Kevin questions

I grew up extremely shy. My parents divorcing at an early age probably had something to do with it. With a single working parent and all older siblings, I spent a lot of time alone waiting for the rest of the family to come home. I remember long stretches of solitude, and so for years most social graces much less the art of conversation was baffling to me. During my 20s and 30s I worked extensively to get better at participating in conversations.

A few years ago, a friend Jonathan said to me, “you ask the strangest questions. We should call them ‘Kevin’ questions.” A typical question from me might be something like:

If we were telling the story of your life, and we did a cold open–at the height of dramatic tensions–what scene in your life would it likely be?


What’s something your significant other has taught you the most about in life?

My friend and I started chatting about these questions, and ended up figuring out that there was a measurable pattern. The first thing we realized is they’re almost always personal. A lot of conversation in life is very impersonal, whether you’re talking about the weather or something heated liked politics/religions, it’s about something out there in the world. It doesn’t require the person to really think about what’s going on in their world. Not surprisingly, people really like thinking and talking about themselves.

I also started realizing that a lot of conversation is really associative. We’re talking about this one thing, say flannel, and it makes me think about a girlfriend who used to wear flannel shirts and how we argued all the time. So then I bring that up, and we spend the next five minutes talking about it. On the other hand, there are conversations where we’re skipping from one thing to the next perhaps under a common theme. For example you bring up something that annoys you about your manager, but then we start talking about the whole practice of management, and it forces us to think about that entire theme. I call this random access memory, where you have to think about everything you know about a certain topic to really contemplate what to say next. When I ask you “what’s your favorite movie of all time?” you have to try to quickly revisit all the movies you’ve ever seen. While you’re busy doing that, it often stirs up a lot of interesting memories. These conversations can require a lot of energy and focus, but they can also be rewarding since they get you think about all your lived experience and hopefully realizing some new insights.

My friend Jonathan and I ended up realizing “Kevin” questions are something like the following:

Ever since realizing this, I’ll take a surface level moment amongst friend and figure out a way to explore something we’re already talking about deeper. If we’re talking about the weather, instead of staying at the shallow end, I’ll ask something like “what was your favorite snow day as a kid?”

These conversations end up having several benefits. Not only do you tend to realize deeper insights since you’re not just fleeting from one associative memory to the next. They also have the benefit of really drawing someone into the conversation, since you’re asking them something personal.

Realizing this phenomenon has taken from me from a shy introvert to someone that draws energy from conversation.

More example questions

What is the TED talk you’ve been preparing to give your whole life? Assume that whatever you have to talk about people will show up, so no filter.

There are some things in life we do that are just to check a box so we can live up to others’ expectations. What box that you checked do you most regret?