Chad Littlefield has studied questions. He knows how to ask excellent questions that lead to open, intriguing, creative conversations. He explains how to ask useful questions that help people be more creative. Learn tips on how to craft the best questions, build team trust, and increase creativity.

What You’ll Learn

  • The essential elements of well-crafted questions
  • The reason “why” questions close off creativity
  • How to use questions to drive creativity

About Chad Littlefield

Chad Littlefield, M.Ed., is the co-founder and CEO of We!™ ( He has spoken at TEDx and is the author of the Pocket Guide to Facilitating Human Connections. As a speaker and professional facilitator, Chad designs fun, challenging, and engaging experiences and tools that break down communication barriers, and increase connection and engagement. He has worked as an instructor at Penn State University and led the design team who created We! Connect Cards™ which are now being used to create conversations that matter within companies and campuses in over 50 countries around the world. Chad has the privilege of consulting, coaching, and facilitating within organizations like JetBlue, Starbucks, Penn State, Cigna, Typeform, United Way, Goodwill, TEDx and dozens more.


The Weekly Challenge

In the next week, talk with three strangers. They could be people in your daily interactions, like a cashier, and ask them an open-ended question that starts with “what” or “how.” The questions need to come from a place of genuine curiosity. In the comments below share what questions you asked and what happened.


Feel like reading instead of listening? Download the free transcript or read it below. Enjoy!

Transcript for Episode #070: How to Ask Questions With Chad Littlefield

Amy Climer: Welcome to The Deliberate Creative Podcast Episode 70. In today’s episode, we are going to talk about how to ask useful and valuable questions. But before we get into that, I want to share with you a brand new iTunes review that came all the way from Australia. This is not the first international review this show has gotten, but it is the first one from Australia, which is very exciting. This is a review by Mark Collard and it is titled “Inspiring and Authentic,” five stars. Mark says:

“I’ve dived into Amy’s podcast on a few occasions and it always strikes me as inspiring and particularly authentic. She walks her talk. As an author and entrepreneur, I’ve picked up useful tips for creativity which would not have popped into my head if not for listening. Thanks, Amy. Keep up the good work.”

Thank you, Mark. I really appreciate you taking the time to write the review. It means a lot to me. If you want to write a review, you can go to That is the shortcut that will take you directly to the iTunes page. You can write a review there and I try to read every review on a show so you might just hear your review on a future episode. It also helps other listeners find the podcast and it is a great way to give back. You can also share the podcast on social media, it’s another way to spread the love or tell your friends about it. In this particular episode, my guest Chad is going to share a number of resources and you can get all of those on the shownotes page which can be found at Go there, you can get all the links to the resources that Chad mentions.

Today’s guest is Chad Littlefield. Chad is creator of We! Connect Cards and co-founder of the company We! and he is focused in on helping teams make connections with each other. He does that by helping people understand how to ask good questions and asking good questions himself. It is pretty fun to get together with Chad because he always has these unusual questions that make you really think and it is great. He is going to talk about how to formulate questions and then how to use those to be more creative. Here is Chad.

Chad, welcome to The Deliberate Creative Podcast. Thanks for being on the show.

Chad Littlefield: Thanks for having me. I am feeling deliberately creative just being here.

Amy Climer: Awesome! Start off and tell us a little bit about yourself, about who you are, and what you do.

Chad Littlefield: Yeah, sure. Maybe I will start by sharing the movie that I watched that shifted the way that I saw the world and thought my world was going, if anybody has seen the movie Patch Adams before. When I saw the movie, I was in middle school. Robin Williams essentially throws on a clown nose and heads out into hospitals with the goal of improving the quality of people’s life rather than the quantity. He does so through human connections. He just has this really magical ability to connect with people. When I saw that movie, I had my whole life figured that I was going to be Patch Adams. I was going to med school. It was happening. After a chemistry class or two, I took a very hard right and said, “Oh my goodness! I am never ever, ever, ever going to be a doctor, but I am still really obsessed with this human connection thing.” That has very much, believe it or not, shaped the way that I see the world and what I do now and where I spend all of my time.

Amy Climer: That is awesome. It is always chemistry that gets everybody.

Chad Littlefield: Yeah.

Amy Climer: I actually met the real Patch Adams. Sorry, I did not meet him, I saw him speak once a number of years ago in Wisconsin. He is amazing.

Chad Littlefield: Really? I have heard mixed reviews. I have heard like he is really crazy and he is really awesome and maybe the two coincide.

Amy Climer: Yeah, absolutely. I thought he was both and incredible. I was like, “Wow! I want to hang out with you.” Tell us a little bit about what is your work? What do you do on a daily basis?

Chad Littlefield: I started a company called We!, like a group of people. Our mission and passion is to create conversations that matter. In anything that we are doing, whether it be training or coaching or designing the next card deck that we are coming up with, the aim is always and the question is always are we creating conversations that matter? Because what we noticed is that there seems to be this national and international deficit of curiosity and questions and conversations that are really good and there’s an abundance of acquaintances and passing connections that serve more like sips of connection rather than gulps of connection.

Amy Climer: When you are doing that work of creating connections that matter, one of the things you do is you are in-person like working with teams, right?

Chad Littlefield: Yeah. Actually flying out like doing a keynote at a conference or I am in the headquarters of JetBlue facilitating a training, working with a group of JetBlue’s facilitators, training them how to create more connection and weave that into their work. Lots of times in-person and a little bit of virtual coaching with clients that are far away.

Amy Climer: Awesome! One of the things that you are basically an expert in is asking questions. Can you talk a little bit about that?

Chad Littlefield: Man, once I am put in the expert box there’s so much pressure.

Amy Climer: Sort of an expert. Is that better?

Chad Littlefield: Thank you. Very humbling. I feel like the rest of the podcast I should just be asking you questions. Question to question to question. A big factor of creativity is trust. This idea of when I share an idea, are you going to build on it and uphold me and my idea or tear it and me down. One of the most profound ways I saw that trust develop really quickly was working for this organization called World in Conversation where my job was to sit in a circle of strangers, six to eight people who’d never met each other, to talk about things you are not supposed to talk about especially with strangers like race, gender, culture, sexuality, long-term conflict, politics.

It was amazing to see that in a 90 minute conversation that was really well facilitated – and facilitation is essentially really good questions and really good listening – and seeing the role the facilitator had to create a conversation that actually really in the moment, in 90 minutes, built bridges across color, across borders, across all this in this room. Having experienced being a participant in one of those dialogues, I was like, “Dude, teach me how to ask questions like that and teach me how to listen like that because whatever you just created, there needs to be more of it in the world.”

Amy Climer: That is cool. I love that inspiration.

Chad Littlefield: Yeah. Just because I like nuggets, one of the things as I was originally going through the training that World in Conversation puts you through, which is this really rigorous — it is actually like a year-long process of how to ask powerful questions, which my now business partner, Will, kind of created and lead. One of the pieces of that training is there is all this self-work involved. If you learn a tool, for example, one of the tools is this concept that really powerful questions tend to start with one of two words: how or what. There are open-ended questions where you ask for a story and more than just a specific answer and how and what and specifically not why questions. We can talk about that later if you want to.

In doing that, my life felt more creative because all of a sudden like my grandmother or my mom, people that I had known my whole life, all of a sudden looked completely new to me because I had this new skill of asking questions. I found out what my grandmother thought about Ronald Reagan. I was not born when Ronald Reagan was the president of the United States and to hear about that and that experience, expanded my own world view and understanding. It was pretty cool.

Amy Climer: I love that because I think about too. All my grandparents have passed away, and I think about the questions that I would ask them that I did not ask them when I had the chance, and like, “Oh, yeah.”

Chad Littlefield: It is called question regret. It is a thing. It is a thing.

Amy Climer: Yeah, it is question regret. That is awesome. Let’s go back to what you said a minute ago about the “what” and “how” questions. Can you talk more about — I was going to say about why those are important and now I am like, “Oh, should I use that word?”

The Essential Elements of Well-Crafted Questions [10:05]

Chad Littlefield: The word is off limits. If people are not familiar, closed questions versus open questions, closed questions tend to bring closed responses. And often times, the questions that we are most comfortable with when we meet someone for the first time are closed questions. For example, where are you from? A person can answer that in one word, one location, one phrase. Most people are generous enough or have answered that question enough to give a little context, a little bit more, but for the most part, there is an end. There is a very clear end to that conversation and it is once they have told you where they are from.

Whereas an open question would invite a much more open-ended story or response that you, in no way, could predict. And so rather than where are you from, what would it look like if you replace that question with what is something you really love about where you grew up? Now you are learning something about who that person is rather than just a factor of chance of their life, for example. Open versus closed questions, “what” and “how” tend to, not always, there are exceptions, but tend to be open-ended questions. “Why” is this really weird thing where when all of us were three feet off the ground and about three years old, if any of you have kids or if any of you have been a kid, you walked around the world asking what question?

Amy Climer: Why?

Chad Littlefield: Why? Why? Why is the grass green? Why is the sky blue? Over and over again. And so that happens in your brain you get these really well-defined neural pathways that know very well how to ask the question why. It is almost, not even almost, it is automatic. It just ekes out. When we grow up, when somebody does something we do not like, “Why did you do that?” When somebody shows up late, “Why are you late?”

The Reason “Why” Questions Close Off Creativity [12:00]

For me, there are two dominant reasons why we actually teach people not to ask questions that begin with “why.” One of them is the idea that there is some level of inherent judgment in most “why” questions because it is a very scientific question and it is basically saying to the person, “Justify and defend why (fill in the blank).” Why this happened, why this occurred, why you were late. The caveat is because we all grew up asking why, why, why, we also have answered the question why, why, why and so we have our defenses and our justifications ready to go. Imagine you are at work and somebody shows up late to a staff meeting and the boss turns and says, “Why are you late?” What was that person who was late probably already thinking about the ten minutes before they showed up?

Amy Climer: What they are going to say.

Chad Littlefield: Exactly. They had this pre-fabricated and granted no one is trying to generate creativity in that moment, but what happens is they just fell into a scripted conversation where all that person had to do was plug in the tape and let their answer play out, as opposed to thinking new novel, creative thoughts and generating new concepts.

Amy Climer: That is great.

Chad Littlefield: The second reason, real quick, going back to the neural pathway is, it is actually just a little brain trick that when you say, “I only ask questions that begin with how or what now and I do not ask questions that begin with why,” it forces you to be really deliberate with your questions. You will notice this as you go to try this in the world or even in the next 24 hours, if you are listening, to ask questions that begin with only “what” or “how” you will eke out, you will start to ask questions that begin with “do”, “when”, “where”, “why”. All these words that either are closed questions or have some level of judgment and what you will do is you will reel that question back, you will peel it back in and then utter it back out as an open-ended question. I was, personally, and all of the people that we have taught, are really surprised at what happens when you peel back the questions and ask a really juicy question.

Amy Climer: That is great. I know because I have tried this because I have heard this from you before, it is harder than you think. Like you think, “Oh okay, that is not that hard,” and then you start realizing how often you used those other words.

Chad Littlefield: Yeah, really simple on concepts. The tool is ask questions that begin with “how” or “what.” Super easy. Anybody probably above a kindergarten reading level can understand that concept, but to practice it is really, really challenging.

Amy Climer: This is making me think of — I have recently learned from my wife Julie, who you know, like you know how so often kids will do something like this one kid hits another kid and you pull them over and you are like, “Hey, why did you hit them?” And they cannot answer that question. Their brain cognitively cannot process why they did that. Which goes back to that judgment like here at this young age you are asked why you did something and you are freaking out because you are like, “I have no idea why I did that. What? I do not know.”

Chad Littlefield: Yeah. It puts you in this panic because if you do not have an answer to that question, there is an assumed some sort of feeling like this person is judging you. They are asking you to justify and you are coming out empty handed.

Amy Climer: Yeah. Then if you ask them what just happened? Let’s walk through what happened. Then they start walking through it and then eventually they can get to why and then kind of identify, “Oh, here is where I should have done something different.”

Chad Littlefield: Yeah, breaking it down a little bit into smaller parts like you are asking people to write a mini dissertation in the moment, on the spot, off the top of their head, which is too much pressure for most people to perform under.

Amy Climer: Especially, if you are tiny.

Chad Littlefield: Yeah, especially if you are tiny.

Amy Climer: If you are ten or six or whatever.

Chad Littlefield: If you want an exercise to flex the how or what muscle, because like any other actual muscle, if you do not use it, it atrophies and dies. One of the exercises that we will do in groups, which you can do solo too, is we will read a passage, like a page or two of a book to them and then we will say not a lot of content. Then, in a group of six to eight people that we are teaching, we will have them whip around in a circle as quickly as possible asking questions that begin only with how or what and frame it as a competition of how many times can you get around the circle. Again, like good creative practice, going for quantity over quality and sort of just the idea of asking those how or what questions over and over again.

Eventually, they get better and the longer you go, the weirder they get as you are running out of things to ask about. But you can do that with yourself. You can just look at an object in your environment or wherever you are listening to this right now and just start asking how or what questions about that object. Just like the Socratic inquiry of asking questions from different angles. If it is an apple, “How did this become red? How does this taste so good? What are the elements in it that make some people like it and some people hate it?” Just start going and push until you get to the place where you are like, “I really cannot ask any more questions,” and then push another like two minutes. Flex that muscle.

How to use questions to drive creativity [17:34]

Amy Climer: Let’s go into this next question of how do you use questions to drive creativity?

Chad Littlefield: Sure. Two things come to top of mind. One is, if anybody has seen this study by Google, a company that really, really likes data.

Amy Climer: I have heard of them, yeah.

Chad Littlefield: They did this huge project called Project Aristotle where they went on this giant quest to build the perfect team. And as a part of the perfect team is obviously a team that is really creative, innovative, high performing. Of all the characteristics that teams show, the number one characteristic that rose to the top that defined teams that were consistently high performing was this idea of psychological safety. Which is the PhD term for do I trust the people that I am working with? And that is over simplified, but essentially that is what it boils down to.

Amy Climer: I wrote about that in my dissertation.

Chad Littlefield: There you go! If anybody wants to read Amy’s dissertation, go to…

Amy Climer: It is a long link. I will put it in the shownotes.

Chad Littlefield: On one hand, questions have this really amazing ability to kind of be keys that unlock information inside of people that allows you to start establishing a relationship or trust. One way that I use questions is to actually build that psychological safety. It is one of the like, “Great, Google found that out. Great, high performing teams need to trust each other.” Way harder to make a group of complex human beings trust each other than it is to just talk about it. And so one really concrete, almost mechanical, way of making it happen is asking really good questions that are rooted in your own natural, genuine curiosity.

The curiosity part is really important because I could give you a list of a 60 really awesome questions and you could ask them in whatever tone you want. But if you are not naturally curious when you ask that question, most people are socially intelligent enough to pick that up and know that like, “Whatever. This person doesn’t care about me, they don’t want to hear me, they don’t want to see me in this moment.” That is, on one hand, using questions and rooting your natural curiosity as a way to learn more about people and develop trust. Because there are lots of aspects of trust, but one huge aspect where trust develops is just through social connections of like, “I spend time with you and I overall have this general sense that you are a cool, good person that has my best interest in mind.” There are other components like are they reliable and all this, but just the social piece questions are really a good way to access that trust.

Amy Climer: It is basically this idea that I know I can be myself with you and you are not going to be a jerk back to me. You are not going to throw me under the bus later.

Chad Littlefield: Yeah. Notice as you go back in your life and you have a staff meeting or you go grab coffee with somebody or something like that, pay attention to the questions they ask and just see if you can be a little bit aware of how those questions hit you or make you feel. And are they the kind of questions like, “Hey, how are you? How was your weekend?” Almost the stock questions that were already formed ten years before they even asked you that question or do they really look at you and say, “Hey, how was your weekend?” Or “What’s a moment from your weekend worth remembering?” Things that create that novel thought right away.

That is on the connection front. I would say that is the indirect method of using questions to drive creativity. The direct way is actually asking really good questions that promote novel thought. One of my favorite questions that – who knows where it was actually coined – it is a question somebody’s asked probably back in 100 A.D., but the Stanford D-School likes to claim credit for this question that starts with three words: how might we… Have you talked about this question before?

Amy Climer: Yeah. And it is definitely a very old question. At least, since the 60s it has been associated with creativity and generating ideas.

Chad Littlefield: Wow! Breaking that down, one, it is a really good open-ended question. The reason I like it is it is one of those tools that you can have in your back pocket. You can say, “How might we…” and then fill in pretty much any context. Whatever you are doing, whatever your specialty is, whatever your focus, whatever your work, your family, whatever you want to drive creativity, fill in the context and you just need to remember those three words. How might we blank, blank, blank? It is a really open question. The word “might” takes off this pressure of judgment and “we” has this sense of collaborativeness that is not always present in meetings in particular where someone is asking how are YOU going to do this? It is like the freedom to be creative feels very limited when somebody puts that pressure on you. So yeah, it takes the pressure off there.

Amy Climer: I was recently facilitating a team kind of strategic planning process where they really want to be creative and I asked that question of how might we blah, blah, blah whatever, and one of the team members said, “Don’t you mean how will we?” I am like, “Oh no, I do not because we are not at that point yet. Eventually, we will look at the list and figure out what are we actually going to use here, but right now I want you to think of just how might we get creative.”  I think of might as a mighty word.

Chad Littlefield: That is a good little memory tool to keep it. My piece too is like one of the brainstorming was letting go of judgment. Because “how will we” is like well, this has to be the perfect idea or we cannot write it down on a piece of paper. There is that element there. That is one specific question. There are a couple of questions that I like to just have in my back pocket to solicit feedback from people as a way of generating creativity.

One of my favorite questions is, “What struck you about (fill in the blank)?” The reason I like the word struck in particular is when I ask that question to a group of people, so I am facilitating a team develop session with a group and I ask that question to a group of, let’s say, 15 people, with that question, I am able to reach both thinkers and feelers, both kind of “sides of the brain” with that. When I do that, I get to expand my own world view and my own perspective of the world because I hear things that I otherwise would not ask about.

Whereas if I ask questions all from my perspective and from my view of the world in my lens, that is exactly what I will get and I will continue to be in this funnel like the way a Facebook algorithm works. The more things you like, the more of that shows up. If you are really liberal and you like lots of liberal things or if you are really conservative and you like lots of conservative things, your news feed will get blue or it will get red. That will show up over time. The same thing with questions. If you have questions that are almost self-fulfilling prophecy questions, that is what you will get. You will not learn anything new.

Amy Climer: Can you give an example of that kind of question that you try to avoid?

Chad Littlefield: Let me ask you, what is something that you really believe strongly in?

Amy Climer: I believe that everybody is creative and has incredible capacity to be more creative.

Chad Littlefield: Cool. If you were to support that view of the world, let’s say you walked down to downtown Asheville and you wanted to support that world view, a question that you might ask someone, if you are canvassing and you are trying to figure out can everybody be creative? Is that really a thing? You might ask more leading questions like, “have you been creative?” It is almost like cherry-picking and you are not getting the whole picture. They are not closed questions, but they have narrow scopes of response. Whereas if you can ask a question that is broad enough — it needs to be clear, but broad enough that it allows people to answer from a direction that you might not be expecting. When you put, basically, your belief in the question, so if you believe something and you find at least, let’s say — this is an estimate — if you find three to eight words of that belief are in your question, it is probably a leading question that is guiding someone towards not a fully open response.

Amy Climer: Great. I love that example.

Chad Littlefield: Is that helpful?

Amy Climer: Yeah, that is.

Chad Littlefield: Cool.

Amy Climer: Before we wrap up, any final things about questions and creativity?

How to Use Questions to Drive Creativity [26:56]

Chad Littlefield: My business partner, Will, just wrote this book called Ask Powerful Questions and the penultimate chapter is on empathy. It has nothing to do with necessarily the structure of questions or mechanics of questions and the tool. One of the tools that is offered in that is as a way of empathizing with people, look at that person or think of that person, imagine that person and in writing or in words, describe the world as they see it. And just go through that experience of clearly articulating the world as they see it.

I think what I have found, personally — I am speaking from a place of I — what I found in doing that is I do not know people’s worlds as much as I think I do. In my head, I have this assumption of who they are, what they want, what they need and so a huge part of human centric design in almost every good design thinking process has this element of empathy in it. And so to have the tool of like describe the world as they see it, then show it to them and see how that lines up.

That can take the place in reflective listening. If you are listening to somebody and let’s say you are in a brainstorming session, you are wanting something creative, a creative outcome and somebody shares an idea, one thing that you can do, because you have listened to this awesome podcast, is just reflect back what you heard to that person in the form of describing the world as they see it and they will, undoubtedly, respond with either like a, “Yeah, that’s totally it! You’re right on point.” And feel really heard or it will be like, “Chad, you just missed the ball so much. That is not even close. Whoa!” That reflecting and describing the world as I see it can be real powerful. So empathy.

Amy Climer: I love that because then they can clarify like, “No, you totally missed it. Here is what I meant.” You are like, “Oh, okay cool.” As opposed to going forward and realizing or thinking that you are on the same page and you are not. That is a mess.

Chad Littlefield: You just kind of created an aha in my brain which has not happened before, which is like part of one of your steps of the creative problem solving process is this step of Clarify, which we were talking about earlier like I am kind of terrible at because I want to go in and implement things right away. But reflective listening does have this really beautiful ability to clarify and bring clarity to what you are even trying to be creative about in the first place.

The Weekly Challenge [29:29]

Amy Climer: Yeah. So true. I love it. We have talked about so much. One of the things I like to do at the end of every podcast episode is give listeners a weekly challenge. One thing that they can do this week to start applying what they learn from you. What would be a weekly challenge you would give people this week?

Chad Littlefield: I am going to give you the weekly challenge that we give all of our students that go through this facilitation training process. They come in the first day, they are scared out of their mind and at the end we leave them with, rather than homework, self-work. Work on oneself. And that is in the next week, go find three strangers — it could be in your daily work flow like a cashier or somebody random on the street — find three strangers and ask them an open-ended question that begins with “how” or “what” rooted in your natural genuine curiosity. Some of you just said, “Oh, heck no! That is never happening.” My invitation would be before you dismiss it, just ponder the perceived risk versus the actual risk. Because the perceived risk is usually pretty high, the actual risk is that you will never see this person again.

Amy Climer: Right. It is pretty low.

Chad Littlefield: And this stranger that you are never going to see again thinks you are weird. And that is about it.

Amy Climer: Maybe that is a good thing.

Chad Littlefield: It could be.

Amy Climer: I love it. That is awesome. Chad, how can people learn more about you?

Chad Littlefield: So the We! website is You can Google We! Connect Cards. We have got this cool deck of cards with 60 really awesome questions on them. You can Google those or you can find them on the website as well.

Amy Climer: Cool. I love it. Thank you so much for being on the show.

Chad Littlefield: Thanks for having me. It was a blast.

Amy Climer: Thank you Chad for being on The Deliberate Creative Podcast. It is great to have you on the show. I appreciated all the insights and resources that you shared for everyone. Again, if you want to get the resources that Chad shared and get links to everything he mentioned, you can go to You will find the links to Chad’s website, the Patch Adams movie, to the real Patch Adams, who is pretty amazing, and also to Chad’s We! Connect Cards. That is actually how Chad and I first met, was through cards. Because I have Climer Cards and he has the We! Connect Cards and as he was creating his, he reached out to me and we got to know each other that way. So it is kind of fun. And then miraculously, we both later ended up living in the same town, which is super cool. Anyway, small world.

I hope you enjoyed this episode and if you work on the challenge, share your comments in the shownotes. I would love to hear what happened. What questions did you ask the stranger and what happened? How did they respond? What answer did you get? How did it feel? Again, the shownotes with all the resources are at If there is a question you want answered on a future episode, feel free to email me. Or if you have a guest you would like to see on the show, let me know. Most of these episodes are based on what would be most helpful for you to help you lead innovation in teams.

Have a wonderful, creative week everyone and I will see you next time. Bye.

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