Information technologists live in interesting times. The Internet continues to bring the platforms and services that mostly eliminate the problems inherent in the PC-based client/server era, such as large upfront capital investments, slow deployment of new or changed services and a daunting set of security issues rooted in its birth as a non-shared technology (i.e. DOS PCs with a dinky floppy drive and molasses-slow modems) attempting to thrive in the interconnected world of email, web-based services and ever-increasing bandwidths. While using the Internet has its own scale issues, it's clear to everyone from the board room to the kid's bedroom that PC knowledge is moving down in value, and knowledge of the Internet is moving up.
Dealing with change is hardly unique to IT people, but perhaps it's the constant, year-in, year-out bombardment of change that is not as prevalent in other fields. The way I've described it to people I've been fortunate enough to work with is to set their expectation, and my own, that twenty percent of the value of their current skill set is lost every year. Just to stay even requires learning a new twenty percent each year. This obviously is an estimate, varies from person to person and is greater in some years and less in others. But overall it's not far off and the point is not precision, it's direction. Stay still for long and your risk of being obsolete gets higher and the effort to retrain to an entire new skill set becomes tougher.
A technology leader must work with each and every person to insure that this does not happen. They must provide the constant push required to change their people, and the education, projects and rewards to pull them forward. It's easier to let people stay in a job and avoid the short-term productivity hit. It's easier to let someone convince you that they're happy where they are and avoid the whining. But it's harder to change attitudes baked in over years of stagnation and retrain, for example, a mainframe COBOL programmer in Java, C++ or Ruby. If they're lucky enough to time their retirement to their obsolescence, they're in the fortunate few. Most take jobs in less demanding parts of IT or leave the field entirely.
One of the most effective methods of gaining people's attention is to purposely, publicly and continually eliminate older technologies. That elimination may take the form of outsourcing the old mainframe systems, replacing dial-up modem banks with an Internet ISP or manual PC software installation with an automated system. This is, by far, not the only benefit you'll gain from this, but emphasizing the constant "out with the old, in with the new" mantra will send strong signals throughout the organization.
Change can be overwhelming to people, particularly ones that are large or arrive as surprises. The previous suggestions deal with the surprises, but what can be done to keep change in manageable chunks? Fortunately, that's where the twenty percent comes in handy. It's not that large if handled on a continual basis. But a totally new twenty percent is much more difficult than one that is somewhat familiar. Asking a programmer that knows several languages to add Ruby to that list is nowhere near as difficult as asking them to configure routers. Asking a network analyst to configure firewalls is probably better than asking them to learn a programming language.
While keeping within one's area and learning new skills is a good tactic, the people that are very valuable have skills in many areas, ready to pitch in on just about any project that comes around. Some people seem naturally born or gifted to play in all areas, or maybe they just get bored more easily. Regardless, your organization needs to move people around departments and the earlier they learn this the better.