The objective of this report is to understand the factors that hinder and those that facilitate the representation of women on boards of directors in South African companies. The insights gained on the obstacles and facilitators in achieving greater representation of women on boards of directors will give companies and individuals actionable knowledge of the key success factors and strategies that can be applied to increase representation. A literature review was done in order to apply existing theory to the research problem. The researcher‟s objectives were to answer three research questions. The methodology for the research is then described. Qualitative research was used with the research instrument being in-depth interviews. Twenty three face-to-face interviews were held with board members, executive search companies, an organisation that trains boards of directors and a women‟s professional body, using a semi-structured questionnaire. Seven respondents completed the questionnaire only. Interviews were transcribed and content analysis performed on them to extract recurring themes related to the questions asked. The results of the interviews are then presented and interpreted. The findings are that there are no conscious or deliberate attempts to keep women out of the boardroom. The factors affecting women representation on boards of directors can be attributed to the interplay of historical and cultural factors that have resulted in women not being top of mind when appointing board members. Legislation is playing an effective facilitation role, but the extent of transforming this trend, in a meaningful way and not just to be compliant, in an equal opportunities environment in which South African companies presently operate, depends on the „natural diversity insights‟ (the natural consciousness to want to do the right thing) of the shareholders, chairpersons, CEOs and/or the nomination committees who play a huge role in either recommending or making the final decision on new board appointments.