A big part about connecting to your subject in portrait photography, or at the very least getting them to feel comfortable, is to know a bit about them. This helps both in the obvious case of conversation, but also in reading their mood and body language. I'm lucky in that I can talk to just about anybody (A gift of my father I think), but knowledge is definitely power. And the way to get that knowledge is through a little research. Now, I don't do this for everyone I take pictures of, but often I'll do it for editorial shoots especially when I'll probably only have less than an hour of their time. Small talk about the weather is fine, but to me it often sounds like practiced banter and that doesn't help the cause. Have something to say about what they're interested in and you've got some power. Not only have you shown them that they're not just another job, but you also get them really thinking about the questions rather than the artificial situation of sitting in front of a camera lens. For example, this morning I was doing a little research on a subject I'm shooting later this afternoon. Author, college professor, ok I could get that information in the assignment email. But that's going to get you conversation about how his books do on amazon and if this years crop of students is up to snuff. Fine and better than the weather, but just so. The magazine also sent me a draft of the article the portraits are running with. So that gave me a little bit about his new book and the trilogy it's a part of, but it doesn't tell me much about him as a person.
Next step is Google. Wikipedia entries, written interviews, etc are all great. Also check Google Images to see if there are other shots of the guy. That might give you some ideas on how to photograph him and at a more basic level whether or not he's photogenic. Sometimes you get a tough subject and need to plan your lighting and equipment accordingly. I also find it handy to see if there's any video of them online as well. Them giving a talk at a conference or getting interviewed for TV and such. Knowing how the person looks in motion and the tone of their voice can make meeting them for the first time less jarring because you know what to expect.
Finally comes a little research into their field. Knowing the guy is in finance is good, but knowing that he works in the international bond market is better. That way you can do a five minute read on the subject and not sound like an idiot when you ask him what he does. I once shot a guy who was an oil market analyst. He had been on Charlie Rose, so I watched that, and read a few bios and interviews, but then I did a little reading on recent volatility in the oil market and what was causing it. Read an article on recent discoveries in Kazakhstan and oil shale in Canada, and learned a bit about the concept of peak oil. So when I showed up the next day, Charley and I hit it off like crazy. I asked him interesting questions and he gave interesting answers. So not only did I make his experience more enjoyable and less artificial, but I got better pictures because he was comfortable AND I learned something to boot.
Some of you reading this must be thinking that I sound bat shit crazy, and that's ok. I'm not looking for cookie cutter in my work, I want each experience to be unique and interesting. In fact, the pictures and the money are all well and good, but in some ways it's the people whom I've met that have made taking portraits rewarding. If the cost of doing that well is an hour or so of browsing the web to do some slightly obsessive pre-shoot research? Well, I think I can live with that.