Formulating a strategy and analyzing the general environment is a subjective and idealized process, and many factors could become obstacles when the strategy is actually implemented. Therefore, these obstacles need to be considered in the analysis process. This article will discuss culture and leadership as the main factors, and explain how culture and leadership influence strat-egy implementation. The first part is about how cultural factors, specifically the internal organizational culture and external culture, affect the company. The second part of the article is about leadership, taking two CEOs of Apple, Steve Jobs and Tim Cook, as ex-amples, and using the Big Five Model of Personality Dimensions to explain how different leadership styles affect strategy implemen-tation.