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This chapter combines new and emerging perspectives on career mentoring in the workplace and its role in failed leadership practice from instigated incivility to manipulative mentoring. While numerous scholarly and practitioner-based works on the topic of mentoring, few have offered the perspective of leaders who facilitate failed mentoring dynamics and its effect on employee subgroups, such as millennials. Based on leadership research, theory, and first-hand experience, this author will share through anecdotal evidence, with a diversity-theme focus on women and millennials, a group that comprises 58 million individuals currently working in corporate positions in the United States (Toosei, 2008) As more millennials join the workplace, professional mentoring plays a significant role in their progress. This research reveals the role that career mentoring can play, when harnessed incorrectly, as a hindrance to the promise and potential of entry-level employees, particularly millennials. The author’s perspective frames this chapter in personal narrative, as she recounts her tale as a Black, female academician and practitioner upon whose own professional trajectory the story of failed mentorship will be loosely based.