If you help other people solve problems, you may have run into this phenomenon: a person gleefully tells you how messed up their environment is. Processes make no sense, roadblocks are everywhere, and all previous attempts to make things better have failed. As you explore the details, you talk about directions to try. But every suggestion is met with an explanation of why it won't work.
I say that these folks are "in love with their own warts." That is, they know there's a problem, but they've somehow been acclimated to it to such a degree that they can't imagine a different world. They will consistently point to outside agents as the author of their woes, without realizing how much resistance they generate themselves.
Over time, by the way, there's a reinforcing process. People who think and talk this way will cluster and drive out the less cynical.
These people can be intensely frustrating to work with, until you understand them. Understanding allows empathy, which is the only way to get past that self-generated resistance.
The first thing to understand is that any conversation about their problems isn't really about their problems. An opening statement like, "We tried that but it didn't work," isn't really asking for a solution. Instead, it's an invitation to play a game. That game is called, "Stump the expert." The player wins when you concede that nothing can ever improve. You "win" by suggesting something that the player cannot find an objection to. It's not a real victory though, for reasons that will be clear in a moment.
Why does the player want to win this game instead of improving their world? For one thing, any solution you find is an implicit critique of the person who has been there. Suppose the solution is to shift a responsibility from one team to another. That requires management support in both teams. If that solution works, then it means the game-player could have produced the same improvement ages ago, but didn't have enough courage to make it happen. Other changes might imply the game-player lacked sufficient authority, vision, credibility, or, rarely, technical acumen.
In every case, the game-player feels that your solution highlights a deficiency of theirs.
This is why "winning" the discussion isn't really a win. You may get a grudging concession about the avenue to explore, but you're still generating more resistance from that game-player.
My usual approach is to decline the invitation to the game. I don't try to find point-by-point answers to things that have failed in the past. I usualy draw analogies to other organizations that have faced the same challenges and make parallels to their solutions. Failing that, I accept the objections (almost always phrased as roadblocks thrown up by others) and just tell them, "Let me handle that." (Most of the time, I find that people on the opposite side of a boundary express roadblocks from the other side that all eventually cancel each other out. That is, the roadblock turns out to be illusory.)
I'd like to hear from you, dear Reader. Assume that you cannot simply fire or transfer the game-player. They have value beyond this particular habitual reflex.
How would you handle a situation like this? What have you tried, and what works?