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The out-of-school time (OST) field often champions new initiatives, given the flexibility, autonomy, and creativity that is inherent in OST programming. An OST program may dedicate many resources – time, funding, training – to new efforts, yet implementation challenges can still impede their efforts. Were they ready? Were there aspects of their program operations or staffing, for example, that needed more support? In this paper, we discuss a two-year project to explore and apply the implementation science concept of readiness to OST programs. We discuss our research-based, field-driven approach to conceptualizing a readiness model, developing a rigorous readiness assessment, and creating an actionable online toolkit that enables OST program staff to measure, understand, and build their readiness to implement new initiatives.