The gamble wasn't so much that he'd set his sights on Harvard Business School but that he applied nowhere else. It was going to be Harvard or nothing....
Skilling graduated a Baker Scholar, a coveted honor bestowed on the top 5 percent of the class. He decided his talent was "pattern recognition" which meant he thought he was good at seeing how the techniques used in one industry could be applied to another.
McKinsey prefers to hire new consultants out of places like Harvard rather than from industry itself. In fact, it's hard to think of a place that believes in the value of brainpower more than McKinsey. The firm spends a great deal of time sorting out stars from the merely superbright; perhaps not surprisingly, those who prosper there often develop a smug superiority.
Indeed, the firm likes to think of itself as bringing enlightenment.... McKinsey ideas often sound incredibly compelling, even pure, in a way that makes them impossible to believe they could ever be corrupted. But like Skilling, McKinsey partners tend to be designers of ditches, not diggers of ditches. When it comes to executing their lofty theories, well, consultants lean toward leaving those messy realities to the companies themselves.
It would be hard to imagine a place that suited Skilling more perfectly. The McKinsey thought process reduced a chaotic world to a series of coolly, clinical, logical observations. Thats precisely how Skilling thought. McKinsey valued sheer brainpower, he had it to spare. It favored people who were quick on their feet and who could "present well." That was Skilling through and through. He had a way of turning practical disagreements into abstract arguments and could outdebate just about anyone. "It was difficult to disagree with Jeff Skilling because he would elevate the disagreement to an intellectual disagreement, and it was hard to outsmart him," says a former partner.
But Skilling also played to his weaknesses. Working at McKinsey only heightened his natural arrogance. McKinsey could be a cold place, ruthless in sorting out the stars from the also-rans. Skilling embraced that ruthlessness. The culture rewarded individual achievement, as opposed to teamwork. Skilling was never much of a team player. If he thought he was smarter than someone--and he usually did--he would treat him harshly if he had the temerity to disagree.
Skilling used to say that a culture that supported innovation...needed to be willing to accept failure. "I'll take a smart, thoughtful guy who fails over a person who is successful," he declared.... Skilling might say he was goint to hold deal makers responsible, but her rarely did, and the deal makers all knew it. Another Skillings precept: a company that worried too much about costs would discourage original thinking. "I don't think we should be doing stupid things," he later explained, "but I don't think a penny-pinching environment is one that fosters creative ideas...."