"How's school?" and "What have you been up to?" are perfectly fine questions, but they tend to produce short, polite answers. There is a different kind of question that tends to open things up: "Can you teach me something?" It works especially well with a grandchild, or any younger person in your life, and it is worth having ready.

Why this question works so well

Most conversations between generations default to the older person sharing wisdom or asking about school and friends — a fine dynamic, but a one-directional one. Asking a younger person to teach you something flips that entirely. Suddenly they are the expert, you are the curious student, and that role is one most people — kids and teenagers especially — genuinely enjoy getting to play. It also naturally produces a much longer, more detailed answer than "how's school" ever does.

What to actually ask about

A phone or app they use. "Can you show me how [an app] works?" is concrete, low-stakes, and gives them something specific to demonstrate rather than explain abstractly.

A game they play. Even watching them play for ten minutes while they explain the rules counts — you do not need to become good at it yourself for the conversation to be worthwhile.

A word or phrase you do not recognize. If you hear a term you do not know, ask directly what it means and where it comes from. This tends to lead somewhere more interesting than expected.

Music or a show they like. "What is this artist you keep mentioning?" is an easy, genuine opener into a topic they likely have a lot to say about.

A skill outside of technology — a sport, a hobby, something they are learning at school. The "teach me" framing works just as well here as it does for anything digital.

This is Learn and Connect at once

This whole idea sits at the overlap of two pillars: it is genuinely new information for you (the Learn pillar's whole point, covered in The Habit of Learning Something New), and it is real, specific connection with someone (see Making Room for Real Conversation) — one small question doing double duty, rather than needing to schedule two separate kinds of time.

Offer something back

The dynamic works even better as a trade — after they teach you something, offer to teach them something in return: a recipe, a piece of family history, a skill from your own life that they have never had reason to learn. This turns a single one-directional favor into a genuine back-and-forth, and it is often the family history and stories side of that trade that a younger person remembers longest, even if the app or game they showed you fades from memory by next week.

You do not have to become an expert

The goal is not mastering whatever they teach you — most people will never become fluent in a video game or a piece of slang after one conversation, and that is completely fine. The value is in the asking itself: a genuine question, a few minutes of someone else's expertise, and a conversation that goes somewhere neither of you expected it to.