companies in German industry. The dissertation is dedicated to this highly relevant set of topics, and it examines the mechanisms of leadership in the digital age from different research perspectives with the aim of creating a profound theoretical basis and thus contributing to the further development of theoretical and entrepreneurial understanding. To achieve this goal, this thesis presents three articles that examine empirical data obtained either by the author or through published scholarly articles. The first article reviews the state of research in the topic area through a systematic literature review and identifies the characteristics of effective leadership behavior in the digital age based on theoretical findings. Papers two and three provide a scientific evaluation of empirical data collected by the author herself. Paper two addresses the identification of leadership trends in the digital age. Since paper one and two conclude that “digital collaboration” in the leadership context is highly relevant from the perspectives of theory and practice, the third paper is devoted to this topic exclusively within the framework of a qualitative survey of leaders and experts. In addition, it is combined with an analysis of the effects of the COVID-19 pandemic on this regard. A brief overview of these essays is provided as follows. Article 1: Effective Leadership Behavior in the Digital Age: A Review and Research Agenda The first article presents the current state of the discussion and research on the emerging topic of leadership behavior in the digital age. In recent years, the number of publications on this topic has increased, but a systematic review of the literature is still lacking. The article addresses this circumstance, and it aims to identify the manifold theoretical contributions, to summarize the results in a structured way, and to derive implications for business and future research proposals. The results of the articles are based on 49 selected scientific articles which present eight leadership behaviors that are rated as conducive to dealing with digital transformation. These are categorized according to Fiedler’s (1966) effectiveness model into task- and relationship-related criteria. To employ the identified behaviors, it is additionally deduced that leaders require awareness, willingness and readiness concerning the opportunities and risks of digitalization. Article 2: New Ways of Leadership in the Digital Age: These Trends are Forcing Leaders to Rethink their Existing Leadership Styles To achieve a holistic and generic understanding of future leadership challenges in the context of digitalization, the next article focuses on examining leadership trends. To identify these seminal implications, the methodology used is a combination of an in-depth expert workshop and a systematic literature review. By selecting the chosen exploratory research design, it is possible to compare leadership trends from theory and practice and identify 21 trends. These are assigned to the following derived, superordinate trends: change of leadership role (individual level), change of collaboration (team level), and change of organizational environment (organizational level). The article thus answers the research question of identifying and characterizing current leadership trends and contributes to the decuviation of common focal areas, as well as differences in leadership trends according to the current state of science and practice. Article 3: Successful Collaboration in the Digital Age and the Potential Effects Caused by COVID- 19 in this Regard Building on the findings of the first and second articles, the leadership topic of “digital collaboration” is addressed separately due to its identified relevance to both economics and science. The author applies a qualitative–explorative research design to obtain a detailed picture of the aspects of digital collaboration. For this purpose, after a systematic literature review, experts and leaders in German industry are interviewed about the success factors and challenges of digital collaboration. Because the survey period took place after the third wave of the COVID-19 pandemic, the resulting effects for digital collaboration had to be considered. After analyzing the qualitative interviews and processing the obtained data, seven key factors for digital collaboration were identified, which are divided among the individual, team, and organizational levels. From a practical perspective, the study shows the need for HR support to professionalize systematically this leadership tool and hence empower leaders. The theoretical contribution consists of the analysis and description of the fundamental factors of collaboration in the digital age.