The purpose of the study reported here is to illustrate how an approach based on a culturally appropriate "shepherd metaphor" has helped Asian students to cross cultural boundaries and to engage in critical thinking online. Asian students are under different levels of influence from the Confucian Heritage Culture, which cultivates students to revere authority, maintain harmony and avoid conflicts in public. This has a significant impact on Asian students' cultural readiness to verbalise critical thinking. This paper partially reports research undertaken in a large English as a Foreign Language reading class in Taiwan, in which "shepherd leadership" was practised. Shepherd leadership involves knowing students individually, offering cognitive modelling, exercising leadership and discipleship, encouraging student leadership and calling on silent students personally to get them to participate. This approach, concentrating on Asian students' affective needs, cognitive modelling, passing leadership to students and reaching out to silent ones, was found effective.