Prior inquiry on politeness tends to explore the deficiency of non-native speakers’ pragmatic knowledge. This inquiry broadens the focus to the impact of different lingua-cultural values on politeness in simulated workplace e-mail requests of Korean and American corporate employees. By examining different perceptions towards power-asymmetry, this inquiry explores how and why politeness strategies are realized similarly and/or differently in and around the speech acts of requests in English. By quantitatively and qualitatively investigating the evoked data, the inquiry proposes that lingua-cultural values affected perception and production in power-asymmetrical situations. Findings disclose that power is a more important factor than familiarity for Korean employees, but to a lesser degree for American employees when doing politeness in e-mail requests. Results dislayed that the underlying reasons for formulating requests diverged not only between Korean and American employees but also between two Korean employee groups that differed according to depth of intercultural experience. This inquiry adds to recent research strands in intercultural pragmatics and communication by asserting that pragmatic strategies to express politeness in relation to power are culture specific with extant and newly reconstructed lingua-cultural values coming into play.