As organizational environment develops, the working environment increases in physical and mental demands. As a result, risk inadvertences could arise, along with organizational emotional and financial challenges. Within their efforts to diminish such risks, organizations strive for developing and training their workforce; a sustainable workforce can only be achieved through cultivating aptitudes and positive attitudes that will lead to organizational but also personal growth. Considered to be an important measuring instrument for social sustainability, workforce sustainability enhances organizational leadership projections and trajectories, along with digitalization initiatives. The aim of the current study is the development of an assessment tool for state and private organizational workforce sustainability, and to study it in relation to leadership and digitalization components. Through a quantitative approach, data was gathered by issuing an online survey that delivered 463 responses. By using structural equation modelling, the authors examined the aims and found that the designed workforce sustainability tool is reliable and valid; as predicted, all the leadership components contribute to organizational stability and a more favorable workforce sustainability development, along with enhancing digital learning. This study stresses the importance for state and private organizations to achieve workforce sustainability, while nurturing and providing the necessary tools for the development of leadership and digital learning.