At work, people quickly realize that achieving personal and organizational objectives largely depends on their political behavior. But little is known about the motivational and cognitive aspects that initiate, shape and make such behavior effective in the long run. This chapter focuses on two largely under-investigated topics: political will and political prudence. Contrary to the established view that political behavior is self-serving in nature, current advances in the political will literature suggest that the willingness to expend political capital can also start from benevolent motives. However, while political will may be seen as the fuel that keeps the political machine running, it also runs the risk if left uncontrolled of depleting quickly, and may thus fail to bring about the intended change to the status quo. It is suggested that political prudence will mitigate this risk. The direction, intensity and persistence of political behavior is set by a decision-making process whereby individuals rely on rationality and realism to assess alternative courses of action and find the one most situationally appropriate. It is proposed that political prudence is a multidimensional construct encompassing five dimensions, and that it may either buffer the effect of political will on political behavior and/or exacerbate it on strategic goal attainment. Finally, the chapter highlights the role of political skill as a quality assurance mechanism that can help prudent decisions not only to be made but also to be effectively implemented.