The purpose of this dissertation research is to examine the interrelationships between transformational leadership, organizational learning, and the five dimensions of organizational innovativeness within Head Start programs. A survey containing 29 questions adapted from validated and reliable scales was administered using a sample of 64. Confirmatory Factor Analysis (CFA) revealed a well-fitting model, confirmed by a chi-square value of X[superscript 2](15) =22.15, p=0.103, Root Mean Square Error of Approximation (RMSEA) of 0.05, and Comparative Fit Index (CFI) of 0.97. Factor loadings were significant at p<0.001, denoting the model's reliability. The model fit showed that the scales were appropriate for measuring transformational leadership, organizational learning, and innovativeness constructs within a Head Start program for the first time. Multivariate regression analysis was statistically significant and explained the variance in organizational learning and innovativeness (R2=0.910). Transformational leadership was found to influence organizational learning and four dimensions of innovativeness: proactiveness, future orientation, creativity, and openness. Notably, risk-taking was the only dimension of innovativeness that was not statistically significant with transformational leadership. Additionally, pairwise correlations corroborated the second hypothesis, showing a strong positive relationship between transformational leadership and organizational learning (r=0.667, p<0.0001). Subsequent correlational analyses partially supported the third and fourth hypotheses, confirming that transformational leadership and organizational learning significantly correlate with multiple dimensions of organizational innovativeness, except for the risk-taking dimension. Creativity was identified in the fifth hypothesis as the strongest predictor of organizational learning, explaining about 61.3% of the variance (R[superscript 2]=0.613). The sample size for this study is a limitation, which may impact the generalizability of the findings. The study concludes with recommendations for future research exploring additional factors affecting risk-taking within the realm of innovativeness, and further validating the survey instrument in diverse settings, such as early childhood programs like Head Start. Finally, this research highlights the critical role of transformational leadership in fostering organizational learning and innovativeness, with creativity being a key driver in the Head Start program context. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]