Purpose: Adolescent students face increased expectations to successfully navigate academic, social, and vocational transitions. As demands increase and support systems fade, adolescents with developmental language disorder and concomitant deficits in executive functions are particularly vulnerable to these high-stakes transitional moments. Limited language systems are not well suited for navigating the subtleties of social nuance, the abstraction of academic and vocational language, and the unfamiliarity of complex planning necessary for self-regulation. Conclusions: This clinical focus article proposes a clinical model of language therapy for adolescents with developmental language disorder and concomitant deficits in executive functions. Therapy emphasizes eliciting the most complex syntactic and semantic skills available to the student as they work to formulate specific, reasoned, predictive, strategic plans. Therapy takes place in small group contexts where pairs of students collaborate to use their language and reasoning to solve unfamiliar, challenging, scientific-like problems.