Although the formulation of organisation strategies is reportedly easier, many organisations struggle when it comes to implementation of their strategies. Given that such strategies are in most cases informed by well researched market data and information, the strategy implementation challenges could then be linked to the role characteristics of strategic leaders, such as the Chief Executive Officer (CEO). The purpose of this research was to investigate the role of a CEO personality in strategic leadership in order to contribute to addressing the challenges of strategy implementation. The main methodology used was qualitative through unstructured interviews with 13 incumbent CEOs. A quantitative methodology was also employed to assess the personalities of the CEOs using standard personality test. The research found that strategic leadership practices are biased towards strategy implementation than the envisioning which typically supports the building of more resilient strategies. The research found that CEO Personality has a role in strategic leadership and this was suggested by the integrated analysis of the qualitative and quantitative data. Interviewed CEOs also provided lived experiences that support this suggestion. Organisations need to invest in envisioning and understanding the personalities in work places to build more resilient strategies. Further research is proposed to look at personality roles in different industries.