Legal risks are a significant part of a firm’s overall risk profile, and is typically guided by calculating the probability of risk and its potential magnitude. Yet this calcuation does not fully capture how risks manifest for organizations. This chapter presents a novel way of evaluating legal risk termed transformative legal risk management. Transformative legal risk management is different from traditional approaches because it incorporates a new layer of understanding legal risk. Using a four-pronged approach to risk management known as VUCA (volatility, uncertainty, complexity, and ambiguity). This chapter introduces two of the four VUCA risks: volatility and uncertainty. The chapter defines volatility, identifies sources of legal volatility, and presents responses that legal experts can use in response to volatility risk. The chapter then defines uncertainty, identifies sources of legal uncertainty, and presents responses firms can use to reduce uncertainty risk. The chapter shows how firms applying VUCA can not only minimize harm from legal risks but also elevate legal risk management into a practice that generates a competitive advantage over rivals.