Chairwork is a psychotherapeutic method that frequently focuses on self-multiplicity and internal relationships. Compassion focused therapy (CFT) uses chairwork to generate and apply compassion toward threat-based aspects of the self. This study explores self-multiplicity in a CFT chairwork intervention for self-criticism. Twelve participants with depression were interviewed following the intervention and the resultant data were analyzed using interpretative phenomenological analysis. Three superordinate themes were identified: differentiating selves; mental imagery of selves; and integrating and transforming selves with compassion. The results highlight how the intervention enabled clients to differentiate internal aspects of themselves in a way that was accessible and helpful, increasing self-complexity and introducing the potential to observe and change patterns of self-to-self relating. The process of bringing compassion to self-criticism was found to integrate both aspects of the critical dialogue, transforming the “critic” by understanding its fears and function. The use of mental imagery facilitated clients’ experience of self-multiplicity and symbolized the kind of changes generated by the exercise. Implications for clinical practice are discussed. (PsycInfo Database Record (c) 2021 APA, all rights reserved)