Despite the vast amount of research that has been conducted on leadership and leadership development, there has been a lack of investigation of first-time leadership. The first career transformation can be viewed as the most challenging one, because, besides learning through experience, it involves a psychological adjustment. Since this is the starting point of all leadership and leadership development, it needs to be understood better in order to be managed properly. The purpose of the current study is to gain insight into how Oslo Municipality’s first-time managers experience their first managerial role. Through semi-structured qualitative interviews, three first-time managers’ perspectives regarding of their first leadership role were elicited, as well as their feedback about the types of challenges and struggles they encountered in this transition. The interviews were analyzed by means of template analysis, which indicated an interpretation of the first-time managers’ challenges and struggles in four primary areas: 1) The transition from individual contributor to manager and self-view as a leader; 2) Learning to cope with stress, loneliness, and redistribution of time and delegation of tasks; 3) Becoming familiar with Oslo Municipality as employers; and 4) The role of support, follow-up and feedback. Their experiences add nuances to our understanding of new managers’ perspectives on becoming leaders for the first time. Based on the analysis of the empirical data, as well as evidence-based support from previous research and literature, the current paper may further contribute to designing appropriate leadership developmental initiatives that take into account the first-time managers’ standpoint in Oslo Municipality.