Mentoring has long been considered important in career advancement in many fields. It is important to pay attention to issues related to mentoring because it appears to be related to a number of organizational and individuallevel outcomes. In this paper, we examine certain factors that may lead to a more effective mentoring relationship, thereby increasing the likelihood that the relationship will be lasting and beneficial for the individual and organization. Specifically, we suggest similarities based on gender and work-family conflict will be related to effectiveness of mentoring relationships. Propositions are presented with respect to these relationships. Although we do not directly link mentoring with retention, the outcomes discussed above will likely result in reduced turnover in IT-related jobs. These outcomes are likely to be negatively associated with women's likelihood of remaining in IT fields and their performance and advancement in the IT field.