In this paper, we investigate the awareness gaps between information security managers and workers with regard to the effectiveness of organizational information security measures in Japanese organizations by analyzing micro data from two Web-based surveys of information security managers and workers. As a result, we find that there are no awareness gaps between information security managers and workers with regard to the effects of the organizational information security in large companies. However, we find that awareness gaps between them tend to exist in small or medium-sized companies. Next, we argue how to bridge the gaps. We propose that information security managers could implement the two-sided organizational measures by communicating with workers in their organizations.In this paper, we investigate the awareness gaps between information security managers and workers with regard to the effectiveness of organizational information security measures in Japanese organizations by analyzing micro data from two Web-based surveys of information security managers and workers. As a result, we find that there are no awareness gaps between information security managers and workers with regard to the effects of the organizational information security in large companies. However, we find that awareness gaps between them tend to exist in small or medium-sized companies. Next, we argue how to bridge the gaps. We propose that information security managers could implement the two-sided organizational measures by communicating with workers in their organizations.