Purpose: School improvement planning has been a central part of school improvement initiatives for decades. Evidence suggests, however, that traditional planning processes are regularly superficial. In the USA, some principals have begun developing short-cycle planning designed to encourage school leadership teams and staff to develop, monitor and adjust plans throughout the academic year. Design/methodology/approach: In this study of eight schools in one urban district, the authors analyzed multiple rounds of short-cycle improvement plans and principal interview data to assess the progress schools made implementing plans over the course of a semester, the ways in which plans were monitored and adjusted and the extent to which principals embraced short-cycle planning. Findings: The authors found that many tasks from first semester plans were completed, which informed the development of plans for the second semester. Observational data were primarily used to monitor plan completion, although principals engaged in monitoring but relied on their leadership team to do so. Principals reported regular engagement with plans throughout semester, but plans were seldom adjusted within a semester. Originality/value: The findings suggest that short-cycle planning is potentially a viable alternative to traditional annual planning as principals communicated being more engaged and adaptive. Still, the evidence also indicated that old habits might be hard to break as school leaders did not monitor and adjust plans frequently enough to guide improvement efforts in relative "real time."