I was in the car the other day with my husband, driving up to a fancy event with some quite established folks in their careers. We knew about each person, their prestige, their work, and their reputations. So I also knew that the default American question “What do you do?” wouldn’t suffice for the dinner party.
We started brainstorming a list of questions to ask people instead, and I jotted them down to remember for later. Asking people better questions is a great way into a more interesting conversation. Here’s some of what we came up with:
What puzzles are you currently working on?
I love talking to people about what they are learning, and what their process is while they are discovering, building, and grappling with a project.
What have you recently figured out? Any fun “Aha” moments in your life recently?
This one is about that feeling of unlocking something. For me, I’ve recently found a good pool and a swim routine, and I’m constantly thinking about how to adjust and iterate on my routines to garner a better day. Each little piece of the puzzle I put together is fun for me to think about.
What are you excited about right now?
This opens the door for people to tell you about their work or their hobbies—whatever lights them up. And even if the answer is, “You know, nothing—I’m in the doldrums right now,” that still gives space to go deeper in the conversation.
What did you do last weekend?
We’re obsessed with what people do during the week, and what they do for work. Flip it on its head and ask people about their weekend and their leisure activities.
Who are you learning from right now?
I like seeing who people are connected to, and who is teaching them, and what they’re learning. I’m always studying different people’s work, and I find that this is a good way to get into people’s research, thinking, and reading, without asking the question “Read any good books lately?”
What’s something that’s not obvious about you right away?
I ask this question in my Mastermind applications, and it’s a wonderful way to go beneath the surface and see who people are. It’s always a fun one, because often the answers aren’t obvious right away—and it’s really cool to hear the answers!
Going deeper: ask three questions
I’ve written about this elsewhere, but after the first question, instead of flipping back to you, ask another question, and another one. It’s the third question with someone else that’s usually at the heart of the subject and gets into the good, juicy conversation. My favorite follow-up questions are:
Tell me more about …
What was that like for you?