I could have sworn when I read this that I'd written something on the subject before. I found a few tangential posts, but the best stuff I wrote was in some private emails I sent.
I got close in this Obamacare post from 2010 about our messaging failures:
Who among conservatives figured this out ahead of time? Why isn't this basic work being done? By anybody. RNC, Club for Growth, Senate Conservatives Fund, CATO, Heritage... Don't care who.
Do we blame the basic infrastructure of the right? The party organizations exist only to win elections short-term, not fight extended philosophical battles. Think tanks exist to make philosophical and factual arguments, and to suggest policy, but rarely step into "campaign mode" against bad ideas. Occasionally an issue group will step up, but it had better be well-funded and organized. Who out there applies campaign principles to winning policy debates and the long-term cultural battles?
I originally thought that the then-newly-spun-off Heritage Action might be able to take up that task, but frankly I've been a little disappointed.
Related reading: Ace of Spades on political conversions.
Frankly, the situation is depressing. We could be doing so much more, so much better, and nobody's interested in doing so. Not that they'd know how if they wanted to.