This research explored the experiences of mentors mentoring institutionalised children under the auspices of Big Brothers Big Sisters of South Africa (BBBSSA). Children who become wards of the state and are placed in Children’s Homes may have had a number of their emotional needs unmet during developmental stages, manifesting in a variety of ways not least of which might be the development of an institutionalised mentality. These children are disadvantaged at age 18 when they enter the world with limited resources, infrastructure or the ability to be self-reliant. Mentoring may represent a means of ameliorating these repercussions and this qualitative research included exploring whether mentors engaged in any strategies to empower their protégé to reduce the effects of an institutionalised mentality, the successes achieved through the mentoring process as well as encountered challenges. The sample was purposively chosen and the seven participants had mentored for longer than a year at a Children’s Home. The data was gathered from them via semi-structured interviews. Data was analysed in light of the research questions, research tool and any subsequent themes that emerged. Mentoring through a programme appeared to enhance relationship longevity because of the structure it created. While growing themselves through the process, mentors reflected that preparing their protégé for adulthood was a concern. The mentors discussed that while not familiar with the concept of an institutionalised mentality per se, they recognised this as a challenge their protégés faced and described their attempts to empower them on mental, emotional and physical levels reporting small successes in often challenging circumstances. The study concludes that mentoring programmes offer a valuable tool in the preparation of institutionalised children for their emancipation from State care and should be capitalised on. Recommendations are made for policy makers, BBBSSA and the Children’s Home in light of these experiences.