I should say that I had a consulting partner who had a cap that said something similar... he was very proud of it because he had worked very hard to recruit a team with a great deal of drive and initiative.
I would agree that, in the context of what your consulting partner had accomplished, the saying reflects positively.
There’s a longstanding axiom of textual criticism that reads: text without context is pretext. The axiom obviates the extraction of a lofty phrase from a high-minded context for use in a dissimilar context, especially if — as is too often the case — the aim is to falsely project the high-mindedness of the known context into the current, dissimilar context, or to otherwise apply a shining veneer of nobility to that which is of lesser character, be it merely pedestrian, mildly ignoble, or utterly damnable.
Thus, your consultant friend would likely object to his favorite hat being worn by some poseur who had merely risen to the level of this own incompetence; like Dilbert’s pointy-haired boss, or his coffee-swilling co-worker, Wally.
In the same way, I think the phrase fits the McCain/Palin pairing. Yes, the pick was great in that she is a very strong Conservative who brought great credibility to the ticket, and to that extent McCain’s team deserves credit for a good choice, but the glaringly obvious result was that she forced him to run after her. Quite unintentionally, the “Leader” became the follower; the Head became the tail. Sarah Palin’s energy, and passion for Conservative policy (read that “the practical application of right-minded thinking, a.k.a. ‘common sense’) eclipsed his own; casting his comparatively dispassionate demeanor into such stark relief that he really had to scramble to try to hide the contrast. THAT effort was a flop, which only served to give legs to the idea that the entire McCain campaign strategy had — from Day One — included a final scene where the Senator would take a canvas nap in the final round so that America could have her first black President.