I recently had the honor of serving as the opening keynote speaker at the Imagine AI Conference, where I delved into the critical intersection of leadership and artificial intelligence. Drawing on insights from my experience as the author of “Big Bet Leadership” and my time at Amazon, my keynote emphasized the pivotal role of leadership in harnessing AI’s transformative potential. With AI rapidly evolving, leaders must not only understand the technology but also guide their organizations through the complexities of its implementation, ensuring that innovation aligns with strategic goals and delivers meaningful value.
In my keynote, titled “Winning with Big Bet Leadership,” I explored the three essential habits that define successful leaders in the AI era: creating clarity, maintaining velocity, and prioritizing risk and value. These habits are not just theoretical—they are the foundation for driving successful AI initiatives that can scale and adapt to the fast-paced digital landscape. As AI continues to reshape industries, the need for strong, visionary leadership has never been more critical. I shared practical strategies for leaders to navigate these challenges, ensuring their organizations are not just keeping up with AI advancements but leading the way.
After the keynote, I sat down with Chris Madden for a discussion about leadership, artificial intelligence and Big Bet Leadership. John Rossman is a keynote speaker, innovation coach, and strategy advisor. The Digital Leader Newsletter is a weekly coaching session focused on customer-centricity, innovation, and strategy. We deliver practical theory, examples, tools, and techniques to help you build better strategies, plans, and solutions—but most of all, to think and communicate better.
Here’s a link to the entire conversation and the transcript below. Well worth the listen.
Chris Madden (00:00:00) – Welcome back to imagine AI podcast, the pop up podcast we have at the imagine I live conference here in Las Vegas. It’s day two and I have with me a very special guest, John Rossman, former Amazon executive and author of the new book Big Bet Leadership. John, thank you for being on the podcast.
John Rossman (00:00:16) – Chris. Great to be here. Thanks for hosting the event. Great event. Thanks for inviting me. Nice to talk.
Chris Madden (00:00:21) – Yeah. Okay. I’m going to start off right away. What’s what message do you have for business leaders today?
John Rossman (00:00:26) – Well, the message relative to a new platform, a new a changing capabilities like AI is like the technology’s cool and the technology is hard, but it’s not the hardest part of actually making business value out of this. The leadership and the operating model, all the things that else need to go around it, that’s the hard part of what changes. My particular focus is on non incremental projects. It’s big moves, things that have substantial upside potential for an organization but come with lots of risks relative to them.
John Rossman (00:01:05) – That’s what a big bet is. And my my thesis my hypothesis is is that a different leadership model a different operating model is needed in order to do that. And we’ve decoded that that operating model, that leadership playbook in big bat leadership.
Chris Madden (00:01:20) – Could you maybe paint a picture of an example that a problem of a business leader might be facing, and what they could take to take action? Yeah.
John Rossman (00:01:29) – You know, a big bet is needed when you’re feeling the symptoms of you’re not differentiated from your competition. Your customers don’t love you. You’re having to battle churn. Your customer acquisition costs are going up. More marketing is needed to win. Not better product, not better value proposition. When you’re becoming kind of a MeToo organization, that’s when a re-imagination is needed. That doesn’t always have to manifest itself in terms of a customer value proposition or a customer experience. Oftentimes it’s on the cost model of the organization itself. How do we become leaner? How do we get more done with less? That’s where a lot of the future going.
John Rossman (00:02:12) – Opportunity comes with AI, but you really have to, you know, not pave cow paths. You have to completely reinvent not just the processes, but the management processes that go around it, the entire operating model, the rhythm of the organization. Those are the different types of big bets. A big bet gets called a lot of things. Things. An organization, an AI strategy, a digital transformation, an operating model implementation, a cost reduction sometimes is a big bet. All of those things can be big bets, high potential upside for the organization, but multifaceted risks. They are truly a wicked problem.
Chris Madden (00:02:50) – What’s the first thing a leader needs to recognize when they’re facing this dilemma? Is it is recognition of the problem and saying it out loud, or.
John Rossman (00:02:59) – That oftentimes is there’s no absolutes to that, to that answer. But oftentimes it’s we’re very vague in both the problem we’re solving as well as like what our hypothesis is for what the future is, the solution relative to that. I get called in a lot of times to do a pressure test, evaluate a current situation and help them understand what it is, what it needs to be in the corrective actions relative to it.
John Rossman (00:03:27) – And I’ll start with just asking ten different people who are deeply involved in the initiative. What’s the problem we’re solving and what’s the future state? I will I will bet anybody I will get ten, not just slightly different answers, ten very different answers. And that clarity. So there’s three habits that big bat legends have. The first is create clarity, creating that clarity around the problem we are solving, making sure that it’s a meaningful problem, that it’s really the root cause of the issue and not the surface level issue, and get getting very refined about what our hypothesis is about the killer feature, what is truly going to satisfy the situation, and making sure that we have a business case and a risk oriented business case so that we can include it in our experimentation log that sets the basis for what we call the big bet vector. And when you can create that type of clarity, then a senior leader can make really good decisions. Do I pursue it? Is it worth worthy or not? That’s the first big decision to make.
John Rossman (00:04:29) – That’s why you oftentimes want to have a portfolio of potential moves that you’re evaluating and then recognizing, like there’s lots of good things we could go do, but you need to place your bets very carefully about the ones you actually proceed. The name of the book is Big Bet Leadership. The big isn’t the size of the bet. The big is the ambition. The whole goal is to de-risk these things so that by the time we are really making big investments, we’ve substantially de-risk the real risk factors relative to it. So it’s no longer an actual big bet.
Chris Madden (00:05:06) – And when you’ve got these potential solutions, where does I like I is part of the solution.
John Rossman (00:05:14) – Absolutely.
Chris Madden (00:05:15) – And how are you choosing like what I solution to go with or I mean like ChatGPT Gemini. Like all these different platforms.
John Rossman (00:05:24) – You know that is a problem statement in its own. But when you are problem oriented versus tool oriented, you tend to solve a much more holistic problem. You solve it from people, process incentives, communication and the technology.
John Rossman (00:05:42) – But if you go along this path, you’ll much better understand. Well, what are the actual operating constraints that I need from whatever tool I’m selecting, whether it’s an AI platform or a sensor of some type or people skill, what’s my real requirements relative to that operating component of my solution architecture that I need? So from my perspective, you’ll be much better prepared to help make that thoughtful decision and to design in a thoughtful way so that you have extensibility, right? Like whatever choice you make. There’s a pretty good probability that, like, it’s probably not the right long term choice or the only long term choice you need designing. This was one of the things I learned as an early Amazon executive was identified the specific use case, but then build in a generalized manner so that you have future flexibility, not just for that use case, but for future things that are kind of come at you. We tell a great story in the in the book about, and it’s a chapter about high stakes decision moments and what are the real obligations that a senior leader has.
John Rossman (00:06:51) – And one of the obligations that a senior leader has is to find what we call the hidden jewels. These are the underlying capabilities that we’re building for a specific use case. But how could I create future extensibility, actually increase the ambition and the potential value of this big bet by identifying a generalized capability that is Amazon’s Playbook 101, which is they build reusable componentry that gets used then in lots of ways, both internally and externally, right. They turn things inside out all the time. That’s one of the things you want to be very thoughtful of is, is you’re not just how do you de-risk that vendor decision? Will you de-risk it by being very clear about, you know, essentially the speeds and feeds you need in and out of it, as well as designing an architecture that allows a much more of a plug and play approach to it.
Chris Madden (00:07:44) – I think one of the biggest problems of making these big changes, right? And people don’t like change. Employees are scared of change. How do you communicate it to the employees that we’re taking this new direction? And AI is going to be a big part of it.
John Rossman (00:07:58) – Communication is a critical capability and obligation of senior leadership. And we we have several chapters, but one in particular in big leadership that addresses that, that need and the mistakes that senior leaders make is they they are vague about the problem. They talk too much about a burning platform, why we need to change, and everything. That’s actually not helpful communication. It’s disconcerting to a participant, to an employee, to a stakeholder. They’re vague about where we’re going, oh, we’re going to improve the customer experience, or we’re going to improve health care or whatever it is. You have to be much more specific, and you have to talk about the journey that you’re going on. Are we certain about this or are we experimenting very different communication tactics. So there’s a very good book called Switch How to Make Change When Change is Hard is by the Heath brothers, and we leverage that destination postcard concept in leadership to take these elements of the big bet vector that we talked about being very specific about the problem, very hypothesis driven about the solution and inserting them into destination postcards.
John Rossman (00:09:11) – But then the job is to be a chief repeating officer. Repeat, repeat, repeat of all of Bezos superpowers. Yeah, it’s his strategic communication and the ability to communicate in the right way to the right stakeholder at the right moment. So I launched the marketplace business at Amazon, and Jeff wouldn’t come to me and go, John, hey, how’s the marketplace going? No, he would come to me and he asked me a question like, can a third party seller register in the middle of the night without talking to anybody, John, yes or no? Well, that’s that’s strategic communication. He’s testing his killer feature hypothesis about what was needed. He’s not just asking me a generalized question.
Chris Madden (00:09:54) – Very specific question.
John Rossman (00:09:56) – And he would ask me that question all the time. It wasn’t he didn’t ask me that question once. He. I mean, I could place a bet about this is the question he’s going to ask me, because he knew that was the apex feature, that if we got that, all these other good things were going to come along with that.
John Rossman (00:10:11) – So he would keep us focused on that simple thing, keep the main thing, the main thing, like that’s that’s a big part of the essence of the book, is about keeping creating a real priority relative to the business.
Chris Madden (00:10:24) – And how long did you work at Amazon with Jeff?
John Rossman (00:10:26) – So I was there for four years. I oftentimes refer to him as dog years, like it was super fantastic. So I was there 2002 through 2005 and.
Chris Madden (00:10:34) – Pretty early in the.
John Rossman (00:10:35) – Very, very early, one of my boys refers to me as an OG You know OG for sure, right? so it’s been almost 20 years now. My entire mission has been about taking many of the practices of Amazon and delicately inserting them into our client’s work. So the first book I wrote was called The Amazon Way about Amazon’s leadership principles. Then I wrote the full playbook of all of Amazon’s practices. It’s called Think Like Amazon 50.5 ideas to become a digital leader. Big bet. Leadership serves a slightly different purpose. It takes a lot of the things I’ve done since Amazon.
John Rossman (00:11:09) – A lot of the work that my co-author, Kevin McCaffery, and I did at T-Mobile in standing up a new business incubation practice, and we decoded many of the things from Amazon, but added in some other lessons from other leaders very specifically focused on big bets. How do we be successful with high ambition, high risk initiatives that companies need? And if there’s one thing that I want people to take away from this conversation and from from the book, it’s this that purely incremental moves are needed but are not enough. In order to win. In this era of AI, you need to have high ambition, high risk. Now you need to approach them very delicately. That’s what the book talks about. But you can’t have just a portfolio of simply incremental moves within a company. That’s the riskiest position of all to be in.
Chris Madden (00:11:58) – Yeah. When you’ve got a bigger ship, it’s really hard to change direction, but you’re going to have to be the captain that.
John Rossman (00:12:05) – You know, especially when it’s a successful ship actually changing.
John Rossman (00:12:10) – Adding to that playbook is very hard. That’s the heart and soul of The Innovator’s Dilemma. I think we’ve prescribed an actual operating model, a leadership playbook that helps solve for the innovator’s dilemma.
Chris Madden (00:12:24) – So with your time from working with Jeff Bezos, what is a big memory that stays with you to this day?
John Rossman (00:12:30) – Well, I told you about one like like his ability to stay specific.
Chris Madden (00:12:34) – Questions.
John Rossman (00:12:35) – But Jeff was always at his best in his happiest when he was actually helping to solve a problem like he loved to just like, problem solve about a solution. and he had high expectations for his senior leaders of understanding the details of their business and the root cause of the issues. And so I thought he was fabulous to work with and work for and everything, but he had high expectations. I wouldn’t want it any other way, honestly. Like like if somebody didn’t have high expectations of me like that says more about me than their leadership style. And so, you know, this playbook isn’t for everybody, I get that.
John Rossman (00:13:13) – But, you know, the subtitle of the book is Your Transformation Playbook for winning in the hyper Digital ERA. I’m interested in winning, like like like really like just surviving, kind of getting along, like interesting. Not my forte. I’m interested in working with companies who truly want to create demonstrated, durable, competitive advantage in whatever their field is. That’s who this playbook is, is for, and that’s who I’m interested in working with.
Chris Madden (00:13:40) – So besides writing this book and being an author, you’re you’re consulting. You’re working with leadership. Yeah. Yeah.
John Rossman (00:13:45) – So we so I get the opportunity to do a lot of keynotes and workshops, and we do offer advisory services. So our goal with our services is to have a ten x power to weight ratio difference from traditional management consulting. So what’s power? Well, power is the impact the value, the speed and the lasting impact of what we deliver. The weight is not just the direct fees and expenses, but the time and the effort that it takes organizations to get there.
John Rossman (00:14:12) – So we have a very flexible set of solutions and services that we believe delivers a ten x power to weight ratio improvement relative to traditional management consulting. Nothing against traditional management consulting. I was one for most of my career, but when you have a really specific perspective and a set of frameworks and tools that supported you, if you focus in on the right problem set, you can actually deliver a much different value equation. And that’s what we’re focusing on.
Chris Madden (00:14:41) – Okay. So you’ve been to a lot of conferences. You do a lot of keynote speaking. How has imagine I live been in your experience
John Rossman (00:14:47) – It’s been unique and great. The energy and the engagement of the participants and the variety of the insights that you get. And remember, this isn’t even day one of AI. This is like the warm up game before preseason, before the first game of the season. Like this is we can’t overstate that enough to see already the real impact, not future impact, but the real impact that AI is having today.
John Rossman (00:15:17) – Better be a wake up call to leaders that, you know. I think what you see a lot of is what we call drugstore cowboys, right? Which is kind of all hat no cattle like, oh yeah, we have an AI strategy here and everything, but really they’re just doing it to satisfy a stakeholder. Like do you have an AI strategy, you know, and everything like, yeah, we got a couple of digital agents or whatever it is. Right. Like that is not enough companies. We wrap up the book bye bye. Our final piece of advice is you need to be an active skeptic. Active meaning like you have to participate. You have to invest a reasonable amount of resources, time and attention and understanding the experimental path that we are going to be on. Skeptic means you have to prove it before you go big on it, right? And so that’s what I see here, is people who are engaging and not waiting until others capture the opportunity. And that that’s what I would encourage everybody to do.
John Rossman (00:16:09) – And this conference has been a fantastic venue for getting to meet both the people making it happen and the people that are figuring out how to how to make it real in the field.
Chris Madden (00:16:19) – Well, I’m glad to hear that, John. John, thank you so much for sitting down with me and taking the time to talk. It’s incredible the caliber of businesses that you’ve worked with and are trying to help. And everyone should check out Big Bet leadership. Thank you, thank you.
John Rossman is a keynote speaker, innovation coach, and strategy advisor. The Digital Leader Newsletter is a weekly coaching session focused on customer-centricity, innovation, and strategy. We deliver practical theory, examples, tools, and techniques to help you build better strategies, plans, and solutions—but most of all, to think and communicate better.