Purpose: The purpose of this study was to determine the effect of intellectual stimulation and individualized consideration of the Chief Executive Officer (CEO) on the performance of senior managers in the private sector in Kenya.Methodology: The study adopted the positivism research philosophy and descriptive correlational research design. The target population consisted of 984 senior managers reporting to the CEOs of 183 private sector companies under the umbrella of the Kenya Private Sector Alliance (KEPSA). A sample size of 284 was drawn using stratified random sampling, and data was collected using structured questionnaires. A response rate of 92% was realized. Data was analyzed using descriptive statistics namely frequencies, means, and standard deviation. Inferential statistics were also used in the analysis which included Pearson’s correlation, Analysis of Variance (ANOVA) and multiple linear regression.Results: Results of the multiple linear regression showed that the CEO’s intellectual stimulation significantly predicted performance of senior managers R2= .610, F (1, 260) = 405.015, p < .05, β = .781, t (260) = 20.125, p <.05. Further, multiple linear regression results indicated that the CEO’s individualized consideration significantly predicted performance of senior managers, R2= .524, F (1, 260) = 285.282, p < .05, β = .724, t (260) =16.890, p<05. Testing the influence of goal orientation as a moderating variable showed that goal orientation significantly moderated the relationship between the CEO’s intellectual stimulation, individualized consideration and performance of senior managers in the private sector in Kenya, R2= .839, F (2, 5) = 265.099, p < .05, β = .111, t = 3.900, p<.05. Unique contribution to theory, practice and policy: The study provides a unique contribution to the theory and practice of transformational leadership in a new context in terms how trаnsformаtionаl leadership behavior associated with the dimensions of intellectual stimulation аnd individualized consideration, affect the performance of senior managers in private sector organizations. The findings are useful for private sector organizations and policy makers in explaining effective leadership behaviors that can be applied by the CEO for improving performance of senior managers. These will be useful in enhancing performance improvement strategies. Researchers and academicians will also find the study useful in defining new research dimensions by using the research results to expand related arguments in future.