His important observation in this article:

As we grow older and more experienced, we overrate the accuracy of our judgments.

This is a subtle insight, and turns the conventional wisdom about experience on its head. It is a warning for those of us who are very confident in our style. It is a red flag for how comfortable we should allow ourselves to become in a work environment, especially when we are in charge of a large organization that can go off the rails without care.

The CEO discussed was well loved:

“When I left,” Cayne told Cohan, speaking of his final day at Bear Stearns, “I had three different meetings. The first was with the president’s advisory group, which was about eighty people. There wasn’t a dry eye. Standing ovation. I was crying.” Until the very end, he evidently saw the world that he wanted to see. “The second meeting was with the retail sales force on the Web,” he goes on. “Standing ovation. And the third was a partners’ meeting that night for me to tell them that I was stepping down. Standing ovation, of the whole auditorium.”

…but at the end of the day, he wrecked his company because he was too confident in his abilities to see market patterns.

Standing ovations are a nice salve for the ego, but they don’t pay employees’ mortgages. So please, make sure that when you making big decisions, always start by evaluating your personal and organizational assumptions. Make sure that you can realize that life can sometimes throw something completely unexpected at you – something like a market crash or a government intervention or a lawsuit that requires a completely different response than you would have had just one day ago. Assuming that what happened yesterday will happen tomorrow can be the downfall of your organization.