I’ve been “interviewing” my close friends and family in a podcast-like setting where I asked them questions that I didn’t find an opportunity to ask otherwise. Here I’m outlining this process as a template.

I’ve done this with three friends and it was a bonding experience with each one of them. At this point, I know these people for 21, 12, and 11 years and yet coming up with questions to ask was not only not hard, I had to limit myself lest the interview would take the whole day.

I have also done this with my parents. Time with parents is limited, very limited once you’re an adult. And perhaps it’s just me, but I don’t have a habit of asking my parents deep questions about their life and most of what I know is what they’ve told me of their own accord. This interview in particular ended up being emotional to the point of tears, and illuminating of the context I grew up in. I’d rank interviewing parents as the top priority, because of the aforementioned time limitation and because of possibly imbalance between how much we might perceive to know about our parents’ lives versus how much we actually do. It goes without saying that parents are a huge factor in our lives, whether they were present or not while we were growing up.

As in a podcast, you should come up with the questions tailored to the person(s) you’re interviewing. Nonetheless, in the interviews I’ve done, some questions were common enough that it was only sensible to ask them to everyone. E.g., roughly in this order:

1. “Tell me about yourself from the beginning, where are you from, what was your childhood like, favourite childhood memory, etc.”
   I’d ask this even if I knew the person since we were kids. I wouldn’t dwell for too long on this question this early, though. And for some people, these can be sensitive topics.
2. I like to proceed here with lighthearted questions, e.g.: “What’s your favourite childhood video game, current or all time favourite music band, cats or dogs or frogs or snakes or… “ anyway
   If the person professionally works in, say, video games or music, it’s not a bad idea to explore these topics deeper at this point, but otherwise you can ask the following.
3. “How would you describe your aesthetic?”
4. “Who are your role models and what do you admire in them? How did they change over time? Who were the role models before, why are they no longer, and who are the role models now?”
5. “What social cause do you care about and/or want to contribute to?”
6. “Of all the things you’ve accomplished so far, what are you most proud of?”
7. “Did you have a moment in life where you felt blissful, like everything is as it should be?”
8. “What’s your most controversial opinion you’re willing to share right now?”
9. And the job-interview-like question: “How do you see your life in the next year, five years, and ten years?”

Based on the interviews so far…

1. Recording the interviews is basically a must, unless the interviewee prefers otherwise. Anyway, If you go at any real length, you’ll absolutely forget a lot of details of the answers you’ve been given. It should also go without saying that these recordings are something to cherish. I keep the recording private and only share them with the interviewee.
2. I’d advise against giving too much of your own opinions on the questions you ask. It easily turns into a discussion that centers on things external to the interviewee. The point here is to understand the interviewee, and in the context of your relationship. Deep discussions about other points should be had separately, except for letting the interviewee express their view as deeply as they desire.

These questions alone can lead you down a long conversation, but none of them are specific to a person. I advise sprinkling in customized questions too.

Happy interviewing! I’ll be back with more insights as I conduct more of these.