This study examines the relationship between leadership mental models (LMMs) and organizational digital maturity, investigating the dual mediating effects of technical empowerment and organizational culture. Design/Methodology/Approach: A quantitative survey of 360 enterprises across various industries was conducted. Data were analyzed using structural equation modeling and bootstrap analysis to test direct and indirect effects, with additional multi-group analysis examining differences across organizational characteristics. Results indicate that LMMs significantly affect organizational digital maturity both directly (β = 0.384, p < 0.001) and indirectly through technical empowerment (β = 0.213, p < 0.01) and organizational culture (β = 0.175, p < 0.01). Organizational size moderates these effects, with stronger relationships observed in larger organizations. Multi-group analysis reveals significant variance across sectors, particularly in technology-intensive industries. The study confirms the importance of leadership cognitive frameworks in digital transformation processes, with technical capabilities and organizational culture serving as crucial mediating mechanisms. Practical Implications: Organizations pursuing digital transformation should develop appropriate leadership mental models while simultaneously fostering technical empowerment and a supportive organizational culture. Strategies should be tailored to organizational size and industry context to maximize digital maturity outcomes.