Australia’s largest employing industry is the health and social care sector. There is currently considerable demand and competition for workers in the nonprofit sector, with disability and mental health services both reporting difficulties in simply filling core vacancies. This chapter explores the challenges facing leaders within the nonprofit disability and mental health service sectors with respect to attracting, developing and maintaining an appropriately skilled workforce. Nonprofit leaders face several staffing challenges. Initially, finding individuals with the right personal attributes to work in the specialised environment of disability or mental health support is difficult. However, this problem is then exacerbated by a potential lack of appropriate supervision, mentoring and access to basic training. It is acknowledged that recruitment and retention of workers is problematic across all locations, but it is particularly difficult in regional and remote areas. This chapter will discuss each of these various issues and highlight possible practical solutions to the above described problems. Specifically, options for innovative and collaborative leadership approaches to nonprofit service provision will be proposed. The specific focus on rural workforce issues in Australia is due to the recognition of the unique issues facing its geographically isolated and sparsely populated locations.