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The devil's advocate in the room

When did you first notice you were the devil's advocate in the room?

He says he was always the one on the opposite side of the table, and he thinks he's always been like that, because his mom always told him it's okay to ask why. So he would always ask people why — and whether or not they could actually describe why they thought what they thought.

When I was always the one on the opposite side of the table. And I think I've always been like that, because my mom always told me it's okay to ask why. So I'd always ask people why. Why, why, why, why. And whether or not they could actually describe what they thought, why they thought.

Source: Round 1, question 6. Michael McCraw, voice transcript relayed by Gideon, Nov 14, 2026, 3:30 PM MT. Pages on this site use only his interview answers or other verified sources. Nothing here is invented.

Questions

When did you first notice you were the devil's advocate in the room?

When I was always the one on the opposite side of the table. And I think I've always been like that, because my mom always told me it's okay to ask why. So I'd always ask people why. Why, why, why, why. And whether or not they could actually describe what they thought, why they thought.