“I don’t hire older CIOs. I like them young.” So barked an experienced and grizzled CEO in a conversation we had a decade ago. Why? Because they don’t know any better, he said. They overestimate their abilities, underestimate the problem, but work hard enough and are smart enough to pull it off. I hope I don’t work for him, I distinctly remember thinking. While overconfidence continues to be a consistent problem in IT, so does too much experience. Those experienced IT folks who may sandbag their estimates (partially out of painful memories from prior battles, partially out of CYA self-protection) constantly run into technology neophytes and amateurs who are deeply convinced that they can move …

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