The ride back to the airport from Captiva Corporation’s annual retreat for the board and top management was proceeding slowly. Cynthia Speedwell and Ben Esperanza sat glumly in the backseat of their limo, checking their watches and making contingency plans in case they missed their flights home. Ben grumbled to his friend and fellow Captiva division president, “At this rate, by the time we get to the airport, Doug Yacubian might actually have figured out what he’s supposed to do as Captiva’s COO.”

A version of this article appeared in the November–December 1999 issue of Harvard Business Review.