There is incentive to stay quiet: getting the paycheck and a stress-free evening with my family.

I mostly said nothing since it seemed no one was interested.

During the contract, I wrote a doc about the shortcomings, problems, and potential solutions, adding to it whenever I ran into something. From code to management to tools used.

When my contract ended, I sent the doc to a couple of people who I felt needed to read it. They loved it, and passed it around to practically everyone. I had emails from offices all over the world with questions about it.

I didn't renew the contract since I had already moved on to other things.

If I had that time again, I would speak up, but I would do so with a well-thought-out document.

But I have to push back?

Just end middle management and the issue from that article suddenly vanishes.

I was an independent contractor for a large bank. My contract kept getting rolled so I ended up there for a few years even if the original piece of work was an 8 month job. A new CIO was appointed during my stint and a huge new IT initiative was launched to replace the decades old core banking system with a "modern" off-the-shelf "bank in a box" product that Oracle had recently purchased. This product was new and had been "successfully" launched by a tiny 8 branch bank in Ghana. The bank I was working for had hundreds of branches in multiple western countries. The product did not fit in any way/shape or form the existing processes in the bank, it's technical infrastructure, the regulatory regime, its retail products nor employment law (employee time is expensive in western countries - so solutions involving throwing bodies at menial repetitive tasks are not viable).

I had been at the coal-face for nearly a month of day long meetings with the vendor to try to get a single niche savings product supported on their system and it was torture. I could see it was never going to work. I had no notions that my lowly opinions would have any sort of impact but I made my opinions clear to my immediate manager - especially over lunch and when we would occasionally go to a nearby bar to watch sports after work. I eventually convinced him of the folly of the entire enterprise.

At some stage, he then spoke up to his manager expressing reservations who then called me in for an aggressive grilling on why I thought the new strategy was bound to fail. I explained - but he seemed unhappy with me and I was sure my contract would not be rolled - not that cared at that stage, I was hating the work at this stage.

I later found out that I must have had some impact because this manager brought up some of the reservations and issues at the next C-level meeting. He was promptly told by the new CIO that either he was either going to be a team player and get fully behind the initiative or else he was out as there was no room for saboteurs and passive blockers.

He got in line. I left of my own volition anyway. Two years later, the project was cancelled, the CIO fired and an $80m lawsuit with Oracle was the result. No real "moral of the story" - just that at some point up the hierarchy "push back" will meet the "owner" of the initiative and the pushback will quickly die.

Putting a price on the decision? This is very bold statement, there are few people on the planet who can give right predictions about the price of the decision.

Imagine engineer saying: "this will ruin our company"

CEO: "What? excuse me, how did you come to this conclusion? what analysis have you run? how did you get these numbers?"

I don't think what you are describing is easy to accomplish in practice, you made it sound simple, but complex systems don't operate this way. You have 100 departments, each can contribute 1 tiny problem and combination of them could lead to catasthropic outcome, but in isolation price feels like negligible or too small, no one can put the price on the decision

And when such negative feedback arrives, they don't get all Colonel Kilgore from "Apocalypse Now" and decide that CHARLIE DOESN'T SURF.

You can push back and change decisions that happen one layer above but can't do much more than that unless you want to become an activist.

You have to have trust that the higher ups are smart enough to be trusted with the decisions.

But make no mistake: this is also a result of so many countries' piss poor work laws. I can push back against my CEO and happily do so and tell him it's a terrible idea, because the worst that happens is that he gets pissy, but I will not get fired because of it, not get fired because of putting it in writing, because firing people for that would be wrongful termination. Boeing scale fuck ups could only have happened in the US because those engineers would be fired for speaking out.