The well-being of a society is enhanced when many of its people question authority
Is it necessary for people questioning the authority? It depends on the characteristic of the authority. The more the authority represent will of people, the less questions people need to raise about the authority's activities.
First of all, well-being of society is improved by questioning authority that doesn't have legitimacy. Because illegal authority normally doesn't try to improve lives of people. Their major concern is maintaining their power. In this situation, people cannot expect the authority would take responsibility of improving people's well-being. For example, Korean people protested authoritarian regime for their legitimate rights and well-being in the 1970s. They demand political rights such as making political parties and so on. Through struggles, they could gather people's attention on the problem and finally attained political democracy. Under the democratic political order, people's well-being was significantly improved comparing with that under authoritarian regime. Without their questioning the authority, their well-being could not be enhanced.
Secondly, the authority could betray well-being of people even if it has legitimacy in some extent. Because the authority could be vulnerable to strong interest groups such as big business owners. Economical moguls can give enormous political funding to political power. Then the political power would be likely to represent not people's general will but will of several powerful persons. In this situation, people need to question the authority and enforce political power to represent their interests. Of course, the easier way of making politicians represent the general people's will is voting for alternative politicians. However, this strategy is not always effective. If we consider politicians and political parities under a democratic political system such as U.S., U.K., etc. we can know how the strategy is not enough for political power to represent general will of people. Questioning the authority and protesting for their well-being, they could gather people's attention and form public opinion that is favorable for alternative political power that represents people's well-being. For example, U.S. citizens succeeded in making major political power legislate regulation of excessive financial institutions after protests in the late 2000s.
In the last place, people need to trust the authority and political process when political parties try to improve people's well-being. In this situation, raising excessive question to the authority could delay a proper compromise and consequence for enhancing people's well-being.
In conclusion, questioning the authority is available to improve their well-being, which contributes to make political power represent people's general will insofar as it's not too excessive to delay the appropriate political process.