Guided by Self-Determination Theory, we offer an integrative and fine-grained analysis of teachers' classroom motivating style (i.e., autonomy support, structure, control, and chaos) to resolve existing controversies in the literature, such as how these dimensions relate to each other and to educationally important student and teacher outcomes. Six independent samples of secondary school teachers (N = 1332; Mage = 40.9 years) and their students (N = 1735, Mage = 14.6 years) read 12 ecologically valid vignettes to rate four dimensions of teachers' motivating styles, using the Situations-in-School (SIS) questionnaire. Multidimensional scaling analyses of both the teacher and the student data indicated that motivating and demotivating teaching could best be graphically represented by a two-dimensional configuration that differed in terms of need support and directiveness. In addition, eight subareas (two subareas per motivating style) were identified along a circumplex model: participative and attuning, guiding and clarifying, demanding and domineering, and abandoning and awaiting. Correlations between these eight subareas and a variety of construct validation and outcome variables (e.g., student motivation, teacher burnout) followed an ordered sinusoid pattern. The discussion focuses on the conceptual implications and practical advantages of adopting a circumplex approach and sketches a number of important future research directions. Educational Impact and Implications Statement The present study suggests that rather than categorizing secondary school teachers as either motivating or demotivating, this approach reveals that an attuning and guiding approach relate to the most adaptive pattern of teacher and student outcomes, whereas an opposite pattern is found for a domineering and abandoning approach. This greater clarity allows teachers to gain a more precise insight into their own teaching style so that they adopt a more need-supportive style that benefits their students and themselves.