Over in the SIW discussion forums, a group of security officers were discussing how they deal with skateboarders and BMX bike riders who come to do "extreme sport" tricks on their property. Some took a soft approach and developed rapport with the kids and requested that they leave. Others put their hands on the gun and threatened to call the police.
Certainly this is something every business has to deal with, since trick riding can drive away legitimate customers and even expose property owners to liability concerns (what if Tony doesn't stick the landing on his fakie 360 pop shuv and instead cracks his head open on your pavement?).
Unfortunately, some of the world's parking lots and stairsteps are better riding terrain than some of the purpose-built skateboard parks (plus often simply a lot more convenient to where these teenagers live), so this probably isn't going away. Actually, you can count on the problem not going away, since the first skateboard tricks were developed in the 1970s and todays' top riders are still pushing the limits of what can be done on a board with two axles and four little wheels.
There's no easy answer to this problem, and since a bit of rebellion is a part of skateboard culture (it was when I rode during junior high, and still is part of the culture today), expect more confrontations. That said, as a corporate security manager or contract security officer, if you really want to earn the respect of your local skateboarding population, you might replicate the moves of the security officer in this funny little video clip from Fuel TV.