School settings are increasingly being targeted as ideal entry points for youth mental health initiatives and naturally, educators have been identified as playing a critical role in supporting youth in distress. The current study set out to investigate how to strengthen the ability of educators to support youth experiencing bullying and mental health difficulties. The study was conducted in two phases: an initial phase in which a mental health literacy and communication skills workshop for educators was developed and refined, and a second phase in which the workshop was pilot-tested. The 2-hour workshop was delivered to two groups of students (N = 35) in a Teacher’s Education (B.Ed.) program at a Canadian university. Participants completed a questionnaire following the workshop to assess their satisfaction with the workshop experience and their degree of change in knowledge and awareness of bullying and mental health difficulties, as well as self-efficacy and perceived confidence in communicating with young people in distress. Results showed that participant satisfaction with the workshop was high and that most participants would recommend the workshop for pre-service and in-service teachers. In addition, participant knowledge, awareness, self-efficacy, and self-confidence in communicating with youth in distress increased from pre- to post-workshop. Taken together, the results of the pilot study provide support for further development and delivery of this workshop to pre-service and in-service teachers to help prepare educators for the complex, demanding, and vital role of supporting young people in distress due to bullying and mental health difficulties.