Some managers are good at managing, some are not. You don't even have to be a top tech wizard to be a good tech manager. (Although, zero tech experience is usually a recipe for disaster.)
And "old stuff" is not necessarily bad stuff. It's often road-tested by time and more reliable than newer stuff. For example, our ASP Classic stuff has proven far easier to migrate to different servers than ASP.Net. ASP.Net is config-picky.
Perhaps because because ASP Classic is a "dead" language, MS doesn't bother changing it every version. It's similar to the reason Latin is used in science: nobody's fiddling with it because it's a "dead" language, which makes it stable.