The study aimed to proposed administrative perspective to develop the digital leadership skills of leaders of Jordanian business organizations to promote digital transformation and entrepreneurship. The developmental descriptive method was used to collect the data from the study sample. The study sample consisted of (75) administrative leaders from various sectors such as telecommunications, services and small and medium enterprises, selected in a stratified random way using statistical tables. The results of the study indicated that the reality of developing digital leadership skills among leaders in Jordanian business organizations to promote digital transformation and entrepreneurship from the point of view of Administrative leaders came to a medium degree. The results showed that there were no statistically significant differences at (α = 0.05) in the responses of the study sample to the degree of need to develop digital leadership skills among leaders in Jordanian business organizations to promote digital transformation and business leadership attributable to the variables of the career center and the business sector. Accordingly, the researcher built a proposed administrative perspective to develop the digital leadership skills of leaders of Jordanian business organizations to promote digital transformation and entrepreneurship and recommended the researcher to adopt this proposed administrative perspective practically by Jordanian business institutions to promote digital transformation and entrepreneurship.