Learning to let go.

• Position: Dismissing workers in North Carolina's 100 largest private companies

An employee who's fired may feel the boss is a Simon Legree with ice water in his veins. But several North Carolina 100 CEOs say their toughest decisions involve dismissing workers. "You have to do it if you're going to be honest with everyone else, but it's the thing you like the least," says G.A. Sywassink of Standard Holding, a Charlotte-based trucking company.

"It lingers in my mind as to the fairness of it," says Richard Hedgepeth of Raleigh-based Electrical Equipment Co., who several years ago fired a midlevel manager because of a personnel conflict.

"Unfortunately, you never get to the point that everyone works out, whether because of business changes or performance issues," says Sywassink, who led a group that bought Standard Holding in 1987.

When a CEO replaces a top manager, it's more than just a personnel decision. Five years ago, Roy Davis of Concord-based S&D Coffee hired a new COO, "replacing an old and loyal friend," Davis says. "We literally loved each other almost like brothers."

S&D had seen two decades of double-digit annual growth, boosted in the '80s by sales of soft-drink fountain syrups to convenience stores. But when wholesale grocers began delivering the syrups at less cost in...