Tom Calloway, nonexecutive chairman of Astar Enterprises, put the phone back in its cradle as gently as he could, given the circumstances. He had just finished yet another difficult and unsatisfactory conversation with Edward Bennett, Astar’s CEO, about succession planning. Calloway wheeled his chair around and looked out over the stunning view of Boston Harbor. His 25th-floor office at Pedigree Investment Partners was smaller than the one he’d had at Puritan Bancorp before retiring as CEO four years ago, but he’d brought his impressive mahogany desk with him, and the table in the corner displayed a career’s worth of “tombstones” from major deals he’d done during his career at Puritan.

A version of this article appeared in the September 2006 issue of Harvard Business Review.