In this chapter, the author tells the story of two comparable projects but with very different outcomes: one failed miserably requiring a rewrite while the other one successful even after many revisions. To me, the most important factor is to have everyone having the same big picture.
This is much easier said than done. From personal experience, even a relatively simple diagram can be interpreted differently by different people, even after numerous meetings and even when everyone agrees! It is very dangerous for an architect to have a false sense of group agreement.
A few words on the technical debt. My experience is that technical debt is hardly ever repaid especially in a large-scale software development. Typically in a large development the responsibilities of each team becomes very specific: with each team responsible for a module or a single aspect of the overall product with separate testing teams, regression teams, system testing teams, etc. Suddenly repaying the technical debt requires buy-in from multiple teams. One would not want the testing manager griping about rerunning the same tests and the schedule impact. It is equally difficult to justify to the upper management the additional time to work on something that's already "working".
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