This article addresses the question, "What organizational conditions foster successful classroom promotion of Learning How to Learn?". Data are reported from the ESRC Learning How to Learn Project's Staff Questionnaire administered in 2002 and 2004. In 2002, 1212 Questionnaire returns were obtained from primary and secondary support staff, teachers and managers at 32 schools. In 2004, 698 returns were obtained from 23 schools. Thirty items in Section A are about classroom assessment, 28 items in Section B are about teachers' learning, and 26 items in Section C are about school management practices and systems. Factor analysis generated sets of factors from items in each of the three sections of the Questionnaire. Levels of teachers' values and practices are reported and compared for each factor. These factors were then used in multiple regression analyses of baseline responses to the Questionnaire in order to explore relationships between classroom assessment, teachers' learning and school management practices. Patterns of change for each dimension of practice are explored by analysing the difference between 2002 and 2004 mean practice and values factor scores. Main findings are: (1) in-class teacher learning practices appear to be a key precondition for the classroom promotion of Learning How to Learn; (2) organizational conditions, understood in terms of school management practices and systems, appear to influence what happens in classrooms through the mediation of teachers' learning, particularly learning that has a clear basis in classroom activity; (3) values remained ahead of practice in 2004 for the four dimensions of school management practices identified in this study. This indicates considerable challenges for schools that decide to develop organizational strategies for sustaining change in the classroom through promoting Learning How to Learn.