Justin, I really like this post. From my perspective the biggest hurdle out of the ten is constantly facing the 'Wall of Process'. This is especially true in larger ITs when we are working in an Agile manner and their processess have been established to 'control' everything. I like to think of this as the Productivity to Risk model. The more an IT tries to control risk the less productive they become. Of course risk mitigation is warranted; however, the problem is that many ITs only have one risk management process which is set to deal with the highest degree of risk making everything terribly inefficient.