The current focus of education is on preparing diverse student populations for college and career readiness. One critical aspect of this preparation is the development of 21st century learning skills that integrate technology to support students in becoming active members of a globalized society. According to the National Assessment of Educational Progress, however, English learners (ELs) and students with disabilities (SWDs) are underprepared to use technology to enhance their learning. Therefore, it is important for schools to find ways to integrate critical technology skills with academic instruction in the education of cognitively and linguistically diverse learners. School leaders are essential to the establishment of this instruction. This paper provides lessons learned from a professional development project focused on training middle school English language arts teachers in the integration of blended learning activities to support these diverse learners. These lessons, with supporting data, are discussed along with implications and recommendations for school leaders focused on providing access to critical 21st-century learning skills. [Note: The page range (35-38) shown on the PDF is incorrect. The correct page range for this article is p44-51.]