In Chapter 1, I provide a general theoretical framework for the dissertation. In Chapter 2, I examine the association between cultural metacognition and intercultural effectiveness. In Chapter 3, I examine the conditions and cognitive mechanisms that facilitate application and updating of cultural knowledge among individuals high on cultural metacognition. I further test whether related individual difference factors can explain the hypotheses I proposed in Chapter 3. Multiple methods were employed to test my hypotheses using quasi-field surveys with executives, 360 degree multi-rater surveys with MBA students as well as experimental designs with lab and crowdsourcing participants.