This article explores the emerging concept of contrast leadership and the role of the strategic sparring partner as a mechanism to mitigate the risks associated with decision-making in the C-suite. It argues that the loneliness at the top and the cognitive biases inherent in power can erode the quality of strategic decisions. Drawing on the academic and management literature, it proposes a conceptual framework for contrast leadership and distinguishes it from other approaches such as executive coaching and traditional consulting. The article analyzes the role of the strategic sparring partner as a core component of this leadership style and examines relevant case examples, including Bridgewater Associates’ culture of “radical truth” and Bill Campbell’s role as Silicon Valley’s “trillion-dollar coach.” It concludes that, although the term contrast leadership is relatively new, it rests on solid principles from organizational psychology and leadership theory and offers a practical, effective way to improve the quality of decision-making processes in complex, high-uncertainty environments.