"Nobody ever got fired for buying IBM." That chestnut has morphed from sales proposition to object lesson on the perils of clinging to convention in less than a generation. We've ditched the dark suits and "sincere" ties of our father's IBM for black turtlenecks and jeans, and we've embraced the "think different" ethos of Apple's celebrated campaign : "Here's to the crazy ones. The misfits, the rebels, the troublemakers, the round pegs in square holes. The ones who see things differently."

As a reverse fairy tale for the CEO set, the reality television program Undercover Boss is fascinating, not so much in the witness-to-a-train- wreck mode of the rest of the genre, but because it is so revealing of our conflicted relationship with "the boss." The premise of the show—that the only way to get a clue about what's really going on in his (or her) organization, is for the boss to go undercover on the front lines—is all too often the actual reality in organizations of any size. Yet, at the same time, the view of the boss as the ultimate authority with the heroic power to swoop in and save the day—whether that means paying down a mortgage, granting an instant promotion, or banishing a reviled policy—holds sway in real life as well as on "reality" TV.

At one time or another, most of us have probably worked for a boss who was self-absorbed, vindictive, or just plain inept — a real-life equivalent to Dunder Mifflin’s Michael Scott. One of my first jobs was for an HR manager who thought the best way to humble a cocky new MBA was to have him spend...