I've worked in both sorts of companies. The constant questioning may work well at smaller scale but kills productivity at larger scales. Putting aside that it inevitably becomes a political exercise as much as a technical one (because the different technical solutions almost always reflect competing priorities), it also requires perfect sharing of information across the organization, which does not scale.
Especially in any sales driven organization, I've seen it cause issues with infra teams questioning the need for certain features. Meanwhile, the answer is that the features are necessary because someone is willing to pay $$$ for them.
Especially in any sales driven organization, I've seen it cause issues with infra teams questioning the need for certain features. Meanwhile, the answer is that the features are necessary because someone is willing to pay $$$ for them.