In other words, to get NGE underway, users need to stop thinking "know-how" (which button do I press?) to "know-why" (what is the underlying information architecture and process design this piece of software is trying to support, and what consequences does this have for my behavior and productivity?)

While I do not disagree with you that that would be nice, the world wants it otherwise. Most people (the least interesting portion of humanity, but nevertheless) is not interested in how things work, or why they work. Even the net generation which is now entering the workforce is not interested in how things work or how they can change them to any higher or lower degree than the generations that came before them. They have access to better tools (Facebook, for instance) and therefore can easily do what it would take a programmer to do only a few years ago, but ability to Tivo, Google, text, Twitter and Facebook does not a reflective and analytic mind make.

Programmers actually hang back a bit on the new tools - they prefer their computing more barebones, but also more flexible. In his brilliant essay "In the beginning was the command line", Neal Stephenson distinguishes between the Eloi (happy to deal with technology at a metaphor level) and Morloks (want to dig down, preferably using EMACS). He makes no judgement as to what group has the more satisfying or productive life (in fact, he cannot see any difference) but concludes that the difference in outlook is immense - and that things that work for the Eloi would not work for the Morloks and vice versa.

Consequently, if we are going to get companies into an NGE state, Enterprise 2-0 and so on, I think we will need to recognize that the vast majority of employees are lurkers in the knowledge and information creation game, happy to listen, use what is useful, push the buttons that get things done, and go on with their lives. The key difference the software makes is that creativity and productivity in a digital domain is more visible across geographical and organizatorial fiefdoms. This will increase the career prospects and influece of Morloks until the tools are simple enough that the Eloi will usurp them.  Which they will do, being the majority.

As I have written myself, not knowing technology is dangerous, because if you do not know how things work, you can make bad decisions. But in the long run, technology fades into the background and the technology providers fade into support roles. In the short run, there is money and influence to be had, but that has to be managed as a temporary competitive advantage - get the most out of it while you can, then commoditize it and move on to the next new thing.