The aim of this study was to qualitatively explore the barriers and enablers to implementing healthy workplace initiatives in a sample of workplaces based in Perth, Western Australia. In-depth interviews were conducted with representatives from 31 organizations representing small, medium and large businesses in the Perth metropolitan area which reported having healthy workplace initiatives. In total, 43 factors were mentioned as influencing the implementation of healthy workplace initiatives. Factors appearing to exert the most influence on the implementation of health promoting initiatives in this sample were culture; support from managers and staff; collaboration with industry providers; financial resources circumstances and the physical environment. These factors appeared to be mutually reinforcing and interconnected. Findings suggest there may be merit in applying an organizational development lens to the implementation of workplace health promotion initiatives as this could assist in leveraging enablers and minimizing barriers.