The integration of artificial intelligence (AI) into a human-to-human coaching relationship presents both fascinating opportunities and significant challenges. This chapter explores AI’s evolving role within the coaching relationship, balancing its potential to support both coach and client in their self-development with concerns related to trust, ethics, and process integrity. Much like involving a human third party, AI raises issues of confidentiality, data ownership, informed consent, and potential conflicts of interest. Additionally, a third party such as AI can influence the process—intentionally or unintentionally—by imposing goals, expectations, or assessments that may not align with the client’s self-valued goals and needs. Furthermore, AI could shift the dynamic from a 1:1 to a 2:1 setting, out-balancing the relationship and creating pressure on the client’s, affecting their openness and engagement. Its involvement further risks introducing bias from training data or becoming overly mechanical, diminishing the human connection central to coaching. The chapter critically examines how AI can be responsibly integrated to complement rather than disrupt the coaching dynamic, ensuring that technological innovation aligns with the core values of coaching.