How To Ask Questions

9/18/23

Missoula, MT

Firstly, while I enjoy trying to write something each day as a mental exercise, I find that the days are filled with so many new experiences and observations that to faithfully recount all of the meaningful ones would be impossible, or at least exhausting. Therefore, these writings are largely reduced to one thing that seems easy enough to write about, based on the amount of time I prefer to put aside for writing. In other words, these blogs are far from travel documentation, and more so a series of unrelated, random entries based on the events of each day. If that explanation is helpful to anyone but me.

When it comes to talking to strangers, there are two key things to keep in mind, assuming you want to walk away with the feeling of a meaningful interaction.

1. For the most part, people enjoy talking about themselves.

2. Every single person on the planet knows at least one thing that you don’t.

With those key points in mind, any time you talk to a stranger, you can leave feeling as though you’ve gotten something out of it. Assuming you want to, and have the energy to. If you want to be curious, which I suggest to should, and want to learn new things.

All you have to do is ask questions that allow you to a) keep them talking about themselves and b) identify the things they know that you don’t, and then both you will probably be at least moderately entertained. And, if you’re really good, you can keep asking these sorts of questions, and never actually have to share a single thought of your own.

To me, this is very simple. And over time I’ve identified some good to-go questions, but I can easily come up with new ones using these guidelines. However I often get the response “wow, you ask such good questions.” I don’t think I do. I just ask questions that are strategically designed to keep them talking about themselves, and keep me entertained. And these comments bother me, because anyone is capable of doing the same exact thing I do.

Today, after meeting two women, roughly in their late 50s, while hiking with my friends Hannah and Will, and us all being invited to join these women for cheese and wine, we found ourselves sitting with them at a rooftop patio of a bar downtown. Jackie, one of the women, has taught and performed violin classically for about 40 years. I asked her, “what’s the most incredible experience you’ve had though music?”

She attempted to answer, but hesitated, unable to come up with something. Later she went to the bathroom, and when she returned, she said that she’d thought more about the question, and had come up with an answer. But she added, “No one’s ever asked me that before.”

It surprised me to hear that. Possibly because, to me, it was a very basic question, based on my guidelines. I don’t bring it up to praise myself, it was almost comical because of how calculated the question was, but more so to highlight how surprising such a question can seem to someone.