How do you ask a question?

I think I have to learn how to talk with people. That’s “with,” not “to.” “To” I’ve got down pat. I love being on stage, I can tell stories, share information, explain, describe, comment at length… But I’m wondering about the “with”.

Today, I went to the store (had to stock up on perishables before the impending storm), and wound up talking to the fellow behind me in the line to check out. He asked one or two leading questions, and I was off. I mentioned science fiction, he expressed an interest, so I said I’m a writer and publisher. He asked if I’d written anything he’d recognize, and then I asked who he liked to read. He mentioned Asimov, and that was it. I told him stories about knowing Isaac, and he only had to make a few “mm hmm”s here and there, while I held forth for probably fifteen minutes (it felt kind of like those days in the office way back when, when Isaac would talk for an hour, and I just listened).

I talked, he seemed interested, we checked out, and as I was getting into the car, I thought “Gee, that guy learned a lot about me, and listened to my stories, and I know almost nothing about him.” It can’t be because he didn’t want to talk about himself. It’s just that he asked a question or two that got me talking.

I’ve had similar sensations in the past, but they were fleeting. Writing this, however, I’m realizing it’s a common occurrence with me. I’m terrible at starting conversations, and I have trouble meeting people in crowds. But once someone asks me a good leading question, I can talk forever, and come away thinking we had a good conversation, when in fact we didn’t. I have never learned the art of asking a good leading question, of sharing that conversational spotlight. Perhaps that’s part of why I didn’t enjoy being a reporter nearly so much as being a columnist.

Now that I’ve become conscious of this failing, I’m going to try to learn from it and correct it, but I fear it won’t be easy, especially during the pandemic. But once we’ve defeated this virus, or learned to live with safely with it, and when we go back to seeing each other in person, I hope you’ll be able to help me with this. Thinking back on conversations, I know how they go: I get a question that requires more than a one-word answer, and I give it, and I keep talking. But I’m not sure how often, at the end of what turns into a monologue, I can return the favor with an equally interesting leading question. It’s not an inability to listen: I can listen as well as I talk, and take it in. It’s just being the encouraging, enthusiastic listener who asks the question to get that monologue back, that’s where the problem lies.

Want to contribute to the “teach Ian to ask questions” fund? Much appreciated, at

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