The pace of commercial graphic design practice presents very few opportunities to conduct user research after a project's launch. This makes the design team's ability to anticipate and address risks during the design development phase even more important, recognized in the astute observation from Tim Brown, CEO of leading international design group IDEO, that sometimes you must "fail early to succeed early." This paper presents the methods and strategies used by the Centre for Design Research's (CfDR) creative team to mitigate risk during three communication design case-study projects. Elements of failure are identified in each of the three cases and presented, with discussion of where and why they occurred, and the possible approaches for reducing the risk of such problems re-occurring. To provide structure to the discussion, the paper frames each contributory issue as either a usability, communication or technical failing. The analysis demonstrates that the factors contributing to design process failures are often complex and multi-layered. To avoid a poor design project outcome, it is evident that consistent risk monitoring is present in all stages of a design project, but might be improved by better understanding how issues change their degree of importance and potential negative impact during the course of the project. Developing a mechanism to enable teams to objectively identify and manage these fluctuating project risks, will contribute to a more coherent and effective strategy for recognizing and managing future design projects. (Contains 3 tables.)