This study examined the feasibility of group interventions using the Direct Skills Teaching (DST) approach to teach interview preparedness skills (“Presenting Qualifications”) and basic work-related conversational skills (“Conversing with Others”) to individuals with psychiatric disabilities. This quasi-experimental pilot study included 87 participants in Study 1 and 55 participants in Study 2, all with various psychiatric diagnoses. Each group intervention consisted of four sessions delivered by graduate counseling students. Participants reported increased confidence in presenting qualifications at interviews in Study 1, and in conversational skills at work in Study 2. Participants in both studies reported high levels of satisfaction with the respective group intervention. The results of the study supported the feasibility of DST group interventions designed to teach work-related skills to individuals with psychiatric disabilities.