Open AccessThe organizational ambidexterity objective encouraging performance of companies through the simultaneous development of alignment and adaptability. Among the contextual factors that influence, stand out the training, trust, discipline, pressure and support on the organization's participants. The objective of this study is to analyze the relationship of the organizational context with the realization of organizational ambidexterity in small business. It seeks to understand if there is a positive relation between the attributes constituting the organizational context and the ambidexterity in small businesses. For both, was held a multiple case study with three small business in the city of São Luís. The main results indicate that the contextual factors influence the innovative capabilities and, consequently, in the organizational ambidexterity in small business. The results also indicate that the absence of such factors can cause the lack of innovation activities.