Authors write annual CEO letters to convey specific messages but may not reflect on the leadership styles applied in their communications. The purpose of the current paper is to explore the usage of authentic, servant, transactional, and transformational leadership styles in leadership letters of Fortune 500 companies as a function of nine industrial sectors. The primary methodology for data analysis comprised content analysis and stepwise multiple regression. Results revealed CEO letter writers used transformational leadership most frequently, followed by transactional leadership. Stepwise multiple regression results revealed direct relationships existed between consumer goods and authentic leadership; services, and servant leadership; and utilities and transactional leadership. Additionally, a proposed template for future leadership letters was incorporated to enrich communication in CEO letters by applying specific leadership styles using new leadership paradigms to bolster the existent transformational leadership style.