Why Your AI Projects Keep Failing (It's Not the Tech) ft. Barbara Wittman

Barbara Wittman has spent 25 years cleaning up broken transformation projects, and the root cause is never the technology. In this episode, she breaks down how AI is exposing dysfunction that companies have been hiding for years: misalignment between business and IT, unchecked assumptions, and a total lack of shared understanding. She explains why boards pressure CEOs into AI adoption out of fear, why the people actually executing get sidelined, and why most “AI use cases” fall apart the moment you pick them apart. Barbara makes the case for “human infrastructure” as a real budget line item, not a buzzword, and shares frameworks so simple they fit on the back of a napkin. If you’re a founder, a transformation leader, or anyone trying to figure out why your AI investments aren’t paying off, this conversation will reframe how you think about the problem.