Human beings are social animals, and people are likely to bristle at someone trying to poke holes in their worldview in that way, unless they have already established some kind of rapport. (Even the Socratic method expressed in Plato’s dialogues was practiced on people who belonged to the same city-state and social class as Socrates – and he eventually got charged and sentenced to death regardless.)
This is why one of the methods advocated for in curing people of conspiracy-theory thinking, is providing them a warm and supportive atmosphere where they feel part of a community, and not trying to challenge their ideas head on.