Nova: We've all been there. You have the perfect plan, the brilliant strategy, the flawless product roadmap. You know exactly what needs to be done. And yet, when the pressure is on, something breaks down. A deadline is missed, a feature ships with bugs, the team isn't aligned. There's a huge, frustrating gap between knowing and doing. What if the secret to closing that gap wasn't in another management textbook, but in the obsessive habits of athletes like Kobe Bryant and Kevin Durant?

Simons: It’s a powerful question, and one that keeps a lot of us up at night. That gap is where potential goes to die.

Nova: Exactly! And that's the core idea of Alan Stein Jr.'s 'Raise Your Game,' and it's what we're exploring today. We'll dive deep into this from two perspectives. First, we'll explore the Performer's Paradox: why it's so hard to bridge that gap between knowing what to do and actually doing it. Then, we'll discuss the Influence Engine: how to lead and build synergistic teams, especially when you don't have direct authority, a challenge our guest today knows all too well.

Nova: And to help us translate these ideas from the court to the world of code and product, we're thrilled to have Simons with us. Simons is a senior Product Manager in tech with over 15 years of experience, a PhD, and a deep fascination with what makes great leaders and innovators tick. Welcome, Simons!

Simons: Thanks, Nova. It's a topic I'm obsessed with. That 'knowing-doing gap' is the daily battle in product management. It's the space between the whiteboard and the real world, and it's where the magic, or the misery, happens.

Nova: Let's jump right into that battle, Simons. The book opens with a powerful quote from the philosopher Jim Rohn: "Success is the natural consequence of consistently applying the basic fundamentals." It sounds so simple, right? But the author, Alan Stein, saw the exact opposite in a really interesting setting. He was working at a USA Basketball fantasy camp.

Simons: A fantasy camp? Tell me more.

Nova: Picture this: it’s Las Vegas. You have these hyper-successful, middle-aged men—CEOs, surgeons, venture capitalists—who have enough disposable income to pay a small fortune to live out their basketball dreams for a weekend. They get drafted onto teams, coached by legends like John Calipari, and play in real, competitive games. Now, you'd think these titans of industry would be models of teamwork and discipline, right?

Simons: You would hope so. They’ve clearly achieved success in one domain.

Nova: But that’s not what happened. Stein observed that the moment they stepped on the court, their raw character came out. Some were incredibly selfish, hogging the ball. Others were completely un-coachable, ignoring the Hall of Fame coaches giving them advice. They knew, intellectually, how to play team basketball, but in the heat of the moment, they just couldn't do it. Their ingrained habits took over. The knowing-doing gap was on full display.

Simons: That's fascinating because it's a perfect microcosm of a corporate environment. You can have a team of A-players, all brilliant on paper, but if their underlying habits—how they communicate, how they handle pressure, whether they prioritize individual glory over the team's goal—are misaligned, the project is doomed. The basketball court just makes it visible in real-time.

Nova: It really does. And the book contrasts this with the true elites. Stein spent years as a performance coach for players like Kevin Durant and Kobe Bryant. He tells this story about working with Durant. He expected to be running him through some secret, complex, next-level drills. But what did Durant want to work on for hours? The most basic fundamentals. Simple footwork. Basic crossovers. The same 'boring' stuff a high school freshman would practice. He was obsessed with perfecting the absolute basics until they were automatic.

Simons: That’s the part that people miss about innovators like Steve Jobs or Jeff Bezos, people I really admire. We see the revolutionary product, the grand vision. We don't see the thousands of hours they, and their teams, spent obsessing over the 'boring' details. Jobs was notorious for his focus on typography and the curve of a device's corner. Bezos built Amazon on the back of ruthless efficiency in logistics and customer service—incredibly unglamorous, fundamental work.

Nova: So, Simons, this contrast is so stark. In the tech world, we worship innovation, disruption, the 'next big thing.' Does this idea of obsessing over 'boring' fundamentals actually resonate, or does it feel counterintuitive to that culture?

Simons: Oh, it resonates completely. It's the hidden truth behind every great product. People see the slick keynote presentation, but they don't see the hundreds of sprint cycles where teams debated the placement of a single button. The fundamentals in our world are things like: Is the user problem we're solving crystal clear and validated? Is our data clean and reliable? Is the communication between product and engineering absolutely precise? These are our 'free throws.' You miss them, you lose the game, no matter how brilliant your long-term strategy is.

Nova: I love that analogy—'these are our free throws.' So it's really about closing that knowing-doing gap by building disciplined habits. The book uses the example of the obesity crisis. As a society, we have more knowledge than ever about diet and exercise. We know what to do. But knowledge alone is useless. The power is in the application. So how do you build those 'doing' habits on a product team that's constantly pulled in a million directions?

Simons: It's about building systems and creating what I call 'guardrails of discipline.' You can't rely on willpower alone, especially in a high-pressure environment. For example, on my teams, we have a non-negotiable rule: no user story is considered 'ready' for an engineering sprint unless it has a clear 'why' statement—the user problem—and defined success metrics. It's a simple, repeatable drill. It's not sexy, but it forces the 'doing' of strategic thinking and prevents us from just chasing cool-sounding ideas that aren't grounded in user value. It's our version of practicing footwork, just like Durant.

Nova: So the system itself becomes the coach, constantly reinforcing the fundamentals.

Simons: Exactly. It automates the discipline, which closes that gap between a good intention and a consistent action.

Nova: That's a perfect transition, because building those systems and holding the team to that standard requires leadership. And the book argues that once you master yourself as a 'Player' by closing your own knowing-doing gap, you have to evolve into a 'Coach.' But for many people, and I think this is especially true for a Product Manager, you're a coach who can't bench anyone. You have to lead purely through influence.

Simons: You've just described the central challenge of my profession. I have all the responsibility for the product's success, but zero direct authority over the people who actually build, design, and market it. It’s all influence, all the time.

Nova: And the book gives a great framework for this. The five qualities of a great 'Coach' or leader are Vision, Culture, being a Servant, Character, and Empowerment. It tells this fantastic story that I think will resonate. It's about a brilliant senior developer named David who gets promoted to team lead. He's technically the best on the team, but he's a terrible leader. Morale plummets, people start quitting. He's just assigning tasks and checking boxes.

Simons: I have seen this movie before. Many times. The 'battlefield promotion' where your best individual contributor becomes your worst manager.

Nova: Exactly. And David only succeeds when he finally realizes his job isn't to be the best coder anymore. His job is to create a vision for what the team is building, to foster a culture of trust and open communication, and to act as a servant leader—to ask his team, "What do you need from me to do your best work?" and then go get it for them. He had to stop being the star player and start making everyone else a star.

Simons: That shift from 'I' to 'we' is the hardest leap for any new leader. It's moving from creating value yourself to creating an environment where others can create value. It's a profound identity shift.

Nova: It is. So, Simons, you live this every single day. How do you create that compelling vision that gets an engineer, a designer, and a marketer all excited and aligned to build the same thing, when none of them actually report to you?

Simons: It's the hardest and most important part of the job. You can't just share a PowerPoint deck and expect everyone to be inspired. You have to be the chief storyteller. You have to constantly, relentlessly repeat the 'why.' You have to connect their individual work—that specific line of code, that particular UI mockup, that marketing copy—back to the larger customer problem we're solving and the impact it will have on someone's life. It's about making them feel like they are co-authors of the vision, not just cogs in a machine executing a plan. That's what the book calls 'empowerment.'

Nova: And that directly ties into another key quality for a great 'Team' that the book highlights: Role Clarity. The author says every member needs to understand their specific place in the whole. How do you prevent the 'that's not my job' problem on a cross-functional team where roles can get blurry?

Simons: You have to be almost pathologically explicit about it. We use tools, of course, like a simple RACI matrix—which stands for Responsible, Accountable, Consulted, and Informed—for every major feature. It’s a simple chart that clarifies who does what. But the tool is less important than the conversation. At the kickoff for any big project, we explicitly discuss roles. I'll literally say, 'My job is to be the voice of the customer and the business. Your job as the lead engineer is to be the voice of technical feasibility and excellence. Your job as the designer is to be the voice of the user's experience.'

Nova: You’re defining their swim lanes.

Simons: Precisely. Defining the swim lanes, as the book would say, prevents collisions. But more importantly, it shows respect for each person's expertise. It tells the engineer, "I trust you to be the expert on this," which builds the psychological safety and trust needed for a team to become more than the sum of its parts. That's how you get to that magical 1+1=3 synergy the book talks about.

Nova: This is all connecting so beautifully. So, what we're really saying is, it's a two-step process to raise your game. First, you have to be a great 'Player' by relentlessly mastering your own fundamentals and closing your personal knowing-doing gap.

Simons: Exactly. You can't be an effective 'Coach' if you haven't put in the work as a 'Player.' Your credibility doesn't come from your title; it comes from your own discipline and competence. People will listen to your vision because they trust that you've done your homework.

Nova: And then, once you have that foundation, you raise your team's game by becoming that 'Coach'—providing a clear vision, serving their needs, and creating a culture of trust and absolute role clarity.

Simons: That’s the playbook. It’s a progression. Self-mastery first, then team-mastery.

Nova: The book ends with this fantastic, visceral story. The author, Alan, is participating in this brutal endurance event called 'Hell on the Hill,' which is exactly what it sounds like: running up a steep, muddy hill 100 times. He's completely broken, physically and mentally, around the 70th climb and is about to quit.

Simons: I can feel the pain just hearing that.

Nova: Right? But then he sees Steve Wojciechowski, a famous college basketball coach known for his toughness, still grinding it out. So Alan stumbles over to him and asks, 'Wojo, how many do you have left?' And Wojo, without breaking stride, just says, 'One. Thirty more times.'

Simons: Wow. That's powerful.

Nova: Isn't it? That intense focus on the very next step, not the overwhelming whole. It's such a powerful mental model. So, for everyone listening, especially those of you leading teams or navigating complex projects, here's the question to ponder, inspired by the book: What is the 'one rep' you can focus on tomorrow to move your most important goal forward? Don't think about the whole hill. Just the next step.

Simons: That's the perfect takeaway. It's the essence of the agile methodology that drives the tech world. Don't worry about the entire year-long roadmap. Focus on the next two-week sprint. Focus on the next user story. Focus on the next conversation with a customer. That's how you build something great. One rep at a time.

Nova: Simons, this has been an absolutely fantastic translation of these principles. Thank you so much for bringing your perspective.

Simons: My pleasure, Nova. It was a great conversation.