I believe and I’ve seen some bumper stickers that would back up the idea and the fact  that we are living in an international critical thinking deficit, right? Live  in this world where people come to conclusions so quickly don’t really research information all  that much. They take something at face value and they run with it and make decisions or  maybe even worse judgments or start yelling at people because of it. In this video, we’re going to unpack how do you ask questions that promote critical thinking. And I’m going to be sharing one really brilliant strategy that I learned from Brandon Stanton,  the founder of Humans Of New York, if you’re familiar with that. 

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And the second strategy,  I’m going to share one of my absolute favorite, I think one of the coolest practical tools in Me and Will’s book called Ask Powerful Questions Create Conversations that matter. The only kind of fluff I like is marshmallowy and sits on a sandwich. Let’s get into it.  

Hearing Brandon Stanton uh speak one time. If you’re not familiar with the Humans of New  York, by the way, he basically set out originally, set out to do portrait photography of 10,000  people in new york city to create this library of stories. He very simply used to… I  haven’t followed him in the last like handful of months. But he used to post a picture with just  a quote from that story. Now, the quote would be usually phenomenal. It would just breathe so much  like depth and humanity into that 2-dimensional image that he shared. The technique of how he  got there, right? Because you don’t just walk up to somebody on the street and say, “Can I take  your picture and can you share this really intense beautiful quote with me so I can put it in my post today?”Right? You’ve got to actually get to there in conversation. And you’ve got to ask questions  that promote really critical thought about things that potentially people have never shared out loud  before that they’ve never thought deeply about. And his technique that he shared, he used the image of a spiral. He talked about spiraling down in conversation. 

From Here to There

Going from, “Hey, how are you doing?” to eventually a story about their grandmother on a chair when they were 5,  that really transformed their life, right? How do you go from here to here? And he used the idea of a spiral you kind of just get deeper and deeper and deeper. But  you might go around, right? It’s you’re not… Oh, you’re not just like drilling straight down  because that feels very invasive. To keep the conversation natural, you’re kind of  spiraling down. And I love that idea in terms of promoting critical thinking. You know, if you’re familiar with the idea of socratic inquiry. Like teaching through questions. When you’re spiraling down in conversation, you start to get more specific too. You start really general  and you get more specific and more specific and more specific. And one of my favorite quotes or  ideas on the planet who I have no idea who said it. I can’t find it on Google. If you can, share  it in the comments and I’ll like buy you a car or something. Not going to happen. But I would really  love to know. But it’s this idea that specificity is the soul of narrative. I love that concept. The more specific we get, the more to the heart of story we get. And the more that we’re talking and like generalities appear, the less usefulthat is. The same is true for critical thinking.  

Critical Thinking

When you’re thinking about… If you want to critically think about something contentious  like the death penalty, for example. You could be thinking about this at a very surface level.  But then the more specific you get into specific cases, right? And instances, that’s  where story and narrative starts to really come to life and you start to be like, “Wow, I don’t  I don’t know what I think anymore”, right? And that critical thinking starts to show up. My language for Brandon’s spiraling technique is to follow one curiosity path, one thread and keep  bouncing to that thread. Wherever it takes you. If you spun a globe and picked a random spot,  the island of newfoundland and you then zoomed in a little bit further to a park in the island of Newfoundland, and then you zoomed in a little bit further and you found there was a dog park inside that park. Then you zoomed in a little bit further and you found a dog and it’s owner. And you found out their name and you found out the type of dog and you found out how they came together and…  Those are stories. But when I’m telling you about the island of Newfoundland, I’m all of a sudden a Wikipedia article, right? That’s more specific you get… You follow that curiosity  path by just kind of Zooming in further. Now, the thing the cool thing with curiosity is it  doesn’t work like a drill like zooming into the island of Newfoundland, you might actually find  that as you’re going to the island of Newfoundland, you learn about Newfoundland  dogs. And then you’re like, “Oh, wait. They were created over here.” And now you’ve got another  curiosity path. Following that path down. The next tool I’m going to share with you is going to help you do that in a really practical way with one very simple word. And that word is “Why”. You might have heard of the uh this technique or this idea of the 5 whys before.  

It’s a cool concept to promote design thinking, right? You ask, why are you doing something. And  then you ask why are you doing that and then why are you doing that? You ask that five layers down  until you get to the core or the heart. Now, that’s cool if you’re talking about ideas. But  if you’re trying to promote critical thinking in people, the way that I would use this one  word is by deleting it out of your vocabulary. It’s by saying drop the why. Because when I ask  questions that begin with why they force people to rationalize and justify which… I can’t  put this back together. But that could promote critical thinking. But it’s going to be way better  if you want to promote critical thinking to start your questions with either how or what.  

Those questions allow people to really expand and answer in a way that doesn’t require justification  and rationalization. Because in order for critical thinking to actually happen, our brains have to be open. Barbara Fredrickson talks about the broaden and build theory and positive  psychology –that when good things happen, our brains actually open up to new ideas. Whereas  when we’re worried about how we’re going to pay rent and we don’t know what’s going to happen  next month and we’re worried for our safety, we can do this. They can make people put up this barrier to try to protect some level of safety because it’s kind of prying for that justification. When you ask questions that begin with how or what, typically, those tend to be more open questions, they invite story. They invite explanations, they’re longer answers, they’re not closed questions that close down responses.

My invitation to you is combine Brandon Stanton’s spiraling technique of following a curiosity path by asking questions that begin with how or what over and over and over and over again until  critical thinking happens. And perhaps, you can offset the critical thinking deficit that exists  right now on planet earth. I’m Chad Littlefield. 


Have an awesome day.


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