In a previous paper, the author identified and recommended solutions to specific hindrances in the development of reliable cost estimates including estimator competency, effective estimating tools, and a lack of reliable historical data. However, the execution of a plan to attain the desired solutions in the corporate world is fraught with obstacles. Experience by the author with owner and engineering contractor firms has identified common roadblocks and mitigation strategies to support the attainment of the solutions. This paper will discuss these mitigation strategies including: developing an identified vision and objectives based on the Total Cost Management Framework, presenting and winning management approval, development of a detailed plan, presentation to and obtaining support of middle and senior management, and implementation. Topics will include understanding senior management’s perspective, communicating the correct information at the appropriate level of detail, setting realistic goals based on business objectives, establishing a sense of urgency, short term wins, and overcoming the challenges of implementation. These principles can be applied in any development scenario.