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Executive and organizational development is among the most fertile areas for applied psychoanalysis. This has led many mental health providers to consider transition to business consultation, including executive coaching, as way of diversifying their practices and extending their clinical work. To illustrate the theoretical and technical underpinnings of a psychoanalytic approach to executive role consultation, a case from the author's specialized practice is presented in detail. The case focuses on transference–countertransference; defenses and compromise; unconscious motivation; and the coconstruction of a reflective, analytic process between client and consultant. The theoretical and technical features that influence the course and progress of consultative work are highlighted. The need to attend simultaneously to psychoanalytic principles and practical concerns of the executive and his or her corporate work environment, and the challenges this task presents, is emphasized. The consultative approach exemplified here that draws on the strengths and utility from all facets of psychoanalytic thinking can demonstrate clear-cut benefits for workplace performance.