Political skill is the essential requirement for individuals to survive in the political arenas of organization, and is a topic that is gaining significant recognition in the area of managing interactions within the organization. The present study investigates political skill influence on helping behavior, compassion, knowledge sharing behavior and job embeddedness under the mediating mechanism of organizational based self-esteem, interpersonal trust, and personal reputation. Moreover, political will moderation impact is also observed among political skill and its outcomes. A quantitative approach is employed involving responses from 219 managers serving in banks of Islamabad and Rawalpindi using a questionnaire. Structural Equation modeling and process macro is used to test the hypotheses. Political skill revealed a significant positive impact on positive behaviors and job embeddedness, organizational based self-esteem, interpersonal trust and personal reputation. The results supported mediation hypotheses however; political will moderation was not supported. Political skill will help managers deal with tough competitions, technological advancements and demanding jobs, and to cultivate a positive environment in the workplace by promoting positive behaviors such as helping colleagues, showing a compassionate response, engaging in knowledge sharing behavior and by increasing job embeddedness. Managers should be trained to develop political skill in their personality as it will help them to enhance self-esteem, add to their repute, and help to develop trust in colleagues. The study was the first to address the unexplored areas of research regarding political skill impact on positive behaviors and job embeddedness in the presence of specified mediators and moderator.