The community college leadership pipeline is a source for concern in the face of anticipated retirements, yet most administrators come only from the ranks of classroom faculty, not from the full spectrum of all faculty. Librarians, whose experiences lend themselves to many administrative duties, seldom advance into administrative positions. This study was centered on the development of a career coaching intervention by which participants from a subset of California community college libraries received guidance from administrators who had previously been librarians. The aim was to see whether such an intervention could increase administrative skills, improve self-efficacy to perform in administrative roles, increase perceptions of the desirability of attaining such positions, and lead to greater intent to move onto such career pathways. The study found that a career coaching program had mixed success at addressing the study aims, but that it also opened space for librarians alone to explore other leadership and professional growth opportunities. The research argues for the restaging of such a career coaching program, centered on librarians only, so as to encourage their advancement, whether into administrative ranks at their community colleges or otherwise.