Boss was a total bully - was not coached, was expected to be perfect from day one. Most of the issues I faced were all considered "my fault" but policies were put in place for people hired after me that would prevent those issues from happening to them.
Two out of four projects that I was assigned out of the gate had scoping/estimating issues and it was on my shoulders to fix it.
Disorganized - lots of disjointed systems that were time consuming with lots of opportunity for error.