At most companies, preparing for a high-stakes presentation to the chief executive involves rehearsing in front of colleagues, refining slide decks, and hoping for the best. At Uber Technologies, employees now have a different option: they can pitch their ideas to a digital replica of CEO Dara Khosrowshahi — one that interrupts, challenges assumptions, and pushes back with the kind of pointed questioning the real Khosrowshahi is known for.

The AI-powered CEO clone, built internally by Uber employees, represents one of the more unusual applications of generative artificial intelligence inside a major corporation.…