DevOps transformational efforts are challenged. In a survey of over 3000 corporate executives, two-thirds reported that their organizations failed to achieve intended performance improvements following organizational change initiatives (Meany & Pung, 2008). In addition, another study (Grady & Grady 2013) concluded that 68% of organizational change efforts fail or experience serious challenges. Adopting DevOps practices goes beyond process and technology usage requiring a transformational change to address cultural issues that create barriers to DevOps adoption. The shift to DevOps expands the scope of transformational change from the software development department in the IT organization to not only the entire IT organization but also to an enterprise-wide fashion. Transformational change initiatives addressing culture have the highest failure rates compared to other types of change efforts. This talk showcases results of recent studies conducted by Microsoft and Henley Business School, Reading, UK on a set of identified traits of DevOps transformational leadership providing both insights to how to learn to lead effectively transformational initiatives at an organizational level and recognize the cultural barriers and process & technology pitfalls that need to be addressed to achieve expected outcomes.