I was talking with a prospective client that had spent the past three years rushing a SaaS solution to market. They even referenced the technical debt as an area they need help with overcoming as they move forward.
Second order change is difficult for any organization or established project, but remaining consistent with your message can drive the process in that direction. Sounds like a challenge for the two of you, but try to bring solutions / recommendations instead of minor resistance that might get misinterpreted. Not easy I know.
Hard space to penetrated but with a lot of federally funded initiatives the past few years. New regulations around EHR is driving the space.
They need to die off, in a career sense. Any help I give them, even when well qualified and executed on my part (i.e. despite them / their attitude) is just adding to the problem.
Seriously. There are a lot of "morons" and "jerks" out there who need, simply if painfully, to be "disenabled".
(And, to some extent, if their/the customers suffer, well, those people voted with their feet in becoming customers. In our "free market" society (this is a U.S./"Western" perspective), it's somewhat akin to our politics: You can bitch all you want about the politicians and how they are screwing you over, but YOU elected them.)
My buddy and I have been resisting "quick changes" on projects that have a lot of technical debt for a number of years, and what has happened is that managers have just gone to some other less experienced developers who have no scruples to get their changes done without the "fuss". Our reputations have taken a bit of a hit as well - we're "too careful" or don't see that the "perfect is the enemy of the good" etc. That's what they say in front of us, I'm sure they're more colorful when we aren't listening. I've learned to mitigate this by working with a couple of managers that aren't clueless but it's a danger when that isn't an option...