Implementation strategies are key to enhancing thetranslation of new innovations but there is a need to systematically design and tailor strategies to match the targeted implementation context and address determinants. There are increasing methods to inform the development and tailoring of implementation strategies to maximize their usability, feasibility, and appropriateness in new settings such as the Cognitive Walkthrough for Implementation Strategies (CWIS) approach. The aim of the current project is to apply the CWIS approach to inform the redesign of a multifaceted selection-quality implementation toolkit entitled Adoption of Curricular supports Toolkit: Systematic Measurement of Appropriateness and Readiness for Translation in Schools (ACT SMARTS) for use in middle and high schools. We systematically applied CWIS as the second part of a community-partnered iterative redesign of ACT SMARTS for schools to evaluate the usability and inform further toolkit redesign areas. We conducted three CWIS user testing sessions with key end users of school district administrators (n = 3), school principals (n = 6), and educators (n = 6). Our CWIS application revealed that end users found ACT SMARTS acceptable and relevant but anticipate usability issues engaging in the ACT SMARTS process. Results informed the identification of eleven usability issues and corresponding redesign solutions to enhance the usability of ACT SMARTS for use in middle and high schools. Results indicated the utility of CWIS in assessing implementation strategy usability in service of informing strategy modification as part of our broader redesign to improve alignment with end user, end recipient, and setting needs. Recommendations regarding the use of this participatory approach are discussed.