People always say it is easier to handle things than handle people. This statement is even truer for middle managers in organizations since they need to handle gaps between the senior level and the subordinate level. Also, these middle managers often find themselves stuck in between various stakeholder groups (Anicich Hirsh, 2017). Though middle managers are critical for organizations, studies which include both how these middle managers interact with the senior level and how they interact with the subordinate level are still few in Taiwan. This study aims to explore the area by understanding challenges and analyzing behaviors of the middle managers in Taiwan. In the beginning, a literature, umbrella management, about middle managers’ behaviors when they face bi-directional pressure will be explored. Three options of managerial roles will be also discussed. Then, behaviors of 26 middle managers in 25 companies through a qualitative method will be analyzed. Findings show that there are three types of protection models which these middle managers are holding: bigger protection against the senior level, similar size of protection against both the senior level and the subordinate level, and bigger protection against the subordinate level. Based on the findings, 5 key factors, including trust from the senior level, authority, positioning, observation capability, and open communication, to decide if a middle manager can be effective or not will be also shared.