How do you know when you’re struggling with technical debt with products from outside vendors?

My view is perhaps a little counterintuitive; the best tech stack is no tech stack. No, it's not really feasible I don't think, but even by using the word stack, it implies that "more is better" (see pancakes, cash, pillows, books). While that may be true in some circumstances, it doesn't always ring true when you consider the second- and subsequent-order effects of technology buying decisions. What does that mean?

It's easy to fall into the trap of thinking we are perfectly capable of making technology decisions. As leaders, we’re rewarded for sounding and acting confident with very little information.