The results are in: observations are not improving teaching and learning. Pertinently, the Gates Foundation’s recently completed effort to improve student outcomes through enhancing the teacher evaluation process failed to achieve substantive improvement. The way observations are currently designed serve as an obstacle to teacher risk-taking. Teachers fear negative evaluations when their pedagogy is rated, and they lack faith in being supported by supervisors because a trusting relationship between them and their observer has not been built. Trust-Based Observations: Maximizing Teaching and Learning Growth is a schema changing evaluation model that understands people perform at their best when they feel safe and supported. It begins with twelve, 20 minute observations per week followed by collegial conversations driven by reflective questions, sharing observed teaching strengths, and the building of safe and trusting relationships with teachers. Add the elimination of rating pedagogical skills and replace it with rating mindset, and teachers trust. When teachers fully embrace risk-taking and innovation, it leads to remarkable teaching transformations and improved student learning.