in: Behavior, Character, Podcast

• Last updated: September 30, 2021

Podcast #465: The Powerful Questions That Will Help You Decide, Create, Connect, and Lead

To move forward in life, we typically focus on finding answers. But my guest today argues we should spend more time asking questions. His name is Warren Berger, and he’s a self-described “questionologist” and the author of The Book of Beautiful Questions: The Powerful Questions That Will Help You Decide, Create, Connect, and Lead. We begin our conversation discussing why having an inquisitive mindset is more important than ever in this fast changing, uncertain world of ours, but why people are afraid to ask questions. Warren then argues that questions don’t necessarily need to have answers to be useful and explains what he thinks makes a question a “beautiful question.” Warren then talks through the importance of asking questions when you’re trying to make decisions, be creative, form relationships, and lead people, while providing concrete examples of questions to ask yourself and others to be more effective in each domain.

Show Highlights

  • How can asking more and better questions improve our life?
  • The value of an open and curious mind 
  • What holds people back from asking questions?
  • Why knowing more should actually lead to questioning more 
  • Are there such things as stupid questions?
  • What makes for a beautiful question?
  • Using questions to make better decisions 
  • How questions can change our perspective and framing of problems 
  • Why we give better advice to our friends than ourselves 
  • How asking questions can boost your creativity 
  • What adults can learn from kids about creativity 
  • How questions bolster relationships 
  • Can good questions build bridges across political divides?
  • Why leaders need to ask more questions

Resources/People/Articles Mentioned in Podcast

Book cover of "The Book of Beautiful Questions" by Warren Berger.

Connect With Warren

A More Beautiful Question website

Warren on Twitter

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Read the Transcript

Brett McKay: Brett McKay here and welcome to another edition of the Art of Manliness podcast. To move forward in life, we typically focus on finding answers. My guest today argues that we should spend more time asking questions. His name is Warren Berger, he’s a self-described questionologist and the author of the book, ‘The Book of Beautiful Questions: The Powerful Questions that Will Help you Decide, Create, Connect and Lead’.

We begin our conversation discussing why having an inquisitive mindset is more important than ever in this fast-changing, uncertain world of ours, but why people are afraid to ask questions. Warren then argues that questions don’t necessarily need to have answers to be useful and explains what he thinks makes a question a beautiful question. Warren then talks us through the importance of asking questions when you’re trying to make decisions, be creative, form relationships, and lead people while providing concrete examples of questions to ask yourself and others to be more effective in each domain.

After the show’s over, check out our show notes at And, Warren joins me now via

All right, Warren Berger, welcome to the show.

Warren Berger: Thank you, Brett. It’s great to be here.

Brett McKay: You are a self-proclaimed questionologist. You’ve been spending a lot of time thinking and writing about what makes a good question a good question. You make the case that to move forward in life in today’s fast-changing world, we need to ask more questions, which is counterintuitive because we think if we want to move forward in life, we’re looking for answers. So, how can asking questions improve all facets of our life, personal, business, et cetera?

Warren Berger: Yeah, I think of questioning as a mindset and a way of looking at the world around you with an open and curious mind. I think it’s more important than ever these days to approach life that way, that I’m open to learning. I’m going to question the information that comes at me. I’m going to question the assumptions about why things are the way they are. I’m just going to go through life with that kind of an attitude.

The reason I think it’s more important than ever is because the world we’re in right now … First of all, think about what’s going on with the glut of information. We all know about the situation of bad information coming at people and distorting their views. In a way, it’s more important than ever that we be questioning just basic things like the news information that’s coming at us or the stories that we’re being bombarded with on websites.

On that basic level, it’s important, but I think it’s also important in the larger sense that we’re in a world now where everything is changing all the time. Maybe in the past, you could coast a little bit on what you knew. You’d sort of go through school and go through college and pick up a trade or whatever, pick up a body of knowledge, and then coast on that for a while. Today, I don’t think there’s any coasting.

Everything changes so fast that all of us almost have to be in constant learning mode and that’s why questioning’s so important ’cause questioning is how you learn. Just that willingness to ask questions and take in new information and consider new points of view, that’s what’s going to enable you to keep learning and the learning will enable you to keep adapting and growing.

Brett McKay: Yeah, I like what you said about it’s an attitude you take towards the world. When you’re talking about all this glut of information, it’s really easy to get cynical. It seems like questioning is a positive alternative to getting cynical.

Warren Berger: Yeah, it is ’cause part of what goes on … I don’t know if you’ve noticed this, but I’ve noticed with cynical people, they have this attitude like, “Oh, I’ve seen it all. I know it all.” They always seem to take this view, “Oh, I’ve seen this before. We’ve heard this before.” Part of what their cynicism is built on is this idea that they’ve already figured out the game and there’s nothing new for them to learn. I think that’s a really bad attitude because that traps you in your current thinking or your current worldview.

I think it’s just really, really important to have that openness. That’s what’s going to keep things fresh in your life. It’s going to keep you open to new people, new ideas, and it’s just going to make you a better person overall.

Brett McKay: What holds people back from asking questions ’cause people don’t like asking questions particularly as you get older? You start asking fewer questions. What’s going on there?

Warren Berger: Yeah, there’s a few things going on there. It’s really interesting. If you look at the research on questioning, we all have heard or we all know from experience that kids are good questioners. Kids ask a lot of questions. That’s a known thing. What’s interesting is if you look at that, the research totally bares that out in terms of numbers. Kids who are three, four, five-years-old are asking just thousands and thousands of questions.

Then, what’s interesting and what a lot of people aren’t as aware of, is that there’s a drop off that happens when kids get to be six, seven-years-old and as they advance through grades of school, they seem to ask less and less questions. Then, that continues into adulthood. I think it’s interesting to think about why that’s happening. I think there’s a lot of things that work against questioning. I think of them as the enemies of questioning.

One of them is that fear of admitting to the world or to people around you that you don’t know something. So, if you’re asking a question, it must mean you don’t know something. Therefore, we think, “Oh, well that’s revealing a weakness. That’s revealing something that’s lacking in us.” Over time, we seem to get defensive about that and we don’t want to admit that we don’t know something. So, that’s a big, big enemy of questioning.

Then, there are just other things like time. We get very conscious of having to get things done and move forward all the time in our lives. Questioning, the very act of questioning to me is a stepping back. When you ask a question, it’s like you’re stepping back. You’re saying, “Hold on a second. I want to know this or I’m wondering about that.” To a lot of people that seems almost like it’s not productive or something. It slows things down. So, that’s another sort of thing that works against questioning is just that pressure for answers and to get things done and to just keep moving forward.

I would say one other thing that works against questioning, and this sounds odd, is knowledge. Kids, when they’re very young, aren’t weighed down by a lot of knowledge and so they’re asking questions all over the place. As we start to know more, we start to feel like, okay, we’re starting to figure all this stuff out. That causes us to ask less questions and I think that’s kind of bad. That’s like the knowledge is good, but the lessening of the questions is bad. Ideally, we want to be knowing more and also questioning more so that even though we’re knowing more stuff and learning more stuff, we still want to know even more and we want to learn even more.

We have to kind of overcome that trap of expertise, that idea that, “Oh, I’ve got this figured out, therefore I don’t need to ask any questions.”

Brett McKay: Your first book was ‘A More Beautiful Question’. What makes a beautiful question a beautiful question? Are all questions created equal? There’s that saying, there’s no such thing as dumb questions, but is that true?

Warren Berger: Well, I think there are dumb questions or there are stupid questions. Often times, I’m in a meeting and the meeting is about how our organization is going to innovate and someone asks a question about their vacation time or something like that. There are questions that are off-topic or that are self-centered, not concerned about what anyone else is working on. There are definitely bad questions, but I think I enjoy … To me, one of the things I really like are naïve questions, which sometimes get dismissed as stupid questions.

A naïve question is when you step back and say, “Wait a minute. Why are we doing this thing we’re doing?” It’s like really basic. Everyone’s already figured out as a group our goal is to do ‘X’ and now we’re working on how are we going to do ‘X’ and how are we going to do ‘X’ faster and how are we going to do ‘X’ more efficiently. Then, someone comes along and says, “Wait a minute. Why are we doing ‘X’ in the first place? I love those kind of questions because, on the one hand, they seem very fundamental and very basic and sometimes they’re annoying to people ’cause they feel like, “That’s too basic. Why are you asking that question?”

What they do is they force you to regularly challenge your own assumptions or reconsider your assumptions, reconsider the thing everyone thought we agreed upon. Maybe it’s time to just step back and say, “Do we really all agree on this? Does it really make sense and have we thought about it lately?” I love naïve questions. To me, those are beautiful questions.

In general, the way I would define a beautiful question is, a beautiful question is a question that’s ambitious. It’s not like, “Oh, what color should we paint the walls in our kitchen?” That’s a fine question, but it’s not particularly ambitious. I love questions that are ambitious, that are actionable and that might bring about some kind of change or they might bring about change in people’s thinking or they might bring about change in the world or the change in your company or your organization.

If you would have asked a question like, “How might I help this organization to do a better job of communicating with each other?” Maybe you’ve noticed that there’s a real lack of communication in your group or your organization and you pose that question to yourself. I love that ’cause that’s a beautiful question. It’s ambitious, but yet it’s something you might be able to actually work on and do something with and it’s a question that if you answer it, it could change things. There could be a change that comes about because of that. That’s the way I define a beautiful question.

Brett McKay: I love it. My favorite questions, I think this is in line with what you’re talking about, are the questions that don’t have an immediate answer or they don’t even have an answer at all, but they just get me thinking.

Warren Berger: Yeah.

Brett McKay: Those are my favorite absolute questions.

Warren Berger: Oh, yeah. Yeah, those questions can come from anywhere. There’s a story that I tell and my first book, ‘A More Beautiful Question’, about the Polaroid Instant Camera and how it came about because the founder of Polaroid, Edwin Land, was out one day with his four-year-old daughter and he was taking pictures with a standard camera back in the 1940s. Of course, in those days, you took a picture, you had to send the film out and wait for it to get processed and all. It would be days and days before you ever saw the results.

So, he tried to explain this to his daughter, his four-year-old daughter and she said, “I don’t understand. Why do we have to wait for the picture?” That question just blew his mind. It just shifted Edwin Land’s thinking because it’s so obvious and so fundamental, but he’d never really thought about why do you have to wait for the picture and what if you didn’t have to wait? What if there was a way to create a camera where you could get the results right away? That became the basis of him creating the Polaroid Instant Camera.

I think what’s interesting is questions have this power, the right question has this power to unlock something in our minds or in our imagination that can be really amazing. You can do this in your own mind. You can do this by asking yourself a great question or sometimes you can do it to other people. When you put a great question out there, it can just trigger something in other people and they’ll say, “Wow, I never thought about that question before, but I’m going to think about that. That’s got me going.”

Brett McKay: Yeah. The great thing about those sorts of questions is that you might not even get the answer you were thinking you would get. If you just go with that openness, you throw it out there and it can go somewhere completely different. It’s because of the question.

Warren Berger: What I think of is the greatest questions, the most beautiful questions, first of all, there’s no simple answer. You can’t look it up on Google. If it’s really a beautiful question like, “How am I going to bring about change in this situation or in my life,” you’re not going to find the answer on Google. As I like to say, you have to do a different kind of search. Google’s not going to help you.

I love that. I love the idea that we can and we should pursue really ambitious questions that don’t have easy answers and we don’t know where they’re going to lead us. They may lead us somewhere that’s not what we expected, that’s in a whole different direction than we thought of starting out.

Brett McKay: In your latest book, ‘The Book of Beautiful Questions’, you get really specific and offer suggestions with specific questions for different facets of our life. The one section I found really useful and I’ve been using it in my own life since I read this book, is the section on using questions to make better decisions.

Warren Berger: Yeah.

Brett McKay: First off, how do people typically … By decisions, let’s say we’re talking about big decisions not what am I going to eat for breakfast today, though you can question that, right?

Warren Berger: Right.

Brett McKay: But, the things like, should I take that job where I have to move my family?

Warren Berger: Right.

Brett McKay: How do people typically approach decisions like that without asking questions that prevent them from exploring different options or even eliminating options?

Warren Berger: Yeah. Well, there’s this very popular expression of going with your gut and that’s what a lot of people do when they’re making decisions. They go with their gut instinct. There’s two schools of thought on that. Through the years there have been a lot of people that really praise gut instinct and say, “Yeah, you should trust your gut and go with your gut.” You remember Malcolm Gladwell wrote the book, ‘Blink’, that was all about amazing decisions people made just in the flash of a second just based on a gut instinct.

There’s a whole school of thought that says, make gut decisions and it’s great, but increasingly, the research, if you look at the scientific research on this, it shows the opposite. It shows that if we are making a lot of decisions just based on our gut instinct, on what we feel in the moment, we’re going to make a lot of mistakes. We’re going to make a lot of bad choices. The reason for that is that we as human beings, we tend to have all these biases.

We have these inherent biases that we’re not even aware of and the biases can be things like we’re biased in terms of short-term instead of long-term. We tend to be much more focused on what’s happening right now as opposed to what’s down the road. We have a bias that’s sometimes referred to as the negativity bias where we’re biased … Negative things have a much bigger impact in our minds than positive things. We have a lot of fear so we make decisions sometimes based on fear.

The point is, you have all these biases and assumptions and things like that that are going to cause you to make a decision that might not be the best decision. I guess the case I’m making in the decision-making chapter, is that you need to slow down the decision making process a little bit if you can. Obviously, if you have to make a snap decision because of the situation, then you make a snap decision. But, if you have time, take advantage of that and think about your decisions more.

One of the ways that you can do that is by asking yourself questions and asking other people questions. It’s one of the ways you can bring more information into the decision-making process and open up more possibilities to choose from, more options. It can also help you overcome some of those biases like the fear issue when you’re making a decision. Just asking yourself questions like, “Okay, what scares me about this decision and what excites me about it?” Just asking yourself those questions to identify these things that are under the surface, it will help a lot.

Or, asking a question like, “What’s the worst case scenario here? What’s the worst that could happen if I make this decision and what’s the best that could happen?” Just getting yourself to think about those things will give you more information to help you make the decision.

Brett McKay: One of my favorite questions, and I’ve used this a couple times on people when they’ve come to me with this question, was the one about overcoming the biases of short-term/long-term thinking. One of the hard things is that you don’t know what your future self’s going to like.

Warren Berger: No, exactly.

Brett McKay: You’re just focusing on what you want now. So, one of the questions that I loved was about whether you should take a job that has a pay raise or whether you should stay where you’re at now ’cause it’s easy on your family, things are good. The question was, I believe … You kind of invert it. You ask yourself, “All right, let’s say you’re already living in that new city. You’ve got that job. Let’s say you get offered to move back home, but with a pay cut. Would you take that?”

Warren Berger: Would you take it? Exactly. What that question is doing and this is the amazing thing you can do with questions. You can shift reality. You can shift perspective so you can basically say, “Okay, I’m trying to answer this question or make this decision based on the here and now, but what if I shift things around and I think about a year from now or I think about it from a different perspective in some way?” That allows you to just come at the decision a different way.

What that example you cited came from someone who actually did that. He was facing the prospect of having to make a move and for a job raise or not. What he did, when he made that little switch and he asked himself the question as if he’d already made the move, as if he already made the decision, and would he regret it, would he go back and take a pay cut to be back home, what he was doing there, one of the things he was doing with that question was he was overcoming his own fear of moving and change. His fear of change basically.

What that exposed to him, what that revealed to him was that the thing that was keeping him really from taking the job was just a fear of making a change. That’s all. When he framed the question as if the change had already been made, then it was no question at all. It’s, “Oh, yeah. Obviously, this is what I want.” The only thing getting in the way was change. Once he realized that, then he realized, “Okay, I should take the job because I shouldn’t let a fear of change stop me from doing what otherwise is clearly the right thing to do.”

That’s what you can do with questioning. You can sort of reframe things. You can remove certain constraints just temporarily. I love the question that’s in the book called ‘what would I try to do if I knew I couldn’t fail?’ That’s a very popular question right now in Silicon Valley. They love to ask that question. What you’re doing with that question is you’re temporarily removing the constraint of failure so that you can then think about possibilities in the boldest, bravest way. You can think, “Okay, I don’t have to worry about failure anymore. I’ve put that off to the side, so what would I do?”

Now, all of a sudden, you start to have very bold ideas. “Well, if I didn’t have any fear of failure, I would do this. I would do that.” The reason that’s so good is it just opens up a part of your brain. It opens up possibilities that might be ignored otherwise. Now, the important thing to note is after you think about that question and you come up with these bold possibilities, you still have to go back and understand that failure is a possibility.

Now, you go back and you bring failure back into the equation. You say, “Okay, I’ve thought of all these bold possibilities, now I have to realize, yeah, failure could actually be an issue here, so how would I deal with it if, let’s say, I did fail on this situation? What would be the worst case scenario? How would I recover from that?” Basically, it’s a really powerful way to allow yourself the freedom to really think and really consider all the possibilities.

Brett McKay: Yeah. Another powerful question that I got out of the book and I’ve used it on two people that came to me with some problems was all right, let’s say a friend came to you with this exact same problem, what would you tell them?

Warren Berger: Right.

Brett McKay: That question, I guess, gives you some mental distance from your problem which allows-

Warren Berger: It’s incredible, yeah. The author, Dan Ariely, has talked about this and has showed the research that shows that we give better advice to other people than we give to ourselves, which is weird, right? It’s like, why would that be the case? Well, there are reasons for it. You know how sometimes you’re too close to a problem to see it clearly? That’s the way we are with our own lives. We’re too close to it to see it clearly, but when our best friend is having a problem, that we can see totally clearly. We can see our best friend’s situation. We know what’s in his best interest.

So, we’re able to make a really great decision for our friend and to say, “Hey, I know exactly what you should do.” Then, when it comes to ourselves, we have trouble. Again, here’s where you can use a little questioning trick just to say, “If my best friend were facing this decision that I face, what advice would I give? How would I advise my best friend to proceed?” The chances are whatever advice you would give your best friend is also pretty good advice for yourself.

Brett McKay: I love that and there’s so many more questions in that section. I love how specific they are. Let’s move on to creativity because with the robots coming after our jobs-

Warren Berger: Yeah.

Brett McKay: … success in today’s economy requires creativity, thinking differently. The problem is, as you said, a lot of adults, not only do they stop questioning, asking questions, they start thinking of themselves as not creative.

Warren Berger: Right.

Brett McKay: I think the same things that are going on why adults don’t ask questions also goes into why adults think they aren’t a creative or they just …

Warren Berger: Yeah, it’s been trained out of us. Just as questioning was kind of trained out of us, creativity is trained out of us. Not intentionally, but just the systems we go through in school and in the workplace tend to discourage both questioning and creativity. I think of creativity is all about asking questions, but one of the things I say in the creativity chapter is let’s start with the most basic question of, am I creative, which that’s the first question to deal with if you want to unlock your creativity. You’ve got to deal with that question that people wonder about as, “Gee, am I really creative? I don’t know.”

The answer to that is yes, you are. We all are. You almost have to stop asking that question and reframe it a little bit as, what are some of the ways I seem to be creative? Try to identify that. Try to identify where your creativity naturally seems to come out or seems to flow. The other questioning you can do around creativity is, one of the big things I talk about in that chapter is that a lot of times creativity is about just finding the right problems to focus and work on. Artists are always trying to do that. Innovators, inventors are always trying to do that. They’re trying to find that problem, something that’s lacking in the world, something that’s missing, a voice that’s not being heard, a device that people need and they don’t have.

You’re just trying to ask, what problem can I make my own? What problem can I take ownership of and work on? That’s a big question and then in terms of finding that, in terms of finding what it is you might want to work on, you just ask yourself questions like, what stirs me or what bugs me? What are things I see out there that drives me crazy? I say, “Why hasn’t someone done this or why doesn’t anyone ever present his point of view?” Look for the things that somehow raise your emotions a little bit or really, really engage. That may be the area where you want to search for a problem you want to tackle.

Brett McKay: Yeah, I think you mentioned, I think it was David Kelley, the guy at Ideo. He keeps a notebook of-

Warren Berger: Yeah, Ideo.

Brett McKay: Yeah, he keeps a list, a notebook of annoyances that come up throughout the day.

Warren Berger: Yeah, so when he’s walking around, every time he finds something that annoys him like the fact that certain kind of doors have to be pulled out instead of pushed in or whatever, he will make a note of that and his company is … They’re always working on innovations. They’re always working on new ways of designing things. He’s just got this long list of things that he thinks could be better designed.

I think all of us can find things like that. Now, it doesn’t mean we’re going to change every little thing that annoys us, but it just means that you’re looking for areas of opportunity. Somewhere in that long list that you start to compile, there may be something that you can actually decide, “You know what? I’m not just going to complain about this. I’m going to try to do something. I’m going to try to take ownership of this particular problem or this particular challenge.”

Brett McKay: One thing I’ve read about creativity is they’ve done these experiments with kids and adults where they’ll give them a box of just stuff, and the kids end up coming up … They had to solve a problem with just random stuff. It could be like a hammer and a piece of cardboard or a paper towel tube. The kids were able to come up with a lot more solutions than the adults and they say it’s because when adults see a hammer they think, “Well, you just hammer nails with that.” A kid sees a hammer, they don’t know that. It’s not encrusted in their brain yet.

Warren Berger: Absolutely.

Brett McKay: Some other questions would just be making assumptions about stuff or asking questions that challenge the assumptions of everyday life, right?

Warren Berger: Yeah, yeah. Yeah, the other thing that kids are really good at, and we can all learn from is that kids will just try stuff. They won’t think about it. They won’t worry and be paralyzed by what should they try. They’ll just go ahead and try it. What they’re doing there, it’s interesting, they’re acting on their questions immediately. If you could see inside their head, they’re saying, “What if I try this? Okay, let’s try it. What if I turn this upside down? Okay, let’s turn it upside down.” So, they’re constantly questioning, but then they’re also acting on their questions really quickly and turning them into little experiments.

That’s one of the reasons why if you give a kid some type of a little building project with some funky raw materials, duct tape and straws and things like that, they’ll be able to build something much faster than an MBA graduate would be able to do it because they’re just natural born experimenters and they’ll start trying stuff right away. So, I think of that as a form of questioning too. They’re always in that mode of, “Hey … ” They’re always in ‘what if’ mode. What if I try this? What if I try that?

Brett McKay: Another area you talk about in the book are relationships, and questions in relationships. That, I think, again, people don’t ask a lot of questions in relationships because questions are scary. They’re afraid of the answers they might find out or they’re afraid that the question will come off as too intrusive, challenging. But, you argue that, no, questions can actually really strengthen relationships both personally and in business.

Warren Berger: Yeah, questions seem to do three things that are important for relationships. Number one, they show interest. So, when you ask a question, you’re showing interest in the other party. Number two, they create understanding because as you ask questions, you get information back. You understand more. The third thing is they build rapport because they create conversation, they generate conversation which in turn builds rapport between the two parties.

I think of those as the three legs of the relationship stool, the three legs that a relationship can be built on. It’s really interesting because it matters and it works both with new relationships, so people you’re just meeting, as well as established relationships, people you might be really close to. It’s important in either case, if you think about it. With a new person, yeah, you want to show interest. Yeah, you want to create understanding and build rapport. That’s all really important to creating a new relationship with someone, but those things are also important with your girlfriend of 10 years or your spouse or your brother or your father-in-law, or whatever.

You want to, even though you’ve known that person for a long period of time, you still want to show interest, you still want to create more understanding, and you still want to have that rapport. So, I think questioning is just … It’s a really, really valuable tool for that. People worry about it that it might be intrusive or something when you ask people questions, but it’s not really the case. For the most part, people are flattered when you ask them questions.

As long as you ask the questions in the right way. The questions should be coming out of curiosity. They should seem somewhat authentic like you really are interested. If you’re asking rote questions like, “What’s up?” Those don’t have that much power, but if you’re asking questions that really seem to show interest and curiosity, generally people love that ’cause, hey, they love that someone’s curious about them.

Brett McKay: Right. Well, I mean you highlight this Arthur Aron. I think his list of 36 questions you’re can ask that can possibly lead to love.

Warren Berger: Yeah, he’s been doing these experiments for years. He’s a psychology professor who specialized in intimate relationships and whether people could build intimate relationships, essentially whether they could fall in love with each other by talking to each other in certain ways. One of the things he found was that asking questions of each other, if two people are getting together for the first time, they’re on a date or something, and they ask questions of each other, it was really, really powerful.

Then, he started trying to figure out what kind of questions are the best ones and he ended up coming up with 36 questions that were … They’re all about if you could have dinner with anyone in the world, who would it be or how would you describe your relationship with your mother. They were these sort of questions that got at deep beliefs and feelings that a person might have. He found that if two people did these 36 questions with each other, it was pretty amazing. By the end of the experiment or the question asking session, they felt very close to one another. A few of them actually did fall in love. One couple got married after they did his experiment.

His point was, again, coming back to that idea that just by showing the interest is really important and then by creating and understanding. The questions, if they’re good questions, will help you start to understand this other person on a much, much deeper level. I think it’s really valuable. I think guys especially, guys can really benefit from this information because I think women tend to be pretty good question askers, especially, let’s say, on a date.

Women will tend to ask questions, but guys a lot of times don’t. I’m not sure. I think it may have to do with guys sometimes feeling like they have to make a good impression on a date and that the way that they’re going to impress someone is by telling stories or by telling jokes or whatever, just showing something about themselves. They tend to forget about asking questions so they’re missing a really, really important thing, a really important element that could really help them build a rapport with the other person.

Brett McKay: Yeah, one of the insights I got from there that was really powerful is that you can start off with the superficial questions that you usually do on a first date like how many brothers and sisters do you have, but then you go deeper. It would be like, “What made you the most different from your siblings?”

Warren Berger: Right. Exactly. The deeper you can go on questions … People worry about asking deep questions too soon, but one of the people I quoted in the book said he believes just jump right into the deep end, the deep end of the pool because there’s no point wasting too much time on a lot of surfacey, shallow questions. They’re really not going to get you that much information. As soon as you start to ask a fairly deep question that really gets at someone’s feelings or what makes someone special or different, as soon as you start asking those questions, that’s when you’re going to start to be making a connection with that person.

I think most people will welcome it and if someone doesn’t welcome it, then maybe that’s a signal too. Maybe that means that they’re really not that interested in you.

Brett McKay: Right. As you said, this works for also established relationships. One of the questions I got from the book … Soon as I read it, I asked my wife this question. It was, what’s something you’ve always wanted to try but haven’t done yet?

Warren Berger: Yeah.

Brett McKay: She’s like, “That’s a great question.”

Warren Berger: Yeah, exactly.

Brett McKay: We had this great conversation.

Warren Berger: Yeah, and what’s so funny is we assume we know so much about people that have been in our lives for a while and what you will discover through that kind of questioning is boy, there’s a lot you don’t know. ‘Cause it just doesn’t come up in day-to-day conversation. It’s a really great way just to surface things that you probably should be aware of but aren’t aware of.

Brett McKay: Related to relationship is this idea that we live in an intense time of political polarization.

Warren Berger: Yeah.

Brett McKay: Do you think questions can bridge the gap between people on different sides of the spectrum?

Warren Berger: Well, they can help. Right now, it’s tough. It’s tough out there right now. There’s a feeling of we’re just … There’s a wall between us and you’re either on one side or the other side. It’s a difficult time, but I think any attempts to reach over that divide are going to have to involve questions. They’re not going to involve statements. Statements won’t do it.

The problem we have right now is that both sides have their statements, they have their ideas, they have their beliefs, and when they try to communicate with each other, the way I envision it is like their statements are butting heads. Their statements are just banging into each other and nothing good happens, nothing good comes of it.

By changing those statements to questions, we at least have a chance of starting to make a connection. Again, going back to that idea of what do questions do when you ask someone else a question. Number one, you’re showing interest, all right? Number two, you’re trying to create some kind of understanding. And, then number three, you’re building rapport.

We have to show interest in people who are on the other side from us. We may be inclined to say, “I don’t care. I don’t agree with them and therefore, I don’t care.” But, if there’s going to be any progress at all, you have to show interest. There’s a great line that someone in the book used which is Lynn Nottage. She’s a playwright. She said, “I try to replace judgment with curiosity.”

When you’re encountering someone of a different point of view, instead of automatically judging them, try to bring curiosity into the equation. Curiosity would be, why do they feel the way they feel? What are some of the factors that might be going into that? Is there anything in their viewpoint that I should think about or I should consider? Is there something I might be missing that they’re saying? Is there something they’re not saying that is kind of under the surface?

I think if you bring that kind of curiosity to your interactions with other people, people on the other side, it’s at least a start. It may work. It may not. It all depends on how receptive they are to your curiosity, but if they’re receptive to it, then they may turn around and ask you some questions too. Okay, why do you feel the way you feel? At least when you get onto that level of conversation, you’re starting to exchange information a little bit instead of just lobbing grenades at each other.

Brett McKay: Yeah, I think that’s a good point to make that you need to go in the mindset that you’re not going to convince someone.

Warren Berger: No. No, absolutely. Exactly. That’s a great point because everyone right now is in that mode of I’m going to beat you up with facts. I have my set of facts here and my set of facts is so strong that there is no way you will be able to resist. Well, sorry. That doesn’t work. We know that doesn’t work. When people have made up their mind about something, yelling at them and citing a bunch of facts at them, unfortunately, it doesn’t have much impact. They kind of have built up a defense against that and they have their counter facts that they will come back at you with.

You need to get beyond that kind of thing, that thing of like, “I’m going to argue you into my point of view.” You need to instead be thinking in terms, “Okay, is there any common ground we can find? Is there anything we can agree on?” Because that will be the beginnings of a dialogue at least. If there is a goal that you’re trying to do through questioning a person of a different point of view, it’s a very modest goal. You just want them to consider your side just a little bit. That’s all. You don’t want them to come over to your side. You don’t want them to accept your side totally.

If you can get them to, just for a minute, think about your side of the issue, that’s a victory. It’s a small victory, but it’s a victory. Because, at that point, they’ve gained 10%. They’ve gained a tiny bit of understanding of your side and that’s a good start.

Brett McKay: Yeah, the question you ask for that, I think you mentioned it in the book, was is there anything about my position that you find attractive?

Warren Berger: Exactly.

Brett McKay: Right.

Warren Berger: That’s a very powerful question. Another trick you can use with questioning is you can say, “Here’s my position. On a scale of one to 10, how much do you disagree with it and how much do you agree with it?” The reason that’s a really effective question is because even if people disagree with your point of view, rarely will they put it at the lowest number. So, they won’t say, “Oh, Your point of view I give a zero.” Usually, they’ll say, “Well, on a scale of one to 10, I’ll give your point of view maybe a two.”

Then, you can say, “Okay, why are you giving it a two? What is it that gives it a two instead of a zero?” At that point, you’re forcing them to articulate the positives in your argument. You’re almost forcing them to articulate your side of the argument a little bit. Again, it’s just a way to make that little shift of perspective where all you want someone to do is to think about your side just a little bit.

By the way, you should be doing the same thing with their side. It’s not fair to think, “I want them to think about my side of the issue a little bit,” without also saying, “I’m willing to think about their side a little bit too.”

Brett McKay: Yeah, that one to 10 trick, that reminded me. It’s completely unrelated to polarization, but Tim Ferris, we had him on the podcast a while back ago. One little trick he had was when he goes to a restaurant and he’s asking the waiter, is this meal good? Is this dish good? He asks, “On a scale of one to 10, what would you rate this dish but you can’t say seven.” That forces …

Usually, people are like, “Ah, you know. It’s a seven.” That doesn’t really tell you anything. But, if it’s a nine, that means it’s really good. If it’s six, then it’s probably not great.

Warren Berger: Yeah, he’s forcing you to sort of make that choice. Yeah, yeah. That’s interesting. Yeah, what he’s doing there, again, is using questioning as a great way to manipulate thinking or shift thinking a little bit or force a different perspective on there. That’s the power of questioning. What it all boils down to is what you’re trying to do with questioning a lot of times is just shift perspective a little bit.

All of us tend to have a narrow perspective. We’re looking at things just through tunnel vision. What you want to do is open it up a little bit. Open up that tunnel vision a little bit so you see more, you consider more, you take in more information, and you have more possibilities to choose from, you have more points of view that you’re considering. You want to do all those things and questioning helps you do all those things.

Brett McKay: The last section was about leadership. Leaders need to ask more questions, which is counter-intuitive because we think of leaders as the people that have the answers. The buck stops with me as Truman said.

Warren Berger: I think that’s-

Brett McKay: Yeah, why do leaders need to ask questions?

Warren Berger: I think that’s the old model of leadership, right? It’s the idea that the leader has all the answers. To some extent, there’s still a number of leaders who still operate that way today, but I think there’s a new model of leadership that’s as you should be a questioning leader. The reason goes back to what we were talking about at the outset about this changing world we’re in now where everything is happening very quickly, change is going on all the time, and the idea that a leader can have all the answers is sort of obsolete.

A leader in today’s world should be very open to new information, should be soliciting points of view from all around him or her, and should just be questioning why are we doing things this way or how should we react to this new change that’s going on. A leader today just has to be a questioner, has to be curious, and has to be open-minded. If not, what the leader’s going to do is lead people off a cliff because what will happen is the leader will be operating with very limited information, with a very sort of biased point of view about what works and what doesn’t, and it’s almost bound to fail in the world we live in today.

Brett McKay: Yeah, this is not to say that leaders don’t have a vision. Leaders have a vision, but they ask questions to get to that vision.

Warren Berger: Yeah, and they question that vision constantly as they go along. So, they ask questions to establish the vision starting with what is my vision? Pretty basic, right? But, you do have to ask yourself that and articulate what do you really believe? Why are you a leader in the first place? Why do you want to be a leader? And, what are your core values?

You need to ask those questions in the beginning and articulate that vision, but then you also need to be questioning that vision as you go along because, as I was saying, it’s like change is so constant now that the vision that you came up with at the beginning of your venture, whatever it is, might not hold up as well now as it did a few years ago. Maybe it needs to be changed or just fine-tuned in some way, but that’s one of the things that a leader has to do now is be willing to say, “Okay. Last year I thought this, but this year, I’m thinking more we should be doing more of this.”

That’s okay. That’s actually what you should be doing now as a leader. You should be totally open to that kind of adaptability based on the change that’s going on. It doesn’t mean you’re wishy-washy. It doesn’t mean you don’t have that core vision. You can still have those core values, that core vision, but it has to be much more adaptable now. It has to be more flexible.

You see people leading companies now who are having to ask questions like, what business are we really in? Last year, we thought we were in the shoe business, but now people aren’t buying shoes the way we used to and maybe we need to adjust the model. So, I think it’s just become kind of a fact of life for leaders now.

It’s challenging because it requires almost a different skillset than leaders are trained and are used to using that top-down model of leadership where you’re supposed to make snap judgments and then execute them. This is a different skillset. The questioning leader has to be someone who’s willing to show a little bit of vulnerability, which old leaders necessarily weren’t used to and didn’t like to do. You have to be willing to admit that you don’t have all the answers and that you’re open to new points of view and you have to be confident enough to do that and believe that people will still follow you.

Brett McKay: Right. I guess a question that a leader should constantly be asking is why. Why are we doing this?

Warren Berger: Yeah, why are we doing this and, again, on a personal level, why. Why me? Why am I leading this organization? That’s a pretty basic thing. You find a lot of people sort of fall into leadership positions or they climb up to them because it’s a natural outgrowth of their career advancement. They just climb the ladder and eventually, they’re the leader. Then, they look around and they go, “Whoa, this is not necessarily what I wanted.”

I think leaders need to be even asking that basic question of, why do I want to be a leader? Do I really want to be leading this group of people and do I want it for the right reasons? Because if you don’t want it for the right reasons, if the answer to the why question is all selfish, if it’s like, “I want to be a leader because it pays more money,” or there’s a lot of glory. I’ll get on the cover of a business magazine. If you have those kinds of selfish reasons for leading, those are not going to serve you well in terms of your followers. Eventually, your followers are going to get wise to that and you’re not going to have loyal followers eventually.

I think it starts with asking, why do I want to be a leader? Do I have the right motivations? Then, it moves to the organization. What are we about as an organization? What should we be about? What should we stand for?

Brett McKay: I imagine it’s scary to ask that question because the answer could be, “Well, maybe I shouldn’t be a leader.”

Warren Berger: Oh, yeah. It definitely could and there’s a lot of people out there who are leaders right now who shouldn’t be. One of the things that you see in companies is the star performer often ends up the leader. The person who was the greatest salesperson in the history of the company ends up being the leader. Sometimes what you discover is that really great salesperson probably should have stayed a salesperson because once they become a leader, it’s a whole different world.

Now, instead of it being all about them and their individual results or their individual performance, now, they’re suddenly responsible for a whole group of people. As a leader, this sounds counterintuitive, but in some ways, you have to step back and step away from the spotlight because being a leader is not so much about being an individual achievement anymore. Now, it’s about sharing credit with other people, worrying about other people’s performance as opposed to just your own.

It’s an interesting thing and not everyone is cut out for it. Some of these star performers at companies, it would be nice that they realized that and, by the way, it would also be nice if organizations figured out ways for those people to still prosper and be very successful without becoming the CEO.

Brett McKay: Yeah, you see that issue with founders of companies. They’re really good at starting companies, but then they want to maintain, still be CEO, but they’re not a good CEO.

Warren Berger: They’re not a good CEO. If they’re smart, they will outsource that to someone who is a good CEO. Some of the smart ones do exactly that. They realize, “Hey, I can’t handle this. I’m going to find someone who knows how to be a leader and I’m going to let that person actually run the company.” A lot of people, there’s ego involved there and a lot of people, I don’t know, they feel like they can do anything and they’re not honest with themselves about what they really are good at or what they really want to do.

Brett McKay: Right. It’s a bias, a curse of expertise. You think you’re good at one thing, you’re good at everything.

Warren Berger: It’s that feeling of, I can do it all.

Brett McKay: Right. Well, Warren, this has been a great conversation. Is there someplace people can go to learn more about the books and also maybe a place to go find some questions that they can start using today?

Warren Berger: Yeah. Well, my main site that I use is So, just take those four words, a more beautiful question, and just squish them together into one word and dot com and you’ve got the site that basically has my new book, ‘The Book of Beautiful Questions’ featured on it. It’s also got all the articles and essays and things that I’ve written, the research, the data. There’s some fun stuff on there like I created a list of all the songs I could think of that have a question for a title like ‘Who Wrote the Book of Love?’ and things like that. I’m up to, I think, I don’t know, 60 or 70 songs now.

There’s all kinds of fun. There’s quizzes you can take on what kind of a questioner are you. It’s basically a clearinghouse for all of my information about questioning and anything that might be related to questioning. That’s the place to go.

Brett McKay: Warren Berger, thanks for coming on. It’s been a lot of fun.

Warren Berger: Thank you very much, Brett, I really enjoyed talking to you.

Brett McKay: My guest today was Warren Berger. He’s the author of the book, ‘The Book of Beautiful Questions’. It’s available on and bookstores everywhere. You can find out more information about his book and his work at Also, check out our show notes at where you can find links to resources, where you can delve deeper into this topic.

Well, that wraps up another edition of the Art of Manliness podcast. For more manly tips and advice, make sure and check out the Art of Manliness website at If you enjoy the show, you’ve got something out of it, I’d appreciate if you take one minute to give us a review on iTunes or Stitcher. It helps out a lot. If you’ve done that already, thank you. Please consider sharing the show with a friend or family member who you think would get something out of it.

As always, thank you for your continued support. Until next time, this is Brett McKay telling you to stay manly.

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