Objective: The coach-coachee relationship is the essential factor for change and development in coaching. However, in times of hypercomplexity, the relational issue gets a new twist. As a coach, it is no longer enough to facilitate through questions; coaching requires becoming involved in a dialogue, where both sides are willing to develop and change. In the presentation, the concrete ingredients necessary to establish a trustful and collaborative relationship will be explored. Design/Method: The study is based on empirical investigations (Stelter, 2014; Stelter et al., 2011) and on an analysis of different theories including experiential, existential, relational, and narrative approaches. Results: The following six factors will be presented and further analysed: 1. The dialogical perspective (Shotter, 2006; Kirkegaard, 2010) 2. Narrative perspective: Outsider witness procedures (White, 2007; Stelter, 2014) 3. The protreptic turn of coaching (Kirkeby, 2009) 4. Mentalization (Asen & Fonagy, 2011). 5. The collaborative dimension of the coach-coachee relationship (Anderson, 2007; Stelter, 2014) 6. Feedback as a collaborative activity (Miller & Bargmann, 2011) Conclusion: The presentation will deepen the understanding of the key factors that strengthen and intensify the coach-coachee relationship: a relationship that from time to time will have a symmetrical character. The symmetrical dimension of in the coach-coachee relationship is worth highlighting as a new and promising perspective for coaching dialogues in late-modern times.