This book discusses the impact of advanced information technologies, such as data processing, machine learning, and artificial intelligence, on organizational decision-making processes and practices. One of the book’s central themes is the interplay between human reasoning and machine logic in the context of organizational functioning, specifically, the fairly common situations in which subjective beliefs are pitted against objective evidence giving rise to conflict rather than enhancing the quality of organizational sensemaking. Aiming to not only raise the awareness of the potential challenges but also to offer solutions, the book delineates and discusses the core impediments to effective human-information technology interactions, and outlines strategies for overcoming those obstacles on the way to enhancing the efficacy of organizational decision-making.