The first question I ask a subject is, "can you tell me about yourself?" This isn't usually asked in person, rather through e-mail or text message, as I'm looking for a thoughtful, truthful answer that isn't typically best gotten when putting the subject on the spot. This also alleviates any issues of the question coming across as disingenuous. I'm not enquiring merely to have have the subject talk, as it can sometimes seem, but rather to learn what the subject would like to portray. More often than not, the final photograph will stem from this conversation instead of fitting them into a preexisting idea. The image below is one that originated from such a conversation.
There were quite a few directions this shoot could have gone as the subject gave a, much appreciated, thorough answer. Some of the ideas her response spurred were discarded as too contrived and others went outside of the time and budget allocated to these shoots. As is ordinary for most brain storms, some were too grandiose in scale to accomplish and many more were simply boring as sometimes it's best to accept that not all ideas are good ideas. Ultimately, I presented an idea that played on her appreciation of the arts and, with the subject in agreement, we decided to use Vermeer's The Girl with a Pearl Earring as inspiration.
Asking the subject to tell me something about themself servers another purpose and that is subject buy in. When the subject believes in or likes what is being made then it's much easier to create something great together. It's no longer just me taking a portrait of the subject but rather both of us working towards a shared goal. Certainly proper direction and explanation to the subject could have create the same photograph but because we shared the same vision there was very little that had to be said. In the end, we both walked away believing we had created something good, something we would both be happy with and, to me, that's the best possible outcome.