Bill Nye once said “everyone you know knows something you don’t.” Take that into an interview or any conversation with you, and you’ll have a much better time than if you hadn’t.
There is an odd thing that happens when you interview someone: objectivity yields subjectivity.
The more you can ask a question in a general way, the better and more personal the answer will be. Making the subject of the question an idea will get a much more thoughtful answer than asking a person about why someone did something.
First you have to find something interesting about that person. The great thing is that there is something interesting about everyone. Everyone has been through some shit. Some people have been through more pleasant shit than others – shit is subjective. But you’ve gotta dig into the shit, because that is when you find the good shit – what people want to hear about. But it tough to physically go through each person’s metaphorical shit. Asking someone a shitty question feels like…shit. But it is worth it, because that is where friends are made.
“Tell me about that dog bite” is a far better way to ask the question than “Did a dog really bite you?” or “How did you get bit by a dog?”, because it creates the subject as the act of a dog biting something, rather than the subject being the person who was bit – that may hurt the ego of the person, which you don’t want to do (at least at first), because you want to keep the conversation going.
Stating a pointed truth, questioning a falsehood, or the opposite of both – one that you know will elicit a reaction, is a great second question. You have to establish report first. You will know that report is established when you can comfortably ask someone to get a beer, and they will comfortably answer yes.
Have a beer, go through some shit with someone, and have fun.