Is it right to question things you do not understand? Should authorities feel challenged or reassured that they are not employing “yes men”? If authorities are humble, they will be grateful for those that are respectfully willing to be truthful and give an opinion that differs from what the authority says. Even the God of the Bible respected men of this sort. Moses, Jeremiah, and others all spoke from the heart.
Regarding Jeremiah, more than once he was told to perform various actions that were actually object lessons such as burying a linen belt, remaining single, and observing a potter making a vessel. But at Jeremiah 32:25 Jeremiah was truly baffled by an instruction he received. He was told to buy a field. Jeremiah complied but then questioned Jehovah because it made no sense. Why buy a piece of land when all this time Jehovah has had Jeremiah prophesying that the Chaldeans (Babylonians) were coming to conquer and deport the peoples, and ruin the land.
In the rest of the chapter, Jehovah responds and goes on to explain that the direction to buy the field was prophetic of what the returning exiles from Babylon would do. So just as surely as Jeremiah completed a simple transaction during a turbulent time, just prior to the nation being captured and taken to Babylon, with the same assurance Jehovah tells Jeremiah that without fail there will be a repopulating of the land. Further, in chapter 33, Jehovah goes on to describe in detail the prosperous state the repatriated Israelites will experience.