Most of the tech industry is built on easy money. Fast growth which required little effort.
All of these people think that they worked hard for their money, but what they call 'hard work', I call 'easy peasy' and what they call 'very risky', I call 'low risk'.
99.99% of the population would probably turn to communism if they had worked as hard as I did for so little reward... That said, my stance is apathetic. It's all the same to me.
If you can get by in one hopelessly crooked system, you can probably get by in a different hopelessly crooked system.
They should have their own judgement on the effectiveness of their direct reports. The problem is that they trust their own judgement while having poor judgement themselves. Trust could also be an issue but assessing effectiveness is something gained over time, not self-declared.
I’ve always seen it as an offshoot of the mentality that fixing something old is often delaying an inevitable new purchase (especially when it comes to tech). Total armchair theory based on how if it’s limping along usually they’ll go “well just keep using it we’ll upgrade later.”
There's a trust factor. For some reason, upper management doesn't necessarily trust the judgement of their lower management, like like lower management rarely trusts the judgement of their engineers.
There's an information disparity. Upper management often doesn't see what people on the lower rungs of the org chart are doing. To upper management, it looks like the one who's getting all the things done is lower management, not the engineers.
There's also a psychological factor. For some reason, humans are much more likely to overpay for something new than to pay far less to maintain something old. I'm not entirely sure why, but I see this mentality affect everybody from upper management to engineers to people buying cars.
There's also the ego factor. I've seen some business owners react very, very poorly to having an employee request a raise. It can be perceived as somebody trying to take more money out of your pocket for no return. This can also be applied to larger companies and budgets, bonuses, etc.
There's also the "fiefdom" factor. Your management might see expanding your team from 1 engineer to 19 as an improvement to their social standing in the company regardless of how much money it costs the company. The larger your department, the more important you're perceived to other departments and the c-suite.
edit: spelling and clarity.