Unrelated comment: I hadn’t heard of de Bono’s 6 hats, and after reading the wikipedia entry linked from your post, showed it to my wife. “Oh, we use Blue all the time,” she said, “that’s why we never seem to understand how people get so caught up in one way of thinking.”

I think it’s a useful insight that CEOs (and managers on down) tend to be motivated by sociopathy (even if not sociopathic themselves) because they are beholden to the shareholders, and the shareholders do not have a compassionate tie or other loyalty. They are working in values of dollars and cents, and they demand results in such terms, so by nature are non-social.

Which is a good thing, as you also illustrated. It still requires a bit of a leap of faith, but evidence also shows that ethical and compassionate behavior (over time) are the most profitable.

It’s a similar problem with politicians, though (theoretically at least) there is an ethical or moral stand tied to your vote, perhaps because the monetary reward is less direct. For lobbiests, however, the path is much clearer, and hence you see more sociopathic behavior.

I used to use the phrase “how will doing / not doing this work affect your bonuses?” as a way of distilling this sentiment and focusing the minds of my colleagues when reviewing the merits of individual features (and when their attention was not all it could be…)

I’m bringing my own evil hat out of the bottom drawer, and giving it pride of place on my desk from now on!

Alternatively, use the Evil Hat to consider what will happen if a different system is put in place. Think, “If I were an Evil team leader, and someone was going to measure me based on the number of obstacles I remove, what could I do? Ooh, I know… I’ll make sure there are lots of obstacles! I can get my mate from Infrastructure to help. And I won’t prevent the obstacles from hitting the team in the first place. ” Etc.