Why You Should Ask "Bad" Questions

Recently in a conversation with a friend, a question came up that I hadn’t thought about in quite some time. 'What's your favourite song?' When you grow up, you stop thinking about your favourites of things, it feels reductive, almost unanswerable as we become more complex. I never found these sorts of questions to be insightful in discovering information about people. For example, asking the question 'What is your favourite movie?' has seemingly been less effective than reframing the question and asking what their favourite genre is, and then movies that they like within the genre. This method has seemingly been a better indication to learn about someone than simply asking them their favourite. There are too many nuances, and the answer seems near random at the end of the day; a randomly selected movie, selected to answer that specific question and provide no further insight.

Or so I thought

When my friend recently discussed their favourite song with me, they mentioned many songs, but one stuck with me. They recited a story about how their mother used to sing them a song. They couldn't recall the name of the song, nor the artist (simply that it had to do something with the Beatles) but they remembered a drum sequence in the middle of the song. They had rarely heard the actual song in their life but it held something within them, and that story stuck with me (The song was 'Silly Little Love Songs' by the Wings). I never expected to learn so much from someone I cared about from a question that was so meaningless, the song has been stuck in my head ever since. Not just because it's beautiful but because of what it meant, and how it had meant that to her.

I decided to continue digging with this question and see the answers I would receive. I asked the question in the simplest way I possibly could. 'What's your favourite song?'

The initial reactions were always interesting, some people named multiple songs, others had one on their fingertips without question, and a lot were frustrated with how limiting the question was (To all those who are reading this now, trust me, I understand, I would have been frustrated as well).

Eventually I got an answer, or multiple, but the process of boiling it down was always fascinating. When looking for one answer, people grab onto a theme or idea related to music and then pick their favourite song related to that idea.

This may seem like an altogether very meaningless exercise, but I would disagree, what I have learnt from this goes a little beyond music. The songs themselves did not tell me alot about the people I cared about, and while the stories were fantastic that was not the main takeaway either, it was how they came about their answer and how within the constraints of that question they were able to associate their favourite. It's the limitations of the question that cause this insight to be achievable, by asking them a "better" question I truly learn what kind of music they like, but I learn less about what kind of person they are and what holds meaning to them. By scrambling within the confines of a limiting question, people come out with a song that fits an idea of what is important to them. Even if the question is about music, their answers may go beyond it.

So, here are some of the responses (and music) that have given me insight into those around me. Starting with my own: