> I just really wonder what the team structures are like... Maybe you're lucky or maybe I'm benighted, but it's rare that an organization consciously decides t

> I just really wonder what the team structures are like... Maybe you're lucky or maybe I'm benighted, but it's rare that an organization consciously decides that this is the quarter to finish off the Java 5 migrations, even if that means delaying the Jabberwocky Project and even if there's a non-zero chance of customer impact. Partly because it's a really hard problem to attach an accurate and objective number to the value of something like that. > ...technical debt and the benefits and costs associated with varied approaches... That's not entirely accurate. Engineers are experts at technical benefits of different approaches. And they should be experts on the entire cost of the systems they are responsible for. But they're not necessarily experts on the benefits. They aren't necessarily qualified to anticipate what different features and different release schedules will do to the revenue for the product. In B2C companies with millions of users, you can run statistics and A/B testing to make this stuff more objective, but a lot of companies live and die by big sales to a smaller number of customers. So determining the benefits of shipping a month early depends a lot on knowing particular people well enough to guess how they'll react to good or bad news.