Lots of IT shops nowadays are struggling to contain a BIG MESS while still providing new features that the business needs. So the skills that are most useful at

Lots of IT shops nowadays are struggling to contain a BIG MESS while still providing new features that the business needs. So the skills that are most useful at director level and above, are how to cope with the BIG MESS and how to extricate the business from the BIG MESS. Most likely this involves lots of compromises and the usual techniques of managing in the midst of chaos by evolving bit by bit to get closer to some overall architectural vision. As far as the technology goes, there are many ways to have an IT infrastructure without a BIG MESS. So technology does not help you here. What matters most is deciding on an architectural vision and leading the whole company towards that "better place". If you believe in silver bullets, then you will fail. If you read Peopleware and it made sense to you, then you are probably on the right track. There is a huge literature on management techniques to guide you. Pick a path that you can walk and just do it.