While addressing social problems, and planning in general, the notion of “wicked problems” (coined by Rittel and Webber, 1973) is also applicable to complex organisational and social change issues that are currently challenging business and community leaders. The relentless drive for solutions, coupled with the desire to `get it right` the first time, is straining the traditional or rational approaches to problem solving and leadership. In an effort to address the above, concepts such as cross-disciplinary, inter-disciplinary, and multi-disciplinary teams or thinking have been developed and deployed. However, these have fallen short of expectations. The concept of transdisciplinary leadership is drawn from systems thinking transdisciplinarity. Using action research and case study methodology, transdisciplinary leadership has evolved through a range of “complex wicked problems”. It also draws from in-depth interviews with a number of business and community leaders in Australia and USA who have successfully addressed “wicked problems”. This paper suggests that developing leadership strategies based on transdisciplinary thinking can benefit leaders tasked with dealing with wicked problems. A transdisciplinary approach offers a more effective approach to building knowledge, consensus, making sense of the complexity of issues at stake and ultimately delivering results with wider support and agreement.