Ask any number of prominent businesses. U.S. Steel. UPMC. American Eagle Outfitters. Leaders from these employers and hundreds of others in southwestern Pennsylvania are concerned about the growing mismatch between skills held by local high school graduates and those needed in various industrial, technical or trade occupations.
Before I continue with my critique, I should point out that the demographic in question tends to be less geographically mobile and not everyone is going to go to college. People with only a high school education (or less) would comprise a substantial component of the long-term local workforce. Connecting chronically unemployed communities with job openings is a worthy cause.
A better strategy is to raid other regions, establishing a line of network in-migration. A good labor pool to tap is that of international migrants, but I would take anyone willing to move for a job over the unfortunate people who are stuck for whatever reason. Facilitating geographic mobility is as important as more education. Reforming local schools takes too long. One component of the current round of economic globalization is rapid change.
The era of captive labor is over. That's a good thing. The concern should be helping the stuck become more mobile, not allowing local business to keep wages low. The sooner Pittsburgh embraces a global labor market, the better.