Through assigning one-on-one instructional coaches, the Teaching Skills That Matter (TSTM) initiative successfully supported teachers in 33 states to integrate the skills that matter into instruction using effective approaches in five topical areas: health literacy, civics education, digital literacy, financial literacy, and workforce preparation. Instructional coaches, who also served as adult education teachers themselves, and teachers engaged in regular dialogues while teachers planned their TSTM implementations as well as after observing the lessons being taught. Rather than being evaluative, coaching conversations created space for in-depth reflection and critical thinking about the complex work of teaching. [Contributing authors include: Susan Finn Miller, Adria Katka, Cherise Moore, Katie Callahan Neginskiy, Lisa Soricone, Kristy Stoesz, and Geoff Woodland.]