Too many to count, my top items:
1) Consistently penny smart, pound foolish. For example trying to lowball new hires saying "you get what you deserve over time" just results in people not being happy and leaving since raises are slow to non-existent. Trying to squeeze into a seeming arbitrary budget but canceling projects to engineer desperately needed replacement systems.
2) Way too much churn around management (no CTO lasts over a year) and direction - nobody wants to be accountable for a decision. Impossible to know what direction to invest in and which to migrate away from since the plan changes every quarter.
3) Following the above - most systems and processes are massively out of date. There are still Windows 2003 servers serving critical roles and most pieces of the infrastructure are multiple revisions out of date.
4) Cloak and Dagger non-sense. "Security" is paramount and there are literally hundreds of people in Security who get to say no to what technologists want to do but they are not responsible for keeping most of the Security tools running. Most technologists aren't officially allowed to know what Security software is loaded onto all desktops and servers, but almost trivial troubleshooting uncovers one of the dozen tools in slowing down performance or breaking something. Nobody is allowed to talk about how their "proprietary" system works since it's a secret - yet it turns out so much is just duct taped together with Excel, VB scripts, and other terrible non-enterprise solutions since nobody was willing to work with and share with another part of the firm and implement things properly. This despite the entire hypocritical focus on What Good Looks Like.
5) 0 development in anything that matters. No training on technology, it's all management principles training - or forced indoctrination into a "way of being" that just does not work with technology.
6) The constant threat of outsourcing. The Bridgewater method just doesn't work for technology - once you have a system it needs grunt work to maintain (as opposed to investing where often the smartest thing to do in don't do anything while you weigh options) - there is a constant desire to outsource the technology teams creating FUD about people's jobs and mental anguish.
