Supercommunication Expert: Ask These Questions To Make People Open Up and Connect With Anyone. A Convo With Charles Duhigg

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Sure, absolutely.

Yeah, I want to talk about the journey of you writing this book. Before you studied Super Communicators, were you good at this communication thing?

Well, first of all, thanks for having me on. This is a huge treat for me. And to answer your question, so I thought I was a good communicator because I'm a journalist, right? I write books for a living. I used to write for the New York Times, and now I write for the New Yorker magazine. And so at the Times, they made me a manager at one point. And I was like, oh man, I'm going to do great at this. Like, I really— I have an MBA from Harvard Business School. You know, I'm all set. And I found out that I was not as good a manager as I thought I was going to be. And it all was because of bad communication that basically I would have people come to me, you know, my direct reports, and they would bring something up and I would fail to hear what they were really saying. Right. Or they would bring to me what was clearly sort of an emotional problem. And I would treat it like a practical problem and would try and solve it for them. And we all know that this doesn't work, right? Many of us probably experience this at home where our spouse complains about their day and we try and solve their complaints and they don't want the solution. They just want the empathy. And so that was one of the things that really made me realize there's a lot to learn about communication. There's a real science of communication. We're living through a golden age of understanding communication for the first time. And so that's why I decided to write the book.

I love it. Um, when I was reading your book, I was always thinking about all the good communicators I knew growing up and all the people that, uh, that influenced my communication style. Was there somebody that you grew up with, a family member, a friend, a neighbor that you thought of as you were writing the book, or somebody that influenced your communication style or what you thought was good communication?

Well, now I'm really curious. Who, who, who did you grow up with that you felt like made you the communicator that you are?

I think it's my dad. My dad was in sales. He was actually a car salesman, but he was not the typical car salesperson. He would actually ask a lot of questions before he would, you know, show them a car. He would ask them like, why are you here to buy a car? Like, what's wrong with your car right now? And people were intrigued by that question. Like, aren't you just supposed to push something on me? And he was like, oh, because he wanted to find out what are the things they valued. And then he would show them those things like, oh, you care about the stereo and you care about the suspension and you care about, you know, gas mileage. So I'm not going to show you all the other stuff, all 5,000 other stuff I can show you. But also just in a casual setting, he was very jovial and made everybody feel like this is fun talking to this guy. But as I was reading the book and realizing, okay, there are some good characteristics of that, but I started to find out that I needed to be a better listener because I'm not really getting enough information to know how to connect. What about yourself? Did you have somebody that you looked up to?

So I think it's really interesting that you mentioned your dad and that he asked these questions because the best, the best salespeople and the best car salespeople are people who do exactly that, right? They are super communicators. You have to be a super communicator to really make a career of that. For me, it was— I found that there were a couple of people in my life, friends of mine, who I just— they just had this ease of bringing people together, right? I have one friend named Greg who everyone loves to talk to. Greg, like, Greg is like any time he enters a conversation, you just know that that conversation is going to be better. And you know that if you have something you want to, you want to discuss, that he's the guy you can turn to and talk about it. And, and I think we all have a couple of friends like this, or we all have people in our lives. And by the same token, oftentimes we are super communicators, right? Every single person who's listening to this is at one time or another a super communicator. If a friend calls you, you you know exactly what questions to ask them. If your sibling calls up and they need someone to like, listen to their complaints, you know exactly how to listen. What's different is that some people are consistent super communicators. Your dad is a consistent super communicator. Greg is a consistent super communicator. And the difference is, it's not that they're more talented at communication. It's actually usually that they've recognized that communication is a set of skills, a set of skills that many of us know without recognizing them as skills. And that if you apply those skills to every conversation, if you treat talking to someone on the bus the same way that you would treat talking to your best friend, then all of a sudden they open up. You manage to connect with almost anyone because you're approaching them the right way.

Yeah. And what I got from your book and also what I got just from this, that little conversation we had right now is it's important to be conscious of being a good communicator. Like when you start opening your mouth, you're not just forming your ideas as you are spitting them out, you know? Which is a huge takeaway for me is like, how can I consciously try to be a better communicator? Just being aware. Yeah.

And to that point, what we know the biggest characteristic that super communicators have, the best communicators have, is that they think about communication. And if you talk to people who are great communicators, if you talk to Bill Clinton or, you know, anyone who's sort of Ronald Reagan, anyone who's lionized as a great communicator, if you ask them, were you always good at communication? They inevitably say no. They say something like, when I was in high school, I had real trouble making friends. I really had to study how kids talk to each other so that I could like work my way into the social scene. Or, or my parents got divorced when I was a kid and I had to become the peacemaker between them, the person who was communicating between them. What they're really saying is there was a time in my life that I had to pay close attention to communication. And it's that act of paying attention. It's that act of wanting to communicate better. That is the first and most important step to actually communicating better.

This is so profound because when I was growing up, I'm the youngest of 3 children. I have 2 older sisters. Whenever my sisters fought, whenever my parents were in an argument or something, you know, I always thought what my role was to have fun and make a joke and bring some levity to the situation. That's kind of where I got my sense of humor is just out of this need of like, this is uncomfortable. Let's smile again. And I think that that makes me think about, you know, how I like to communicate, not to take things too seriously, because at the end of the day, you know, we're all going to be 6 feet under.

That's exactly right. And my guess is that for you, thinking about communication, practicing communication, it became a coping mechanism, right? It became a way for you to manage your emotions and the emotions of people around you, to ameliorate tension. Oftentimes communication does that because communication helps us connect with each other.

Right.

What's interesting is that we think of communication as this thing that exists for information exchange, but that's not actually why communication evolved. Communication evolved to help us connect with each other, to help us feel closer to each other, to, to basically service the pro-social instinct that all of us have hardwired into our brains. And if I was to ask you about all the conversations you've had today, my guess is No more than 10 or 15% of them would have had to do with information exchange, right? When you like ask your wife, like, how was your day? Or you ask your kids, what are you excited for at school today? Or you see a coworker and you say, how was your weekend? You're not actually, you don't actually care how their weekend was, right? You're, you're looking to connect with them. You're looking to say like, I want to know you and I want you to know me. That's why communication has evolved. It's our superpower as Homo sapiens. Is that we can connect with each other through language.

I definitely feel that because growing up as a minority, even when I travel abroad and go to different countries, when I try to communicate with somebody, even if they have English as not their first language, my first intention is not, I need to tell them where, ask them where the bathroom is. I'm trying to just first tell them, hey, I'm safe. I'm not trying to hurt you here. And it's just a sense of like, I want to connect with you first. Hey, listen, I'm sorry to bother you. Can you help me? Where's the bathroom? You know, and it's not really about the bathroom. It's about like, how can I first make sure we're on the same page first?

Yeah, that's absolutely right. That's absolutely right. And, and there is something very human about that, right? There's something very human about— well, it's interesting when we're in a conversation with another person, our body and our brains start to change. So even in this conversation, you're in Australia, I'm in the United States. We're separated by thousands of miles. But in this conversation, without either of us noticing it, our heart rates will start to match each other. The rate at which we breathe will start to match each other. Even the dilation of our pupils of our eyes will become similar. And if we could see inside our brains, what we would see is that your thoughts and my thoughts are becoming more alike. They're actually achieving somewhat of a synchronicity, which you can actually see on these brain graphs. And that kind of makes sense when you think about it, because If I tell you about an emotion I'm feeling, you actually feel that emotion a little bit, right? Or if I tell you about an idea, you experience that idea. So it makes sense that our brains would become more similar. But it turns out that within neuroscience, this is known as neural entrainment. And it's the thing that makes us feel connected to each other. When you and I become entrained, even if we disagree with each other, even if we're from different backgrounds, our skin is a different color, When we become entrained, we will feel closer to each other. We will feel more connected to each other. And as a result, we'll trust each other more. We'll be willing to listen to each other more. That's what's really happening when we communicate.

When you mentioned entrainment in the book, I went down this rabbit hole of like learning about like, is this actually real? Like it physically changes things in the room. And then I read the study about like the room full of grandfather clocks where the, the clock with the largest pendulum basically pulled all the other— all the other clocks in the room were all on different times and they were moving in different directions and da da da, but over time they all entrained with the largest pendulum. And yeah, you'd walk into the room and they're all in sync. What in the world? What are you talking about? Is this for real?

Yeah. Yeah. And in that case, what's going on there is it has to do with gravity, right? That they're all converging on a similar gravitational impulse. And you can think about communication the same way that like, When I tell you something that's meaningful, it has a certain gravity to it.

Yeah. Yeah.

And when you acknowledge that gravity, when you, when you're willing to, to match me, to also be authentic, it exerts a gravity on me and we sort of move to the same place.

I love it. If somebody is listening right now or watching and they want to become a better communicator, they're buying what we're selling right now and they're like, okay, I want to do this, but what's some of the worst advice they're probably following right now?

Oh, that's a really good question. I don't know. I mean, probably the worst advice is just try and impress the person you're talking to, right? Like, like, like really concentrate on being like really witty and saying the smart thing. The much better advice is to say to someone, look, there's a couple of skills that you should invest in to become a good communicator. One of them is you should figure out what kind of conversation is actually happening right now. Because when we're in a discussion, we tend to think we know what that discussion is about, right? We're talking about our kids or we're talking about where to go on vacation next week or budget for next month. But actually, when researchers look at people's neural activity when they're in that conversation, what they see is that people are having many different kinds of conversations all at the same time. And in general, these conversations tend to fall into one of three buckets. There's these practical conversations where we're making plans together or we're solving problems. But then there's also emotional conversations where I tell you what I'm feeling and I don't want you to solve my feelings. I want you to empathize with me. And then there's social conversations, which is about how we relate to each other and relate to society, the identities that are important to us. And what researchers have found is that all three of these conversations are all equally important. And during a discussion, you'll probably have all three conversations, right? But if you're not having the same kind of conversation at the same moment as the other person, you cannot fully hear each other. You will not feel connected to each other. And within psychology, this is known as the matching principle. Successful communication requires having the same kind of conversation at the same moment. And so that's what I would say to people that they should do instead of thinking about how do I impress you? How do I come off as debonair?

Right.

Ask yourself, what, what is this other person? What kind of mindset are they in? Are they asking me like practical questions? Are they asking Are they talking about emotional issues? How do I match them and invite them to match me? That's going to make you feel much more connected to each other, and it's ultimately going to make the other person feel like you're great, like there's someone who they like as opposed to someone who can just say witty things.

So in that moment when you're trying to evaluate what kind of conversation this is, obviously if you have a close friend or you're speaking to a close friend or a spouse, you can just ask them, you know, like, would you like this conversation to be about this or that or the other. What if this person's just like at a dinner party, and are you supposed to make a hypothesis and then just like try it out? Let me just empathize with them and see if they resonate with that. Let me try something else.

So yeah, it's a great question, and you're exactly right. In actually, in a surprisingly large number of settings, we can just ask the other person. When I come home and I start complaining about my day at work, my wife will often ask me like, Do you want me to help you solve this or do you just need to complain? And I'm like, no, no, no, I just want to complain. I just need to get this off my chest. And it's easy to ask that even at a dinner party. But let's, let's say that it's not right. Let's say it's one of these situations where it doesn't feel like you can ask someone as directly. At that moment, what's important is to look for clues, right? And oftentimes we miscategorize an emotional conversation as a practical conversation. And the way to figure out if this is an emotional conversation is listen to what words the person is using. If they say stuff like, you know, I'm really worried about the budget for next year because I feel like if we don't get it right, we're going to have to lay people off.

Right.

Right. So now what we're talking about— this person just used two emotion words. They said, I feel like, which shows me a little bit what frame of mind they're in. And then they mentioned, I have to lay people off, which is probably going to make them anxious. It's going to make them feel guilty. It's going to make them upset. So they're actually telling me that even though they're talking about layoffs and they're talking about budgets, it seems like a practical conversation. They're actually telling me, I need to have an emotional conversation about this first. I need, I need to hear that you understand that I am feeling anxiety and that you empathize with that before we can move on to the practical conversation. We need to get aligned on this emotional conversation. And once you start looking for it, it's not hard to see.

That's great advice because in business, often decisions are emotional. You're dealing with people, you're dealing with livelihoods. And from a practical point of view, you probably know what you have to do just from a P&L, profit and loss sheet kind of situation. But it still doesn't make it easy for you to make those tough decisions. And maybe that conversation in that moment with your co-founder or somebody that maybe an advisor is just about, hey, this is tough. You're going to have to deal with it. We're going to— let's talk about how you can deal with it. And once you know you can deal with it emotionally, then the decision is actually clear.

Yeah, it's a lot easier. And think about hiring, for instance. We tend to think of hiring like, if I offer them a higher salary and I give them a better title, they're going to come join, right? It's very— it's a very practical calculation in our head. But anyone who's hired knows that when you sit down with a candidate and you make them an offer, they're overjoyed that you're going to give them more money and they're overjoyed they're going to get a better title. But then they're going to have all these questions like, you know, I really get— I have all these good friends at my existing work. Like, can I make friends here? You know, am I going to offend the guy who hired me at my last job by leaving? Do I want to see myself as someone who works for your company as opposed to working for this old company?

Yeah.

And if that person— if we offer that person a job and they turn us down, our reaction is emotional, right? It feels like they've rejected us, not just the job. So emotional conversations happen all the time in the business world. They might masquerade as practical conversations. They might sound like practical conversations, but the really good communicators know how to see underneath the hood and say, this is actually an emotional conversation.

Yeah, 100%. One piece of advice I heard from Naval Ravikant is if you're interviewing somebody and you want to hire them and you want to convince them that this is a good place to work, just ask them to have a coffee with one of the people that work at your company so they can just get to know what kind of people am I going to be working with? Oh, these people seem cool. They seem smart, you know, and it just kind of greases the wheels a little bit.

I think that's exactly right. And, and what you're really doing there is you're acknowledging that someone needs to have an emotional relationship to how they make this decision, that it's not just about numbers and titles. It's about sitting down with someone and in understanding them and seeing what the emotional temperature of this workplace is like.

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Yeah, it's because empathy is at the core of how we learn to trust each other. So to explain empathy, I need to talk a little bit about vulnerability, right? Because vulnerability is this misunderstood word. We hear the word vulnerability and we think about like people crying on each other's shoulders or talking about your moms. That's not what vulnerability is. What vulnerability is, is if I tell you something that you could judge it sets off a neural cascade in my brain. And I might not care about your judgment. I might say something like, I think Star Trek is better than Star Wars, and it doesn't matter if you agree with me or not. But as soon as I say something that you could judge, I have this instinct. It's, again, hardwired into our brains. We can't stop it to pay very close attention to how you react. And in that moment, If instead of judging me, you withhold your judgment, and even better, if you tell me something that I could judge about you, then what you're doing is you're exhibiting empathy. And at that moment, we will feel closer to each other. Our brains have evolved to be on a hair trigger to look for threats, and the way I test whether you are threatening or not is to tell you something you could judge about me that's small and not that important and see if you do judge me or if you exhibit empathy and you withhold judgment and you tell me something about yourself that I could judge about you. If that happens at that moment, even if we disagree with each other, even if we're negotiating over what's the right prices, even if we're fighting over who gets this assignment, at that moment, we will feel more connected to each other and we trust each other more. And because business is built on trust, this ability to empathize, this ability to show the other person that you will withhold judgment, is at the core of how we convince others to trust us.

I love that. Let me ask a question. Like, is a good example, like, let's say, for example, you're having a sales conversation and somebody says, I think this is too expensive. And you say to them, well, I actually thought that too when I started working here until I started to see the success stories that came about from the service. Can I share some of those success stories with you?

That's perfect. What I love about that— now, the one thing I would say is that could even raise it up is to ask a question. But you're, you're exactly right. So this person said, this is too expensive. And instead of saying, oh, you're a cheapskate, or you, you don't, you don't really understand what I said— yeah, what I say is, I say, you know what, I thought the exact same thing. Like, when I first started selling this, I was like, how am I going to sell this? This is too expensive. But then I talked to all these people and they helped convince me about why it's so valuable to them. And, and you know what, actually I was wrong. Like, I, I'm not a very good salesperson because I'm telling you that I, I was wrong at figuring out what this was worth, right? When we do that, now the other person might not be convinced by us. They might say, oh, this just seems like you're trying to sell me something. But they are going to trust you more. They're going to listen to you more closely. And particularly if you ask them a question, and especially what's known as a deep question, right? And this gets to what your dad did. There are, what we know about super communicators is that they ask 10 to 20 times more questions than the average person. And some of those questions are just like invitations, right? Like, oh, you know, what'd you think about that? Or, oh, did you see that movie last week? I'm just inviting you into the conversation. But some of the questions are what are known in psychology as deep questions. And a deep question is something that asks about my values or my beliefs or my experiences. And that can sound a little intimidating, right? But it's as simple as like if you meet someone who's a doctor, for instance, instead of saying, oh, what hospital do you work at? You can ask, oh, what made you decide to become a doctor? Right? That second question that draws this person out, it gives them a chance to tell you who they really are, what they value, what experiences they had. And so very similarly, if I'm talking to someone and they say, look, I can't afford this, the first thing I would do is to ask a deep question and say, I totally understand that. Tell me like how you think about evaluating value. Like what's the thing for you when you do spend a large amount on a product or when you do commit yourself to an investment where you feel like this is a big investment, like what's the thing that's going on inside your head that makes that feel right to you?

Right.

And when I ask that, that's a deep question. When I ask that and I listen to the other person, what they're going to do is they're going to tell me how they see the world. And at that moment, much like your dad talking to some people who want to buy a car, I'm going to know how to sell to them. I'm going to know what aspects of my product I should highlight for them because it's really important to them.

Yeah, I want to add that when I was reading that portion in the book about asking deeper questions, it really got me thinking, am I just asking these questions that elicit autopilot responses? Like the question of like, I work at this hospital instead of like, am I asking questions for them that they have to pause and think for a moment where they're like, oh, why did I become a doctor? Well, I think my parents kind of convinced me, you know, I think that's exactly right.

And I think that the way that we find those questions is instead of asking people about the facts of their life, we ask them about how they feel about their life. Right? Like, for instance, Omar, you've been podcasting for a while. I'm sure it takes a ton of time. Like, what is it about a podcast that you really enjoy? Like, why do you think that you enjoy doing— spending your time this way as opposed to any of the other ways you could spend your time?

I love it because I am forced to become a better person so that I can share what I learn along the way.

Yeah. Yeah. And, and actually, you just told me so much about who you are, right? You're someone who, like, values self-improvement. You also value feeling like a good person. Like, there's something about— there's something about that, that sense of improvement and of struggle that to you feels rewarding. Because what you could say is you could say, actually, I'm doing this because I get paid a huge amount of money, right? Or I like doing this because I get recognized on the street sometimes. And then you'd be telling me about other things that you value. But just asking that question, asking you how you feel about why do you podcast, a why question, often is the way that we invite someone to tell us who they really are.

Charles, we're going to shift gears a little bit. We're going to play a little game.

Okay. Okay.

This game is called Super Communicator or Bad Communicator.

Okay. I love it. I love this.

So I'm going to name a person, a well-known person, and just based on what you know, I want you to tell me if they're a super communicator or a bad communicator and tell me why in one sentence. You ready?

I love it. And I will warn you, oftentimes we don't know how people communicate in real life based on their public persona. But I'll try my best.

Let's just say publicly and what you know based on your interaction.

Okay.

All right. First person, Kamala Harris.

So that's a great question. So I've seen her in person before. I actually think she's not a great communicator. And every time I've seen her, and again, this might be completely different if you're one-on-one with her, if you're someone who's having a real conversation. But whenever I've seen her working a crowd or on a stage, part of me feels like she's like reading from a script in her head. She's not asking me questions because she's curious about how I might react. She's not proving to me that she's listening to me. And I think that's one of the reasons why the election turned out the way it did is that people didn't feel like she was super authentic.

Next, Chris Williamson.

I think he's great. I was on his podcast and I think that like Chris is a great communicator because one of the things he does is he's actually very quick to be vulnerable, right? Like if you mention something from your own life, he goes there with you and he says like, oh, I'm sorry to hear that. Let me tell you about a time that I made a mistake that's similar. And that's really, really valuable.

Elon Musk.

Oh, that's a good question, right? Because I would actually say that Elon Musk is a pretty good communicator. Now, we might not like what he's saying, but I feel like he's being authentic with us on a regular basis. I mean, if anything, he's being too authentic and too honest all the time because every crazy idea that moves through his brain, he feels like he needs to express to the world. But I do think that there's something to be said there about why that authenticity resonates with so many people. The truth is, there are a lot of people for whom Elon Musk can do no wrong, even if they don't agree with him. They just think the world of him. And it's because they feel like they have a real relationship with him, like they really know who he is because he's really good at authentic communication.

New York City Mayor Zoran Momdani.

Oh, Mamdani is actually a great communicator. I have to say, like, for anyone who hasn't seen him in person, one of the things that Mamdani does that's really, really good is he works really hard to prove that he's listening to you. So it's interesting, the fact that he always wears the same dark suit, right? The entire campaign, he was never in anything besides this dark suit. He's actively showing people, I know that I'm young. I know that you think I'm young. I'm going to try and prove that I deserve this by not giving up the formality. Like, I know I need to prove this to you. I'm proving to you that I'm paying attention to what you think of me and how you think of me. And I think that's a really powerful tactic that people can use to, to, to really connect with others.

Kanye West.

I mean, again, like Elon Musk, I think he's being authentic, right? Just because you're a good communicator doesn't mean you're going to say smart stuff. But he does do a good job of like getting across all the crazy that's moving through his head.

Oh boy. Last one, Malala Yousafzai.

Oh, I actually thought you were going to ask about Donald Trump. Can I answer for Donald?

Yeah, go ahead. Yeah.

So, okay, let me, let me preface this by saying I'm not a fan of Trump. Um, I, I think what's going on inside in the U.S. and what internationally is really worrisome to me right now. And it just feels very anxiety-producing. Yeah, but I've been to a number of Trump rallies and I've been in rooms with Trump where it's a small audience. And one of the things, things that people underestimate about Trump is he is a great communicator. So if you go to a Trump rally, one of the things that happens is that he's proving that he's listening to the crowd. So he'll say something and if the crowd like claps or roars their approval, he will lean into that and he'll start just saying more and more things about whatever he was talking about. That's why he says so many crazy things is because he's listening to the audience. He's proving that he's listening to the audience. He's leaning in and matching the audience. So he goes off script all the time. And one-on-one, he's a very charming person. I mean, he's a total egomaniac. He just talks about himself the entire time. He'll never ask you a profound question about yourself, but he will ask you a lot of questions, and he'll ask you deep questions. Now, they're always deep questions sort of about him. Why do you think they're treating me so bad? Like, why do you think the media doesn't treat me better? It's actually kind of a deep question, right? Like, what's my analysis of what's going on inside the media right now. It's all about you. But it is still a deep question. It gives him a chance to see who I am.

Yeah. Yeah. And there's a performative aspect of him. People forget that he was a reality star for many years.

Yeah.

He has a star on Hollywood Boulevard. People forget that. Like, you know, he knows how to perform.

He's been an actor his whole life, right? He's been performing the Donald Trump character since he was in his 20s.

Yeah.

Now, what's worrisome is that, as anyone knows, it's worrisome when your performance becomes who you think you really are, right? I think many people who perform roles, they kind of know, like, yeah, that's like 80% who I am, but there's a 20% that's more real, it's more deep. And I do wonder with people like Elon Musk and Donald Trump if they've forgotten about that 20%. And they start believing their own kind of patter.

Yeah, yeah, yeah. Off camera, before we started this conversation, we were talking about why all this hoopla and hate for the Super Bowl halftime show where Bad Bunny is singing in Spanish. It's just Spanish, guys. It's okay. But often I see these pundits that are going off on how I'm saying this is horrible and this is like anti-America and all this other stuff. It's like, do you really believe that? Like, do you— are you just, you know, farming for clicks?

I mean, obviously they're farming for clicks, right? Like, and I feel like if you watch like cable news both on the left and the right, people just say like the most extreme things because they know that that's, that's what draws attention. But then there are people who start believing their own BS, right? I think of like Tucker Carlson who like just 20 years ago. Like, yeah, Tucker was a journalist. He was a, he was a really thoughtful guy. And, and now he's so simplistic and he's so incendiary. And I think part of it is that he just fell in love with the character he had created. And as a result, his version of authenticity is very shallow.

And it's a very powerful force when that character pays the bills.

Absolutely, absolutely right. You should— like, the— you should never try and convince someone to disavow an ideology that makes them rich because it's always going to be a losing battle.

Yeah, totally. All right, thanks so much for playing with me in that game. That was fantastic. I had a great time. I want to ask about— have you ever thought about a conversation you wish you can redo back in your life?

Oh, all the time.

Is there one that sticks out and why?

So, and I want to ask you the same question because I'm curious what you would say. Yeah, all the time. Like, I just think about— so my, my dad passed away about, I guess, 7 years ago now. And there are so many, like, there's so many conversations that I think of where I was like, why didn't I spend more time talking to him? Like, he mentioned this interesting thing, and instead of asking him a question about it. What, like, I just like kind of barreled through to talk about the thing I wanted to talk about. And like, I would give anything to go back and have those conversations, right? Like when, when you lose a parent, all you can think about is the, is the, the conversation you wish you could have with them today and how sad you are that you can't have that conversation. But also with my kids, I have a 14-year-old and a 17-year-old, and there's a lot of times that they said something that looking back on it, I was like, oh, I could have gone deeper with them. I could have asked them why they felt that way, or I could have asked them what it meant to them. And instead, I just tried to solve their problem for them. Yeah. So there's lots of conversations that I wish I could go back and redo. What about you?

Oh, there are some conversations when I was growing up that I wish I had. Like, you know, growing up, my parents are immigrants from Egypt, migrated to the US. And, you know, when you're immigrants, you got to study, you got to work hard because you know, you can't mess this up. We sacrificed too much for you to throw this away with a liberal arts degree, right? You have to do something with this that makes money. But we never actually had a conversation about like, what are the possibilities in this thing called life? It was more of like, you know, just we have a saying in Arabic. It says like, walk beside the wall, like just be safe, walk beside the wall, don't create any fuss. Don't create any, don't kick up dust and just kind of, you know, play your role in society and try to be productive. Right. And as I grew older, I know I had a decade where I was a schoolteacher because I walked beside the wall and I just, okay, everybody needs teachers. I'm going to become a schoolteacher. And I was a schoolteacher for 10 years. And throughout those 10 years, I loved the experience and I learned so much and it's informed so much of what I do, but I, started to discover this whole world of people that create things out of thin air called entrepreneurs. I was like, what is this craziness that people just create businesses and make money and travel and come up with ideas? And, and then I started to realize, like, there are really no rules in the world. Like, you can do whatever you want. Like, and I'd never had this conversation before with anybody. Now, you know, I recently visited my sister who lives in Egypt, and she's got 4 kids and they're all in their 20s. And I try to have these conversations with them because I never had this conversation. I literally felt like you can literally do whatever you want. Like you can achieve anything you like, you know, like don't let anybody think, say, or you're behind or whatever the possibility. All these people that you look up to, all these people that have achieved things, you know, they didn't listen to all the naysayers and they just figured it out, you know. And I think that is needs to be kind of said, and that conversation I wish I had.

Yeah, yeah, I think that's really profound and, and very, very apt that it's, it's oftentimes, particularly with our parents, it's hard, right? And I think for, for immigrant parents, it's even more difficult because they have made so many sacrifices. They're so focused on giving their children a better life. And so these conversations that can feel a little navel crazy, right? Like, what do you want to do with your life? Who do you— what do you care about? Those can feel unproductive. But what we know and what you know is that those are actually the most productive conversations we can have. Because if you are optimizing for the wrong thing, if you are optimizing to be a teacher, if you're optimizing to walk besides the wall, then all of that work is for nothing. Because you could have chosen a better goal. You could have chosen a goal that feels more appropriate to you. I'll actually say I used to live in Egypt. I lived in Cairo for a year and a half.

Amazing.

And one of the things that like— is your sister in Cairo? Is she?

Yeah, yeah, she's in Cairo. She's in New Cairo.

Oh, oh, oh. So I was in Bab el-Lou down by AUC in Midan Tahrir.

Okay.

I don't know if she's probably in Zamalek. She's probably in like—

she's in the new, like, It's called the Fifth District. Like, it's a, it's a new development in Cairo.

Yeah, right, right. It sounds really nice.

Yeah.

Like, the thing that I love about Egypt post-Arab Spring is it does feel like there is— and this is true, I think, for the whole Middle East to some degree— it does feel like there's this new openness, right? And like, when I talk to, when I talk to young people in Egypt and in other parts of the Middle East, I do feel like they are asking those kinds of questions about like, what do I want this world to be as opposed to it's been handed to me. There's only one path I can walk.

Totally. Yeah. Running a business is complicated. There's dozens of software programs that you need and they're all so expensive. And since they come from different companies, they don't always play nice with one another. But what can you do, right? Odoo. That's what. Odoo has all the software business owners need. We're talking sales, CRM, manufacturing, websites, literally every kind of software. And it's an all-in-one platform, so it all works together. And it's quality software, so you're not sacrificing. It's simply a better experience than a hodgepodge of programs trying to fit together. You'd expect to pay a premium for it, right? But that's the most amazing part about Odoo. This interconnected suite of business software costs less than the mismatch of disconnected programs you're currently using. So the question is, why spend more on software programs that are less efficient when Odoo's simple software program can handle everything for a fraction of the price? Discover how Odoo can take your business to the next level by visiting odoo.com. That's O-D-O-O dot com. Today's episode is sponsored by Upwork. Listen, hiring help shouldn't be a headache or a drain on your budget. Upwork makes it easy to hire specialized freelancers quickly so you can get the expertise you need now. I know this firsthand because I've used Upwork for over a decade and we made some of the best hires through Upwork. This is because they're a one-stop platform to find, hire, and pay expert freelancers across web and software development, data and analytics, marketing, business operations, and more. It's free to sign up and posting a job is easy. Upwork helps you grow your business by giving you fast access to specialized talent across more than 125 categories. So you can fill skill gaps, launch projects faster, and scale support up or down without committing to full-time headcount. I've hired software engineers, managers, marketing specialists, copywriters, social media experts, Upwork is truly amazing. And with Business Plus, you can access the top 1% of talent on Upwork. And with AI-powered shortlisting, you can get matched to the right freelancer in under 6 hours. No endless searching required. Visit upwork.com right now and post your job for free. That's upwork.com to connect with top talent ready to help your business grow. That's U-P-W-O-R-K.com, upwork.com. I want to go back to— you mentioned the 3 buckets, the 3 types of conversations, and I just want to get a little practical for our audience so they kind of know how to apply this after this episode. So I'm going to give you a situation. I'm going to give you like maybe a little soundbite, and you tell me which kind of conversation actually needs to be had in this situation. So the first one is, let's say your co-founder says to you, I think this business is a mistake.

So, so I think based on that, I would need to ask a question, right? Because they haven't used— they haven't necessarily used an emotional word. They haven't said, I feel like this business is a mistake. I feel like we're wasting our time. They said, I think. And so the question I would usually ask is— I mean, the simplest one would just be to say, tell me why. Like, tell me why you're feeling that way right now, or you're thinking that way right now? And inevitably they're going to say something like they're going to say, look, like, you know, we went into X and what we should have done is gone into X, Y. And I think it's— I think it's still time. There's— we still have enough time to make this adjustment, but it's going to be hard. But I see this new opportunity. Okay. They're in a practical mindset right there. They're talking about making decisions together, making choices about strategy. But they also could say, like, I just, you know, I could have spent the last 5 years like in a normal job earning money. I'd already have a bunch of stock options. All this AI stuff is going on and I've missed out on that. And I just feel like disappointed and I feel frustrated that the things haven't— okay, so now I know that you're in an emotional mindset, right? Right. You're talking about emotions that you're feeling and I need to meet you there. And that doesn't mean the whole conversation has to be emotional conversation. But I need to say something like, what I hear you saying is like you are feeling disappointed that, that you made the best choices you thought you could make with the information in front of you, and the world has not served up your rewards the way that you deserve. And I, I hear that. I feel the same way. It is really disappointing.

It's a bad beat.

That being said, yeah, it's a bad beat. It's a bad beat. We had bad luck. But that being said, Now, like, let's talk about how to make the best of this. Yeah, because, because we can't undo the unfairness of the world. In other words, do I have your permission to move from an emotional conversation to a practical conversation? And now we're, now we're matching each other.

I love it. What if your partner, your partner in life says, I feel like we never spend time together?

So, okay, what's interesting is that could seem like a practical conversation, right? Like, 'We never— I feel like we never spend time together. So let's come up with a plan to spend time together.' But the fact that she said, or he said, 'I feel,' is a real clue that the first thing we have to do is we have to acknowledge what they are feeling. Because what they're feeling is not like, 'We don't spend time together.' But what they are feeling is, 'I want to spend more time with you, and I want you to want to spend more time with me, which probably means that I'm feeling a little ignored, or I'm feeling a little left out of all these things that are happening in your life, or I'm feeling overwhelmed because we both have so much work to do, but I'm feeling something. So, so the first thing I would do, again, I would ask a question is to say, what do you love about the time we spend together? And what do you feel like keeps us from doing that? So that actually even sounds like a like a little bit of a practical question, but actually it's an emotional question because I'm asking them, what do you love about spending time together? And what are the things that are preventing us from that? How do you feel about those? Right? Like, why are those— why do these exist and are they frustrating to you? So now we're having an emotional conversation together with these practical overtones that allow us to both move into the practical and talk about a plan to make this better.

And most of all, you're just having a conversation about it. Yeah, some people just don't have a conversation. They're just like, yeah, whatever, you know, like, just deal with it kind of thing. That's the rail out point. All right, last situation. This is a bit of a tough one because if people are managing people in person in the office, let's say an employee looks upset and you ask them, you know, is everything okay? And they say, I'm fine, but they're clearly not fine. How do you approach the situation?

So I think what's really important is, particularly if we are someone's boss or we're the team leader, we want to create opportunities that invite them to tell us what they're thinking and feeling without mandating what to describe to us what they're thinking and feeling. And so in a situation like that, if you look really upset and I come up to you and I say, hey, you look upset. Is everything okay? If you say, yeah, I'm fine, I'm totally fine, what you're telling me is even if there's something upset that's upsetting me, I don't want to discuss it with you, at least not right now, right? And it could be something that has nothing to do with work, nothing to do with anything I can help with, right? It could be that like your kid just called and they left their bag at home and it's, ah, why, like, why can't my kid like do a better job of like remembering stuff in the morning? So what I would say in that situation, I would say, okay, I'm glad to hear that. Just want you to know that if you do ever want to talk about anything, my door's open and I'd love to talk with you about how to— what's going on. Right. What I'm doing there is I'm inviting them to say, if you want me to match you, if you want to have this kind of conversation, I'm all for it, but I'm not going to force you to do it. You have control over, over this discussion as much as I do. And I'm going to respect that.

I love it. These are great. These are great. And I think everybody who's listening is going to love starting to apply some of this stuff in their life and their work. I want to get a little bit real about my community of entrepreneurs. My friends are all entrepreneurs, our listeners, and some of us are kind of wrapped up in our own delusion, to be quite honest. And I want to talk about, you know, especially when we're like at conferences or we're having like some sort of like speaker dinner or whatever it might be, why do we confuse as entrepreneurs, why do we confuse confidence with connection? Like we often feel like we're having a connection with somebody, but it's just us believing that we're great.

Yeah, that's exactly right. This happens all the time. If you ask people, what is your goal in this conversation? Particularly in something like entrepreneurial settings, what they'll often say is they'll say, my goal is to convince the other person that I'm smart, or my goal is to convince them that I'm successful, or my goal is to get them interested in my business because I want to ask them to invest.

Right.

And that's okay. It's okay to have those goals. But what should also be a goal is to say, my goal is to connect with this person. And if you think about who you, you've connected with in the last month where you just like felt like, oh, this is— person's so great, they're probably not the most impressive person that you met in the last month, right? They're probably not the best conversationalist or the funniest person, or they didn't have the best idea. But because you connected with them, there's something there for you to build on. You can improve ideas or you can improve pitches together. And so I think what's happening is that oftentimes when we go into a conversation, we know what we want to say, but we spend less time asking ourselves, what do I hope the other person says? Like, what question do I want to ask the other person? What am I hoping that the other person will reveal about themselves that seems meaningful? We think about ourselves because we have control over ourselves. But we also have control over the conversation, and we can be as curious about the other person as we want to be, and that's going to help us connect with them.

You know, I chuckled at the start when you said, you know, trying to impress the other person and all that kind of stuff. I chuckled because that was me. That was me for many years. And a lot of people ask me, like, how did it feel when you sold your— I had a software company for 10 years and we sold it and got acquired. And a lot of people ask me, how did it feel when you you had this incredible accomplishment. And the number one feeling I felt was relief. I just felt relief. I don't feel that way anymore when I have a dinner. I don't feel like I need to prove anything anymore. I don't need— I feel like I could just be a human being again and just enjoy the conversation just like we're having right now. Because I, for some reason, realized, oh, like, all that work and all that sacrifice, okay, now I'm secure financially. But at the same time, it's like, didn't really matter. Didn't— like, I was trying to prove something to myself, really, outside of anybody else. And I, you know, I just want to make it clear, I wasn't laughing at anybody that may be feeling that way, because I can resonate with that, because that was me for years. And it just felt like the sense of, oof, all right, now I— you know, there's oftentimes we'll have a conversation with somebody and I feel like they're like kind of on guard, and I just, I just say flat out, buddy, I don't want anything from you. I'm good. Yeah, just let's have a good meal. Relax. Yeah, they're so used to it.

I just want to learn about you. Yeah, yeah, no, absolutely, absolutely. And, and that's totally legitimate, right? Like, yeah, until, until we've proven to ourselves that we are worthy of our own love, it's hard for us to, to believe it, and it's hard for us to relax. But the thing I will say is this: the best conversations that you've had look like a mess. Like, if I could get a transcript of the best conversation you had with your spouse, your parents, and I looked at them, it would be a mess. It would be people bringing up ideas and then like getting distracted in some other idea and then never coming back to the first idea and interrupting each other. And, and the words that we use aren't very eloquent, right? They sort of like we say things in sort of a dumb way, but those are great conversations because they're real. The best conversations are not about eloquence. They are not about saying the smartest thing possible. The best conversations are about saying something that really reveals who you are and showing the other person that you want to understand who they are. Yeah, that is how we have a great conversation. And when that happens, when, when I say to someone like, you know, I want to tell you about my product because I think it'd be a great investment for you, but before before we do, I want to tell you like who I am and why I made this thing. And more importantly, I want to understand why you're at this dinner, like why, why you're willing to sit down with me. And that'll help me figure out if this is actually a good investment for you. Like, tell me what, what matters to you. That's when we're going to have a real conversation and we're going to walk away from that. And even if the person says this isn't the right investment for me, they're going to feel connected to you and they're going to remember more and they're going to like you more. They're going to remember you. And so the next time you come up with an investment that does make sense for them, it's going to be so much easier to have that, to get your foot in the door and have that conversation.

Totally. When it comes to communication and just investing in becoming a better communicator, how much of it is a superpower now that everybody's just outsourcing communication to AI and those muscles are atrophying?

So I don't think they're really atrophying. It's interesting. There's been a bunch of studies done. On AI, and obviously people are using it a lot. And there's these kind of parasocial relationships, right, where people have like AI boyfriends or girlfriends, they feel like. So what's interesting is if you look at the data on like how those relationships go with the AI or, or when AI is intermediating between two people, they tend to be relatively shallow and they don't last very long. Like even people who have like an AI boyfriend, they have an AI boyfriend like 4 or 5 months. That's a long time for them. Now, if I told you that, like, somebody had, like, a boyfriend and their relationship only lasted 4 months, you would be like, that's not a very long relationship, right? Like, that's— it's probably not your light year soulmate, right? And the reason why is because when we're having a discussion, part of what's happening is that I am paying attention to my effect on you, and you are paying attention to your effect on me. I'm looking for that effect. Part of the exchange of a conversation is me feeling like you are feeling something or you are thinking something because I provided that to you.

Right.

And giving you those clues back that like when I say like, oh, that's an interesting question. What I'm really saying is like, oh, your question is impacting me, right? Like I'm, I'm thinking about it and I'm, and it's making me realize something. That's an integral part of a conversation. When you do that with a machine, you know that the conversation— the machine isn't thinking or feeling anything. When you use AI to write all of your emails, the person on the other end, they kind of can pick up almost subconsciously on this little thin layer of a lack of sincerity, a lack of authenticity. So it's fine to use AI like, yeah, a little bit of pandering, right? That's why ChatGPT keeps telling me like, not only is that a great question, that's the best question you could possibly ask.

That's the right question to ask right now.

Exactly. Exactly. And I don't trust that that's true. Nobody does. But I think it's really important. AI is a really powerful tool and we should use it as a tool. But is it going to replace the connections that we have, the conversations we have? All the evidence says no. It's the people who can combine using AI and also knowing when to step away from AI and have a real talk. Those are the people going to succeed.

Succeed. Yeah, it's going to be even more valuable. Yeah, totally. I have so much more I want to discuss with you, but I know we're short on time. I really enjoyed our conversation. We didn't even get into your other book that really changed my life, literally changed my life, Power of Habit. It actually got me into just being as consistent as possible going to the gym and using some of the tips that came out of it. I don't miss a day now because of some things I learned there. But it also helped me too from a business point of view. We implemented a lot of the strategies in our onboarding in our software, Webinar Ninja, when we were building it and just figuring out how can we build a habit of people coming back in and, and using our software. So fantastic.

That's wonderful.

Yeah, you've been a great help throughout my journey. So I got one more question and it's a very simple one. You know, you have done a lot. You've studied history at Yale. You have an MBA from Harvard Business School. You worked for The New York Times, you work for The New Yorker, you have a Pulitzer Prize, you have a New York Times bestselling book. Where do you go from here, Charles?

Oh, thank you for asking that. As if, like, as if all that prelude, like, forgive, makes it easier to go forward. I mean, honestly, like, I'm actually like trying to figure out like another book topic right now that I'm, that I'm just starting to work on. And the truth of the matter is all of those accolades much like you selling your company. When I won the Pulitzer, I thought it would change my life and it didn't at all. Right. It was just an— it was just a prize. It was people saying like, you did a good job and that feels really good. I definitely wouldn't turn it down. But the thing that actually like is more meaningful is trying to find something new to write about that I think is important and that will resonate with people or having a conversation with my kids and, and learning something about them and feeling like we really connected with each other and, and that we're, we're building a friendship that's going to last throughout our life. Those are the things that, that really matter. And, and those are the things you get to do every day. It doesn't matter how good a conversation I had with my kid last month. It's the conversation we're having right now that matters. And so I feel like I like learning things. I'm happy that I've been successful because it means that some of the lessons I've learned are lessons that I can apply going forward. But it really is all about like, you know, what are you doing today? Do you do something that makes you happy and that makes you passionate and that you feel like makes the world a better place today? That's the thing that matters much more than anything else.

That's lovely. I got a movie recommendation for you that I feel like you would really enjoy. Given where you are in your life right now. It's called Perfect Days. It's a Japanese movie. Oh, interesting. Yeah, I think you can— it's streaming somewhere. Uh, it's called Perfect Days, and I don't want to tell you too much, but I think you're really going to enjoy it based on what you said.

Oh, good. I'll go look that up tonight. Thank you for that.

Thanks, Charles, for being on the show. Thank you. You've been a fantastic— not only guest, but person to speak to and get to know a little bit. Uh, you've influenced me so much from afar. I say, you know, I'm in the process of working on my first book, and when I was reading your books throughout my journey, I realized, oh man, I got to get better because I got to write at least as good as Charles.

Yeah, it takes forever.

The—

if the first draft is terrible and the 13th draft is terrible, that's okay. Like, that's, that's how you write a good draft, is you have terrible, terrible drafts in the beginning. I hope it's nothing but bliss writing in the book, although I know that it will be an uphill struggle and that, that, that's part of the process. And hopefully it brings its own kind of bliss.

It's— I love it. Thank you so much, Charles. Appreciate it.

Thank you, Omar. Take care.

That was a brilliant conversation. I enjoyed every single moment with Charles Duhigg. You should definitely, if you have not already, put his books in your Amazon cart and hit checkout. This book is incredible. We talked a lot about it in the conversation, Super Communicators. If you want to just get better at life, his books help you tremendously. So this one, pick it up. The other one, of course, we didn't talk about it too much, but it's The Power of Habit. This book has helped me so much when it comes to being consistent and having habits become part of my life. It's like my lifestyle, the things I always want to do. So if you have a hard time like being consistent with exercise or something in business, or maybe if it's just consistent with the promises you tell yourself, right? You want to keep your promises to yourself, then The Power of Habit is going to help you tremendously. Put these Both these books, both of them, put them in your cart right now. Make sure you check out and buy them. Incredible, incredible pieces of work that are well-researched and really fun to read. That's it for me today, guys. Who do you want me to bring on the show next? Let me know in the comments if you're watching on YouTube, or put it in a review on Apple Podcasts if you're listening to the podcast, or just send me a message on Instagram or Facebook or whatever it might be. I'm always looking forward to having great conversations with great people that can help us all get better like Charles. So if you know somebody like that, if you've been following somebody like that, let me know so that I can reach out to them and get them on the podcast. Until the next episode, take care and do yourself a favor. Implement one thing you learned today so that you actually take action and actually make your life better with the content you just learned. If you found today's episode helpful and you want more practical business lessons to help you start, grow, and scale your business, the best thing you could do is subscribe to this podcast. Hit subscribe or follow on your favorite podcast app, the one that you're using right now, whether it's Apple or Spotify or wherever you listen to podcasts. By hitting subscribe, you get our next episode automatically, and it's the best way to support the show. It's absolutely free and it's a way for you to commit to growing your business. And now that you've subscribed, I'll check you in the next episode.

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