James Somers recalls working for a CEO who would ask him one question, over and over: “What are you worried about?”

He wanted me to worry, if only because worry is such a great proxy for interest and urgency and basically that whole portfolio of feelings that kick in when you give a damn. He wanted me to give a damn. […]

This is why the question is so useful in the workplace. It cuts to the heart of the matter. Ask your systems guy or accountant or security team what they’re worried about and you’ll find out all you need to know about your systems and accounts and security. Want to become a better programmer? Ask your boss what worries him about your code. Want to be a better boss? Ask your programmer what worries him about his code.

Not surprisingly I’ve found that this question bears fruit in all sorts of other contexts. If you’re talking to a friend about a new girl he’s been seeing, and he seems to be waffling, or he’s inarticulate about it, asking him “well, what are you worried about?” will drive right to the point. It’ll dredge up all the stuff he’s actually been thinking about, not just any old stuff, but the stuff that stood out enough to scare him.