We conceptualize strategic flexibility as a strategic paradox that entails tensions between stability and dynamism. Furthermore, we develop a framework that disentangles the nested tensions of the strategic paradox as system-inherent, cognitive, and social. Integrating our framework with a strategic leadership perspective enables us to reveal mechanisms between paradoxical cognition, strategic action, and firm performance. CEO´s paradoxical cognition increases the ability and willingness to be strategically flexible. Additionally, a deep understanding of contradictory demands and a disposition to develop both/and-strategies positively moderates the relationship of strategic flexibility and firm performance. To test our propositions we propose a quantitative research method based on a computer aided text analysis algorithm (CATA).