tl;dr:Max discusses the implications of letting things go sideways, as opposed to stepping in and creating a short-term fix, and the longer term positive impact this strategy can have on the business as a whole. “It represented an important learning opportunity for the broader business which would generate broader buy in and allow us to dramatically improve process.”
tl;dr:"Now with a complete list of your tech debt as it stands go through each and answer the following questions: (1) If we choose to do nothing, will this issue become worse, remain the same, or improve? (2) If it'll become worse, how quickly will it degrade? (3) If it remains the same, how much disruption is it causing today? (4) If it'll improve, at what point will it improve to the degree it's no longer an obstruction?"