[tstrimple]

Have you mostly worked for younger tech companies or were they "traditional" businesses who had to be forced to adopt technology? The places I've seen with the biggest challenges are all large old and well established companies. Think insurance, transportation, agriculture or healthcare. Places where the people who managed the entire system out of file cabinets a decade ago now manage the document repositories they don't understand and they are still bitter about it.

The insurance company was known for hiring contractors and keeping them on the bench for months to years just in case they needed them. I also remember while working there a particular Big Three consultant kept showing up in people's meetings and never speaking up. No one could figure out what he did or why he was there, but the agency was billing $500 / hour for his time and no one could figure out how to get rid of him. It was a complete shit show. This doesn't even touch on some of the major technical blunders they made throughout the years. Just a few small personal anecdotes.

The transportation company was even worse. Literally the worst company I've ever spent time at. It only employees around 15k people, so it's quite a bit smaller than the above insurance company. All signs indicate that this company was well run by the founder. But not by his sons who inherited it. They had a driver turnover rate of over 100%. If they needed 100 drivers for the year, they would have to hire 105 drivers throughout the year. They just constantly churn through brand new drivers, train them up and lose them to other companies through incompetence. One of the consequences of constantly burning through brand new CDL drivers is you have higher accident rates. The project I was brought in to consult on was a driver monitoring system. So if the driver braked too hard or swerved too fast it would create an incident and the driver would have to talk to someone after their route to explain what went wrong and how to prevent it in the future. I can't imagine why they had turnover problems! Their entire IT org was run in a similar dysfunctional way.