Overthinking is not a skill, it's an art.
Start by asking yourself a million questions, and then question your ability to ask those questions.
And then, of course, there's the art of rephrasing the question.
But don't just rephrase, overthink. Overthink, rephrase, overthink, rephrase...
For a more... obvious approach, see: Overthinking the Obvious
And don't even get me started on the art of overthinking the obvious.