102: Work on Your Game and Step Up, with Dre Baldwin

How are the leaders at all levels of management tackling the toughest challenges each day? That's the question, and this podcast is the answer. I'm Rob Fonte, and I'm bringing on the brightest minds in management to share practical solutions to those challenges you're facing. Let's get ready to jam. Hello, everyone, and welcome back to the Leadership Jam session. Today's guest is Dre Baldwin, CEO and founder of Work on youn Game. Dre has given four TEDx talks on discipline, confidence, mental toughness, and personal initiative, and has authored over 40 books. Dre sits down with me today to talk about his journey from playing professional basketball for nine years to today, where he works with entrepreneurs and leaders to help them establish mindset, strategy systems, and accountability. Dre, welcome to the jam session.

Excited to be here, Rob. Thank you for having me on.

Yeah, I'm excited to have you on. And you ready to jam?

Yes.

All right. So the. You have a fantastic journey. The way I understand it, you correct me wrong, is you. You started playing basketball when you got into high school, basically, from what I understand, sat on the bench even your. Your senior year. But then after high school, five years later, you make it to playing professional basketball internationally for nine years. Is that about right?

That's about right. I dabbled in basketball. I mean, it's not like I never heard of it before.

Sure, yeah.

Wasn't really, like, seriously playing until I was 14, which is my freshman year, and didn't make the team till my senior year, so. That's right.

Wow. So. So how does that happen? How do you go from, you know, making a team senior year and then making it professionally?

Well, we have to say it was just because I just outworked the rest of the world for five years. That's probably not the entire case. That's part of it, but that's not the whole. Yeah, I had some natural abilities, inclinations for basketball that I just happened to be tapping into at a little bit later timeline than the average kid who might have started playing when they were 6 or 8 years old. I didn't start until I was 14. Good thing about basketball, Rob, is that you can practice by yourself. You don't need another person, and you don't even need all. You needed the ball.

As long as you have a ball and court, you have the necessary equipment. And on top of that, I had the discipline, which was to just keep going to the park and trying things out and practicing and putting those three things together. I eventually was able to piece together becoming a no Serviceable player. It's not like I was playing in the NBA at that point. I was still a Division 3 college player. So it's not like people are looking at me like this guy's the next superstar. It wasn't in the cards yet, even then, at that point, but I was able to kind of sell and hustle my way into a pro opportunity. That's how I got started.

And then you played for nine years, which is pretty incredible.

Thank you. Yes, that's true.

And then you go on to become CEO and founder of Work on. Work on your game. Right now you work with a lot of organizations and companies bring you in. How did you make that transition?

My first introduction to entrepreneurship was as I got invited to a network marketing meeting. And that's how I first started learning about just entrepreneurship in general and that there are other ways of building business. And I dabbled a little bit in that, and that just helped plant the. The business minded seed into my head. Didn't stay in network marketing. Went to college. No. Finished college.

Played pro ball. Started putting videos on YouTube and built an audience of basketball players. And the players started asking about the mindset aspect of basketball. This is where it started because I was showing them how to do the dribbling and the dunking and how to shoot, the technical skill. And they were saying, hey, Dre, you seem to go to the gym every day. You seem to stay motivated, for lack of a better term. And you're practicing all the time. I don't always feel like practicing.

And I have the skill or I'm developing some skill, but I don't always use the skill when it's necessary in the game. So can you help with the. The internal. The mental side of the practicing, the playing and all that stuff. So I just started talking about mindset and Rob. I didn't even think there was anything special about it. Because unlike with playing basketball, in which you can look at someone and tell where they're deficient, you cannot tell the mental deficiency another person has by looking at them. You only know when you start to converse with them and get to know them.

And you can't really tell that you don't know a person, and especially if you don't know what questions to ask. So when I Started talking about discipline and confidence and mental toughness and believing in yourself and persistence and why you got to practice even when you don't feel like it. And all these things the player said, I've never heard anyone describe these aspects of basketball, let alone life in a way that you're describing them. So that was a light bulb moment for me. And secondly, it was people who didn't play basketball started hearing it and saying, well, Dre, I don't play basketball. But the way you break that stuff down, that stuff is applicable off the court. So that told me that, okay, there's a whole world of people who don't play basketball who I can serve with this. And remember back to that network marketing experience, I always had it in my head that I wanted to do something outside of sports.

All right, so I know you wrote a lot of books, right? One of your books, work on. Work on your game.

Yeah.

I believe you came up with like a four part model or like a roadmap. Is that right?

Yeah, the four pillars of where it originally started.

All right, so why don't you walk us through what that looks like?

Sure. First one's discipline, showing up every day to do the work. And that's really the first thing people noticed about me. And next one is confidence. Putting yourself out there boldly and authentically. Especially important in a performance based line of work like playing sports. Third is mental toughness. How do you stay disciplined and stay confident even when things aren't working the way you expect them to go? Very important as well when you have big goals and big dreams, because you're going to spend a lot of time rob having not achieved the goal, even though you're still working on it and you still have to keep showing up.

And the last one is personal initiative. How do we actually put this stuff to work and go make things happen instead of waiting for things to happen? In other words, being a self starter or being A go getter. So those are the four foundational pieces that were all based around mindset, and we've evolved it over time. Mindset still our foundation. But basically what work on your game is all about is codifying and systematizing professional performance and discipline for results, which.

Obviously translates into the corporate world, right?

That's right.

So let me ask you this. I love the mental toughness piece. Right. And so in your experience, how do you build that in a team environment without, you know, pushing people too far to, like, burning out? Right. Because there is that balance at times when you're managing people.

You did well. The biggest thing as a manager or leader of a group of people is you have to know how hard to push on which buttons for which people, because then everybody's the same. And something that you learn a lot playing sports, especially a team sport, because you're in a locker room with a bunch of other players. And a good coach understands, and a good player understands as well that there are certain players on the team who you can yell at in front of everybody and they can take it and they'll come back better. There are other players. If you do that, you will lose them mentally for the next three weeks. And you have to understand who you can do it to, who you can't do it to. And when you play sports for long enough, like up to the pro level, as I did, you get a lot of experience seeing people.

You see the good, the bad, and the ugly when it comes to that, when it comes to coaches and teammates using it the right way and using it the wrong way. So a lot of athletes are not able to articulate and explain it, even though they have seen it, but they're not. May not be thinking about it on that level, but I thought about it on that level. So I've seen it from all angles, done right, done poorly, and just done in a confusing way, let's say.

Yeah. So you really. You really gotta take your time to get to know your people. Right. Kind of understand what their boundaries are, where to push them and when. When to kind of dial back.

Yes. And the faster you can figure it out, the better you get at reading people. The faster you figure it out, the faster you can get moving.

Yeah. Yeah. It's amazing how many managers you know. Yeah, I work with a lot of managers and how many I come across that don't really take that time up front to do it. And then they're trying to play catch up along the way or trying to figure out what went wrong. So it's so imperative to, to spend that time and invest it up front.

Right. And something I hear from even teachers, interestingly enough, and youth coaches, they say things like, hey, the main reason that I can get on my students or my players or these kids, even with youth say it, is that they know that I care. And when they know that you care, then you can get away with things with them that you couldn't get away with if they think you're just using them for the job.

Yeah, so true. All right, well, let me ask you this. Like, we have a lot of, we have a lot of leaders that listen in obviously on this podcast, first time leaders who are new to managing people. What would you say, you know, in your experience the biggest mistake that new leaders make out of the gate or within their first year? And, and how might they course correct that?

New leaders meaning new to leadership.

Yeah, new to leadership. Yeah.

Well, they're operating out of the book. They're operating out of textbook hardly ever works. So textbook's often written by people who might not have even done the thing they wrote the textbook about. So you, to be the leader, you have to actually get some real life experience, get your hands dirty, and you got to get, as we say, ten toes deep in what you're doing, ideally learning from someone who's already in that leadership position who has the ability not only to just show you what to do, but also explain to you why they're doing it. So unfortunately, sometimes you have the blind leading the blind. You have people who are not really good leaders, but they have a title and they have seniority, so they get told, hey, go train this person. But they're training you the wrong way because they don't even know, but they have the title, so you learn from them. And unfortunately, if that person who is doing the learning, the trainee, if they don't have the insight to understand this person is training me improperly, you might be fooled into thinking, I guess this is the way it's done.

And then you copy it and then you get a whole culture just like that. So ideally you have a really good leader who's already in the game, who can explain it and tell you why they're doing what they're doing, not just what they do because you're not them, but if you can understand the why and apply it in your way, then you, we can start to multiply leadership.

Yeah. Yep. Totally agree. All right. And what about the more experienced leaders, right? Maybe perhaps the ones, let's say even middle mid management, who are Feel like you're kind of stuck in between upper leadership and their teams. Right. And trying to feel like they gotta please both, but might feel like they're not. Might feel like just how many days you're just failing both.

Both. Both ends of it. What advice can you give them?

Well, number one, they're right. They do have to please both. Because you're conservancy, you have to please your bosses, the people who are above you. And at the same time, you need to. Number one is embrace that mentally. Embrace that. This is where you're at. This is part of the game.

Yeah.

Why we call it work on your game. Because the game means, first of all, you need to understand what game you're in. And a lot of times people have an inaccurate assessment. Rob. Of what game they're actually in. So then when the game is not going the way they want it to go, they get frustrated because their expectations are off.

Yeah.

Expectation when you're in the middle is that, yes, you have these people down below you, so to speak, and yet these people above you. And yes, this is the game that you have to play. So let's figure out how we can best play this game. And the biggest thing is the communication. And it's the first of all, the internal communication with yourself. Okay. I have to get this message across to my team that came from up above. And I don't even like the message, but this is the way it has to go.

So how can I get this across to them to where they understand that it's not me being a jerk to them, but at the same time, I'm not. I'm not throwing the upper management under the bus. Right. How do I do that at the same time? And that's a communication skill. That's the smoothness of communication that you have to learn how to get that message across in a way that they all get it. And if word gets back to your superiors, you don't look bad. So that's. That's a skill.

So you have to learn how to. You got to learn how to say it. Say it sometimes without saying everything that you really want to say. And.

Which is hard.

Yes, exactly. Very hard. But it's a skill, which means it can be developed.

Yeah. I love what you just said about, you know, sometimes not even realizing the game you're. You're playing.

Mm.

Right. Which I think is very fair. Sometimes you're just too close to it. How does one try to figure out when they don't realize the game? They're not Even playing the right game.

Well, it goes back to what we talked about a couple questions ago is hopefully you have some people around you who understand it and they can explain it to you and they can translate to you what's happening so that you don't make a misstep. Now, short of that, let's say you don't have that person around to help you understand and you don't have the language skills to explain it to someone who might not work with you. But let's say you had a coach outside of work.

Yeah.

And you can't. You can't quite explain it to them in a way that they understand what the problem is. If you have a good coach, they should be able to figure it out. But let's say you didn't have that. Either is. Then you would have to have to go through some trial and error, which means getting in the hot water with the bosses, messing up with your subordinates, maybe getting fired or time or two. And then over time, through those scars, you learn how to actually do the job the right way. So you learn through your own personal experience.

Yeah, yeah. I mean, you know, you do learn from your mistakes, right?

That's right.

Exactly. So even with yourself, just curious, because you've had a lot of success, but I'm sure you've had some missteps along the way, too, even as you were building out your business. And so anything that you can share what you learned about missteps along the.

Way, that helped you, I think with hiring. For example, if I've ever been wild in a job interview once I was. I was wild in an interview, hired a person, and because they sounded so good in the interview, I did not do my due diligence in terms of training, in terms of preparing them for the job, and making sure I took the time to get them up to speed on the job. And the reason why I did that was not because I didn't know how to do it, because I had had an. Had an executive assistant working for me a few years ago. And she started off as someone who had never been an executive assistant. She had been a marketing assistant. I taught her.

I made her into an executive assistant. I made her really good. I made her so good, in fact, Rob, that she got hired away from me for three times when I was paying her. And when she left, I had a hole. I needed. I needed a new ea and I wanted to get one quickly. But we all know the saying hire slow fire fest.

That's right.

I hired fast. Then I had to fire fest because the person I hired, I wanted to fast track her to be what I needed to replace. She wasn't there yet. I needed to take the time and train her the same way I trained the previous one. I was too lazy to do that because I wanted to get back to where I was and recreate the past. And she ended up fumbling the job and I probably shouldn't even have hired her. Had I been doing my due diligence and following the process the right way, she wouldn't have made it through the vetting. But because I was so in need of a new person and because personality wise, she kind of.

I got her. I hired her on personality, not on skill and nobody. And then I ended up having to fire her. And it wasn't really her fault. She wasn't good at the job. But again, she should never got hired. So it's my fault for hiring her, not her fault for being who she was. So that was the lack of due diligence on my part and actually following my own process.

Yeah, I appreciate you sharing that. But it happens so often though. It really does. It's a common theme that. That happens to many, many of us. Hiring. Right. Not spending the time.

Right.

To do it. Right. Right. And doing your due diligence. So, I mean, my first hour is my first fire 25 years ago.

Yeah.

Screwed it up right out of the gate. So let me ask you this. So I mean, you obviously work with a lot of organizations and. And what would you say is a. Is a common theme you see across managers, across, you know, all your clients and companies.

You work with managers in terms of what they need or what they want for their teams now in terms of.

Well, maybe even both. But let's just say even some common, you know, common mistakes that you see across the board.

A common thing I see with managers. And most of the managers I work with, I'll give context. They're usually men in some sort of leadership position, but they have a good amount of autonomy. Is that they want everyone on the team to get up to their speed and up to their level. And when those people are not, they get very frustrated. So they come venting to me, hey, the people on my team are doing this, this and this, and the people above me are asking me to do all these things that I don't even have the time to get done. And they're just like, might be time for me to quit my job. Right.

That's where they get to that point. How do I deal with all these different people who are just not on the same page that I'm on. And I basically spend a good amount of time trying to talk them off the ledge, so to speak, rob from where they are and help them understand. Okay, let's make sense of where you're at because no, you're not going to quit your job. No, you're not going to divorce your wife. No, let's figure out, all right. What's actually going on here. And let's break this down into manageable bite sized pieces.

So sometimes it's just calming people down from the situation that they're in. The good thing is they have someone like myself to kind of hold space and be a place where they can say what they want to say, get it out, and then we can figure out what to do with it. That's with them individually. Now, as far as people in leadership positions with their teams, the biggest challenge, and again, this is the challenge that they bring to me. So it could be different with different people. Challenge that gets brought to me is that our people are just not following through. There are certain things we want them to do. We have a process for them to follow.

The process is all set up for them to be successful. If they follow the process but only know 30% of the team is following the process consistently, how do we get that other 70% to follow the team or how do we get that 30% who is performing to influence the other 70% to perform. And again, they bring me in because they know my specialty is around this mindset and discipline and I guess motivation, if you want to call it. So again, if they were talking to someone else, they may offer a different problem because they feel like that person has a different solution to that problem. But those are the two common things that I come across.

All right, fair enough. So you talk about, you know, the mindset. Right. And, and I know we talked about this earlier, but I just want to go back to it for a second in terms of trying to like impart this on employees. The reality is though, one can only really motivate themselves. You can only provide so much, I guess, guidance. And so.

Right.

What do you do with individuals that you know that it's difficult to even try to impart this type of mindset into them?

Ideally, you fire them and get rid of them and never had them on the team in the first place and you just work with the motivated. That's the ideal way to do it. But let's just say you're stuck with this person.

Yeah.

And they have to be there. And contractually you can't get rid of them. If you have a person like that, then the first thing you want to do is try to get on the same side of the table as them. And I've worked with leaders who had people like this on their teams. And based on the way things were set up, business wise, they couldn't actually fire this person. Person had to quit if they were going to leave. So I helped them understand, okay, let's. You need to get on the same page as this person.

You're their superior. They know that you're the boss, you know that you're the boss. But if you go breathing fire at them, all they're going to do is go even further into their shell and they're going to be even less of what you want. They're already giving you less than what you want. They're going to give you less than less if you do that. So don't do that. Get on the same side of the table as them. Let them understand that you're on the same team as they are.

And when someone feels that you care and that you give a damn and you're on the same side of the table as them, they will come around, usually relatively quickly to giving you what you want. And what you want is usually for them to either step their game up or just leave. And that's usually what ends up happening. The person will start coming around and saying, hey, what do you need from me? What else can I do? Or they just start performing the way they're supposed to perform, or they just say, you know what, I don't really want to be working here. So you know what, I'm going to leave now. They leave now. You can replace them with a person that you want. But the, the default that I see response by most, especially men, is that men go on the offensive and you want to just beat them into submission.

But that usually doesn't work. They will submit, but their performance is going to be just like that. It's going to be beat down into submission. Their performance still going to be bad, even worse. So you have to do the opposite of sometimes our instinct, which is to go on the attack, get on the same side as them, and then get them to see things. You show them that you see things, how they see things, and then they'll start trying to see things the way you see things. So it goes back to the old no zig zig, or give people what they want, they give you what you want.

Okay, fair enough. I mean, it is amazing how, how long in some organizations, how long it takes to get rid of people.

Yeah, it is, right?

I mean it's, it's my mind. I mean I have several clients that they walk me through it. I'm like, wow. I'm like this individuals could have been gone months ago.

Right, right. And you can't really do anything. It depends on the way it's set up.

Some curious. You work with a lot of men. Do you see a big difference between, you know, leaders who, who are men and those who are women and how they approach their employees?

Yes, absolutely. There's a big difference because, well, if a woman is a leader in an organization, unless she's working in an all female organization, you have the dynamic of a woman sometimes leading men. And there are some men who've never been in that situation where they had a woman leading them other than maybe their mom at home or a teacher at school. So it's a different type of dynamic in how do you communicate in a certain way. You have just this different sexual dynamic. Not in an intimate way, but just a sexual dynamic. You have a man and a woman talking to each other. They're both the heterosexual.

That's a different, it's a different thing that has to be dealt with that you don't have to deal with when you have all men in the room.

Yeah.

When a man is in a leadership position, it's the women and the men in the organization who are subordinate are usually used to there being a man in a leadership position. But when there's a woman in a leadership position, even the women in the organization, it can be a little bit of a different thing. And a woman is navigating in an area that who knows, depending on her background, maybe she hasn't been in that position before and she has to deal with these different people and talk to people in different ways and she has to turn on her. Depending on her normal baseline behavior, she may have to turn on her masculine when she walks into the office. And that might not even be her normal way of behaving, but I haven't seen any leaders do it. Not with men around by standing their feminine. Not what I've seen.

You know, it is interesting how I think women unfairly get, get described as a certain way when they're, they're very direct and. But yet you would never, you know, think twice about that as from a male coming from a male.

That's right.

Think. Right. It's, it's, it's kind of like a double standard at Times unfairly. Right.

Well, it is a double standard. Woman's a woman.

Yeah, yeah. But you know, I mean, I would probably say most of my career, I think I probably had more female leaders than male leaders.

Interesting.

Yeah, three quarters were mostly, you know, were all women. Quarter maybe were males in what industry? Healthcare Industry.

Okay, okay, well that would make sense. I know healthcare, but it makes sense in healthcare. Yes.

Yeah. Right. And, and I've seen like the progression over time and actually the last team I ever managed before I launched my company, all the managers were all women on the team.

Healthcare.

Healthcare. Yeah, yeah, yeah.

Okay.

For a biotech company. And, and you know, it was interesting how I would have to defend sometimes, like, you know, I would have managers come to me and say, oh, well, you know, your, your manager's just way too, too strong. Right. They need to kind of dial it back. And I would sit back and I would tell that the, the person who was coming to me complaining, I would say, well, if, if this individual is a male, would you and I even be having this discussion?

Right, right.

So just interesting just to see some of that dynamic. But it's interesting to hear your side of it where you're, you know, you've worked with a lot more of male leaders too.

Right. And it depends on industry as well.

Yeah.

Antidote that you just gave the person coming to you complaining, is it usually a male or a female?

Believe it or not, in that case, the last case it was a female.

Oh, I wouldn't think that.

Me neither. But in most cases. Right. It's usually a male coming complaint.

Right, that's what I would think it would.

Yeah. Yeah. That was the one unique scenario, I gotta be honest, that did surprise me.

Right.

But 99% of times it's a male complaint. Of course.

Interesting. A lot of the industries, most of the people that I work with are in these industries that are kind of aligned with the way that I talk and think, with objectivity, rationality, logic. So yeah, finance, accounting, these things are everything black and white because that's kind of how I communicate. So those seems to be the type of people I attract.

Which makes sense. Yeah, totally makes sense. So I do think we take that for granted sometimes that we think, you know, leadership, I mean, leadership is leadership. Right. When you're managing people, there are fundamental. Right, same fundamentals, but there are nuances. And haven't thought of it as, as much as, as now until you said it. Different industries are going to have some, some of those nuances.

Right?

Yeah. And you see, you see Certain types of. You see certain archetypes of people in different industries, in different positions.

Absolutely.

Yeah.

Very interesting. All right, so finally, so last question for you. So if you could embed just one practice for, for our audience that they should incorporate into the organization or their culture, what would it be and why.

They got to step up their people skills, the communication skills. Communication people. Slash communication skills. So let me explain what I mean by that, Rob. That communication is not just how you talk. A lot of people want to hear the word communication. They think about what you say, what you can write down, what you send in an email.

Yeah.

50% of communication is what you receive, what the other person is saying, what they wrote, how they're feeling, what they're not saying and how they're saying it. All the context around what they're actually saying, which is the non verbal communication, which we all know is the bulk of communication. At least 51%, depending on who you ask, is 99%. But most of communication is not what somebody says, it's everything else around it. And a lot of human beings are really bad at reading the signals coming from other people.

So.

True. And one reason that people just generally don't listen, another reason is that we are consistently distracted and that distraction is only getting worse as we go along because the technology is getting better and the options to distract ourselves are growing every day. So people are getting worse and worse at communication. At least the receiving of communication, which means, I tell audiences all the time, Rob, that the opportunity is always in the opposites. So the biggest opportunity for a leader these days is to become a much better communicator, a much better listener and receiver of communication because there are fewer and fewer and fewer people with who have the skill. So the better you are at it, the more valuable you'll be because nobody else has it. And that ability to connect with other people and get them to voluntarily want to follow you makes you a leader rather than just a manager. Because you don't want to be a manager or a boss because that's when people have to listen to you because of the.

The org chart leader. Right. The leader is the person that people want to follow you because of who you are as a person. Doesn't matter what position you occupy in the hierarchy. So that's the number one skill moving forward again, especially as we get more and more technology that can replace human communication, the people who keep it become more valuable because everybody else is losing it.

You know, I, I really appreciate you said that because. And how you define the Communication piece. Because it is really, you know, from. From a manager's perspective, it is. So, I mean, we talk about the. The importance of listening, but I think you described it very well because it is important to tune everything else out and focus on what the employee is telling you in front of you.

That's right.

Really hard to do. Right. Especially in a virtual world nowadays where, you know, you're going from one meeting to the next, your email's up on the screen, things are dinging in the background.

Right. It. It is hard depending on who the person is. I mean, some people, it's a. Some people like doing it. I can tell that someone like yourself, I mean, just by the fact that you have this show, you like communicating with people. Right. Because you don't have to do this.

Right. And there are other people who. They like to have conversations with people. I like talking to people and finding out where they're at. And I'm naturally inquisitive. I ask questions about just random things that I pick up. But not everybody's like that. Some managers are, I gotta hit these numbers.

Okay. So just. Just get these things done. All right. So they don't have that. They don't have it innately. They have to learn it.

So true. Yeah. And what they don't realize is, you know. Yeah. If you're managing people, you're not going to hit your numbers unless you're in tune to what they're doing and their needs.

Right. Unless if you're lucky, because I've had managers who weren't that good, and I was a good performer, so they were still able to hit their numbers because they happen to have some stars, but you don't have stars, then. Yeah. You won't be lucky.

Yeah. That's where the real work comes in. Right, Right. Getting those who, you know. And let's be honest, a lot of times managers, when you first become a manager, in most cases you're inheriting a team, you really get.

Right.

To, you know, hire your whole team. So. Yeah.

Right. So it's just getting that. That fingertip feel, so to speak.

Yeah.

For who people are. And again, the faster you can get a read on who somebody really is, the better you can operate with them or get rid of them if you need to.

Yeah. It goes back to what we were saying before. Right. You really got to invest that time up front. Right, people?

Exactly.

Yeah. I love the discussion, and I appreciate you coming on and kind of sharing your insights with my audience.

Thank you for having me on the show. I appreciate you sharing your platform? Rob?

Absolutely. Thanks so much for listening today. If you enjoyed this episode, be sure to share it with a friend or colleague who you think might also get some value from it. I'm Rob Fonte, and I'll see you on the next episode of the Leadership Jam Session PO Podcast.