Ask better questions, part 1

If I had to break down what it takes to be a good conversationalist, I’d say the 3 components are:

• Listening
• Storytelling
• Asking questions

Whilst being a good listener is probably a more important skill to master in life, I find it much more interesting to write about asking good questions. And sure, there’s some overlap between the two, but to me it’s two distinct skill sets.

In general, it does seem like women are better question-askers than men — maybe because women are more relational, and therefore more comfortable asking personal questions that men tend to shy away from. Either way, in my experience the ability to ask good, thoughtful questions is a rare quality in people today.

For the record, I’m not a fan of small talk questions — “What are your plans for the weekend?”, “How’s your week going?” — but I view them as a necessary evil to start conversations, which can then lead to other more interesting topics. I also noticed while traveling in Europe that people very rarely ask what you do for a living, whereas it’s a standard question in the US and in particular the Silicon Valley. Nowadays I try to avoid asking that question as much as possible, if for nothing else then to force myself to think of other questions to ask.

Having said that, it is ironic that one of my favorite questions to ask is just a variation of “what do you do?” In fact, it’s two versions of the same question:

1. What did you want to do growing up?
2. What do you want to do when you grow up?

I love asking both versions for different reasons — for #1, it’s to learn more about the other person’s childhood hopes and dreams. For #2, I like that it’s tongue-in-cheek since most people I ask are already grown up…and yet, the question reaches beyond what they do now, and seeks to understand what they might want to do in the future.

Growing up, my favorite TV shows were courtroom dramas — it started out with shows like Law & Order and Picket Fences, and branched out into The Practice, Ally McBeal, and a few others. I was fascinated with how courtroom proceedings and jury trials were portrayed on television, so much so that I wanted to become a lawyer. Well, almost every single person in my family told me that was a terrible idea, so I resigned myself to study engineering like most all good Asian sons. In the end I’m glad I didn’t try to follow this particular childhood dream, as I don’t think I have the aptitude or personality to make it as a lawyer.

And now you know a bit more about me. I would love to know your story, too, so feel free to let me know in the comments, or just message me. On future installments of this series I’ll be exploring other questions I find interesting, so don’t be surprised if I randomly reach out to ask odd questions.

Thanks for reading!