The globalization of Chinese economy has a major impact on local companies worldwide today. Leaders of Chinese global mergers & acquisitions (M&As) face various cross-cultural dilemmas. This chapter captures the research on three Chinese-owned Dutch companies, examining critical M&A success and failure factors from a cross-cultural perspective. The data collected through interviews among Chinese and Dutch leaders allow us to get a better understanding of the leadership and cultural dilemmas within Chinese–Dutch M&A companies. Our findings contribute to the literature about cross-cultural dilemmas in a globalizing workplace. In particular, the findings contribute to the understanding of cross-cultural key constraints such as miscommunication, feelings of distrust, and nontransparency. We argue that these cross-cultural constraints may be caused by the perceived divergence of Chinese versus Dutch values toward, among others, the dilemma of “money and control” versus “trust and loyalty.” How to anticipate these Chinese–Dutch dilemmas in M&As? This chapter concludes that a more servant-leadership style is needed when anticipating these dilemmas to reconcile organizational cultural values.