>but in our case, the purchase decision was rarely made by the person who actually had to use the software. And you have to get those people on board. If anything, they're more important, because they're the ones who are going to make the bosses life hell if the software they buy isn't doing the job - or worse - is doing the job too well.

>Over and over again, we saw internal sabotage. People would simply refuse to change processes, and would find any excuse. "Oh, the software didn't work, so I had to go back to doing it manually".

This one resonated with me, from a former workplace. Even when their jobs were nowhere near at risk, people don't want to change habits. The employees did not get paid more for being more productive, so they would find fairly pointless excuses for not using tools that made their lives easier.

Ultimately, it's a problem with management and their incentives (or lack thereof).