Often, 'leaders' make mistakes and people below suffer the consequences. It is important to let these leaders deal with the pain caused by their decisions from their cluelessness about how things work.

I’ll ask for something preventative or that otherwise hardens our systems. They ask “is it a need?” and I’ll say something like “we can function without, but that means we have a 5-10% chance in the next 6mo of having a major failure and embarrassing ourselves in front of a live audience in the thousands as well as our client.” They then decide how much that risk is worth to them, and whatever they decide is kind of out of my hands at that point. If the thing I warned them of comes because they didn’t pay for it, I can point to the receipts (though I’ve never had to, we’re small enough people remember those conversations).

60% of the time they just get what I need maybe? But ultimately it’s about CYA. Tell them what’s up, tell them what the solution is, tell them what the consequences are if they don’t do the solution, and make them decide.

Again this obviously depends on company culture and structure, but I can’t imagine on the only person who can do this!

I don't think that's it. Emergent problems require attention and action from leadership, who in turn can make the problem visible to higher ups. This creates signal, and positive feedback when the problem is fixed or mitigated.

If the problem doesn't exist to begin with, there is no signal. Managers don't get to show their fast-acting skills, and there are no heroics to speak of.

So ultimately poorly maintained and managed projects who deliver fixes for problems of their own doing create a perverse incentive, whereas no one is lauded or promoted for doing normal day-to-day things.

At some point in one's early single-digit they learn that touching hot stuff hurts. They start to avoid stuff that they know is hot, but still come in contact with hot stuff accidentally. Later they learn techniques minimizing probability of touching hot stuff even by accident. By the time one reaches twenty or so, the only times a person burns themselves is really by being way too reckless.

> Like it or not, sometimes the best thing for an organization isn't to just fix every problem and prevent it from bubbling up; it needs to be treated like a learning opportunity for org leadership, which means sending the pain signals upward before just repairing it.

Should we accept that management as a whole is in general more clueless than your average teenager? The "learning opportunity" should, ideally, happen exactly once, realistically once in a very rare while.

> It's important to coach people on the idea that in large group sizes, it's more efficient to let certain kinds of problems play out and not be so reactive to them.

You are conflating two things here, I guess. Yes, some "problems" are not worth to be fixed proactively or at all, but that has very little to do with group sizes, it's a "simple" cost-benefit tradeoff. As groups grow the left hands tend to become increasingly unaware of what the right is doing and that is the primary reason why we have management class in the first place.

The problem OP raises is attention span of the metaphorical gold fish in the management layers. Even if a department does everything in their power to communicate impending problems, do risk weighed cost-benefit analyses, get proactive treatments pre-approved by higher management, the same higher management forgets the risks and costs savings once they have been mitigated, effectively incentivizing firefighting. Some teams gradually fall into eternal firefighting and burn out, others start manufacturing fires to get rewarded. The biggest problem is that it is nearly impossible to tell the two apart.