We examine how the combined effect of leader’s personal need for structure and digital self-efficacy influence employees’ autonomy experiences during digital workplace changes. In addition, we test the impact of employee work tenure as a second-stage moderator in this relationship. In this chapter, we aim to explain how the cognitive framework of the leader in terms of digital self-efficacy and need for structure can influence his or her reaction to dynamic and uncertain situations at work (i.e., digital work changes). We argue and empirically establish that leaders’ low adaptive capacity (i.e., low digital self-efficacy and high need for structure) can negatively affect the autonomy perceptions of employees. In addition, employee’s work tenure co-shapes the relationship between leaders’ cognitive framework and employee’s autonomy. Our findings emphasize the need to differentiate between these leaders who have the capacity to deal well with digital changes from those who struggle; they also point to the importance of the leader’s high digital self-efficacy, especially for employees with high work tenure, for nurturing employees’ autonomy. Given that the need for autonomy is central to employees’ happiness and well-being, understanding how leaders’ cognitive framework affects autonomy is an invaluable contribution to our knowledge of leaders’ well-being supportive behaviors at large.