The journey from individual contributor to effective manager is often called the most significant transition of a career a shift not just in responsibilities, but in identity. Yet, the foundations of great leadership often start with a more personal, foundational practice: curiosity and continuous self-improvement. In this deep-dive interview, we sit down with leadership expert and podcast host Ryan Hawk of The Learning Leader Show, to unpack his best-selling book, Welcome to Management, and the surprising lessons he’s gathered from interviewing hundreds of the world’s most successful leaders.

Ryan shares the critical mindset shifts every new manager needs to make, why leading yourself is the necessary first step, and how embracing a learning leader mindset fueled by relentless curiosity was the unexpected catalyst that propelled his own professional journey from cold-calling sales rep to full-time entrepreneur and author.

If you’re looking to master the art of management, cultivate psychological safety in your team, or simply unlock the compounding power of daily personal growth, you won’t want to miss these powerful insights on how curiosity shapes success.

Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/ryan-hawk

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How Curiosity Shaped My Career Journey, With Ryan Hawk

Host Of The Learning Leader Podcast, Best-Selling Author, And Keynote Speaker

The transition into management is a topic of this episode’s discussion and it is arguably one of the most significant moments in your career. It’s not just a change in role, it’s a change in identity. At the same time, many managers struggle with the transition because they see the role the wrong way or they haven’t had the right kinds of training or role models.

We’re also going to talk leadership, in particular what Ryan has learned from interviewing literally hundreds of impressive leaders on his own podcast. I’m sure there’s going to be a lot for you to take away, so let’s get going. Ryan, welcome, thanks for joining the show with me, really great to have you on.

Yeah, thanks for having me, I appreciate it.

Yeah, so we’re going to focus on a couple of things that I mentioned in the introduction. We’re going to talk about your book, Welcome to Management, and then we’re talk a little bit about your experience as a podcast host, which you’ve been very successful at. Before we do that, just give us a quick background on you and what you’re up to at the moment.

At the moment, always writing, always working on distilling down the excellence that I’m learning from others in order to hopefully share it with people. Now I’m super lucky I get a chance to work with 4 others on my team, 3 of them coaches. They’re all coaches, but three of them are active coaches with the clients that we work with. It’s been a cool growth and evolution when it comes to like the business side of what I get to do.

I’m surrounded by I think people who make me better. This is Garron Stokes, the Hall of Famer Sherry Cole, Brooke Copps and Eli Liker. It’s super gratifying and exciting. We have a team meeting coming up in a couple of days. I’m prepping for that to get prepared for a ton of work we have. The combination of all the podcast stuff and how I love preparing for that mixed now with having a team where we get to go out and work with clients, again, I feel super fortunate to get to do it every day.

The Management Transition & Welcome to Management Origin

Your podcast prep certainly was evident in the ones that I’ve listened to. Definitely want to come back to that. Let’s start with your book, your first book, Welcome to Management. You went through your own management journey. I remember reading the early part of the book, you were describing getting hit with a personal situation and you’re like, “What the heck? This isn’t what I thought management would be about.” what was the broader impetus for writing it and why did you feel like the topic was so important to get out there?

It’s honestly the book that I needed when I got promoted from individual contributor to manager for the first time. I think a lot of books are written for that purpose. People draw from their own experiences and write the thing that they wish they had. A lot of it comes from because I was trying to help other people and giving that, whether it’s advice or having those conversations.

You combine my own personal experience with the fact that I at that point, I guess, I don’t know, learned from hundreds of other exceptional leaders from interviewing them on my podcast to learning leader show, and so that combination seemed like the right time. The title, which I still love, comes from my dad. It speaks from that original story you’re talking about, within the first week on the job where I’m leading a team that I was previously a member of.

I was peers with all of these people and now I’m the manager, they report to me and I’m sitting in my new office admiring the Herman Miller chair and looking out an actual window that I now have because I used to be in a cubicle. I turn around and there’s a woman who’s in her mid to early 40s looking like a troubled look on her face, she walks in my office, she closes the door, she starts crying and tells me that her husband cheated on her and he wanted a divorce.

I sat there thinking, “Why are you telling me this?” ultimately, you learn if you lead people is that everybody has different relationships with different people. They’re willing to share certain amounts of things about their personal lives. I would not have shared that with my boss but she needed some time off, she had some stuff going on and she wanted me to allow her to do that.

I immediately called my dad after she left my office and told him what had just happened and that’s when he said, “Welcome to management.” to me, there’s a lot of those moments you hear like “Welcome to the NFL,” “Welcome to whatever,” and so that to me was just jarring and really hard. I’m hopeful that now, when somebody gets promoted from individual contributor to first-time manager, they get a nice handshake, a pat on the back and their boss hands them my book. That’s my hope that happens for others, that they can be better prepared and make fewer mistakes than I did when I had that first job.

Mindset Shifts & The User Manual Concept

Coming back to this manager transition, you talk about the fact that, arguably, one of the biggest transitions you make from being a typically a high-performing individual contributor to being a manager. What do you think the biggest mindset shifts are that somebody who is aspiring to be a manager or is a new manager needs to make?

That everybody is different. They all have different modes of communication. We actually created this exercise that I learned from a mentor of mine named Tom Augburn and he named it something different but we shifted it and we called it a User Manual. Essentially, there are manuals for everything in the world that you buy, a refrigerator, a computer, a phone, a camera, like whatever is out there are manuals, but there are not manuals for people. That just doesn’t make sense for me.

To get very practical immediately with this answer, one of the things I like to do is we built out basically a Personal User Manual that each person fills out and then you have conversations about it. It’s basically like how to best work with me, how to communicate with me, when to have meetings, what I value, what I don’t value, all these types of things that pop up there. Tom, who initially gave me the genesis of this idea, just has the one-pager, “How to best work with me.” He was like a senior VP level guy and so he was leading leaders and others.

I just tweaked a little bit and created a user manual. I think one big thing is realizing everybody’s different. When I got promoted at 26, I was still pretty selfish and ego-driven and saw the world through my eyes like I was the star of the movie. I didn’t do a great job of understanding their perspectives of other people. I needed to mature and grow up and understand the world didn’t revolve around me. I just thought it was stupid if somebody did it different than me, which is obviously like really stupid in itself to have that thought, but that’s what I did.

It’s about getting to know your people, caring for your people and realizing it’s not about you, it’s about the team, and in your job as the leader is to understand the individuals on your team, how to inspire them, what to do to be there for them, how to prove and show them that you genuinely care for them. When you do need to get on them, they’ll respond well.

You need to tell somebody you’re not meeting the standard. That doesn’t go well from a coach or a boss who doesn’t first prove that they love you and care about you. That is a never-ending element of leadership and of managing a team is making sure your people know that you care for them genuinely. You get to know them, you get to know their husbands and wives and kids and you know their names. You really understand who they are as a person, their aspirations and their longer-term goals.

You have conversations about all those things. In addition, then yes, you can then go deeper on the daily grind of the work of hitting the number, whatever the objective is. I think it’s really tough to hold someone to a really high standard if you don’t first and foremost and always prove to them that you care and love for them.

That foundation of psychological safety, I think Kim Scott talks about the same thing in Radical Candor, you’ve got to have that established as a baseline right or a foundation before you actually need to draw on it. I think that’s what you’re saying. If you deliver that hard message without having built that foundation of trust and respect and demonstrating caring, it’s going to be a lot harder for people to believe that the message that you’re conveying to them is actually in their interest to listen to.

Everybody reading I hope at least has had either a great coach or a great boss or even a great teacher and everybody I’m almost certain, unfortunately, has probably had a bad boss or a bad teacher or a bad coach in their life. To me, when I think of the two greatest coaches outside of my parents are Bob Gregg and Ron Allery in my life and they were also the hardest on me by far. They’re my high school head coach and offensive coordinator when I played football.

They demanded so much from me. They were verbally abusive at times when you were allowed to be, I don’t know if some coaches still can do that, which I think is okay, as long as you first show them that you love them and care for them and that’s what those guys did. They still do. Coach Allery and I still have conversations about it to this day that you can be demanding, you can have really high standards, you can push and push but only if the person knows that you actually care for them. That’s what those guys were really good at. That’s what I try to model my leadership after same as my parents are where, again, you could push it and you could hold the line with really high standards but you got to care. You got to genuinely care and love the people that you’re serving.

I think that’s absolutely true. You talked about having to learn that not everybody thought the way that you did and that other ways of thinking or doing things might actually be okay. I went through a similar epiphany, if you want to call it that. I’m very logically driven by nature. If I think back to when I was in my twenties, I was working at McKinsey at the time, Ryan. I went to this one-week training program that had a heavy focus on influence and it talked about all of these different influencing styles and only one of them was logic.

I was like, “Wait, there’s eleven others? I thought that was the only way to influence people.” I’m exaggerating obviously, but learning and then practicing these different ways of influencing over the course of that one-week workshop, it was like, “Okay, I get it now. The way that my brain works is just different than the way everybody else’s brain works and I got to make sure that I understand how their brain works if I want to have influence with them.”

That was like the big takeaway and I think as a manager, there’s a lot of influencing when you’re a manager and you’ve got to be able to have the conversation in a way with each person that’s going to work for them. That may be yelling at one person and putting your arm around somebody else and having an, “I’m here for you” moment because everybody needs something different from you as a manager.

Yeah, it’s similar to being a parent. If you have multiple kids, you just assume well they’re all going to be the same, they’re definitely not. It’s showing that you at a foundational level as you’re mentioning, you love and care for them and you’re genuinely interested in getting to know them and who they are. I think that just takes high levels of emotional intelligence and awareness of people and the good leaders have it and the ones who you probably put in that column of bad bosses or bad leaders are ones that are not your favorites they don’t.

Leading Yourself: The Importance Of Continuous Learning

You start the book with a section on leading yourself. Why is that inner work, if you want to call it that, so important also foundational to being a great manager?

The fun part about leading yourself is that it never ends. You never have an arrival moment. It’s something you have to continuously work on. As Charlie Munger has said, I think all of our goals, and it’s definitely one of mine, is to go to bed a little bit wiser than you were when you woke up, reflect, understand yourself, understand strengths and weaknesses, understand what you need to do to get better, be a work in progress, don’t apologize for that, that’s part of the deal.

That doesn’t mean that you can just make mistakes all the time and not strive to be great, it just means that you’re in this always becoming mindset. To me like that’s what a learning leader is, that’s why I named my podcast after that. It’s all about this always becoming mindset of striving to get a little bit better, and watch the beauty of compounding take over.

I’ve written whole books about leading yourself. That’s what I focus on pretty much. For the most part, there’s elements of leading teams and senior leadership when I speak with CEOs of big companies, but we still get back to the importance of always working on yourself, understanding your purpose, understanding your core values, critical behaviors that make those values true. All of that has to be, again, a constant work in progress if you want any chance to be good and effective at inspiring and leading other people.

Curiosity: Great leadership starts with self-work knowing your purpose, living your values, and practicing the behaviors that make them real. It’s a constant work in progress.

Lifelong Curiosity & Learning

When did you realize in your life that you were a lifelong learner? When did that become important to you?

I was not a big reader outside of kids’ sports books growing up. I wasn’t very curious, I wasn’t very talkative until probably I got my first real job after my football career was over. I got hired by a family friend named Rex Caswell to be a telephonic sales rep at Lexus Nexus. I had some insecurities about having a real job because I never had one before I just played football but I really wanted to prove Rex right.

I didn’t have kids when I started. I didn’t have really anything else going on and so I just worked 24/7. I found the number one rep in the company and asked him if he would come in with me on the weekends to help me with scripts and to practice and roleplay and get all my email templates set up and do all this extra work so that during the working hours, I wasn’t spending any time doing anything other than trying to get in front of customers.

He also was a reader and so I started reading books. I remember when I read Good to Great. That became like my Bible. I was just amazed at a guy like Jim Collins could take you into other worlds and you could learn and you could improve and you could implement stuff. That led to the next book, a book that shook me was Give and Take by Adam Grant.

I was like “You can win,” because I played football as a quarterback it’s a very zero-sum game. If one guy plays the other one doesn’t get to play, at least not quarterback. In that book, you learn about like that the people who win the most are people who are giving and adding the most value to other people and it changed my entire perspective of how to approach my job and life in general. What happens, that’s the cool thing about reading, is not only does it help you like in the immediate moment, but it opens your eyes to the fact that there are all these other books out there.

One then creates more curiosity and then more curiosity and then that opens up to, “There’s all these great performers around me at work, I should just ask them what to do.” Rex Caswell, again, the guy who hired me helped me come up with interview questions so I just started interviewing all of the highest performers at Lexus Nexus and just writing down everything they’d say. I would just try to take bits and pieces from all the different people, mash it together with my personality and it worked.

This idea of interviewing the best of the best started a really long time ago for me. I just do it professionally now, but I started doing it in my mid-twenties once Rex helped me with that idea. I just think understanding the power of being a curious person actually makes you more curious, like learning from other people, learning from books, learning from TED Talks, whatever it is it just makes you want more.

That’s why if I could put a skill in somebody like a child of mine that I hope that they have and they keep and they develop, it’s being curious because it compounds so much over time and it could lead you to places that you never thought possible. We try to do that. We’ll see how that continues to work but to me that’s a good question because it really starts as I got older because some people say “I was just really curious kid always asking teacher questions.” that was not me. I never said a word in school. I was the quiet one who got in trouble because I did not talk. Now I would just say the becoming curious and developing that skill has really served me well as I’ve got older.

It’s interesting also that it came after your football career. You weren’t a watching tape junkie. I’m hypothesizing that that’s the case based on the fact you talked about it happening when you took that job at Lexus Nexus.

I have regrets over that because I think I would have probably been a better player and had better performances and been better for my teams if I was. I could lie and say that but that would be a lie. That wasn’t me. Some people I guess are later bloomers with some of the skills they develop and that’s definitely the case for me.

That’s true of a lot of people and that we all go through these journeys as you said earlier, always becoming, and part of always becoming is you’re never done but it also means you probably didn’t start as soon as you should have.

Everyone has a different timeline of what they do. I went back to Ohio University where I graduated from, I did a live show with James Clear. I know they probably brought like the best of the best because they’re all these kids from leadership programs that they had to apply for and it was insane to get in there. There are 250 kids and we met with a number of them before and after and I was just blown away.

It made me very inspired for the future because these kids are just light years ahead of where I was at their age and they just ask great questions and they got amazing internships and they seem totally with it. It just blew my mind at where some of these kids are when I compared them like to me and all of my friends. They’re just light years ahead of where we were.

You’re younger than I am. In the pre-internet era, it was a lot harder to learn things. I grew up with three television channels, CBS, NBC and ABC. There was no cable television in our house, there was no YouTube, there was no internet available. All these things that these kids now have the ability to learn from watching all these videos that all these people around the world create, the TED Talks, all of the things that just did not exist for me in childhood. I see this in my own kids, my kids are adults, and they were way more worldly than I was when I was that age.

Why is that?

I think some of it we made an effort. We took our kids to foreign countries when they were kids because I did not do that other than go into Canada. That was the only place I’d been, Ryan, as a kid. I came home for my first year of college and said, “Everybody else seems to have been to Europe, like we need to do a trip to Europe.” my dad, to his credit, booked a trip and we came over here to England and saw England as a family.

I was what almost nineteen at that point. My kids were probably in 10 or 12 different countries in different parts of the world before they got out of high school. We made that effort for them. I think just in general, what’s available to them, and not just my kids, like available to kids in general, is way greater than what was available when you were a kid or when I was a kid.

I think that helps. It’s funny that you talk about how engaged these kids are that you were with because I think there’s a lot of people that are in their 30s, one of my great frustrations with people in terms of how they think about their careers is how apathetic most people are about it. They don’t put the work in. You think here’s a kid who’s the ones you were dealing with, 18, 19, 20 years old, what happens to them in between there and 35 where they just stopped caring? They don’t want to get better, they don’t have that curiosity anymore? I think that’s true of so many people. Curiosity, for me, is very important attribute because if you’re curious, you will always get better.

It’s like having a fascination with people, with ideas, with places. I think it’s a skill, I think you can develop that skill. I think it’s a valuable skill to develop to be curious and to be fascinated by understanding stories and people and what makes them, them. If we weren’t recording right now, we would be going down rabbit hole of like I want to plan the next European trip to take my kids on,” because that sounds like a really good idea instead of just going to the beach or something. Sometimes you think of those trips and you’re like, “That would be a pain, it’s a long flight, then you got to like deal with whatever,” and it’s like, “No, that’s the good stuff.” That’s all the good stuff of doing that especially with your kids because they need some extra adversity in their lives beyond just like sports or whatever random stuff is happening at school. Anyway, you just got my mind thinking about that.

Daily Practices For Personal Growth & Leadership

What are some of the other things that are part of your personal practice repertoire to lead yourself?

I think every leader, if they want to be effective, should have some form of a writing practice. You don’t have to publish that, but there should be some documentation and reflection on what’s going on, what you’re thinking, how you’re feeling about that as well as sharing and getting the fuzzy, messy thoughts out of your head onto the page about any and all topics.

You should have a clear understanding of what you believe, you should have an understanding of what your values are, you should have an understanding of why you do what you do, you should have a belief set on all different forms of leadership. If you don’t have a regular practice to get those thoughts out of your head onto the page, I think it’s a huge mistake. I don’t think you’re going to be as clear as you need to be if you want to be effective.

The first thing I do every day is get up and hydrate and then it’s time to get those thoughts out of my head onto the page, whether I’m working on a book or I’m doing a Homework for Life, Matthew Dicks style of journaling, which is just documenting the days and the key learnings from those days as well as I like prompts. I mentioned one already that I think anybody could implement or you could come up with your own, but I do think it’s useful that at the end of the day you ask yourself, “What specifically did I do to be a little bit wiser going to bed than I was when I woke up?”

That works as a forcing function for you because you know you’re going to ask yourself that at the end of each day and so your days then are spent saying, “I want to make sure I have a good answer at the end of that day. I’m going to do things to get a little bit wiser, to be a little bit better, to push outside of my comfort zone to increase the level of comfort and competency in my life,” whatever it may be for you.

Create prompts that work as forcing functions that set you up into the direction that you want to go. It’s all about breaking down big goals into smaller ones and doing them day by day and again, watch the beauty of compounding take effect. I just am a big believer in stacking day after day after day and then you look back like “I’ve done quite a bit here and I feel much better now 6 months later than I did 6 months previous from now.”

When you do your writing, on one end of the spectrum I guess I would think about writing a book. It’s a long effort, you got to continually work at it, refine it. It’s got to have structure and all of that. On the other end, you probably have something just pure journaling where it’s stream of consciousness. When you’re not writing a book or the writing that you’re doing, the things you’re getting down on paper are not specifically about writing a book, how do you organize those thoughts and distill and get the essence of them versus just having a bunch of random musings day to day?

I could even read some of it now, it isn’t structured at all. It’s a lot of what looks like semi-rambling at times or jumping from wildly different things, whether it’s the documentation of what we did with our kids versus something I learned on a podcast after I did an interview. Sometimes, those go back and forth. It is a stream of consciousness, it is a get the words out of my head onto the page. There isn’t editing. Books, you edit a ton. There isn’t editing when that happens. It’s just get it all out.

The funny thing is, though, there are parts and pieces of books that are taken from that type of journaling because there are key learnings or there are something happened and so again that’s another good reason to do it or they turn into blog posts on Substack or social media posts or whatever like that. I just think you got to do it. I know there are some forms of it.

Brian Koppelman talked where you write with a pen or a pencil into a notebook and you never lift your hand off the page and you go all the way down the page and you go to the next page and you do the whole thing all the way down to the page. I don’t do it like that. I type it. Usually it’s on my phone but usually it’s on a computer and I just type out stream of consciousness of what happened, what I learned, what I’m thinking, how I’m feeling. I think it’s important to document all those things.

Curiosity: Typing out your stream of consciousness what happened, what you learned, what you’re thinking, how you’re feeling documenting it all is important.

I go back and read it all the time. Sometimes I smile, sometimes I cringe, sometimes I go “Oh wow,” and sometimes I find things that are key learnings that maybe I had not thought about and then that ends up like in a book or in a speech or something. Yeah, it is very stream of consciousness, just get it all out style of writing.

I tend to jot ideas down in the Notes app on my phone. That’s where a lot of it starts. I’ll go back. I don’t have a morning writing ritual like you do. We’re going to talk about morning ritual in a minute, but I don’t do that but just as ideas come to me when I’m working, when I’m engaging with somebody, I just try and do a quick note. I’ll come back to them and think like, “Is this a social media post? Is it a newsletter topic? Is it an article? Is it something more than an article?”

It forces me to start distilling how much is there to this idea. Is this just like a very simple quick suggestion or is there a bigger idea here that could be developed further? I spend time pretty regularly going back to my list and looking for writing ideas like when I’m doing a new newsletter and trying to think like, “Where’s this idea and is this idea ready to be birthed to the world yet or does it still need a bit more of that continued refinement?”

A lot of it does need that work. I just pulled out the notes on my phone and like, “Figure out the cost of success and don’t bargain over the price,” “Every thought that you have is a downstream of what you consume,” “Grit is fit,” “Good humor,” because I’m thinking about humor, “Good humor and good writing, good speaking is usually strong opinions sometimes about random stuff. Part of the key to good humor is extreme opinions. Good writing would be something that really aggravates them.”

These are just random notes that I heard whether from a book or from a podcast or a conversation I had and there are just tons and tons of, “You don’t fall prey to the arrival fallacy.” that’s another version of “you’ve never arrived you’re always becoming.” different types of things that are throughout these notes that I think are helpful. As with you, I go back and review it and say like, “What is this? Is this anything? Is it just for me? Does this turn into something?”

Nikki Glaser talked about it, an amazing stand-up comedian and roaster and she will stop mid-conversations while out with friends because somebody said something or she thought of something that could be interesting, could be a bit, could be a story, could be a joke and just get it down. I think that practice of getting it out of your head onto the page or writing it down the second that you think of it is useful because if not, you’ll probably forget.

We probably all have those regrets where you were thinking something and then you went onto the next thing without stopping and writing it down or putting in your phone and then it like never came back or maybe if you’re lucky it did but it like took a week or something. I just think that’s a good practice for all of us to have is to document those thoughts as much as possible.

I’m not sure my notes list is quite as interesting as yours but there’s some very random thoughts in there. You know, “Going big and how you test your thinking,” which came from a discussion I had with Chris Voss, “Being open-minded and clear-eyed about opportunities presented to you.” the idea of eustress, which is a word that most people don’t know. I didn’t until probably a year ago. Bureaucratic jujitsu, streaks and how they can work against you, I was thinking about that in the context of Wordle, so again, it’s a pretty random list. You have a very regimented morning. I was listening to your conversation with Arthur Brooks, it was like, “Who is more regimented?” It was like two pretty regimented guys.

That guy’s crazy in a good way.

You’re up pretty early, hydrated, writing, working out.

Yeah. Sometimes I think people are tired of hearing about those things. I’m happy to go into it because the whole morning routine thing got overblown. That stems again from my high school coaches, Bob Gregg and Ron Allery. They’re very regimented guys. They studied all of the military institutes. They went to Army and basically that’s the offense that we ran and we practiced the same way and we got up super early. Yeah, it’s ingrained.

In college, it was the same thing. I played for guys who all went to the Air Force Academy, Brian Knorr and Steve Russ and a bunch of others. Anyway, it’s pretty regimented. I like to own my mornings, especially in a loud home with kids and everything that we have. Getting up really early is my time and so I can have complete control over what I do because nobody else is awake.

There’s an element of stretching, hydrating, reading, thinking and then punishing my body physically because I’m trying to stay strong and get stronger. I try to do all of those things first thing in the morning, wake up pretty early. To do that, you got to go to bed I think earlier to get enough sleep. By the time everyone else is up and at it and ready for breakfast and the bus stop and all that, I’ve accomplished all of those things that I need to do to get done to make sure that I’m in a good place both mentally and physically.

To me, working out is my medicine. It’s a drug. I do it every day. I don’t have off days. There might be a chip missing or something that I’ve got but if I don’t work out, I’m not right. I just have to punish myself there and that then sets me up for the rest of the day to be better. I think everybody’s got to figure what is that for you and then try to just be disciplined to do it every day and set your environment up so that you can do it every day.

I think it’s a very personal thing and people need to really experiment and try and figure out what’s best for them and then do it. I know some exceptional people that just sleep in and don’t do any of that, but then maybe they stay up and they’re very creative late at night or they work out then or they write then or whatever. I think everybody’s got to find what their version of that is and then try to stay consistent.

The Genesis Of The Learning Leadership Show Podcast

Let’s talk about your show. You started this what back in 2014, The Learning Leader Show?

Yes, I started recording then. We published in 2015.

I suspect there was some linkage to what you were talking about earlier in terms of interviewing all of the leaders at Lexus Nexus, but how did the idea come to you and what did you want your show to be when you started it?

I’d gone back to school and gotten my MBA. It took me six years. My company paid for it, they reimbursed me for doing it and so I thought, “This is crazy. My company reimburses me. I should always go to school because I’m going to get reimbursed.” I was looking into even on the beginning stages of applying to go and maybe get a PhD in Management or Leadership or whatever. There were programs out there like that.

I didn’t love the element of getting my MBA. You got to take all these classes and some of them I didn’t really care for and they were really hard. I got tutors for a number of them. It was really hard and I wasn’t super curious about all of it, but I was told by a higher-up guy, “You should get this. It would help you in your career.” I’m glad I did. I’m glad I went through it because I was a Communications major undergrad.

I thought, “Is there a better way to get a leadership phd program than going to some school or then they tell me the curriculum I have to take and when I have to be there and where I have to go and you know all that stuff?” I was a podcast listener at the time. There were a few early ones like my buddy Todd Henry who lives down in Cincinnati who’s still doing it and is great, Joe Rogan, Bill Simmons, there weren’t a ton. Terry Gross, she was crushing it still.

I thought, “I’ve done a bunch of interviewing in my professional life to hire people both for my own teams as well as others and I developed I think some good skills for that.” I developed some more curiosity by that point and thought like, “What if I do it? What if I just start my own show?” fortunately, once I made that decision, then I was very committed to learning like how does the whole podcast world work.

Not only was I trying to develop my skill as getting great guest and asking great questions and even better follow-up questions, but I also was like trying to understand iTunes, which is what it was called at the time, and how the whole algorithm works and all of that. I recorded 22 episodes pre-launch. I released 3 episodes per week for those first 8 weeks because that’s when your opportunity to hit New and Noteworthy in iTunes at the time. It may still be like that, I’m not even sure.

I set it up to where I would give myself the best chance to do that. I hit it within the first week and stayed there the whole eight weeks and it’s been steadily growing ever since. It’s pretty cool to see how that has happened. My intention was purely selfish and for me. I just thought it would give me a better chance to get in touch with more well-known people who are super accomplished if I asked them to be on a podcast instead of just asked them to talk to me. I think that’s still true.

That really was the genesis of it and now it’s still my favorite thing in the world to do to have a deep long-form conversation with a person who’s far wiser than me and I can basically ask them anything I want. Fortunately, enough other people like it that it’s been my full-time work since the end of 2017 going into 2018. I never would have guessed or thought it was even possible to make this my life’s work that provides my family but here we are and it’s pretty cool.

Looking back, even in some of your early episodes, Ryan, you had some pretty big-name guests. You were very early able to attract some fantastic people onto your show. What’s your secret for getting them on?

It really helped me that I had a sales job at Lexus Nexus. I was making 60 cold calls a day. I was writing tons of cold emails. I was always trying to wordsmith those emails with my mentors and teammates and friends at Lexus because it was a more efficient way to get in contact with a prospect than just dialing the phone. I was trying to do both. I was sending out emails all the time and I was making these cold calls in order to try to crush my number. I had a lot of practice at cold emailing and cold calling.

I tried to craft really well-written cold emails to all the people that you’re talking about. I don’t have any fear of being ignored or being rejected. For every guest that you saw in those early days, I was probably cold emailing twenty others or more. To get those first 22, you do the math and it’s a lot of emailing a lot of people on that list, the list I still have to this day, which now has thousands of people on it that I’ve tried to get on my show.

That’s definitely changed over the years. Now it’s almost flipped where I just have relationships with a bunch of PR people and we identify who would be good fits and who I’m curious about and then we decide to have them on the show. In the early days, the first few hundred episodes, it was pretty much all a bunch of cold emailing, being ignored, being rejected and then just keep going.

What’s interesting, I’m sure you discovered this in the early days, I’m coming up on 200 episodes so not nearly as far into this as you are at this point, and it’s become a much more crowded space than when you started back in 2015. Some people who are very well-known they’re very generous with their time. They’re like, “Sure, I’d love to do it,” and then you get people who you think, “There’s no way this person’s going to turn me down,” because they’re not even up at the top of your high-profile list. They’re like “No, I don’t have time for this.”

It just really comes down in part to whether people want to make the time for it or not. As you say, I stopped taking it personally. I had to learn to stop taking it personally pretty early on because you just realize I’m going to get people and at this point, like you, I mostly get PR people reaching out to me and I can be more selective about who I get onto the show.

I have people who I still pursue, I wanted to have a conversation with you so that’s how I reached out and appreciate you saying yes. That mix definitely shifts it’s not really doing too much cold outreach anymore. I look at some of the people you had on your show. I would love to get some of those people. You work your way up the ladder.

That’s the other part of it too, I would say, especially in the early days and it’s still true now is every time you do it, is really interviewed Rex Caswell again and bringing Rex up again. I love him. He says, “You’re interviewing for your next job every day.” Basically, what he’s saying is however you choose to show up, whatever the output that you have, that is what’s going to get you whatever the next thing is.

I think the same is true in podcasting. If you host somebody and you do an excellent job and you’re prepared and they really enjoy it and maybe you got things out of them that they hadn’t talked about before and they finish the recording they’re like, “Thank you, that was a lot of fun,” like sometimes, they’ll do the recruiting for you. I remember Will Guidara. He told me this story because he wanted me to know. I love Will, Unreasonable Hospitality, I’ve had him on a few times. I had him on before the book because I’d heard about him through Brian Koppelman.

Anyway, I sent him a cold email because I heard him on some other show and I’m like, “This guy’s great.” he’s good, really close friends with Simon Sinek. He just forwarded the email to Simon and said, “What do you think of this?” I mentioned Simon in the email that I had him on I knew they were friends. Simon said, “Absolutely do it,” and then Will forwarded that to me and it was like, “Let’s go, dude.”

Part of getting the people and like how it compounds and how it grows and one great one to the next great one is doing a great job with that person so that then they become your advocate they become your champion. Now having whatever 600 of them out there, that is very helpful. The beginnings are really, really tough but as you get going and if you do great work, then I think it really opens up a bunch of doors and creates some cool opportunities that you never would have thought possible. I just try to just be as prepared as possible for every opportunity because you really never know what’s going to happen as a result of it.

Preparation & The Art Of The Deep Interview

What do you do to prep?

I read a ton. It’s very boring-looking if you’re from the outside. I just read and I just take notes and I think a lot about openings. I think a lot about how I can take people to specific moments in their lives. I think a lot about loved ones of the people that I’m talking to. People usually like doing that. I was promoting I don’t even remember which book it was a while, maybe like The Pursuit of Excellence, I went on a podcast. I wish I remembered the person who did it. He asked me about my grandpa, my dad’s dad, Dean Hawk, who’s still the most selfless human on the planet because I’d written about him.

That’s what he opened with and it changed the whole feeling that I had for that host and for the whole conversation. I just took a note after that of saying like, “Try to find loved ones or people that they really care about and see if it fits and see if it would make sense.” I don’t do it all the time, but I do it some of the time. There are little things like that that you pick up that makes it feel different, feel personal. It gets them out of interview mode and more into like, “I’m having a conversation with a guy who seems to care about me and want to get my story out.”

There could be a book written about all of that, but to me, that is part of the fun. Peyton Manning took every prep in practice when he played football and he said when he couldn’t continue to take every prep in practice, that’s when he knew he was done. To me, I’ve had so many random people say, “You could outsource all of your prep. You can use ChatGPT, use a combination of people.”

I have no desire to outsource any of that. I love that. That is part of the fun. It’s reading the book, watching the TED Talk, like finding that passage on page 67 that was such a cool way to open, stuff like that. I guess it would be a sign. If I don’t want to do that anymore, if I lose the love of that element of it, I probably should stop because I think that’s the good stuff. I think that’s what makes it good. Part of it is doing the deep research of thinking of ways to put my guest in a position to share openly and shine a bright light on all the useful and good things about them so that it certainly helps me because it starts with me, but then hopefully helps all the people who are listening to.

The Impact Of Deep Conversations & Final Advice

Is there any one guest who hit you with a particular lightning bolt that’s really had a profound impact on your life?

That happens all the time. It’s hard to say is there any one. One of the moments that it tore me up in maybe a good way was when I drove to Columbus, Ohio and I was welcomed into the wrestling room of Tom Ryan, Ohio State’s legendary wrestling coach. I’m really glad I went there in person because I considered just doing it on Zoom because it would be less time or I could just stay here and do it.

I went there, he was the nicest guy ever, he had some of his best wrestlers were actually practicing and I just got to stand there next to Tom watching. I don’t know wrestling. I’m a football, baseball, basketball guy. My kids are mainly soccer and lacrosse and volleyball. I don’t really know anything about wrestling. I’m just being curious and asking questions and he was super cool. He didn’t make fun of me or think the questions were dumb. He was really into it and describing all the way from warm-ups to when they got going. It was amazing.

We sit down to actually record after we watched practice for 30, 40 minutes and he tells me the story of his 5-year-old son Teague and having a heart attack and dying at 5. He told the story a lot before and never to me directly. I’d seen him talk about it, but just to see a fellow dad just break down and lose it. I look over at Corey my camera guy who’s there and he had all these cameras going and Corey’s losing it, I’m losing it.

Just to see the way that this guy turned the biggest tragedy I could ever imagine, not something certainly I’ve dealt with, and how he’s used it and responded from it because you’ll never ever get over something that. I was so inspired it knocked me back. That drive home is an hour and twenty minutes and I was a combination of inspired, of grateful, of sad, a big mixture of emotions.

What I was most feeling as I got home and I texted coach after I was, “Just thank you. I feel so lucky that what I get to do for a living is have these types of conversations with brilliant people you.” we’ve maintained a pretty cool relationship. Getting to meet my heroes and they somehow exceed my very lofty and high expectations and then build actual real relationships with them is literally the coolest thing ever.

We’ve been talking for 45, 50 minutes, whatever it’s been, you’re citing them regularly. It’s sticking with you people that you’ve talked to.

It’s my life’s work. Outside of family stuff, it’s what I want to do. We do other things we have a leadership development all these other businesses and it’s awesome. Don’t get me wrong, I’ve built some amazing relationships but if you map out your perfect day, part of that perfect day is to have some of that Tom Ryan time. Be with somebody, have a conversation, maybe not that hopefully there isn’t the tragedy that involved there, but get close with a person and have a conversation. There’s nothing cooler in the world for a job, to me at least, than doing that.

One of the things I love about doing this, it’s work, was when I was doing this while also managing a corporate job. People say to me, “How do you have time for this?” I’m like, “I make time for it.” I want to learn from other people. You probably have conversations with people at the pub over beers that you’re learning from. I’m just preparing a set of questions in advance and recording it and releasing it, but it’s the same process.

It probably makes you better than when you are having those conversations at the pub or at the sidelines at the soccer game or whatever. How has it impacted you as a listener and as a conversationalist?

It’s different. You know better than I do. This is work. Getting ready for it, being able to ask good questions, knowing your guest, having the right follow ups that draw new information. You made that point a minute ago. That’s very different than the way a lot of conversations go at the pub. A lot of conversations that go at the pub gets ignored at the UK probably. You forget half the stuff that you may have talked about at the pub. Things don’t click as well because you’re not fully present in a way that you are than when you’re doing an interview like this.

Why not? You can choose to be that present, though. You can’t control them. You don’t think it has made your conversations richer and better because you’ve gotten so many repetitions doing this?

Absolutely.

My point of that was I think it makes you better in all other areas of your life because you become a better conversationalist, you probably become a better listener. You’re used to listening. You get a lot of practice listening. Most people don’t get that practice. That’s taken me a while to realize. I’m in this chapter of life where you spend time watching your kids play sports. When you do that, there are other parents who are doing the exact same thing.

Inevitably, you strike up a conversation and ask questions. To me, that’s where it comes out. We had a Halloween party. I just met a guy who owns all these car dealerships and we’re dressed up like idiots but I’m basically doing like this, having an interview with a guy, learning about that. We developed a much deeper relationship because it’s built on curiosity. I don’t know if I’d do that years ago. That’s what I’m saying for you. I think getting all of the reps makes you better as a husband, as a friend, as a random dad in a soccer game. I think you can really benefit. I felt it. I’m guessing that you felt it and you’ll feel it even more as you keep going.

Last question. What’s ahead for you?

Being a visionary is not one of my things. I want to keep doing this. The work is the win. In order to do that, it has to continually get better. Whether it’s writing books or giving speeches or recording a podcast, all of that work is the win and so the standard just has to continually to get better. You have to keep pushing it, keep being challenged, keep being uncomfortable. My hope is if we talk five years from now, there may be some evolutions and some tweaks and maybe the team grows, but for the most part, I’m still going to have deep, long-form conversations with brilliant people and trying to learn from them and then take what I’m learning from others and share it with the world.

Any last advice you want to give to our audience before we break?

Document your days. Matthew Dicks, Homework for Life. You can search that up. He’s given a TED Talk he’s on my podcast multiple times, but document your days. Always do things that your future self will thank your current self for. Your future self will thank your current self because you documented your days. Get the thoughts out of your head onto the page. If you implement that practice, I don’t see any possible way you won’t be glad that you did. Do it.

Great. Thank you for doing this. It’s great to get to know you.

This is awesome. I appreciate it.

I appreciate it too. Thanks. Have a great day.

—

Thanks so much to Ryan for joining me to discuss his transition into management, how that translated into his book, Welcome to Management, what he’s learned from literally hundreds of interviews with some amazing leaders, the idea of excellence and how he has worked on developing that and building it into his daily routine. A lot to learn from him. As a reminder, this episode was brought to you by PathWise.io and if you’re ready to take control of your career join the PathWise community now. You can also sign up on the website for our newsletter and follow us on LinkedIn, Facebook, YouTube, Instagram and TikTok. Thanks.

Important Links

• Ryan Hawk
• Welcome to Management
• Radical Candor
• Good to Great
• Give and Take
• The Learning Leader Show
• Unreasonable Hospitality
• The Pursuit of Excellence
• PathWise on LinkedIn
• PathWise on Facebook
• PathWise on YouTube
• PathWise on Instagram
• PathWise on TikTok

About Ryan Hawk

Ryan Hawk is a bestselling author, keynote speaker, and host of The Learning Leader Show. Over the past decade, he has interviewed 650+ of the world’s most influential leaders: Jim Collins, Simon Sinek, Adam Grant, Tony Robbins, James Clear, Ryan Holiday, Kat Cole, John Maxwell, Jocko Willink, Susan Cain, Ramit Sethi, Kirk Herbstreit, JJ Redick, Coach John Calipari, Admiral William McRaven, Liz Wiseman, George Raveling, Tom Peters, Daniel Pink, Patrick Lencioni, John Mackey, Robert Greene, General Stanley McChrystal, Seth Godin, and the list goes on. The Learning Leader Show has been named an Apple Podcast “Best-Seller” for the past four years and regularly ranks as the #1 Business Podcast in the world. It earns millions of downloads per year.

Ryan travels the globe teaching the world’s largest companies, universities, and associations about personal excellence, leadership, storytelling, sales, teamwork, and more. When Ryan speaks, you’re listening to everyone he’s ever interviewed. And he’s interviewed more than 100 NY Times Best-Selling authors in addition to Special Forces Operators, Fortune 500 CEOs, entrepreneurs, professional athletes, and front office executives.

Ryan has also published three books: Welcome To Management – How to Grow from Top Performer to Excellent Leader, The Pursuit of Excellence – The Uncommon Behaviors of The World’s Most Productive Achievers, and The Score That Matters – Growing Excellence in Yourself and Those You Lead.

Born in Dayton, Ohio, Ryan spent his earlier years playing sports. He earned a college scholarship to play quarterback at Miami University where he got beat out for the starting QB job by Ben Roethlisberger. He finished his career as Ohio University’s quarterback and team captain. He then spent 12 years in Corporate America where he rose to the level of Vice President of Sales of a multi-billion dollar company. He now spends his time preparing for his next podcast guest, working with leadership teams, and sharing what he’s learned on stages all over the world.