How I Stopped Being the Escape Hatch for My Team | Ep. 354
20m 5s
This transcript discusses the core principles of effective leadership, using the contrast between Phil Jackson and Michael Jordan as a central example. Jackson, who won 11 NBA championships by refusing to call timeouts and letting players figure out problems, demonstrates that true leadership involves letting go of direct control. In contrast, Jordan's demanding, star-player mentality made him an unstoppable athlete but a poor coach. The speaker shares a personal story of hitting $50 million in revenue but feeling exhausted and resentful, realizing they had been acting as the star player rather than a coach. A mentor's blunt feedback—"If it's your business, it's your fault"—forced them to take accountability and restructure leadership. Key lessons include: track your time to ensure you're building your team's problem-solving ability, not just solving problems yourself; measure success by your team's KPIs, not your own; and identify tasks only you can do. The "iceberg illusion" of leadership reveals that bosses handle 90% of unseen work, so followers should shift from resentment to curiosity and ask how to help. Finally, leaders must create systems (like Jackson's triangle offense) that force collaboration and psychological safety, where team members feel safe to take risks and make mistakes. This approach multiplies team efforts, leading to greater success and growth.
If people don't listen to you, don't respect you, don't see you as leader. You are probably making the same mistake that I make for yours. This is what everybody gets wrong about leadership and it has nothing to do with what you do and everything to do with how you think. Become a great leader comes down to really three steps. It's changing how you think about yourself, how you think about the person leading you, and how you think about the people that you lead. I only understood this when I studied the strategy behind one of the greatest leaders in history. I'm talking about the Phil Jackson paradox. The reason that Phil Jackson won 11 NBA championships more than any coach in history is because he knew something about leadership that most people don't actually know. Phil Jackson coached Michael Jordan and Kobe Bryant. He was also famous for something that drove people insane, which is he refused to call timeouts when his team was struggling on the court. So he would literally sit there on the bench and watch his players fight it out, figure it out, whatever, and he would not jump in. And so he said one time at interview, he said, the more that I tried to exert power directly, the less powerful I became. So instead, what did he do? He used indirect actions to lead his team, which we will talk about more later. The results though were what is insane. He had 11 championships and players who could perform with the highest level, even when he was not there directing every play. He has gone down the hall of fame. People know who Phil Jackson is anywhere you go. Compare that to Michael Jordan, who is also the greatest player of all time. But he has openly said he could never be a coach. And he has admitted that he has no patience for it. He has said that in multiple interviews. And it shows because his leadership style as a player was to demand that every single person match his intensity and work ethic. There's even a time where he punched him, Steve Kerr in the face during practice for not defending hard enough. So that temperament that made him an absolutely unstoppable player. It's also why coaching was never in the cars. Because coaching requires patience, delegation, letting other people make mistakes, understand that they are their own people. So the same drive that made him the greatest player also made him incapable of being the greatest coach. That's why the best leaders learn to let go of control. While the ineffective ones, ones who never actually make it to the top, they try to hold onto the power at all costs. And that is the paradox. They believe stuff like nobody cares as much as I do. It's probably one of the most common self-delusion of ineffective leaders. Because the truth is that you haven't created the conditions for anyone else to care as much as you. You've set it up so that only your effort matters. And then you're really surprised when nobody else steps up to the plate. What I want you to get from this is that when you're a leader, not the star player, but a leader, your job is not to be the star player. It is to be the coach. Nobody ever won a championship because the coach could dribble faster than the point guard. Number two, how do you think about yourself? Now here's what nobody tells you. The hardest part of letting go of control is not the part where you step back. It's the part where you have to take accountability for things that you didn't realize were under your control. So the day that I hit 50 million revenue was actually one of the worst days of my life. That afternoon when we realized it was like, wow, we hit 50 million. It was like our highest one ever. I went on a walk that afternoon with Alex. We're talking about, oh my gosh, we've hit 50 million revenue. This is crazy. And I remember as we're talking about it, he was all excited talking about like how crazy that is and how it's amazing. I remember feeling this hero excitement. I actually felt depressed because I was like, wow, I'm so tired. I'm so resentful. I feel like I've literally like carried 120 people on my back across the finish line. And it felt like none of them were at my level. I felt like I had done it all by myself. And he was like, that's not good. You should talk to someone who got that. So I went to one of my mentors and I told her what was going on. And I was like, I need help or something. And it feels like everybody's wrong, but like this company's so big. And like it feels like it's just getting away from me. And I don't have control over it anymore. And I just kept complaining to be honest. And I remember she looked at me and she said, if it's your business sense, your fault. And I was like, and then she said, so what are you going to do? Let it burn down or fix it. And I was like, I'm not going to let it burn down. I remember thinking like in that moment, I was like, I kind of want to. I kind of wish I was the person who could sometimes, but I can't. I can't do it. And I remember in that moment, just feeling this immense feeling of clarity because I understood like, no, I'm not going to let it burn down. So like, I have to fix it. And also anxiety because I realized that I and nobody else was going to undo what was done. I agree to say she said, I was like, this is my fault. And it's not like I did it intentionally. It's like, I didn't know what I was doing when I was building my business. Like I was new. I was inexperienced. Like I had hired people who were probably like got in above their bridges. And now I have to be the one to either demo them, move them, put in people above them. And that's me who has to do it. Like there's nobody else. And then I remember thinking to myself, like, what's the alternative? I'm like, I can't. Like I just, I don't have it. I'm not going to shut it down. I'm not going to be done with the business. Like the thought of the humiliation was enough to keep me going. Like, I'm not going to do that to my team. I'm not going to do that to the people that rely on us. Like I'm just not going to do that. So I asked myself, like, how did I get here? Because I felt like I had tried to do everything right. And when I went home that night and I was just kind of reflecting on right and end of day to day for like the first few years of my business, I realized that I had been playing the game as Michael Jordan when I need to be playing it as Phil Dexon. I had been trying to be the star player. Not because I wanted the credit, but I was always saving the day. I was always being the rescuer. Me, me, me, me. I was the one that was imperative to the business running. And so I remember committing to. I said, I'm going to commit to fixing this, making sure that there's no freaking way in hell that a year from now, this is the case in my business. I did that and it was terrible because basically what I had to do was like turn over an entire level of leadership, which a year before I had hired and I felt like about it and I still feel like about it. Because it sucks. Like nobody likes to fire people, especially somebody who claims themselves to want to be a great leader. It really got tested because about a year into this and I'd finally brought in new leaders I had other ones out, but the team still didn't feel great. Like they were like, man, there's a lot of change with a lot of stuff going on. We saw that somebody from our team, this person, left and they created a business that was essentially the exact same business hours. They were trying to steal all our clients and they had relationships with a lot of clients. And so thinking we really need to innovate the product, we need to redo our packaging and pricing because they essentially copied all our stuff. And I said, this looks gross. I don't want to, when you're number one, you don't want to look like number two in the marketplace. And so I started thinking like, how do we revamp everything? So it doesn't look this way. It was the first time that I recognized, I could not be the one to come with the idea to fix this. And so I remember I went to my leadership team and I said, guys, this one's for you. I know how to fix this. I know what I would do, but I want you guys to tell me what you should do in this situation. I want you to give me the plan and you have until Monday. And I was so terrified because there's like everything in my body was like so uncomfortable. I just like wanted to jump in and do it. And instead, I waited and then on Monday, I was actually really impressed. Like they came to me. They had a really good plan. And it actually ended up turning everything around. Like we put together a brand new marketing campaign and they were able to execute it with me meeting with them once a week. That really taught me so much of the time until we allow other people to do something on behalf. We just don't believe it's going to happen. You kind of have to just let yourself be proven wrong by the universe, by just letting go and just saying like, if it doesn't work, it doesn't work. But I can't keep doing this. And that's kind of where I got to. There's a research study on high performing teams and it talks about how one of the number one factor for high performing teams, it is not talent, it's not intelligence, it's not experience, it's literally just psychological safety, which is the belief that you can make mistakes and take risks without being punished. Now what did I do in that moment? I showed them that they could take a risk and I wasn't going to punish them. The thing is is that when the leader is the star player who always says the answer, they without meaning to it, without knowing, destroy that psychological safety because the team thinks I should depend on them. They are smarter than me. They should do this. By you stepping in constantly, you're showing them with your actions that you don't trust them. But when you give them space and you coach them and you say, you do it, that signals confidence. It says, oh, they think, if my boss gave that to me, then they believe I can do it. Maybe you don't believe they can do it. But you're willing to give them a shot. And they're going to feel a lot better and they're going to perform better when they think that's the case. To be clear, that doesn't mean that you're not going to hold them to a high standard or push them to their max capability. I think psychological safety and high standards are not two opposite things. You need both of them to have a great organization because without safety, teams are going to essentially go quiet and they're not going to bring things up to you and they're probably not going to try and push themselves. Without standards, teams are going to be really comfortable. And so you need both of these things. If you want to avoid that, I recommend that you follow a few steps. One, track your time for two weeks. And this is all I want you to think about. Categorize all the chunks of time and then beings you're in and things you work on as either solving today's problems or building the team's ability to solve problems. If more than 50% of your time goes to you solving it directly, you're still the star player. And listen, it's hard to make this change over time. Like, I get it. It's much more satisfying to solve problems on your own. But I also, if you watch my channel, maybe you want to build something that goes far beyond you, that's what I would like to do. And you have to learn these lessons early on. The second thing you want to do is you want to redefine your KPIs. One of the worst things you can do is business is only measuring individual KPIs. Your measurement of your success is your team's performance. If your team hits their KPIs, then you did your job. If they don't, then you didn't do your job. So stop focusing on your KPIs and start looking at who reports to you. Their KPIs are measurements of your success because what a leader does is a great leader multiplies the efforts of their team. They are there to remove friction and increase leverage for their team. That's it, which makes success easier, faster, and more fun. Now, the third thing I want you to do after you've done these two things is just identify and write down three things in your company or on your team that only you can do in nobody else. And ask yourself why. And now you could say, well, anybody could typically technically do anything. Well, what are three things that if you do, they get a four or five times greater return for your company than if somebody else does them? And then you look at everything else on your calendar. You're like, why am I still doing it? If you have capital and you've got capacity, why do you hold on to it? Maybe it's an identity. Maybe it's because you don't trust people.
Either way, it's your problem to solve. The next step is to change the way that you think about the person's leading you, your boss. So this is for you, those of you who work in a company and you have a leader. Now, in order to do this, you need to understand what I call the iceberg illusion of leadership. The best way to become a great leader is to become a great follower. When I worked my first couple of jobs in gyms, I remember that I had a boss that would leave earlier than me and come in later than me. I felt resentful. When my boss came in, they were in a great mood all the time and they were always well-rested and had a good frame of mind. My thought was, "Well, a good boss should be there all the time. They should be able to do my job better than me." If they can't, then they're fucking bad boss. If they don't know how to make the sale better than me, if they don't know how to train better than me, if they don't have the same skills and clients that I have, then that means that they're not going to their job. How can somebody who's worse at my job be my boss? I did not understand the point. What clicked for me was when my boss, I remember I walked into their office and I saw that they had tears in their eyes and I said, "Is everything okay?" And they said, "I'm just dealing with a lot right now." And I said, "Well, what are you dealing with?" Suddenly, I hear everything. It's like there's a huge staffing issue. There's a huge budget issue where they can't bring enough resources. Their boss is asking to do something that they don't have the resources to do and there's a bunch of construction issues with one of the new locations. I remember in that moment that was when the paradigm broke for me. I realized, holy shit, I did not realize how much this person was holding. And it was the first time I had empathy for my boss. From that moment, I was like, "How can I take things off their plate?" Instead of resenting them for not being able to do my job, I started saying, "How could I help them do their job better?" It's interesting because that one little shift in seeing that moment, like that glimpse of, I'd say, like vulnerability, it changed how I was treated, how they developed me, and ultimately my entire career trajectory. Because they offered me a management position not even 10 months into the job. Now why was that? This is what a lot of people don't get. There's this iceberg illusion of leadership. You think about any organization like an iceberg. There's the work you see, the tasks, the meetings, the client-facing or team-facing stuff. It's like above the water line. Just assume that what you see is 10%, the other 90%, is strategy, politics, financial decisions, preventing crises, managing up, managing sideways, negotiating hiring, creating culture, firing, protecting the team from, they'll never know about. And so when you judge your boss by the 10%, you see, you will always be underwhelmed by their ability. The whole point of them being above you is to shield you from all the things that they deal with because you're supposed to focus on your job and they are supposed to protect you from everything else. So when you understand your boss's job is not to do your job better than you. It's to do a different job. Their job is not to do your job better than you can. It's to make decisions and operate and do a completely different job than you do. And to see ahead and deal with problems and open up opportunities for you that you didn't even know that they will do and that they will never get credit for. What I've learned from that experience is how you think about the person leading you, will determine how readable you are and how readable you are determines how fast you grow and the people who rise in the organizations, they are not the ones who think they're smarter than the boss. They're the ones who figure out how to make their bosses job easier and how to be a great direct report. So when you shift from my boss should serve me, my boss should be better than me at these things too. How can I take things off my boss's plate? My boss should be better than me at their job, not mine. Two things will happen. One, you're bossing a trust you more and then you give you more stuff. And then two, you're going to develop more skills because they give you that stuff. Your son leads to three, you're going to grow way faster and you're going to get more skills than everybody else around you. So one thing you could do this week is you could literally ask your boss one question, what's on your plate right now that I could take off? A lot of people think to themselves, they're like, well, why would I help them do their job? So you can learn, motherfucker, what are you talking about? If I could take something off of Elon Musk or Jeff Bezos, play a f*** and do it. If they were like, hey, you can be my janitor for a week. I would do it because I want to learn. Most people never ask these questions and they never do it because they let their ego get in the way and they believe all the s*** they see on social media about how bad boss is on, how bad it is to work and come these blah, blah, blah. Those people don't get noticed, they don't grow and they certainly don't have lives they want. So replace resentment with curiosity instead of saying, must be nice that they leave early. Try thinking, I wonder what they're dealing with that I don't see that they have to get down with more time to recoup from work. That one reframe is the difference between an employee mindset and a leadership mindset. Number four is how you think about the people that you lead. Now you are ready for the higher level of leadership. This comes when you change how you think about the people that you lead. So if you want to become a top one percent leader, you need to understand another key aspect of what we call Phil Jackson's strategy, the triangle offense. So this is not just a basketball strategy. It's a very, very good leadership philosophy. In most offenses, there's a point guard who controls the ball and makes all the decisions. The triangle eliminated that. Every player had to read the defense and make their own decisions. So what that meant was there was no single decision maker. So Kobe Bryant couldn't just like ISO ball his way through the triangle and Shaq couldn't just demand the ball in the post. They actually had to trust their teammates. And more importantly, their teammates had to develop the basketball IQ to make real time decisions under pressure. Phil Jackson forced this not by giving speeches about teamwork, but by designing a system where individual talent, dominance, authority wouldn't work. He literally created the conditions where the collaboration was not optional. It was the only path to success. Now the result in the first few weeks was always panic because people were so used to being told what to do. I'm escalated to Phil Jackson and then what he would do is send them back. And the first month, I remember they talked about like how frustrated everyone was. Why won't you just tell us what to do? Why won't you tell us what the play is? But then by the second month, because you knew you have to wait, something shifted with everybody. The players started talking to each other. They started solving problems together essentially being their escape hatch. The real work in leadership is learning to delegate not just tasks, but decisions. If you delegate a task, it means go do this thing I've already figured out. That's the two degree I trust you. When you delegate decision, it means here's the outcome we need. I need you to figure out how to get there, which means I trust you. If you want to create doers, then give people tasks. If you want to create leaders, give people decisions. I had to let people make decisions that I disagreed with and I still do. There's so many things I don't fully agree with in my company. I have to watch them take approaches that I wouldn't always take and still won't. Sometimes they fail. I'm like, I thought that would fail. But sometimes they don't. I'm like, wow, I suck. I can't believe I was going to tell them not to do that. Sometimes their approach actually works better than what mine would have. I'm like, I'm getting old. But here's the thing. Both outcomes were very valuable because in both cases, they are building the muscle to think and lead independently. I have stopped asking the question, did they do it the way that I would have done it? I start asking the question, did they achieve the outcome we wanted? That has changed everything about how I lead because it just, it completely removes me as a person from it. And it makes it all about what we do for the company because we are all stewards of the company. And remember this, companies plateau at the competence of the founder. If you are the genius with a thousand hands, then your ceiling is always the company's ceiling. So if you want to avoid that, take these few steps, audit your delegation. Look at everything you've delegated this month for each item ask yourself. Do they delegate a task or did I delegate a decision? And I'm going to go ahead and tell you it's probably mostly tasks. It's probably building people who come to you from every decision point. They can do the task really well, but they don't think. So you have to ask yourself, how do I switch that? How do I create decision makers? The second one, going with that, is create a decisions I no longer make list. Okay, look back at the last week, two weeks of your life. What are all the decisions that you make? Walk through your day, go through your calendar. Remember the meetings you're in, what you were talking to the conversations you had. What decisions did you make that you don't need to make? Somebody else can make them. And then hand them off. You don't need to approve them, just let your team own them and end and resist that very compulsive urge to overrule everything, unless the building is actually one five. And then the third thing is replace, how would I do this with did they achieve the outcome? You need to stop measuring your team's success by whether they did it your way, measure them by if they got the result. Now I'm not saying disregard all values. I always tell people, listen, our values are there because we abide by the values to get the results. But your way in my way, you're going to look different. And there are usually multiple paths to the right outcome. And sometimes their path is actually going to be better than yours. But you're never going to find out if you don't give them the shot. And the last thing I would say is schedule your own absence. Okay. So for every role that you play in the business, identify who could do this next. I'm doing this right now. Who could do this next? If the answer is nobody, that's probably like your most urgent priority is to find somebody who can or bring somebody on who can. Because the goal is to always be training your replacement, not because you're leaving, but because that is what's going to free you up when the next opportunity comes. And if you're not growing your business, your department, your team, who is? And so next time there's a crisis, don't just jump in and rescue the team and rescue the thing. Go to your team and say, I trust you guys. You guys are fucking smart. Come to me on Monday with your plan to solve this and then sit on your fucking hands. I don't know. Go on a hike, lose reception, go camping, distract yourself. I know it's getting hard. I get it. By the second time you do this and the third time you do it and the fourth time you do it, you're going to see that people really rise to the occasion. Because you stop being the escape patch. If you are serious and actually interested in becoming the kind of leader that your team wants to follow, you can go ahead and check out Latest Letters. I know it's cheesy. This is a weekly memo that I sent to my leadership team. So I sent it in our Slack channel. I just send like once, maybe twice a week sometimes, when I'm feeling inspired. It's not filtered. We don't write it for this. I've been doing it for years and I decided to repackage it for my newsletter. Has the frameworks, how I'm thinking to build people and build businesses. So if you're interested in that, you can go ahead and grab the link in the description. You can sign up for it. So you just learned how to think like a leader. But if you can't speak like one, none of it's going to stick. So go ahead, watch this next video. Learn the top five skills and make you sound like a top 1% CEO.
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Podcast Summary
Key Points:
Leadership is about how you think, not what you do; it requires shifting your mindset about yourself, your boss, and your team.
The Phil Jackson paradox shows that trying to exert direct power reduces effectiveness; letting go of control and using indirect actions builds a stronger team.
Ineffective leaders try to be the star player (like Michael Jordan), but great leaders act as coaches who delegate, accept mistakes, and create psychological safety.
Taking accountability for team failures is crucial; the hardest part is realizing that problems are your fault to fix, not your team's.
Measuring success by your team's KPIs, not your own, and tracking time to ensure you're building the team's ability to solve problems are key steps.
The iceberg illusion of leadership
To grow, shift from resentment to curiosity about your boss's unseen burdens, and ask how you can take things off their plate.
Phil Jackson's triangle offense forced collaboration by designing a system where individual dominance wouldn't work; leaders must create conditions where teamwork is the only path to success.
Summary:
This transcript discusses the core principles of effective leadership, using the contrast between Phil Jackson and Michael Jordan as a central example. Jackson, who won 11 NBA championships by refusing to call timeouts and letting players figure out problems, demonstrates that true leadership involves letting go of direct control. In contrast, Jordan's demanding, star-player mentality made him an unstoppable athlete but a poor coach.
The speaker shares a personal story of hitting $50 million in revenue but feeling exhausted and resentful, realizing they had been acting as the star player rather than a coach. A mentor's blunt feedback—"If it's your business, it's your fault"—forced them to take accountability and restructure leadership. Key lessons include: track your time to ensure you're building your team's problem-solving ability, not just solving problems yourself; measure success by your team's KPIs, not your own; and identify tasks only you can do.
The "iceberg illusion" of leadership reveals that bosses handle 90% of unseen work, so followers should shift from resentment to curiosity and ask how to help. Finally, leaders must create systems (like Jackson's triangle offense) that force collaboration and psychological safety, where team members feel safe to take risks and make mistakes. This approach multiplies team efforts, leading to greater success and growth.
FAQs
The Phil Jackson paradox is that trying to exert power directly makes you less powerful. Phil Jackson won 11 NBA championships by using indirect actions, like refusing to call timeouts, to let his team figure things out themselves.
The speaker felt depressed because they realized they had been carrying their team like a star player, feeling resentful and exhausted, instead of acting as a coach who empowers others.
Psychological safety is the belief that you can make mistakes and take risks without punishment. It's a key factor for high-performing teams, as it encourages open communication and risk-taking.
A leader can shift by tracking their time to ensure less than 50% is spent solving problems directly, redefining KPIs to measure team performance, and identifying tasks only they can do with high return, delegating the rest.
The iceberg illusion is that visible work (like tasks and meetings) is only 10% of a leader's job; the other 90% involves strategy, politics, and crisis management. Understanding this helps employees appreciate their boss's role.
An employee can grow faster by shifting from resentment to curiosity about their boss's challenges, asking how they can take things off their plate, which builds trust and develops skills.
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