The present study investigates how fathers realized their parental leave plans with particular consideration of fathers’ leadership responsibility as a potential hindrance. Applying the social cognitive model of career self-management, we expected that fathers with leadership responsibility and those who perceive that they could lose qualifications resulting from a career break would plan shorter leaves before childbirth. Furthermore, self-efficacy beliefs were assumed to be supportive and leadership responsibility to be hindering factors in the final realization of leave plans (after childbirth). A sample of 147 men from Germany, Austria and Switzerland (33% with leadership responsibility) participated in a longitudinal questionnaire study (first measurement before childbirth). Results confirmed that men who expected a loss of qualifications planned shorter leaves. Planned leave length was positively correlated with the actual leave taken. Although leadership responsibility did not predict leave plans in the first place, it had an impact on the realization of leave plans: Fathers without leadership responsibility were more likely to realize their leaves than were fathers with leadership responsibility. Remarkably, men with leadership responsibility shortened their leaves as often as extended it. Self-efficacy beliefs were neither predictive of leave plans nor of realizing them. Our research highlights the importance of organizational support for men in their parental leave planning and realization.