Trust is a fundamental constituent of financial market interactions. As well-known cases of corporate failures in past and recent history have illustrated, betraying the trust that investors and other stakeholders put in corporate leaders can bring drastic consequences for the organisation concerned as well as for markets and society at large. A low level of trust in the market makes it more difficult also for sound and ethical business projects to be funded and supported. Research in accounting has highlighted the link between poor/unethical business practices and unsound/deceitful corporate communications, which leads to two interesting implications for business communication researchers and practitioners: (1) discourse analysis and evaluation can become a source for detecting – and possibly avoiding – unreliable business endeavours; (2) improving financial communication skills can enhance the quality of strategic thinking and decision-making as well as help corporate managers to build long-term trust while persuading sceptical stakeholders to support a business initiative. This chapter takes a rhetorical argumentation perspective advocating the crucial role of argumentation skills.