Tammy is a smart enthusiastic 28-year-old union electrical apprentice and single mother. Despite an undergraduate degree, she could not find a career that allowed her to challenge herself, support her small family and provide time and attention to her child. Her father, a longtime union journeyworker suggested that she join the IBEW (Construction Electrical Apprenticeship) union apprenticeship program at Gateway Technical College. Unfortunately, her father and chief cheerleader died suddenly, just as she was getting started in her electrical career. Tammy’s instructor said that she was excelling in the program. During coaching sessions with the National Board of Certified Counselors certified coach Liz, Tammy began by describing her enthusiasm but confided two things: (1) She had been harassed and discriminated against for being a woman, (2) She lacked confidence and didn’t know if she could ever be as good of an electrician as her father was. We find that these are common reasons why apprentices prefer the confidentiality afforded in the coaching relationship. During coaching, Tammy described a situation in which a journeyworker refused to work with her because she is a woman. Coaching involves asking questions that guide apprentices to reach their own best decisions. Tammy realized that the journeyworker’s statements only revealed his own weaknesses. Tammy continues to work with her coach on overcoming her confidence issues and the company is working on addressing the discriminating issues and working to become a more inclusive environment.