Employment can provide numerous benefits to quality of life, mental health, and social inclusion, which can be particularly important for people with disabilities. In a pilot study, the feasibility of Conversing with Others, a direct skills teaching (DST) group intervention to teach individuals with disabilities a work‐related soft skill focused on conversational skills, was assessed. This mixed methods study delivered the Conversing with Others curriculum in‐person or via telehealth to 119 participants. The intervention was based on the DST method of teaching skills through smaller, digestible, structured lessons. Both modalities showed improvement in participants’ perceptions of their conversational skills. A non‐inferiority test indicated that the telehealth and in‐person group interventions were comparable. Overall, the study supported the feasibility of in‐person and telehealth interventions for teaching workplace conversational skills.