The results are in, observations are not improving teaching and learning. Pertinently, the Gates Foundation's recently completed, seven year, $200 million effort to improve student outcomes through enhancing the teacher evaluation process failed to achieve substantive improvement. The reason is, observations as currently designed, serve as an obstacle to teacher risk-taking. Teachers play it safe because: 1) they fear negative evaluations when their pedagogy is rated, and 2) they lack faith in being supported by supervisors because a trusting relationship between them and their observer has not been sufficiently built. There is a path though to using observations to dramatically improve teaching and learning, Trust Based Observations, 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, trusting relationships with teachers. Add the elimination of rating pedagogical skills, replace it with rating mindset, and teachers trust. Finally, have empowered teachers lead small professional development communities connected to good practice and teachers fully embrace risk-taking and innovation, leading to remarkable teaching transformations and improved student learning.