The broad range of skills associated with practicing therapies of depth, insight, and relationship (DIR) can be applied to many settings outside the traditional private consulting room. In this article, we will focus on an important patient subgroup – organizational leaders. The leadership role is often the locus of intense emotions, setting the individual’s needs, conflicts, and defenses in relief. We outline a hybrid approach to working with this population that blends elements of DIR therapy with leadership coaching. Describing our experience with cases, we argue that this dual set of skills (DIR therapy and leadership coaching) enables the practitioner to stay closer to the leader’s emotional experience and to more effectively facilitate his or her growth. While we note the potential pitfalls of this hybrid approach, we suggest that interested DIR therapists would do well to acquire knowledge and experience related to organizational role functioning.