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This study explores a complementary approach; short-cycle improvement planning, implemented by 20 schools participating in a two-year, improvement-oriented program (2023–2024). Through a qualitative analysis, we examine how school and district leaders compare traditional yearlong SIPs with short-cycle planning, and how their improvement mindsets evolve in the process. The findings suggest that short-cycle planning fosters greater agility, collaboration, and more authentic engagement with improvement goals. The study highlights five key elements: (1) alignment of short- and long-term goals enhances planning effectiveness; (2) compliance-driven planning undermines authentic change; (3) collaborative, improvement-focused planning yields better results than sanction-driven approaches; (4) joint work across school and district improves plan quality and use; and (5) support structures enable more meaningful planning processes.