I'll go first.

In my experience, it seems that just about every engineer I've worked with is on board with reducing tech debt, but the struggle mainly comes from convincing upper management that these things are worth working on.

I'm fairly convinced it's due to some combination of the following:

• inability to persuade on my part
• inability of middle management to fight for prioritizing reducing tech debt
• inability of upper management to understand the consequences of ignoring tech debt until it's too late

I'm curious to hear others' experiences fighting this fight.