First, the method and it's good intentions:
Socratic questioning—Here, you leave people to draw their own conclusions by simply asking a set of helpful questions to take them to the realization that there’s an issue (and the hope is that they’ll then ask you for a solution or even stumble on your solution and offer it up as if it were their own). This, we’re told, increases ownership of the issue because the other person—the person needing to change—came up with the idea himself.
Then, how it often doesn't work out as exploration, more as pointing to an existing point:
Socratic questioning—This one is trickier, because it often looks open and curious. You’re asking questions, so aren’t you already doing what this different-questions approach suggests? Our experience is that generally people who use this approach are not actually curious about something new they might learn from the other person. (This lack of curiosity starts, we’re sorry to point out, with the great Socrates himself, who was a smart fellow who might be forgiven for thinking he had the solution concealed inside his cloak.) Instead, the questioner leads the person down a familiar path (designed by the questioner) and entirely inside familiar (to the questioner) territory. We can spot this in our videos with leaders because they will generally ignore any new information that comes their way and continue their set of questions. When someone gives an unexpected answer to the question, the leader looks more exasperated than confused—because the other person is missing the point. The leader is using questions to search for particular answers, not to get more information on the table.
I always want Socrates to just tell me what he wants the conclusion to be and work backwards. Plato needed an editor, perhaps. But chopped down, Socrates proofs wouldn't have seemed proofs.
Both quotes from Simple Habits for Complex Times.