In North American society we have arranged our working and political relationships according to adversarial models which frustrates the ability to examine problems in context. Instead we prefer the one size fits all model and slavish adherence to the rule; whether that rule is a policy or law.
Certainly we need ethical decision making and publicly defensible decisions. However, that does not preclude using our wisdom to choose the best option in any given instance for the situation at hand.
The Catholic tradition, borrowing from Greek philosophy, identified four cardinal virtues - prudence, justice, temperance, and courage. Cardinal is a derivative of the Latin term "cardo" meaning "hinge". Our moral activity hinges on these four natural virtues. They are referred to as natural virtues meaning all human beings are born with these virtues. The aim of education should be to further develop them in meaningful ways.
Prudence has been referred to as the charioteer of all the other virtues. What is prudence? While he does not explicitly use the term, the talk by Barry Schwartz goes a long way in defining what and how prudence is exercised and how we have lost this virtue and the impact that loss has had in our civic life.