Day One Leadership: Delivering Core Leadership Values with Drew Dudley

Ask yourself, “What have I done today that might not work but tried anyway?” Drew Dudley’s goal with that question is to try to reinvent a willingness to take chances to make mistakes in his life and to help other people do the same. Drew is an internationally-acclaimed author and speaker and the CEO of Day One Leadership. Day One Leadership explores what leaders should do on “Day One” to build value-driven cultures of leadership in their lives and organization. Drew observes that unfortunately, leaders embrace the idea that asking questions makes them look stupid. As we grow older sometimes it gets beaten out of us that the last thing you ever want to do is show that you don’t know something and you don’t want people to figure out that. He says truly great leaders make it very clear what it is they don’t know and they’re good at figuring out who they need to go to to find out. Drew helps some of the world’s largest and most dynamic organizations in the world discover, define, and deliver on their core leadership values.

TTL 248 | Day One Leadership

I’m so glad you joined us because we have Drew Dudley and Drew is the TED King. He has given some of the best TED Talks. In fact, he is one of the most watched TED Talks. He’s in the top fifteen of all TED Talks watched. He is known as the Lollipop Guy. He’s known by a lot of different things, but he is funny. You’re going to enjoy him. He is very much a leadership guru and this is going to be a show not to miss.

Listen to the podcast here

Day One Leadership: Delivering Core Leadership Values with Drew Dudley

I am here with Drew Dudley, who is the CEO of Day One Leadership. His clients have included some of the most dynamic companies and organizations in the world. He has talked to 250,000 and more people on different continents than anybody I’ve had on the show. He is fascinating. His TED Talks are everywhere. I don’t know whether to introduce him as the Lollipop Guy, the guy who must have loved my last name because he randomly raps Hamilton lyrics, or to refer to him as the guy who has an embarrassingly large number of stuffed penguin collection. Welcome, Drew.

It’s wonderful to be here, Diane. Yes, when I saw Hamilton, I immediately began playing the soundtrack in my head and I will do my best to include no more than three Hamilton quotations snuck into the course of this particular interview.

I haven’t seen it yet and I’m going to be in New York. Can you believe I haven’t seen it? Isn’t that great?

I could believe you haven’t seen it because maybe you wanted to pay rent or buy a car or something. I understand why people have chosen not to but I have seen it seven times. That’s why I don’t have a new car because I spent it all on Hamilton tickets. Especially for someone who talks about leadership, they had me about three minutes in. They started dropping a couple of great leadership insights early on. I knew right away, I thought, “This is something that is going to teach me and resonate with the way I like to look at the world, not just something that’s going to entertain me for a couple of hours or so.”

It’s on my list. I want to see it. That’s so funny. You do focus on leadership. I love how you started your one TED Talk asking people how many of them feel comfortable calling themselves a leader. That’s a unique way to start it out. Why do you think people don’t or they either do or they don’t want to consider themselves a leader?

They straight up don’t. I’ve asked that question over a thousand times, less than 1% of the time do we get half the people in the room raising their hands and be comfortable calling themselves leaders. If you do it anonymously, I’ve done it a couple of times where you can text in your answer and you get about 50%, more often than not but as soon as you say to people, “Claim the title right here in front of everybody in room,” people won’t do it. What it comes down to is how we got taught about it. I’m from the education system. When you want to teach people about something, we use examples. The examples we use growing up were all giants and we’re still doing it. They’re presidents, scientific groundbreakers, and they’re people who conquered empires, most of them were white dudes. The examples you use to explain anything form and shape how people think of that thing for the rest of their lives. We taught leadership as giants. We’re still saying, “Look at Steve Jobs, Mark Zuckerberg, and Warren Buffett.” That’s what our kids are hearing. What happens is there is a break, a gap that forms between our identity, who we feel we are and what a leader looks like.

Part of leadership is trying to empower other voices and create opportunities. Click To Tweet

Honestly, so much of my philosophy on what I try to teach in terms of leadership came because I got angry at that. Not necessarily that was what had been happening, but that so many of the most dynamic, caring, and compassionate people that I knew, particularly the young people that I work with at the university, wouldn’t call themselves leaders. That annoyed me, that someone who I know had made my life better. Earlier that day, I was having a bad day and went out of their way to come by and do something kind for me. The next night at a workshop, they wouldn’t call themselves a leader. Eventually, you get annoyed at that you start. You start to realize most of the leadership on the planet comes from people who don’t see themselves as leaders. I said, “Let try to address that fact.” Most people don’t do it because we were taught not to.

It’s interesting because I’m trying to think of some examples of leaders that I’ve used in the course I teach. There’s a lot of men. Do you think that it’s harder on women because we don’t do that? Do you deal with women groups at all? I’m curious where they fall when you talk about this.

Women, in almost anything that involves power and including our society, has been systemically marginalized. Yes, it’s starting to change but you can’t reverse basically thousands of years of the way society has worked quickly. Yes, most people in society already feel separated from the idea of leadership because we’ve associated with power, influence, money, and prestige. Most people don’t feel they have enough of that. That is even more exacerbated for women and visible minorities because historically, there have been these structures in society that do marginalize them from power, influence, and authority. If most men don’t see themselves as leaders and they live in a world that has been designed to benefit men, then women and minorities are going to have an even bigger gap.

If you wanted to understand how big it was and people sometimes nod along and say, “Yes, we understand that it’s hard.” I don’t want to understate it, but if you want to know how society uses any concept, do a Google image search of the concept and when you see what images come up, that tells you what society thinks. It was three years ago, I did a Google image search of the term leader to see what came up because that does give you some insight into what’s being portrayed within our broader society when you do a Google search of it.

I saw a penguin, a chicken, and two different types of fish all portrayed as a leader before the first image of a woman appeared. Kermit the Frog showed up before a woman appeared. The first woman that appeared was a blue avatar without a face. It was shaped like a woman. Two years ago, I did a search for the term CEO because someone came up to me after I told them what I told you at a speech and she said, “Go online and look for CEO.” Two years ago, the first woman that appeared when you did a Google image search of CEO was the 43rd image, and it was CEO Barbie. I’m happy to say she’s not even at the top 40 anymore.

TTL 248 | Day One Leadership
Day One Leadership: Most of the leadership on the planet comes from people who don’t see themselves as leaders.


Ultimately, it’s hard. The power of how we first talk about leadership to young people plays a big role. Words are one thing but when young women look around when people who are not straight white men look around, it’s what they see and how it’s portrayed that has an impact. When we give examples, we have unconsciously tended to make it about white men. Look at leadership conferences, without people even realizing it, 60% of the people speaking are always a straight white guy, and so am I. I recognize that who I am speaks louder than what I say. All of us have to identify that issue so that all of us can play a role in starting to change it.

It’s important because I was associated with a company that set up a meeting and they caught the attention of the women’s group who are not happy with them having so many men in the lineup. Their thought process was, “That’s the group that does what they’re trying to talk about.” Can you appeal to people with the all-white men in any setting or is it never appropriate to have it set up that way?

That’s a tough question because life and the world are too complex to ever say you can never do this or you can never do that. What’s key though is that only when we become aware of the fact that it tends to happen a certain way, I don’t think anyone ever sits down and says, “We’ve got a leadership conference here. Let’s make sure the panel is all straight white guys.” They don’t do that. What we do though is we say, “We’ve got a million things we have to do to get this conference. We want to have great speakers. Who knows who we should get?” You want to fill out that panel.

What happens is until we start to realize that part of leadership is trying to empower other voices and it creates opportunities, until that becomes an instinct that when we say, “We’re going to have a voice to share,” until it instantly pops into your head saying, “How diverse are those voices going to be?” If we allow ourselves to keep acting unconsciously, things stay the same. That’s a big part of what I talk about in my book is that, if you allow yourself to operate unconsciously, you tend to have things stay the same and not necessarily reflect the values you want to. It’s only when you stay conscious about what kind of voices that you’re projecting and helping to empower others to project, what opportunities you’re creating, and whether or not you’re behaving in a way consistent with who you want to be, only when you pay attention to that can you adjust it and change it.

If we allow ourselves to operate unconsciously the way we always have, we marginalize certain groups, we tend to stay homogeneous in the messages that we hear, where we hear them from, and who we hear from. We tend to have our behaviors keep being what they are over and over again. I wanted to give people a step-by-step process on how to make sure how they were behaving every day was consciously tied to the type of values they wanted to embody because leaders can point to specific things they did each day that embody their core values.

I loved how you have made a comment about they want people to think outside the box but they’re doing this wearing the same suit. You’re also addressing the fact of how much money is spent on leadership training. You said $46 billion a year, but Gallup is showing 82% of employees find their leaders uninspiring. You were talking about a process and I know you have the six key values you talked about and accompanying questions that drive leadership and behaviors. I’m interested in them because I’m writing a book on curiosity and I wrote it in assessment to touch on that. You’re dealing with some of the things that I’m writing about. I talk about courage, I talk about fear, different angles of what holds us back and what I’m talking about. I want to know about your six key values. How do you determine those six?

Ultimately, my argument is that leadership is trying to close the gap consciously and actively between the person that you want to be and the person that you see yourself as and how you were behaving. There is a gap for almost everyone on the planet between the person they’d like to see themselves as and how they are actually behaving. Leadership is when you consciously say, “I’m going to act every day to close that gap.” My argument is if we stripped away everything, money, power, prestige and our memory of who had them, and we went back to day one.

Figure out what has to happen on the first day of that voyage and then commit to doing those core things every day. Click To Tweet

You’ve got to go back to the day one of your life as a leader knowing what you know now and you can say, “I’m going to start building myself into the person and a leader I want to be. What are the non-negotiable behaviors that I would make a part of every single day of my life?” That’s ultimately what they warned us about. My argument is that those behaviors should be tied to the values you care about the most. What you do on day one is you start to ask yourself, “What are the values I want to stand for?” For me, there’s a specific process that I outlined in the book because just asking people what your values are, people give you the words that they think sound good, integrity, courage, and empowerment. They sound great.

I once had a girl after my first ever day in front of a classroom, walked up to me and say, “I’m a little confused because this isn’t how leadership was taught where I’m from.” She was an international exchange student. She said, “Could you explain what leadership means in the simplest English terms possible?” Have you ever been asked a question which you are certain you have an answer until someone asked you the question because I utterly choked on it? It was upsetting. I covered it up by doing what educators do, you look at the student and you say, “What do you think?” I was covering my ass.

I could talk about how leadership has been studied, understood and explained throughout history, what the research said were leadership traits that made people more effective, but no one had ever straight up looked at me and said, “Could you explain what it means in simple English?” If you’re reading this, I also challenge you to do the same thing. If someone followed you around for 30 days out of your life, and at the end of it, I sat them down and said, “This person you followed, they had no idea you were following them. What three values do they stand for above all others? What three values do they pivot to whenever they have to make a difficult personal or professional decision? What three values do they hope their kids take out in the world having learned from them?”

What I found is that hundreds of people, who are by every measure objectively successful, people cannot give me their three. When they do, it’s the same ones over and over. It’s integrity off the top. When you ask people to say, “Respect is a core value of yours. Could you explain what that means in the simplest English terms possible?” start it with the word, a commitment. Values are what leaders use to make decisions. The problem is we don’t know what our values are because we were never asked about them going through school.

No one threw a system that taught us to pay attention to the things you’re going to get tested on. We never got tested on our values or how we make decisions. Ultimately, people don’t know what they are. That means they don’t know how they’re judging themselves. They don’t know what criteria they’re using to judge other people. As a result, if you don’t know what your values are or what they mean, you can plan to live them every day. There’s a process to go through to surface your values. I walked through it in the book. I went through that process for myself because the idea of the book is to make sure that when you’ve finished it, you have a specific set of leadership behaviors customized to you that you engage in every day. The six that I gained through this process are in fact impact, courage, growth, empowerment, class and self-respect.

The whole idea of the day one process is that these values that you learn what yours are, are converted into a leadership test. Each individual value is turned into a question and the background of that has to do with some psychological research that I stole from some psychology professor friends of mine. Ultimately, I have a question tied to each of those six values. The book will teach you how to add one to each of yours. The idea is every day I have to pass the leadership test, which means I have to get three out of six of those questions answered. If I do that, I earn yet another day one on this planet and you restart. The reason it’s all about day one is this idea that every morning that you and I get out of bed, we have done absolutely nothing to earn the title of leader. Not a damn thing.

TTL 248 | Day One Leadership
Day One Leadership: We never got tested on our values or how we make decisions, so ultimately people don’t know what they are.


Whether you’re the CEO or you just got hired to clean the floors of the company, when you get out of bed in the morning, each one of you has done exactly the same amount to earn the title of leader. Instead of giving people these titles of leaders because of what they’ve done over the last five years or ten years, what I want to reframe for everyone is the idea that if you get up every morning and you say, “I’ve done nothing to deserve the title,” every day you’ll recommit to behaving in a way that ensures that you deserve that title. Whether or not you end up running a company or whether or not you’re creating these powerful moments of impact for other people. That’s a long answer I gave you. I like talking about that.

I liked hearing about it. I didn’t think it was. I thought it was perfect. It brought back my sales training. I always told, “You’re only as good as your last deal.” What have you done for me lately it is something you got to think about in sales a lot, but I don’t think it’s put that way to leaders. When you were talking about your six values, courage was interesting to me because of my research on curiosity, I found that fear, assumptions, technology, and the environment were the four real factors that held people back. What you said for courage is, “What did I try that might not work but I tried it anyway?” I love that for developing curiosity. Have you always been a curious person?

No, I’ll be honest with you. I fell into a trap that too many young people fall into which is, “It doesn’t matter what you think. What matters is how well you can tell the person at the front of the room what they think.” Unfortunately, when we’re young and we go through the education system, all of your rewards come from how well you please someone else. All the tests you do are about giving someone else their answers, that’s where you saw reward, that’s where you saw accolade and that’s where people patted you on the back. That’s where I got my self-worth from.

Let’s be honest here. Looking back now, no one’s ever asked me that question straight up before. I didn’t care about what I wanted to know. What I got good at when I was younger is figuring out what the person at the front of the room wanted and delivering it to them. I didn’t bother spending time on anything else because that’s how I got told that I was doing it right. That’s how I got told that I was smart. I talked a little bit in the book about courage that question, “What have I done that might not work but tried anyway?”

My goal with that question was to try to re-embed a willingness to take chances and to make mistakes into my life, and to help other people do the same because our courage is eroded as we go through our education system, because our education system says to us, “How smart you are right now, how skilled you are right now, how wise you are and how strong you feel about yourself right now, isn’t what we’re grading you on.” Your final result is determined by how few mistakes you’ve made along the way. Instead of focusing on how good we are at any given moment and engaging in behaviors that continually improve us, what we’re taught to do is avoid mistakes. What we’re taught to do is try never to make an error and we don’t take risks anymore. Ultimately, what that does is it narrows our focus too often into simply figuring out what our teacher wants or our boss wants and delivering it to them. That will get you success, but it will not get you the freedom and it will not get you leadership.

I was not a curious person because I didn’t see any value in curiosity when I was younger because that’s not where the rewards came. A lot of those kids that I rolled my eyes at thought, “Why don’t you get your crap together?” They were the ones who learned early on that it was their thoughts that mattered, not simply regurgitating what other people think. We have to ask ourselves that if we’re going to be leaders as parents, “Are we pushing our kids to simply try to avoid mistakes and please other people or are we fostering that curiosity? Are we seeking it?”

In the book, Curiosity, I say it’s a commitment to asking questions and seeking answers. Asking questions that you don’t know the answer to, unfortunately, leaders embrace the idea that asking questions does make them look stupid. As we grow older, sometimes that gets beaten out of us. The last thing you ever want to do is show that you don’t know something. What leaders are truly great at is making very clear what it is they don’t know and being very good at figuring out who they need to go to find out.

We often hear they don’t want people to figure out that they don’t know things. They keep thinking they’re going to be discovered that they’re not as much of an expert as they think. It’s interesting that all that you said was a big part of what I research for the environment and the impact of teaching and parenting and all the things of how it directs people in certain ways. With the advent of so much AI and everybody’s looking to be more innovative right now to get new ideas for the jobs that will be lost, we need to develop a very curious culture and I don’t know that a lot of that is being focused on. Where would you start with leaders to get them to see the importance of curiosity?

Leadership is figuring out what those foundational behaviors are and creating a process to live them. Click To Tweet

What an interesting idea. No one’s asked me that question before. “Where do we start with leaders to get them interested in curiosity?” How about this. This is something that I’ve been thinking about lately. I’m so glad you asked that question. What you did is a perfect example of how to get more interested in asking questions, when you realize that one of the great leadership traits is how great your questions are. A lot of reasons that I’ve found that wonderful people aren’t willing to embrace the title of leader is they don’t think they have enough answers. They’re afraid that they’re going to be put in a position where they look ignorant or foolish and so people think I’m not smart enough, I don’t have all the answers.

What great leaders do is they ask incredibly good questions. What I mean by that is that their questions have a particular trait that we can all learn, but you have to be conscious about it. That is, they ask questions where the person being asked learns more than the person doing the asking. We create an environment where people assume if you’re asking questions so you can gain information. What great leaders do is they use questions as an incredible way to help the people being asked gain information. What I’ve started to encourage young leaders to do is to try to go through entire days without offering a directive, without giving advice, and without basically giving an order, only asking questions. If someone comes and asks you for advice, try to have an entire conversation where you do nothing but ask questions. Only when you start doing that do you realize how much more effective you are and questions become a bigger part of your life if we want to embed curiosity in leaders.

In the book, I commented that somebody said to me, “If you’re bad at anything and you want to get good at it, you have to practice.” I’m so glad you asked it because I never thought about it in the specific context of courage before. I would give a challenge to everyone out there, go for an entire day where you don’t give a single piece of advice and don’t offer one piece of anecdote. No directive. All you can do is ask questions. What you’ll discover is, people’s response to you will be so much more powerful, your influence on other people will be so much more powerful. What you did is ask me a question where I’m thinking of coming up with answers and realizing things that I didn’t know. That means that what you’ve done is engage in leadership because you made it more likely to someone would learn something. If we practice that, go into an entire day and say, “Nothing tomorrow. No advice. No stories about my life. Only questions.” What you’ll discover is, you start to practice that and you start to see the power of seeking out answers from other people.

It’s funny what came to mind when you said it first. I don’t know if you’ve seen the movie, 40-Year-Old Virgin, where he can’t talk to women and his buddy gives him an advice, “Just keep asking her questions.” It keeps going on to this unusual path of him and she thought he was so amazing because he was so interesting. It’s going to be well-formed questions that get somewhere. We can’t just ask any questions. I love that suggestion. That it’s very challenging for everybody right now with trying to become more innovative. You hear so much about thinking outside the box and there’s a lot of key terms that are thrown around that everybody’s been trying to do forever but now the jobs are more at stake. Jobs are always at stake with computers and different things, but it seems like more so now than ever.

TTL 248 | Day One Leadership
Day One Leadership: All you can do is ask questions, and what you’ll discover is your influence on other people will be so much more powerful.


This is the biggest time that we need to be aware of fear, environment and some of the things we’re talking about. A lot of it is assumption though. A lot of people assume they’re not going to be interested in something, that’s why they’re not curious. Maybe when they were young they tried something and failed or they have a negative family experience or something. It’s interesting to me about how everybody looks at all that. I love the way you look at leadership and all the talks that you’ve given. I want to talk about your TEDx Talks and different things. Traverse City was your favorite, you said. I flew into Traverse City. We used to go up there every year when I was a kid up to Northport Point, Michigan, which is so beautiful up there. Why is that your favorite talk? What about it made it be your favorite?

That would be The Games Has No Winners. A couple of things struck me about that talk. One, it was one of the first times I’ve ever been on stage where I slowed down because I talk very quickly but ultimately, that talk emerged from speaking at business schools. For me, that talk represented a fundamental shift on how we view what success is and I loved being and having the opportunity to share that because it wasn’t necessarily about leadership as much as it was about how you choose to view your role in the world. It came from talking to business students because if you make money, you’ll get invited to come and speak at a business school graduation. As if how much money you have in your bank account indicates that you are more worthwhile to teach these people than others are.

I’m like, “Do you realize that I’m a recovering alcoholic person with bipolar disorder, who for most of his life was 150 pounds overweight?” Just because I made money along the way it doesn’t mean I was making good decisions. I wanted to talk about that challenge, the idea that we need to reshape how we view goals. The reason I like it is that I hope that it resonates with everyone to say this, we cannot treat jobs and money as goals in and of themselves. Jobs, money, and prestige are tied so tightly to leadership, I wanted to break away from that because I can’t convince people that they should embrace their leadership as long as the concept of leadership is always tied to where you fall on the spectrum of financial compensation. What I wanted to do is embrace this idea that money and jobs make lousy life goals because you’re not in charge of either one of those things.

How hard you work and how well you work will always play a role in how much money you make. As long as you work for somebody else, most people will spend most of their lives working for somebody else, how much money you make is someone else’s decision, whether you get promoted is someone else’s decision. That leads to a feeling of powerlessness. If your life goals are tied to somebody else’s decisions that tightly, it’s hard to feel like you’re a leader. That’s why no one puts their hands up because whether we’re aware of it or not, too many people I work with are living a life where their biggest life goals have to be handed to them from somebody else. That pulls away a lot of our agency.

A big part of the leadership I talk about is consciously deciding everyday act in a way that impacts others to say, “I’m not always in-charge of what I have to do every day, but I’m always in charge of who I am.” That has to be your priority. What I loved about that talk is the best way that I’ve ever articulated the idea that money, jobs, prestige and all the things that we’ve been taught are goals aren’t goals at all. They are the natural byproducts that come to people who behave every day in a way that lives up to their core leadership values.

For me, that’s impact, encouragement, empowerment, class, self-respect, etc. My idea is all the money that I’ve made, all of the success that gets me on podcasts like this or gets me on bookstores, when I used to chase that as my goals, I did not get closer to them. When I stopped chasing those things as goals and simply focused on my day-to-day behaviors, all of those things, the natural byproducts that come from my everyday behaviors.

Ultimately, the talk and the book are about the idea that there is no one day in your life that doesn’t start with a day one. Whatever your career wants you to be and whatever your financial situation wants to be or your health, figure out what has to happen on the first day of that voyage and then commit to it. Doing those core things every day. Those won’t be the only things you do every day, but they have to be the non-negotiable ones. For me, you were talking about innovation before we talked about this question. Innovation is thinking outside the box, which is great. What I talk about in the book are the things that have to stay consistent so that innovation is possible because we talk about innovation and thinking outside of the box.

As a general rule, we see ourselves as less than people around us see us. Click To Tweet

The fact is sometimes things are in the box because they work. That means they should stay the foundation. When you tie in a strong foundation, that’s when you can do these amazing things. When someone does a spacewalk, one of the most extraordinary innovative things in the world, they’re still tied to something. If you look at a kite that is flying and doing these amazing things, it still has a foundation. My argument is that leadership is figuring out what those foundational behaviors are, the things that never change, the things that are part of your life every day.

Figuring out what they are, creating a process to live them and then building on that is all your career success, all your relationships success, all of your innovation and new ideas. These certain things have to stay the same. Everything that we’ve been taught to chase, they’re not goals in and of themselves. They are the natural byproducts that come from consistent value-based conscious behavior every single day. The leaders are aware of what they’re trying to accomplish every day in terms of their character and they give themselves evidence that they’ve done it.

You’ve talked about the lists, so you’re talking about these things as goals that we look at life in certain ways like a scavenger hunt. Is it the same with this that there’s a list of things that we need to determine? How do you determine the things that you need to keep the same?

What we end up doing is chasing a list of accomplishments that are laid out for us at the beginning of life as opposed to a list of behaviors. That is it. Leadership as positions, leadership as accomplishments and leadership as acquisitions. That’s how we’re taught about it. All of those things come about because of behaviors. The list I talk about in the book is this encoded roadmap through life. Go to kindergarten and play nice. Go to elementary school then go to high school then college and get married. If that’s not the path they’re on, then they’re somehow screwing up. Ultimately, my focus is it’s not accomplishments that we should be focusing on, it’s how you’re behaving each day. Let’s evaluate leadership on a daily basis instead of over blocks of time.

How do you start doing it? The first thing is surfacing those values. There is a process that you go through. Let’s pick one specific instance because I feel as if while I’ve been chatting with you, I’ve been keeping at relatively high level. The first time we ever put the process in the book into action, we picked the value, impact. This is me with my students. Impact is defined as a commitment to creating moments that cause people to feel as if they are better off for having interacted with you. That was what we wanted. No matter what else we had to do over the course of the day, that had to happen. What happened was we turned that into a question.

We want to think of a very specific type of behavior, so we said, “Let’s create a question that’s carefully crafted so that in order to answer it you have to do something and if you did that something, you would have lived value.” Now we’re not chasing some definition, we have a very specific act to do. Answer this question, “What have I done today to recognize someone else’s leadership?” The idea was because leadership is on a pedestal. If I said to you, “Diane, the fact that you share your ideas with so many people, that you do this research, that you write books, that you share ideas with like-minded individuals inspires me and makes me want to be a better person. That makes you a leader. Thank you.” It’s unlikely anybody who hears that acknowledgment isn’t going to feel better off for having heard it. By the end of the day, have an answer for that.

TTL 248 | Day One Leadership
Day One Leadership: Sharing your ideas with like-minded individuals inspires them and makes them want to be a better person.


The cool thing about that question was you can’t answer it yes or no. It’s just, “What did I do?” You have to be specific. What happened was as a result of that question, we started being much more aware of how many opportunities for impact surrounded us. We became so much more aware of how many leaders surrounded us that we were not recognizing and we became less likely to allow those opportunities to recognize it to pass by. That question and that strategy, we called it operationalizing a leadership value, identify it, define it, convert it into a question. We found that that adjusted our behavior so significantly that we added another question and then another and then another. Each one of those tied to those six values I talked about earlier. What we found is that we were far more likely to actually engage in that behavior.

The ultimate idea is you figure out what your values are, and there’s a process to do that, define what they clearly need, and then create these questions that drive your day to find an answer through your work. It’s not on top of your work, it’s through your work. Find an answer to these questions. What have I done to say to recognize someone else’s leadership? What did I try that might not work but try to anyway? What have I done to make it more likely someone would learn something? What have I done to move someone else closer to a goal? How did I elevate a situation when I could have escalated it? What have I done to be good to myself? That’s my leadership test.

If I get three answers out of six to those, I’ll go to bed every night knowing that even if everything outside of my control, in my career, in my personal life blew up in my face, I still did at least three things that were consistent with the man I wanted to be. Through answering each one of those questions, I engaged in the act of leadership. What I tried to teach to my students and now what I’ve written a book about is how each individual can figure out what their values are and then create their own questions so that each person can go home and answer their own leadership test.

It reminds me of a personality test I took in the ‘80s where on the left side of the page we had to put the words we would use to describe ourselves on the right side, what other people would use to describe us. At that time, I was like, “Should they match?” I was overanalyzing. “Is this good? Is it bad? If they aren’t the same I assume that one would be the same or there’s something wrong here.” Do you think that most people view themselves as other people view them? Imagine a room full of people, but what words they use to describe you, do you think we see ourselves as other people do?

No, I don’t think at all. Two reasons, I say that specifically. The hardest value and question to answer for almost everyone is self-respect. What have I done today to be good to myself? Because people ignore that all the time. If you sleep less than five hours a night, you are clearly choosing to hurt yourself, to make yourself less effective. We do it in the name of working harder or hustling. People have a real hard time answering that question. That right there tells me that people don’t see themselves as others do. It’s the other question that’s opened my eyes to that, is that if I look at somebody in every audience I speak to, I look at somebody and I ask them, “Why do you matter?” Nobody can give me an answer.

It’s creepy how few people in this world if you look at them and say, “Why do you matter?” They stand there and they blink, terrified. If you ask their best friend, there’s this list. That means that as a general rule, we see ourselves as less than people around us see us. We continually devalue how much we matter or the impact we have because we evaluate our lives based on how much money we make or what our titles are. Instead of looking and saying, “What did I do that sent someone away for me feeling better off for having interacted with me?”

People ask me, “What leaders do you look up to?” When you do this job, you can’t help it. People will always say, “Give us some leaders.” Every one of your leadership heroes should be people that you know personally. Because you get to see how they make decisions every day. What criteria do they use? How do they make the toughest choices in their lives? When we look at famous people, when we look at Martin Luther King or RFK, and we say, “Look at what they did,” what we’re seeing are the outcomes of their decisions. I’m not denying that they were, in many ways, great, but we don’t see how they made them. When you can see how someone makes decisions, watch how they consider other people, watch how they identify their values and live by them, that is someone to look up to because you know how they made choices. When you start evaluating the greatest leaders in your life, make sure the list has people that you know because what defines a leader is how well they understand their values and act on them consistently, not what the outcomes are.

Every one of your leadership heroes should be people that you know personally because you get to see how they make decisions every day. Click To Tweet

That’s interesting because I was thinking I had several guests who have talked about Enron and different scandals on the show. If you look at what Enron’s code of ethics was, it sounded great. They were making money. If the world ended that day, you would’ve thought they were great leaders probably. What you’re saying is so important because you don’t know what’s going on behind the scenes. Something could all blow up the next minute if you don’t know the reality of it and I like that that you should know your leaders. You’ve talked about so many different leadership examples. How many TED Talks have you given?

They’re not all online due to various technical glitches and sound issues but it’s been eight.

They’re great talks. I was interested you mentioned that you used to weigh more. You said you were about 150 pounds overweight. Is that what you said?

Yes, give or take.

How did you overcome that? I noticed the difference watching your TED Talks that you are a lot healthier. That’s a huge transformation. Do you ever talk about what you went through with that?

I do. I touched on it in the book as well. I used the day one approach. I guess the easiest way to explain that is to tie it to a different health struggle that I had. The day one approach comes from a distillation of a number of great pieces of advice from brilliant fellow leaders, but also from personal experiences. One of the most transformative was I am a recovering alcoholic. One of the things that I learned in recovery is that if you don’t want to have a drink for the rest of your life, you have to choose not to have a drink today. That’s non-negotiable. It’s the only thing that matters; not yesterday, not tomorrow, today. Then you have to treat every day of the rest of your life as if it is your first day of recovery because if you’ve got ten years in, it doesn’t matter if you don’t make that choice today. If you messed up, everybody messes up on day one, you don’t throw it all away, you recommit the next day.

TTL 248 | Day One Leadership
Day One Leadership: Every day when I get up, even if I don’t know what the future holds, I do know that I have six questions that are supposed to drive me today.


There is an inherent commitment, humility and forgiveness on every day one of a voyage. When it came time to lose weight, I took the same approach. Day one of this voyage, what are the non-negotiable behaviors that have to happen every single day, no matter what else is going on for me to lose weight? I went out. I used the three most powerful words in leadership “I don’t know.” I asked some experts and they gave me questions. These are personal questions for me so not everyone can use this, “Have I eaten less than 1,800 calories? Have I burned more, in total, than 3,000 calories? Have I done fifteen more seconds of cardio today than I did yesterday?” Here’s the thing. I’ve got to start at 60 seconds. If you’re 300 somewhat pounds, that’s a long time. The idea was every day I got up on day one. It didn’t matter if yesterday I didn’t manage to ask those questions. It won’t matter tomorrow. All that mattered was today. The cool thing was we also built in failure into the process. What kills momentum is when things happen that we didn’t plan for.

Everybody messes up on day one. You don't throw it all away; you recommit the next day. Click To Tweet

Any day that I didn’t answer those three questions was a failure, but we built into the process 65 days. The idea was if I answer those questions 300 out of 365 days, I gave myself two months of failure, two months of being on the road and having no option except some junk food, two months of, “I’m at this banquet and I haven’t eaten all day and I have to give a speech.” Whatever the case may be, one of those things happened, I simply said, “Today was day two.” I get 65-day twos, but tomorrow is day one. Once you pile 300-day ones on that pile, I would be 100 pounds lighter and that’s exactly what happened. It’s all my mental health, physical health, my company. The idea is this. Every single day, there are non-negotiable behaviors that have to happen.

There’s a bunch of other stuff too but these are things that you do if you had extra time or your emails are finished or you don’t have a meeting. These have to happen. I used it to lose weight. We used it to build this company. I used it to deal with what used to be an untreated mental illness. What I do is every day when I get up, even if I don’t know what the future holds, I do know that I have six questions that are supposed to drive me today. If I answer them, I’m going to build a better company, I’m going to build stronger relationships and I’m going to have a bigger impact on the world. That is the type of leadership everybody can live whether you’re a CEO or you just got hired.

I can see why your talks are voted one of the most inspirational of the TED Talks and your book sounds amazing, This is Day One: A Practical Guide to Leadership That Matters, Drew Dudley. It’s been so nice to have you on this show, Drew. Can you share how people can reach you, buy your book, find out more and all that stuff?

The best way to find anything out whether you want to see the videos or buy the book is You can get the book wherever, at fine bookstores everywhere, and also at some Speedy bookstores. They’ll probably all have it.

You’ve got time for one last lyric.

My friends, I had the honor to be your obedient servant, Drew Dudley.

It’s been so nice to have you on the show, Drew. Thank you, Drew. This has been so much fun.

It’s been an absolute pleasure. Thank you so much for having me.

Thank you so much to Drew. What a great show. He’s so fascinating. I hope you take time to go look at his TED Talks. He is great. Each one of them is so unique. He’s got so much energy and what he’s talked about in every one of them is so important. You could see why he’s one of the top TED Talks ever for good reason. He talks about a lot of things that I was interested in for my book, Cracking the Curiosity Code, I used a lot of the same thought process behind the four factors I found that hold people back from being curious, which are fear, assumptions, technology, and environment. We put together the Curiosity Code Index, which is an assessment that determines the levels that those factors hold us back from being curious. It’s important because we’re hearing so much as we talked about with Drew about innovation, engagement, productivity, and all those things begin with asking questions. If you don’t know that you’re not curious, sometimes you’re missing out on asking the right questions.

A lot of people have a fear of looking stupid. They don’t want to have somebody think they don’t know something that they should know so they have a fear that holds them back. Other people just assume that they’re not going to be interested in a certain job or topics, so they don’t pursue it when that could be a great future career or position for them within the company. Sometimes technology is doing things for us that we don’t know what’s going on behind the scenes and we rely too much on it that we don’t even think to ask questions. Sometimes it’s our environment of what we grew up with or family or teachers or friends, anybody that we come into contact with maybe didn’t develop those ideas. I loved how Drew talked about that in our conversation because environment can be huge as far as how much it impacts where we look for ideas and what we think is okay to ask and what is even on our bucket list of things to try.

I have a lot of information out there on, it’s the website. You can also find more at If you go to my website, at the top there is also a way to get to the blog which is the radio show. It has been transcribed into a blog, so you can actually read it as well as listen to it, which is nice. You could sign up at the site in different ways. If you want to sign up for the radio show to find out when we’re having new shows, you could sign up to find out about when the Curiosity Code book and Curiosity Code Index are going to be available. All that is available on my site. I hope you take some time to do that because there’s so much great content there.

If you go to, you can listen to past episodes and there are so many great guests who’ve been on the show. I hope you take some time. Check them out. There are so many episodes. Sometimes I ask my Echo device, if I ask her to play Dr. Dianne Hamilton Radio or Dr. Diane Hamilton podcasts, sometimes she’s questionable whether she’s listening to me or not but usually, if I say, “Play Dr. Diane Hamilton podcasts,” she will. There is no excuse. It’s easy to find past episodes. I wanted to thank all of our guests for being so wonderful. This is such a great opportunity to learn so much from so many unbelievable minds out there. I hope you enjoyed the show and I hope you join us for the next episode of Take the Lead Radio.

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About Drew Dudley

TTL 248 | Day One Leadership

Drew Dudley is the former Director of one of the largest university leadership development programs in Canada at the University of Toronto. He helps some of the world’s largest and most dynamic organizations in the world discover, define, and deliver on their core leadership values. As the CEO of Day One Leadership, his clients have included some of the world’s most dynamic companies and organizations, including McDonald’s, Kohl’s, Hyatt Hotels, Proctor & Gamble, JP Morgan Chase, and over 75 colleges and universities. Drew has spoken to more than 250,000 people on 5 continents, been featured on The Huffington Post, Radio America,, and, where his “TED talk” was voted “one of the 15 most inspirational TED talks of all time” and has been viewed millions of times around the web. TIME, Business Insider and Inc. magazines have all included his talk on their lists of “speeches that will make you a better leader.”

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