Via the New York Times, this little Jeff Bezos anecdote:
Jeff has an uncanny ability to read a narrative and consistently arrive at insights that no one else did, even though we were all reading the same narrative. After one meeting I asked him how he was able to do that. He responded with a simple and useful tip that I have not forgotten: he assumes each sentence he reads is wrong unless he can prove otherwise.
I've met my fair share of skeptical bosses, but I'm not sure I've met one that's skeptical in detail.