I think the entire point is that they say the same thing while projecting a completely different attitude.
The way that someone responds to the question of "can we do this" is very important.
We typically call this middle management.
Regardless I'm not really interested in the blame game on who's responsible management or engineering. Both are irrelevant to this discussion. "Can" or "can't", as the article discusses, is an issue of leadership in a business. If it isn't there, it isn't going to matter whether the engineer says "how high?" whenever their asked to jump.
Cynics always have scapegoats. It's always everyone else's fault. Dumb colleagues, idiotic managers, stupid customers. Just remember you control your situation and how those around you interact with you.
The 'Yes, if' thing is one of the major reasons I love startups.