What Makes A Great Question? (When Talking To Someone Who Knows More Than You Do)
Until recently, I didn’t think questions were very important.
It’s probably because in high school, having no questions meant that I knew everything that was going on. To have questions was to admit that I was falling behind in class or not paying attention. With these beliefs, I didn’t care too much for asking questions, much less hearing other people ask their questions. Worse, I didn’t view asking questions as a viable way of learning.
Fast forward to the start of college, and I immediately felt that questions were everywhere. I was expected to ask questions when networking with professionals. I was expected to ask questions at the end of interviews. School clubs frequently hosted Q&A career panels with upperclassmen and alumni. Professors even graded my class participation based on how often I was asking questions.
I accepted that questions had to be important. I found that they were especially important when I was talking to someone who knew more than me or had more expertise than I did (essentially everyone), as these were the types of situations where questions could serve me best as a college student looking to learn more.
So I spent a couple months listening closely to anytime someone asked a question, whether it was during class, a Q&A panel, professional recruitment event, podcast show, or video interview on Youtube
I found that my beliefs needed a bit of revision again. Yes, questions are important, but they are not all made equal. There were genius questions that made me wish that I had asked them myself, and other questions that made me feel second hand embarrassment. Here are a few (out of probably many more) things that I think make an awesome question.
Great Questions Help You Learn
For the longest time I thought that questions were meant to impress. I think we’ve all been at a panel or speaker event where someone raises their hand to ask a question, provides three minutes of long-winded buildup where they flex their knowledge about a topic that the guest speaker is familiar with, which then culminates in a very anticlimactic question (hogging all the Q&A time as a result). As annoying as these questions were, I thought they served a purpose in impressing the recipient of the question.
I continued to believe this, especially when I was networking with professionals. I had the preconceived notion that my job was to impress the professional I was talking to, and I spent considerable amounts of time preparing questions that demonstrated how knowledgeable I was.
After a few less than subpar conversations, I decided to revisit the questions I was asking them. I was talking to professionals who were very knowledgeable about their fields and yet, I left some of those calls feeling as though I had learned very little.
I think that when talking to people who know more than you, asking questions is about trying to learn, not to impress. I once asked a professional I really respect about what makes a great question. He responded by saying that asking about things that you are genuinely curious about is not only a better use of your own time, but also will naturally come off as impressive to the person you’re talking to. Knowing what you want to learn and asking experts about those things is impressive. Asking questions about things you don’t care about is not and a waste of time.
This was all very eye-opening to me. In the past, when I was preparing to talk to professionals and creating a list of questions, I never stopped to think about what I actually wanted to learn! The first time I consciously tried to think about what I genuinely wanted to learn from someone who knew more than me, I found that 1) It was taking me a lot longer to come up with questions because I really had to do some internal reflection and also research the professional’s work, but 2) My questions were more specific and unique to me, and I was able to learn way more from my conversations.
Great Questions Can Get People To Tell Stories
During this past semester when I was thinking about what makes a great question, there was seemingly no one who asked simpler questions (but got deeper answers) than Guy Raz, host of the How I Built This podcast.
In a piece written by Dave Schools of Inc where he talks with Raz, Schools talks about Raz’s ability to get his celebrity guest to tell a vivid story.
“Raz frequently asks binary questions, such as the questions he asked Kevin Systrom and Mike Krieger, the co-founders of Instagram: “Were there moments, especially in the beginning, where you thought this could fail?”
His questions may seem limited, as in, a yes or no would answer the question, but what’s really happening under the surface is Raz has embedded a bigger story in a seemingly simple question and it requires the guest(s) to unwrap the layers.”
Guy Raz may be a podcast host talking to celebrities, but I believe that Raz’ goal in asking questions to his guests can be the same as any student’s goal in talking to someone who has more knowledge than they do: to learn from the unique experiences and stories of that person.
I’ve found that stories are a desirable way to learn from others because 1) they’re just more entertaining and make for a better conversation, and 2) they involve specific experiences that you can gain actionable insights from. The least informative answer that you can get from someone after asking them a question is an answer that’s generic and without examples. In those situations you don’t really get their unique perspectives on things.
Even Guy Raz receives generic answers from his guests, but he digs deeper.
“I’m sort of a — you can call it a master or an annoyance,” said Raz. “I’m very persistent. I often say to people, I know you’ve been asked this question but I’m asking it in a slightly different way because I think there’s a different answer here.”
Sometimes a great follow up question can unveil even more insights than the initial question. I’ve found that some professionals I’ve spoken with often give a high level answer to my initial question (that they’ve probably told to dozens of other students), but if I ask a follow up or even try to summarize back to them what I heard, sometimes they’ll peel back more layers to their answers and share something more specific and interesting.
Although I’ve talked about asking questions in the context of talking to professionals, I think that interesting questions can be great in all sorts of relationships. (For me they’ve made for some philosophical FaceTime calls with friends at 3 am)
If there’s an aspect of asking questions that you think is super important, I’d love to hear about it at alexyyang15@gmail.com!
