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.
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.
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.
The entire idea of "can do vs can't do" is such a platitude anyways, it's not even remotely interesting. It takes all nuance away from communication. As if just because someone has to make their position clearer than a statement like "yes, if" in order to manage the expectations of others that they just don't have a "can do" attitude and by implication are destined to fail.