When you talk to someone like John Rossman, former Amazon executive and author of The Amazon Way and Big Bet Leadership, you’re not just having a conversation about business principles. You’re getting a guided tour of how one of the most influential companies of our time was built from the inside out. John joined me recently on the Transform Your Workplace podcast, and we dove into the real mechanics of Amazon’s rise, and I learned about not just what they did, but how they thought.
John was at Amazon in the early 2000s, during a pivotal shift. “We were starting to realize we weren’t just a first-party e-commerce retailer,” he said. “We were a platform company.” This reframing — thinking of Amazon not just as a seller but as an ecosystem builder — was critical. But as John noted, during those years, the now-famous 14 Leadership Principles weren’t yet codified. “We were hammering them out every single day… asking, how do we think about this? How do we hold each other accountable?”
The principles may not have been written down yet, but they were lived. And eventually, those lived behaviors became The Amazon Way, the leadership playbook Rossman would later bring to life in his writing and consulting.
The Two Types of Customer Obsession
One of the most striking aspects of Amazon’s culture is its deep-rooted obsession with customers. John broke this concept down in a way I hadn’t heard before: “There are really two types of customer obsession,” he explained. “One is tactical, making sure this particular experience delights the customer. The other is strategic, being curious about the entire customer journey, including things that happen upstream and downstream of your product or service.”
That second type of obsession, “strategic curiosity,” is what allows Amazon to see what customers don’t say and what they might want next. This is where real innovation begins.
Rossman credits this kind of thinking with the culture of simplification that Amazon is known for. He pointed to a phrase that stuck with me: The best customer service is no customer service. Originally coined by Amazon’s first VP of customer service, Bill Price, this mindset flips conventional wisdom on its head. It’s not about being great at solving customer problems. Instead, it’s about designing systems so good that customers never need to contact you at all.
Invent, Simplify, and Transform
One of Amazon’s lesser-sung principles is “Invent and Simplify,” and John believes the “Simplify” part is more powerful than most people realize. “Every company’s internal systems are full of calcified layers,” he said. “Especially if they’ve grown through acquisition. The most valuable thing many organizations can do is radically simplify their internal work.”
It’s a discipline that goes beyond adding AI or new tools. As John put it, “Don’t start with the technology. Start with a zero-based redesign of the work itself. Rethink your job definitions, your data flows, your policies. Then, and only then, should you add technology.”
This point hit home for me. As someone who’s spent years talking with business leaders about digital transformation, I’ve seen firsthand how tempting it is to slap a new tool onto an old process and call it innovation. But as John said plainly, “You can’t incrementalize your way to transformation.”
Big Bets Require a Different Playbook
John’s more recent book, Big Bet Leadership, is a direct response to this challenge. It’s a practical manual for leading major, high-stakes change inside a modern enterprise. “If it has significant upside, risks, dependencies, and unknowns, that’s a big bet,” he said. “And most companies try to manage big bets using an operational playbook. That doesn’t work.”
John co-developed this new playbook at T-Mobile, helping incubate and scale new businesses from within the company. The takeaway? You need a separate team with fresh perspective, a clear outcome to design toward, and permission to think beyond today’s fires.
Ownership and Frugality
Among all the leadership principles at Amazon, I learned that “Ownership” is one of John’s favorites. He referenced the infamous Christmas party where someone nailed a tree into a rented floor. “That’s how a renter thinks,” he said. “An owner wouldn’t have done that.”
“Ownership,” in Amazon terms, means thinking long-term, acting on behalf of the whole company, and never saying “that’s not my job.” It’s a counterbalance to the short-term pressure that dominates most businesses. “Over 75% of CFOs said they’d reduce long-term enterprise value just to make this quarter’s numbers,” John noted. “They’re not bad people. They’re under immense pressure. But leadership principles like ‘Ownership’ exist to provide that counterbalance.”
And that brings us to “Frugality,” another principle that many overlook. “‘Frugality’ forces you to rethink things,” John explained. “It’s not about being cheap. It’s about being resourceful and efficient. That’s how you invent.”
John made the distinction clear: instead of cutting corners, “Frugality” is all about respecting what you’ve been given and finding better ways to use it. “There’s a big difference between being frugal and being cheap. It takes wisdom to know the difference.”
Building Culture with Principles
When I asked about hiring and development, John emphasized that culture means shaping an environment where the right people thrive, not trying to make everyone successful. “Culture is what happens when the parents aren’t in the room,” he said. “It’s not the poster on the wall. It’s how decisions are made when no one’s watching.”
One of Amazon’s tactics for preserving that culture is the “bar raiser” interview process, a role with veto power over hiring decisions. The goal isn’t to fill a role quickly but to raise the average capability of the organization over time.
But John is candid: Amazon hasn’t always done enough to invest in development. “There’s more they could do. But where they’ve succeeded is in codifying expectations — principles, paragraphs, mechanisms — that help the right people thrive.”
The Golden Rule and the Next Era of Leadership
In the third edition of The Amazon Way, John proposes a 15th leadership principle: The Golden Rule. He wrote it during the pandemic, as Amazon came under scrutiny for its treatment of workers and environmental impact.
“Amazon sometimes still acts like the startup we were in the early 2000s,” John said. “But they’re not that company anymore. They need to act their size.”
Interestingly, Amazon added two new principles shortly after: Strive to be the world’s best employer and Success and scale bring broad responsibility. John doesn’t claim credit, but he doesn’t entirely dismiss the timing either.
Ultimately, Rossman wants leaders to embrace the paradox Amazon has mastered: being both a world-class operator and a systematic big bet machine.
“If you double the number of experiments, you double your inventiveness,” he quoted Jeff Bezos. But experiments must be thoughtful, disciplined, and tied to high standards. “We don’t say ‘fail fast.’ We say ‘experiment and do it with excellence.’”
That’s the heart of John’s message: success in the modern world comes from studying Amazon’s principles and applying them wisely, not from trying to copy the company itself. Principles, applied with wisdom, can reshape a business from the inside out.
As we face an era of unprecedented change, that kind of thinking might be our most valuable asset.
Dig Deeper
John Rossman’s books, The Amazon Way, Think Like Amazon, and Big Bet Leadership, are available now. You can follow his work at JohnRossman.com or connect with him on LinkedIn.
Brandon Laws is a workplace culture and leadership enthusiast, host of the Transform Your Workplace podcast, and VP of Marketing and Product at Xenium HR.