> This is only because they are focused on some narrow aspect of the business

Is this a bad thing though? If some technical decision has downside risk, I’d reasonably expect:

- the affected stakeholder to bring it up

- the decision maker to assuage the stakeholder’s concern (happy path) or triage and escalate

I think you are right. It's still worth encouraging people to question decisions even though most of the time it won't be the right compromise for the business.

One of the most regulated industries, aviation requires crews to go through crew management training where it's explicitly trained for lower level staff to raise concerns in spite of perceived superior knowledge.

Some of the biggest accidents have happened directly due to this. Like Tenerife where the flight engineer had been listening to the radio and raised doubts about the runway being free but was ignored by the overconfident captain.

I don't know how to calculate "usually", in my experience people who question decisions in my company are shot down because the decision makers are usually (no pun intended) very incompetent and the questions make that visible, even if not intended. Many companies that I know are so corrupt that competent people are considered to be dangerous for the status quo.

This is definitely a best case scenario.

As important as I think questioning is, there’s another side of it where people push their own agenda with questions on topics that were decided by other/more senior people hashing it out. At some point this does need to be dealt with. All I see is the yapping questions wasting meeting time, though.

This thinking pattern exactly illustrates how a group of very intelligent people can make disasterously bad decisions without anyone challenging them. Don't look for holes in the the arguments of people saying you are making a bad decision, look for the information they have that you do not have or have not explicitly analyzed. If you think you have all the information that the org possesses, go right ahead and make your choices without others; you might be lucky and be Steve Jobs post 2000.

> Usually the people who question decisions are shot down because they don’t have a wholistic understanding of the decision and (respectfully) don’t have good arguments.

It takes months of dysfunction until the customer says "I do not want to work with you anymore" or until the "overtime and over budget" thing suddenly becomes too large and problems show up in numbers. Or until key team suddenly completely decomposes. Every single time I have seen that, multiple people tried to communicate about the issue and were shot down.

It is not like management was always "wholistically" right and everyone down there just dont see big picture or have bad arguments - they usually just do not know what is going on on lower levels. Failure to actually listen, whether because it feels bad or because it would take time is quite common.