Retirement surge

The issue is an important one for CIOs, DiMatteo and others say. Many workers, including a high number of executives, are part of the baby boom generation that's set to retire en masse in the next decade or two. At the same time, fewer people are coming into the workforce; some CIOs are already seeing a talent shortage in the IT field. Meanwhile, the CIO's role continues to expand, requiring not only updated technical skills but also, increasingly, business acumen to successfully perform the job.

"The challenge for the CIO is to be really forward-thinking about this, to get the message across that [it] is really important" to train the next generation, DiMatteo says.

Regehr's already there. He's thinking about who will replace him. He's building succession plans for the two levels of management below him. And he's taking steps to make sure rising stars within the Boys & Girls Club can step up when needed.

How is he doing all this? He hired a professional career manager to work with one potential leader. He sends some workers to management seminars at the Georgia Institute of Technology . And he gives board-level assignments to others to help them develop new skills.