This paper is on comparative leadership philosophy. It explores the ancient Asian wisdom for leadership development from the Kautilyan and Confucian perspectives. Every now and then, there is a need for us to look and re-look at ancient wisdoms to be applied effectively in the modern context. In this paper, the authors provide an inside-out leadership development approach. This has practical implications and lessons for contemporary leadership development from an Indian and Chinese cultural perspective. It is also becoming highly relevant due to the growth of both the Indian and Chinese economy. The reference in the Indian context is made from the Arthashastra by Kautilya, while reference in the Chinese context is made from the teachings of Confucius.