Part II: Master of Questions 1.1

*If you haven't yet, check out the first section of this part on Closed Questions

Opening the Door

So now let’s turn the car lights on. There we go. Hopefully you can see a little better, maybe look at the signs of the roads you pass to better avoid dead ends. Welcome to the world of open questions. These are questions that lead to richer answers, and strengthen relationships. Let’s go rewind your date for a moment, and try again with open questions.

Date: “What do you like to drink?”

You: “I’ve been obsessed with drinking Moscow Mules lately.”

Date: “I wasn’t expecting that - How did you come to like that drink?”

Now this is a bit reductionist. Perhaps you’ve never heard of a Moscow Mule. The point I want you to take away from this is to see all the different directions this conversation can go even from the first question. Asking open questions invites stories and more conversational options. Try to think back to a time when someone asked you a great open-ended question. When you felt not only the desire to talk, but the need to provide an answer. On the other side, think about a time when you asked a particularly powerful question that elicited a deep response.

Open-ended questions usually begin with what, who, where, and why. What questions most often lead to gathering facts. How questions can be used to explore a process, a feeling, or an emotion. Where and who likely won’t be used too often, but do act to signal curiosity. Imagine your date plays a guitar. You ask the question, “Did it take you a long time to learn?”, which leads to a conversational dead end (essentially yes it did, or no it did not). Instead you could ask, “Where did you learn to play?” or “Who taught you?” These questions may also yield a simple response, but open up pathways to conversations instead of ending in a dead end or further unwieldy questions..

Note #1: Be careful with questions that begin with why. Why questions have the possibility of being interpreted as interrogative, and could create unintentional negative reactions. “Why” can carry a connotation of judgment, so be aware of how and when you use it. Instead of why, it may be a good idea to use the phrase, “What is the reason?”

Start playing around with open-ended questions and see what sorts of responses you get. When you notice yourself asking close-ended questions, try to switch it up. This takes practice! Asking the right questions is an art, and you’re not going to get good at it overnight. Notice the small victories, though, and when your questions crash into conversational walls, think about how you could ask the question differently next time.

Lastly there are questions somewhere in between open and closed. These questions often begin with the words could, can, should, or would. These are your “Could you pass the salt?” or “Would you mind if I borrowed your charger?” In essence they are a form of asking permission, or checking an assumption. Some effective uses of these words for questions would be, “Can you tell me more about your obsession with “My Little Pony?” or “Would you mind repeating that, I didn’t quite understand?” These are useful for checking in, and signal your respect for the person as well as your curiosity.

Note #2: Should is perhaps the most vile and toxic word in the English language beyond derogatory slurs. Worse than any swear at least. If you choose to only play one game of hide and go seek, this is the one. Notice when you use the word should, especially as it pertains to you. I like to call this “shoulding all over yourself”. Should implies judgement, and judgment is going to negatively impact your ABCs (affect - behavior - cognition) of self-awareness pretty much without exception.

But don’t take my word for it...try it out! When you use the word should, check-in with yourself about how it feels. “Should I go for a run today?” versus, “Can I go for a run today?” Just think about how one word changes your approach to that answer. Should opens you up to the possibility of developing shame (the belief that ‘I am bad’, which will be further explored in our conversations about ego). The answer is almost always going to be “Yes, I should go for a run”, but it puts you in a position where not running says something negative about your identity. You might win that little battle, but you’ll inevitably lose the war.

Can leads to more generative questions. If the answer is yes, you can ask, “When could I go for a run today?” If you can schedule it in, the next question is, “Will I go for a run today?” If the answer is no, there is no judgement attached to it, or at least the possibility for further questioning - “What is stopping me from going for a run?” Maybe the answer is you feel lazy today...but even that leads to more questions. This is not to say you cannot ask these same questions when you start with “should”, only that the nature of the word tends towards the negative and will be a hurdle for generating the more useful questions above.

                   When an Unstoppable Force Meets                   an Immovable Object

A particularly powerful question I use, both with myself and others, is “What is stopping me (or you)?” This has a dual purpose. The first is to identify obstacles toward action in a desired direction. If you can identify the obstacle, it also means you have the option of working toward removing it. If you choose not to do that, this will hopefully lead to further insights about yourself. That’s the second purpose. This is a perfect way to catch the you on the other side of the mirror in a mistake. If you “know” what’s stopping you, and remove those obstacles, and you still don’t act...then those things weren’t really stopping you. For example, if you have to wait for your parents to call before starting a project, but after the call you still don’t start...well then it wasn’t the waiting for your parents to call. This is a great place for a “why?” or “what is the reason?” for yourself. “Why didn’t I start my work after the call?” These questions will yield answers that will have utility for you. It will help you drill down to your ABCs, and give them a good naked look. You might not like what you see, and you’ll find all kinds of clever ways to elude yourself. Respect that, though. This is a game of hide and seek, remember! If these truths were easy to find, the game would be pretty boring.


This is a brief overview of how to ask effective questions, both to yourself and others. As the true focus of this blog is on self-discovery, I will refrain from talking about other clinical interviewing techniques like paraphrasing, silence, nonverbal communication, etc. These are all useful and interesting techniques that I suggest you google, as they can do wonders for your conversational skills.

If you take only one thing away from this post, it should be that asking questions that begin with the words what and how are going to be your best friends in developing your self-awareness. Specifically “What is stopping me?” and “What is the reason for (blank)?” As you grow more curious about your inner self and how it operates, do your best to frame questions as open ended so it will lead to deeper discussions, and more nuanced thinking.

Bias Check #1: For those of you who are astute and may have thought you caught me in a hypocrisy. I applaud you for your effort, but that was a test. For those of you who did not notice - I used the word “should” to describe the takeaway questions. If you didn’t worries - that’s the point. I want to keep you on your toes, and questioning me, your guide. Perhaps that sentence does not elicit feelings of judgement or shame, and it likely won’t until you start actually asking yourself these open-ended questions more frequently. You’ve spent a lifetime asking yourself many of the same questions, and it will be tempting when you catch yourself using a close-ended question, or an ineffective open-ended one, to say to yourself “Damn, I should have phrased it [blank].” In the beginning this is understandable, but even here I want you to work on berating yourself for making a mistake more effectively. Instead of saying to yourself “I should….”, ask yourself, “How could I have said that differently?” You are in the midst of a revolution, the kind that marks change, and change takes a lot of work. It is exhausting. Try not to burden yourself even further by judging your progress.