Coaches are practicing within an increasingly complex context: a globalized world, a hyper-complex society, and diversification of knowledge sources (Stelter, 2012), requiring the situationally appropriate exercise of judgment (Murphy, 2006). Graduate professional education programs transmit the necessary technical knowledge (the “how” of coaching) and cultivate proficiency in reflective evaluation of context in order to apply that technical knowledge (the principles and decision protocols of coaching). This article explores the impact of one graduate coach education program, the Evidence-Based Coaching Certificate (EBC) program at Fielding Graduate University, on the professional judgments of program graduates. Results indicate three different catalysts for coach judgments: client characteristics, coaching tasks, and elements of the coaching engagement (including time frames, expected outcomes, organizational or other situational contexts). Through reflective learning, coaches gained insights into four aspects of their coaching: managing boundaries and ethical challenges, self-awareness and self-management, understanding responsive processes, and situational application of theory.