This study uses content analysis as a qualitative method, as an unobtrusive technique to observe intercultural communication during the decision-making process. The research question was as follows: Is there evidence of an influence of high-context and low-context cultural orientation on the decision-making process when it involves globally distributed collaboration using email? I utilized a secondary dataset of archival email messages (n = 1760) among participants during the World Summit on the Information Society. Using content analysis qualitatively results in rich findings and in-depth descriptions about people's decision-making behaviors in terms of the mannerisms, values, and preferences arising from their diverse cultural backgrounds. Nonetheless, several challenges arose such as the difficulty of discerning meaningful cultural patterns from the dataset given the massive amount of data that had to be read, digested, analyzed, and interpreted, and the need to determine whether to use a deductive or inductive approach. In essence, the findings establish that culture does matter in the form of intercultural communication styles and the cultural values to which participants subscribe. Analysis revealed distinctive patterns of online cultural behaviors among high-context and low-context individuals, as evident in the strategies, approaches, and communicative mannerism displayed by participants in the distributed decision-making processes.