This article provides a conceptual framework for asymmetrical relationships between family therapy educators and trainees. Our framework is based on contextual family therapy, and we apply the concepts of trust, entitlement, self‐validation, and loyalty to training relationships. We highlight the value of educators modeling responsible uses of power in addition to teaching trainees clinical concepts and skills. We propose that training can be a process where trainers earn constructive entitlement through their interactions with trainees, who then give to future clients, supervisees, and trainees to continue the cycle of intergenerational trustworthiness. We also provide examples that illustrate the application of contextual therapy skills such as multidirected partiality, I‐Thou relating, acknowledgment, validation, and accountability to family therapy training.