So I went, in my wayback machine, to the early days right after the crash. Hugo needed the manifest so he could compare it with the census he'd taken. (Of course, it was Hugo who alerted the survivors that they had a mole among them. Key.) James had the manifest, only he wasn't James then; he was Sawyer. Sawyer was a mean guy who hoarded all the goods he could get his hands on, and anything you wanted from him came with a price. So Hugo told Sawyer that he should just give up the manifest for free, "because, Dude, you could use the points." Sawyer gave it up with a comment about how Hugo knew how to talk to people. What did Hugo say? "It's a gift."
Later he conned Sawyer into being nice to everyone by telling him he was about to get banished from the beach camp, and let's not forget when he conned Sayid, Kate, and Miles when they came to the Barracks looking for Charlotte. Hugo knows how to talk to people, how to appeal to their better nature and make them see that it's in their best interest to do what he says. These are the qualities of a natural leader.
We've seen a couple of times now that Hugo is the one Jacob has chosen to talk to, dead though he is. Jacob appeared to Hugo shortly after the time-travelers had returned from 1977, just after Ben had killed him, and told Hugo that he had to lead everyone to the temple. This week, Jacob told Hugo that he had to take Jack out of the temple to the lighthouse, because someone was coming to the Island. Jacob works in mysterious ways, though, and it seems he was not altogether honest; he wanted Hugo to take Jack and get out of the temple because something bad was about to happen. Not Dogen, not Lennon, not Miles or Cindy or anyone else, Jacob made sure to protect Hugo and Jack. We've seen now for 6 years that Jack is a leader of men, and it's safe to say that he will lead the good fight against the Man In Black once the sides have been chosen for good, but doesn't every king need a viceroy? Doesn't every godfather need a consigliere, every captain a first officer? We've recently learned that although Ben made the decisions, it was Richard and Richard alone who talked to Jacob, who brought the word of God down from the mountaintop. Now that the Others have no leader (Dogen's position is unclear,) and Richard is on the run, hugo will have to step forward and take the advisory role Richard has played. That's my take on it, anyway...
(I stole the picture you see from Jorge Garcia's blog...)