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In Chile, school improvement is a centrally guided process, wherein the central government provides guidance through standards of quality, evaluation tools, data, and management tools. Government external support agents play a crucial role in supporting the implementation of these components, fostering an externally conditioned learning model among schools. Under this model, schools perceive their problems through the lens of government tools, learn to improve by following established standards of quality, and enact external improvement suggestions to align with those standards. This learning model would be effective if the external components were aligned with the practical problems that schools experience. However, literature has shown that the connection between external policy components and local needs is often weak, leading to ineffective improvement processes (Bryk et al., 2015; Coburn & Stein, 2010; Mintrop et al., 2018; Penuel & Spillane, 2016). In Chile, the Unit of Supervision of the Ministry of Education in the Metropolitan Region has observed this prevailing learning model in the work of Technical Supervisors (TS) – government agents who assist schools in organizing their improvement processes. Aware of this pattern, the Unit partnered with a team of university researchers to revise their approach to supporting schools. This partnership emerged as a professional development (PD) project aimed at understanding the needs and practices that TS should develop to mitigate the externally induced learning model. The partnership took the form of a six-month ongoing PD sequence co-designed with the Unit of Supervision, which included shadowing, coaching, and training sessions based on design-based school improvement ideas (Mintrop, 2016). The PD aims to help TS develop dispositions and skills to foster inside-out improvement processes that focus on schools’ practical problems and needs. This work reports data collected during the need assessment stage and the initial steps of the PD sequence. To define the next level of work (City et al., 2009), we ask: What are the current dispositions and practices that supervisors express in their work with schools in need of improvement? The research methodology is action research (Coghlan & Brannick, 2007), wherein researchers collect data on change processes in which they themselves are involved. We report data collected from four need assessment sessions with the team of technical chiefs (7 people) who guide the work of TS, along with 20 hours of shadowing sessions during school visits conducted by three TS. Findings show that technical chiefs provide broad guidance to support TS work without setting neither clear goals nor specific practices, leaving an ample space of discretion to them. TS show dispositions and practices to open developmental conversations at the practical level, but they struggle to facilitate open-ended interactions around school emergent problems and needs. School leaders disclose scarce evidence of problems or needs at a practical level. As a result, practical conversations fade out and external artifacts and requirements structure the conversation fostering an implementation mindset (Spillane, 2009). Implications for competencies development and job design adjustment are discussed.