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The aim with this study was to examine how middle managers in their position in the middle of an organization perceive their occupational role and its possibilities and limitations in the light of leadership in social work. Our study was conducted by qualitative research through semi-structured interviews in a middle-sized municipality in the southern part of Sweden. A total of eight middle managers were interviewed, four operating within the care of older persons and four operating within the care of persons with disabilities. The results showed that the middle managers felt like several groups had different expectations of their occupational role and most of them found that the solution was to prioritize and to be able to decide themselves how their work should be executed. Role conflicts could arise when the expectations between different groups or between other expectations and the middle managers’ expectations of themselves collided. These role conflicts became especially clear when the middle manager did not agree with what the political administration demanded. Conversely, the middle managers also mentioned advantages with operating in a political organization. Generally, the middle managers expressed adequate opportunities to influence their organization and occupational role, despite having several rules and guidelines to follow. Furthermore, the middle managers operating within the care of older persons had their offices together with the staff, whereas the middle managers operating within the care of persons with disabilities had their offices together with other middle managers. While their geographical positions were this different, both sides were generally content with their current position and expressed that it was positive for their leadership and role. Steadily having to balance different tasks and live up to different expectations was expressed as both a difficulty and as the aspect that made the profession enjoyable.