
The Winning Paradox
14 minProven Principles and Practices That Make Great Teams Great
Golden Hook & Introduction
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Olivia: Most teams believe that focusing on winning is the key to success. But what if the single-minded pursuit of victory is the very thing that guarantees you’ll lose? That’s the paradox we’re exploring today. Jackson: That is a bold start. It sounds like something designed to make every competitive person in the audience immediately uncomfortable. I love it. Are we about to dismantle the entire concept of ambition? Olivia: Not dismantle, but rebuild it on a stronger foundation. That paradox is at the heart of The Power of a Positive Team by Jon Gordon. Jackson: Jon Gordon, right. He's the guy who works with all those elite sports teams and corporations—the Los Angeles Dodgers, Clemson Football, Southwest Airlines. What's interesting is that his focus on positivity isn't just a business strategy; it comes from a really personal place. I read that he had this period in his early 30s where his life was falling apart, and he credits turning it around to these very principles. Olivia: Exactly. It’s born from experience, not just theory. And his first big principle is that you can't build a winning team by focusing on the win. You have to focus on the culture. As the saying goes, culture eats strategy for breakfast. Jackson: Okay, "culture." That’s one of those words that gets thrown around in every corporate meeting until it loses all meaning. It feels a bit like a cloud—everyone sees it, but nobody can really grab it. What does it actually mean in this context? Olivia: That’s the perfect question. Gordon makes it tangible. For him, culture isn't a poster on the wall; it’s the collection of shared beliefs and actions. It's the root system of the team. If you only focus on the fruit—the wins, the profits—without tending to the roots, the whole tree will eventually die.
The Unseen Architecture: Why Culture and Vision Come First
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Olivia: And he has this incredible story that makes it crystal clear. It’s about two elite college tennis programs: The University of Southern California (USC) and the University of Virginia (UVA). For years, USC, under coach Peter Smith, was a dynasty. They won four national championships in a row between 2009 and 2012. Their culture was legendary—built on love, accountability, and a true family feel. Jackson: So they were the team to beat. Olivia: Exactly. Meanwhile, you have the University of Virginia, coached by Brian Boland. Year after year, he had incredibly talented teams. Top recruits, future pros. But they could never win the big one. They’d get close and then fall apart. They had the talent, the strategy, but something was missing. Jackson: The culture. The roots. Olivia: Precisely. The turning point came in 2013. UVA had just lost early in a major tournament. They were stuck in a hotel during a blizzard, flights canceled, feeling miserable. Instead of just letting them stew, Coach Boland gathered them in his room. He asked them, "Do you guys think we're a connected team?" And they all said, "Yeah, of course." Jackson: Which was clearly the wrong answer. Olivia: Well, he pushed them. He asked, "Who are the most important people in your lives?" They all said their families. Then came the killer question: "Okay, tell me about your teammates' families." And there was just... silence. They were a team of individuals who played together, but they weren't truly connected. Jackson: Wow. That’s a tough realization. So what did he do? A trust fall? Olivia: Something much more profound. He put all their names in a hat. Each player had to draw a name, and their assignment was to learn everything they could about that teammate's family. They had to call their parents, their siblings, interview them, and then present what they learned to the entire team. Jackson: Hold on. So they just... talked about their families and suddenly became champions? That sounds a little too simple, a bit too much like a feel-good movie. Olivia: It does, but you're right to be skeptical. It wasn't the talking that was the magic bullet. It was the outcome of that exercise. It forced vulnerability. It created genuine empathy. They learned about their teammates' struggles, their parents' sacrifices, the 'why' behind the person standing next to them. They stopped being a collection of talented tennis players and became a group of humans who cared deeply for one another. Jackson: It shifted their culture from professional to personal. Olivia: It completely rewired it. And the results were staggering. That same year, after that snowstorm meeting, UVA won its first-ever national championship. And then they won three more in the next four years. For over a decade, Boland couldn't win one. After he shifted his focus from outcomes to culture, he built a dynasty. Jackson: That’s incredible. It really proves the point that talent isn't enough. You can have all the five-star recruits in the world, but if they aren't playing for each other, it's just a bunch of individuals wearing the same shirt. Olivia: And it’s not just sports. Think about a company like Southwest Airlines. They were advised to start charging for checked bags, like every other airline. It would have meant millions in instant revenue. Jackson: A no-brainer for any CFO. Olivia: But they looked at their purpose statement, which is about connecting people through friendly, reliable, and low-cost travel. They realized charging for bags violated their core culture. So they didn't. Instead, they launched the "Bags Fly Free" campaign. They gained market share, their revenue went up anyway, and they strengthened their culture. They chose the root over the fruit. Jackson: Okay, I get the culture part. It's the soil everything grows in. But a positive culture can get crushed by reality. How do you maintain that, how do you fuel it day-to-day, especially when you’re genuinely failing? Isn't that where you risk tipping into 'toxic positivity'?
The Engine of Belief: Fueling the Team with Optimism and Positivity
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Olivia: That is the perfect question, and it's where many people get stuck on Gordon's work. This is where some of the more critical reader reviews pop up, arguing the book can feel a bit surface-level or over-simplistic about negativity. But Gordon makes a crucial distinction. He's not advocating for fake, blind positivity where you ignore problems. He's talking about cultivating genuine, gritty optimism and belief. Jackson: What’s the difference? "Gritty optimism" sounds like a great marketing term. Olivia: The difference is action and perspective. Blind positivity says, "Don't worry, everything's fine!" even when the ship is sinking. Gritty optimism says, "Yes, the ship is sinking, but I believe we have what it takes to patch the hole and bail the water out together. Let's get to work." It’s not about ignoring reality; it's about believing in your team's ability to overcome it. Jackson: It's a choice of focus. Olivia: Exactly. He tells this fantastic story about Dabo Swinney, the head coach of Clemson's football team. For years, there was a running joke in college football called "Clemsoning." It meant finding a way to lose a big game you were supposed to win. It was a label of failure, a cultural curse. Jackson: I remember that. It was a meme before memes were a thing. Olivia: Totally. When Swinney took over, he could have ignored it or just told his players not to think about it. Instead, he confronted it. He told his team, "We are going to change the definition of 'Clemsoning.' From now on, it's going to mean winning." He didn't ignore the negative narrative; he hijacked it. He and his team built such a powerful belief system that they started winning those big games. And eventually, they won two national championships. They created what some might call a 'reality distortion field' through sheer, collective belief. Jackson: So it’s about feeding the right mindset. Gordon has that analogy, right? The two dogs inside you, a positive one and a negative one. The one that wins is the one you feed. Olivia: That’s the one. And it’s an individual responsibility that becomes a collective strength. Each person has to choose to feed the positive dog, to talk to themselves instead of just listening to the negative voice in their head. He tells this amazing story about Dr. James Gills, who completed a double triathlon six times, the last at age 59. When asked how, he said, "I've learned to talk to myself instead of listen to myself." Jackson: That’s a powerful reframe. But again, how does this work in a business setting, when say, a recession hits and you lose half your business? You can't just 'believe' your way back to profitability. Olivia: You can't, but belief dictates your actions. Gordon highlights the story of PPR, a human capital company, during the Great Recession. They lost a huge chunk of their business. Instead of panicking and laying everyone off, the leadership team got together and reframed the problem. They asked, "What opportunity does this crisis create?" Jackson: A question most people are too scared to ask. Olivia: But they did. They realized that while their main business was shrinking, the chaos of the recession was creating new needs in the market. They identified an opportunity to expand into other human capital solutions. They founded three new divisions during the recession. They didn't just survive; they came out of it more profitable and diversified than before. They saw the obstacle as the way. Jackson: They chose to feed the positive dog. They believed they could find a solution, and that belief drove them to actually look for one. Olivia: And that's the perfect bridge to the final, and maybe hardest, part. Because maintaining that belief isn't about ignoring problems or just thinking happy thoughts. It’s about having the courage to confront what's broken. It's about tough love.
The Tough Love Toolkit: Connection, Commitment, and Courageous Conversations
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Jackson: This is where it gets real. Because a team can have a great culture and a positive attitude, but if there's one person who is constantly negative—an energy vampire, as Gordon calls them—they can poison the whole well. Olivia: They absolutely can. And Gordon is ruthless about this. He says you have three choices with negativity: confront it, transform it, or remove it. But you cannot ignore it. He tells a story about Mark Richt, then the coach at the University of Georgia. After a rough start to the season, he put a giant drawing of an energy vampire on the wall. Any player or coach who was being negative would have their picture put on the vampire. Jackson: That’s intense. Public shaming as a management tactic. Olivia: It sounds like it, but the team said it worked because it wasn't about shame. It was about accountability to the culture they had all agreed to build. It was a visual reminder: are you helping or are you hurting? They went on to win ten straight games. But the ultimate expression of this commitment comes from the military. Jackson: I have a feeling you're about to mention the Navy SEALs. Olivia: Of course. Gordon talks about Hell Week, the infamous five-and-a-half-day ordeal where trainees get only about four hours of sleep total. It's designed to break them. And what the instructors see, time and again, is that the guys who make it aren't the strongest or fastest individuals. They're the ones who, in their moment of absolute exhaustion, stop thinking about their own pain and start focusing on the guy next to them. Jackson: It's the ultimate "We before Me" test. Olivia: It is. They start singing songs to keep spirits up, they literally carry each other when someone falters. They learn that their survival depends entirely on the person to their left and their right. They forge a bond and a commitment that is unbreakable. They become a team in the truest sense of the word. Jackson: Wow. That's a powerful, almost primal example. But how does that translate to an office environment without, you know, carrying logs on a cold beach? Olivia: It translates through courageous conversations. It's about creating a culture where you can have what USC coach Pete Carroll called "Tell-the-Truth Mondays." A time where the team gets together, not to blame, but to honestly assess what went wrong and how they can get better. It’s about having the trust to disagree, to challenge each other, to hold each other accountable to a high standard. Jackson: That requires so much psychological safety. To know you can criticize an idea without criticizing the person. Olivia: And that's the 'love' part of the 'tough love' equation. Gordon argues that the best teams have both deep care and high accountability. You can't have one without the other. If you have all love and no accountability, you become a nice, friendly social club that underperforms. If you have all accountability and no love, you get a culture of fear and burnout. Jackson: You need both. You need to care enough about someone to tell them the hard truth. Olivia: Exactly. You have to be willing to have the difficult conversation because you are committed to their success and the team's success. It’s the ultimate act of commitment and care.
Synthesis & Takeaways
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Jackson: So when you boil it all down, the real 'power' of a positive team isn't just about smiling more or putting up inspirational posters. It's an active, difficult, and continuous process. You have to consciously build the culture, you have to fuel it with genuine belief, and then you have to do the hard, daily work of connection and accountability. Olivia: That's the perfect summary. It’s not a passive state; it's a continuous action. Gordon's work is so influential because it gives teams a shared language for this process. It makes these abstract concepts—culture, belief, commitment—discussable and actionable. Jackson: It’s a blueprint. And it seems the core message is that greatness is a team sport, always. No one creates success alone. Olivia: Never. So the takeaway for our listeners isn't just 'be positive.' It's 'build the system that allows positivity to thrive.' And a great question to leave everyone with, inspired by Gordon's 'One Percent Rule,' is this: What is one small, one-percent improvement you could make to your team's culture tomorrow? It doesn't have to be a grand gesture. Just one small thing. Jackson: A powerful thought to end on. It makes it feel achievable. Olivia: This is Aibrary, signing off.