Five years ago, I was asked to take a portrait of Joe Namath before a golf tournament for the Orlando Sentinel. I was 18 years old and didn't know much about the football legend. So I called my grandmother, a New York City native, who knew everything about him. I took 20 photos, all of which he wouldn't take off his sun glasses. So I asked him to take one without his sunglasses and then asked, "what was it like to call the Superbowl in Miami?" This was the result.
So what is the lesson here?
Well first, always listen to your grandmother, but it is just as important to get to know your subject - even if they are a football legend. Do the research, and then, make a connection. Don't just ask a silly question about their best day ever. Connect with your subject in a way that makes them feel something - this will certainly show in the photo.