Today, every firm and organization must digitally transform in order to survive and deal with increasing competition and dynamic market conditions. Digital transformation is not easy to achieve, and many factors play an important role in the successful digital transformation of firms. Leaders' leadership styles and characteristics play a crucial role in digital transformation. This study examines the effects of generative leadership and digital literacy of executive management on the digital maturity of micro and small firms based on the Upper Echelons Theory. Sub-dimensions of digital maturity are also considered and searched to provide a more detailed analysis. The research utilized a survey method and was conducted with 121 upper, middle, and first-line managers of 93 micro and small-size firms operating in the Marmara Region of Turkey. Frequency, factor, regression, and validity and reliability analyses through the SPSS package program were used. The results are two folds. First, generative leadership and digital literacy of executive management help flourish digital maturity when searched independently. Second, the study results indicate that the digital literacy of executive managers has a mediating effect on the relationship between generative leadership and digital maturity. Furthermore, the study proves the mediating effect on digital maturity's technological, strategic, and cultural maturity sub-dimensions. With these findings in micro and small businesses, the study comprehensively contributes to the current knowledge in this domain.