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Behiavioral competencies are key determinants of individual performance and literature has recently started to devote attention on those methodological approaches that can effectively promote their development. According to Dewey, individuals do not learn from experience, but they learn from reflecting on experience. In this paper, we draw on the Dewey’s idea and we investigate if reflective practices through journaling and peer coaching can improve the learning experience of individuals engaged in a competency development program. After introducing the prior research that emphasized the positive impact of these two reflective techniques, the paper illustrates how journaling and peer coaching has been introduced as a part of a competency development program. Preliminary insights from the empirical case show that self-directed learning requires a reflection process that helps individuals to better understand their current behavior, their progresses, and opportunities for change. Journaling was found especially useful to increase one’s self-awareness and self-confidence, whereas peer coaching allowed students create a social bond, share their experiences and receive a direct feedback from a peer. The paper also illustrates the limits of these reflective practices, discussing the interventions that can be implemented to maximize their learning benefits.