Part II: Master of Questions 1.0

*Make sure to check out Part 1 if you haven't already*


I apologize in advance...this may be a little dry. I’ll try to spice it up a bit, but building a strong questioning skills foundation is essential to the rest of this blog and your experience of it. My hope is that you understand the utility of this skill beyond this blog, and start playing with some of the ideas in other areas of your life beyond introspection and self-awareness. As I stated in the problogue - when you learn to ask the right questions, you’ll be golden. This style of questioning is largely drawn from clinical interviewing skills, but can be applied to any aspect of your life that involves communication. I’ll do my best to make this as engaging and relevant as possible, and will also provide a cheat sheet of sorts that you can refer back in the future. Throughout I want you to think of a conversation (both with yourself and others) as if you were driving a car through a town you are not familiar with in the middle of the night.




Imagine you are on a date with someone. Maybe you’ve been happily married to this person for 50 years, maybe you both swiped right on your dating app of choice, and have decided to grab a few drinks. The person across from you starts off the conversation, “Do you like wine?”


You of course respond, “Why yes, I do.”


“Red or white?”


You don’t particularly care, but you are in the mood for, “Red”.


I could outline further conversation, but I think you see where this is going. If you don’t, that’s fine too, because we all fall into this trap of asking closed questions, even when we are skilled conversationalists.


At the heart of an open versus a closed question is: What response are you looking for? Closed question yield binary answers. Yes or no, white or red. Closed questions lead to closed answers. You are driving around a new town at night with your lights off, blindly guessing left or right, and wasting times having to turn around when you reach dead ends. You’ve probably been in a thousand of these conversations that feel more like you’re on the witness stand and a lawyer is interrogating you. You have no doubt been that lawyer, asking questions that seem to lead to nowhere, or shepherd someone down a path of conversation you dictate.


This is particularly clear with people we do not know, or at least do not know well. It can also lead to greater binary thinking within ourselves when we ask closed questions. Should I go to the gym? Is it time to start my work? These questions leave no room to maneuver, explore, or find alternatives. Like all things, there is a time and a place for closed questions, but it can be cumbersome when you ask yourself or others these sorts of questions.

Closed questions often start with the words do, is, or are. This will be another strand of awareness I want you to begin weaving into your game of hide and go seek. Notice when you ask questions that begin with these words, or lead to binary or shallow answers.