[alumic]

Along these same lines, it is common at my organization for people to gleefully say "welcome to ${ORG}!" or "It's the ${ORG} way!" in response to some failure that comes down to managerial knee-jerk or some fundamentally broken process.

It always seemed so perverse to me to promote this sort of tacit approval--as you say--passing it off as "cute" instead of... improving things.

[aljgz]

Throughout my career, I spent too much time trying to change organizations. I later realized that changing culture is prohibitively difficult when one person or a minority are trying it. I now know that it's better to "choose my battle". Only focus my energy on things that really matter, give a friendly comment, maybe coated in humour in all other situations. Cultural problems happen for reasons, and those reasons are usually very hard to change, like personality of the executives.

[alumic]

On swaying culture in any meaningful way: I thankfully learned that lesson early. It's one of the reasons I'm grateful for having worked here. As someone building a product on the side, it's been very useful to see how much influence executives can have on the business' culture. I've spent a fair amount of time reflecting on the problems my own personality might cause.

[squigz]

Are the people making those comments often in positions to be able to improve things?

[alumic]

I've heard it spoken by members of upper management, which obviously serves to reinforce the culture (and was a massive red flag for me at the time). I will say, though, that management is very open to improvements in procedure so it's more that the rank-and-file have accepted the status quo. They also have a habit of promoting a spirit of entrepreneurship within the company, which seems to be the thing that keeps me coming back for more.

[squigz]

Let me put it another way: Are the people making those comments responsible for those procedures?

Having seen this sort of thing many times, and being in that position myself, it seems more about it not being the "rank-and-files" responsibility to fix these things. I'm not going to deal with the process and bureaucracy in order to (try to!) fix processes that are above my paygrade - and with no guarantee things will change in any way

In short, this is a sort of coping mechanism

(Obviously this is less applicable to upper management)