I wanted to post on this thread, because it's something I had to deal with early in my career.
First, I strongly believe that the idea you can't be successful in this field if you are shy/a poor small-talker is complete and utter bull****. There is one thing and one thing only that will determine your success -- your ability to do your job professionally. You can be the best small-talk artist in the free world, but if the athletes/coaches/executives you cover have no respect for the job you do, you are not going anywhere. It's amazing to see how people will chat with you once they trust your work.
I've had a couple of occasions where people I cover have said to me that I'm standoffish. I laugh when that happens, and just explain how I don't want to bother anyone and just like to be professional. I tell them that I want them to know that when I ask their time, they know it will be for something relevant and not a waste. Never once has anyone been offended by that. I've never, ever received a negative response to that.
I would say to you: the first time you see someone in a certain day, always acknowledge their presence, even if it's just a quick hello. I would also give you this advice: My first big job was in sports radio in toronto. I was a big basketball fan, and handed the beat reporting job for the Raptors, then an NBA expansion team. I was 25, and not heavily experienced. It meant all practices, all home games and a couple of road games. I had very little in common with the players. But, during training camp, I did a quick one-on-one with every player. The questions varied, some job-related, some not. (Things like: your dream car, world's best-looking woman, best road city, first impressions of canada, etc.)
It's amazing how much little material that gave me. Damon Stoudamire said he couldn't believe how much curling was on television. Once in a while, if I knew curling was on, I'd ask him if he watched. He always smiled at that, and it opened up a door. Willie Anderson made a joke about one ex-teammate said no one ever looked better missing a layup than Anderson did. So, if he missed one in a game, I'd wait a day or two, then asked what that ex-teammate would have said about the one he missed the other night. He'd always laugh.
It also helps to know a bit about their backgrounds. Villanova had a brawl one night that year, so I asked Ed Pinckney about it. He launched into 10 minutes worth of great stuff. The key is, always start with your notepad/recorder away, then midway through, say, "This stuff is so great, can I do a story on it?" Unless it's something you shouldn't be using anyway, most guys will have no problem. Also: I was planning a golf trip through a certain area recently. A player I knew from there was coming into town. So I pulled him aside quickly explained my situation. He was happy to give me 15 minutes worth of material.
Anyway, hopefully that will give you some help. You will also find that if you are good at your job, the more time you spend around the same people will make you more comfortable chatting with them.