This is really difficult. Perhaps the best thing is to track the proposed technical debt stories, and do not discard them when they are rejected. Instead, also keep track of how much pain is hit that can be associated back to that particular technical debt.
3 years into major project, my team finally got prioritized to work on and improvement that will take us a couple weeks, that we were not able to work on previously because we could not justify its value. But for the past 3 years the organization has lived with pain that this would have resolved. So now we can justify it. And the thing is, it's not like we didn't know 3 years ago when we said we wanted to make this happen but things are going to be terrible if we were not able to prioritize it but in many organizations it's not good enough to just say how bad things will be. People need to actually have felt the pain.
Honestly, I think that's okay on its face. My bigger issue is that frequently there is no or very little trust around engineers who predict what the major problems will be an advocate for them and then it's not like when they're proven right management now listens to them the next time. I think that's the real problem.
3 years into major project, my team finally got prioritized to work on and improvement that will take us a couple weeks, that we were not able to work on previously because we could not justify its value. But for the past 3 years the organization has lived with pain that this would have resolved. So now we can justify it. And the thing is, it's not like we didn't know 3 years ago when we said we wanted to make this happen but things are going to be terrible if we were not able to prioritize it but in many organizations it's not good enough to just say how bad things will be. People need to actually have felt the pain.
Honestly, I think that's okay on its face. My bigger issue is that frequently there is no or very little trust around engineers who predict what the major problems will be an advocate for them and then it's not like when they're proven right management now listens to them the next time. I think that's the real problem.