An early proponent of leading from behind

was Nelson Mandela, according to the New York Times obit (by Bill Keller):

In his autobiography, Mr. Mandela recalled eavesdropping on the endless consensus-seeking deliberations of the tribal council and noticing that the chief worked “like a shepherd.” 

“He stays behind the flock,” he continued, “letting the most nimble go out ahead, whereupon the others follow, not realizing that all along they are being directed from behind.” 

That would often be his own style as leader and president.

[Update via Smartypants, citing Mandela's biographer Richard Stengel: Mandela used the term directly:

Mandela loved to reminisce about his boyhood and his lazy afternoons herding cattle. "You know," he would say, "you can only lead them from behind." He would then raise his eyebrows to make sure I got the analogy.

[Update 2: Note that the original association of Obama with "leading from behind," in Ryan Lizza's New Yorker analysis of his foreign policy, incorporates the shepherding metaphor (and in Mandela's case, experience):

Nonetheless, Obama may be moving toward something resembling a doctrine. One of his advisers described the President’s actions in Libya as “leading from behind.” That’s not a slogan designed for signs at the 2012 Democratic Convention, but it does accurately describe the balance that Obama now seems to be finding. It’s a different definition of leadership than America is known for, and it comes from two unspoken beliefs: that the relative power of the U.S. is declining, as rivals like China rise, and that the U.S. is reviled in many parts of the world. Pursuing our interests and spreading our ideals thus requires stealth and modesty as well as military strength. “It’s so at odds with the John Wayne expectation for what America is in the world,” the adviser said. “But it’s necessary for shepherding us through this phase.”

The Times obit also stresses Mandela's supreme self-confidence:

Unlike many black South Africans, whose confidence had been crushed by generations of officially proclaimed white superiority, Mr. Mandela never seemed to doubt that he was the equal of any man. “The first thing to remember about Mandela is that he came from a royal family,” said Ahmed Kathrada, an activist who shared a prison cellblock with Mr. Mandela and was part of his inner circle. “That always gave him a strength.” 

Leading from behind is a mark of strength, embraced by those who don't need to preen or posture.

Of course, such leadership techniques are as old as humanity, as humans don't easily cotton to being led (at least, a significant proportion of us don't). Only political partisanship and a cult of the imperial presidency transform "leading from behind" into a term of opprobrium.

Nor is the term particularly paradoxical.  Etymologically, the association of "leading" with being in front is a late accrual:

lead (v.1)

"to guide," Old English lædan "cause to go with one, lead, guide, conduct, carry; sprout forth; bring forth, pass (one's life)," causative of liðan "to travel," from West Germanic *laidjan (cf. Old Saxon lithan, Old Norse liða "to go," Old High German ga-lidan "to travel," Gothic ga-leiþan "to go"), from PIE *leit- "to go forth."

Meaning "to be in first place" is from late 14c. Sense in card playing is from 1670s. Related: Led; leading. Lead-off "commencement, beginning" attested from 1879; lead-in "introduction, opening" is from 1928. (Online Etymological Dictionary)

"Steering from behind" would not even suggest a paradox:

steer (v.)

"guide the course of a vehicle," originally by a rudder or something like it, Old English steran (Mercian), stieran (West Saxon) "steer, guide, direct; govern, rule; restrain, correct, punish," from Proto-Germanic *steurjan (cf. Old Norse styra, Old Frisian stiora, Dutch sturen, Old High German stiuren, German steuern "to steer," Gothic stiurjan "to establish, assert"), related to *steuro "a rudder, a steering," from PIE *steu-ro- (cf. Greek stauros "stake, pole"), extended form of root *sta- "to stand" (see stet).

The notion is of a stiff, upright pillar or post used in steering, or else perhaps "establish," hence "direct, steer."

"A firm hand on the tiller" is a fit image of leading from behind.

So, come to think of it, is "the Lord is my shepherd."

Update 3: via Google, I see that ThinkProgress's Ben Armbruster made the connection between Mandela and "leading from behind" back in June 2011.