This project contributes to the understanding of dialectical coaching by critically examining how it differs from the current understanding of the systems of effective coaching, which are good yet still limited in consequentialist mindset. By posing this conceptual question and developing a prototype, we aim to open up theoretical exploration for coaching that centers dialectical exploration of values and growth. Ultimately, we envision a new HCI paradigm in which human interaction with technology centers on encouraging our dialectical engagement with our life.