Sound BITES: E47 - John Rossman | Rossman Partners

Speaker A: Today's episode is brought to you by our company, nanochomp Marketing Strategy and Analytics. We help product and marketing teams solve problems and experience growth using data and approachable AI. Visit nanochomp.com to learn more. Hey everyone. Today on Soundbytes we have a great guest, John Rossman. John is an author, business advisor and keynote speaker. He was an early Amazon executive who helped play a key role in launching the Amazon Marketplace business. His books include the Amazon Way, Think Like Amazon, the Amazon way on IoT, which is a favorite of mine, and Big Bet Leaderships. Most recently Big Bet Leadership is an actionable guide for leaders who want to succeed in complex transformations. Really excited to have you on today. How are you doing, John?

Speaker B: Derek, thanks for having me. Been nice to get to know you and Lauren.

Speaker A: Really appreciate it. Thanks so much for coming. Um, yeah, it's, it's almost hard to pick a point of where to start. So let's start at the beginning. Like how did you get to the point where you're at now? Where did you start and what got you on your tech journey? Journey?

Speaker B: Well, um, God, I'm 60 years old now. Like how, how far do you want me to go and stuff? But um, so I studied industrial engineering at Oregon State and I've always been interested in kind of this intersection of efficiency, ergonomics and, and kind of flow integration. Right. Like how do you get people, processes, machines, outcomes that, that work together and always target both a better, you know, outcome for the, the customer but also efficient and have quality levers. Right. Like that's, that's kind of the arc of my entire career. Uh, my, my first job out of college, um, I was a programmer um for Accenture. It was Anderson Consulting at that time. It was actually MICD when I started and, and I got to do just the edgiest work. I got involved in really early graphical user interface, user Unix, uh workstation, uh, design and really kind of that, that design and systems integration work that I did the first five years of my career really is what got me into, into tech. And then I've kind of migrated to more like um, re engineering and strategy work. But it, it, it all builds on you know, that understanding of actually both how to design ar that matters and kind of in, in the book I talk about the IDs right of, of architecture, um, that, that you need which are the, the capabilities of an architecture. So I have a deep appreciation for that but I have a good enough understanding of actually like you know, from the, the, the metal up, like how systems Work and stuff. And that's, that's been, you know, helpful at times in, in the work that I do.

Speaker A: I think it's really important to understand things at a systems level, a building blocks level. And you see the interaction and interplay on how they all come together.

Speaker B: And that's not a throwaway, uh, line there that you just said, Derek, I'm going to, I'm going to slow down and double click on it like that. That concept of reusable capabilities, whether it's a technology capability or uh, a functional capability, that's really the Lego block concept of Amazon, right? And how they keep modularizing their, their teams and their organizations and it's one of the key ways that allows them to maintain smallish teams and to be relative for a very big company, now a fairly entrepreneurial and fast moving company is because of this connection between service oriented architectures and the teams that actually own and run services at uh, Amazon. And it really is a key concept. Amazon calls it a two pizza team. There's lots of ways to design this, but carefully designing processes and then functions and then steps like that is an artistry and a capability that is essential to creating businesses that both scale but uh, can also be transitioned along the way. They aren't brittle in nature. Right. You have this essence of kind of being antifragile. Things that actually get better with chaos versus breaking with chaos.

Speaker C: Do you think the, the minds or, or the, the people who are really good at designing those processes and steps, do you think that's like a respected, um, uh, skill set? Or is that just something that people take for granted?

Speaker B: You know, I, I, I, I, I don't think it's what people take for granted, but I also don't think it's highly respected. Um, you know, one of my favorite books is the Elon Musk biography that was done a couple years ago by, and one of the things, there's two key concepts in that book that they kept coming back to and I've used these a number of times with my clients, is Elon's focus on the machine that makes the machine. Right. And so he wouldn't just focus on the rocket or the car, he'd be focused on the process that builds the rocket or the car. Right? So then the machine that makes the machine and putting in intense effort into designing that flow. Right. And so that's the art that we're talking about here. And then the other is kind of Elon's algorithm which is delete, delete, delete, Right. Like challenge Every requirement, challenge, every step, everything should be rethought. And, and that is a big combination of what we're talking about. Amazon's third leadership principle is invent and simplify. It's the and simplify part of that leadership principle, uh, uh, in your processes and your approaches and your requirements and your procedures and your jobs and your data structures. Like it's of those things that need to be rethought and simplified. Because simplified not only scales, but again it can be transitioned over time.

Speaker A: Yeah, I think that makes a lot of sense and I think a lot of people miss the simplified component of it. And even worse, when the people are trying to build a process, there's a lot of sunk cost into the way things have previously been done without questioning the first principles about what needs to be done versus what's been done.

Speaker B: Yeah, simple is not easy to get to.

Speaker C: Right.

Speaker B: And it kind of gets to Lauren's question like, like this is not highly respected, but it's the edgiest work I do is kind of the decalcification of all the buildup of all this stuff over time. And especially in bigger companies that have grown through acquisition and you know, they're just hustling to get things done, they don't take time to really rationalize, you know, their processes, the outcomes. Why do we do this? Shouldn't we partner to have this done? Like that kind of core versus versus context discussion and everything. And that's, that's the type of work that we're talking about here. And you know that is operating model redesign and transformation. Right. And so you know, the book is Big bet leadership and it's about transformations. Sometimes these are innovations like outward facing things, but a lot of times it's how to get to a more efficient operating model and it's the, the redo of how we get work done. And I think that you know, and this gets to the premise of the book, you know, the subtitle of the book is your transformation playbook for winning in the hyper digital era. Well, what's the hyper digital era and why do I think this is important? Because in the advent of AI and a couple of other mega forces like the aging of our population and the indebtedness, uh, and committed spend of our country, I think what you're going to see is companies that are being able to be redesigned for a 10-100x level of productivity like white collar, back office, mid office, front office productivity. And if you think about the past 25 years of digital transformation, we've really reinvented customer experiences really well. We've had a plethora of new business models but the way work gets done, productivity, core productivity has been on a very mild upswing. Right. Like 2% a year. I think that's going to change. You're going to see an upswing in productivity. Now that's going to be painful because that means a lot of displacement and everything. But the companies that can figure out how to be systematic about their operating model transformation are going to be the big winners through this. And if you can't, you're going to be the loser. And that's why I think this concept of having both an, and uh, being a world class operator but also a systematic transformation organization. And there's only a few out there that have been able to do that. That's kind of the ones that we know of are, you know, we've talked about one extensively. Elon Musk, Jeff Bezos in Amazon, John Ledger at T Mobile, Satya Nadella at Microsoft. They have a playbook. We, we think they have three critical capabilities that differentiate them from other good operators. And that's really both why we wrote the book, why we think it's important because you have to make transformation a core competency and it's not today. And there is a pattern, there is a, there is an approach to this that is different. And that's the tricky part is it sounds similar to the things you do as a good operator but it's done with distinctly different kind of essence and focus areas.

Speaker A: Yeah, one of the um, well, a lot of things I liked about this book to start, I'll go back like before I even knew you, we had read the Amazon Way and the Amazon Way on IoT. We were, you know, we were running an IoT business that was a playbook. Try to treat it as a bible. So it was really easy, uh, approachable and consumable. And then when we got this new one I was super excited. And when we were talking about uh, right off the gate about outcome based business models are kind of the future and you're talking about these extreme digital transformations. Resilience is going to be a big piece of the pie and a core competency of being adaptable. One of the things we're looking at with all these AI tools is it's basically like a white collar combine harvester. Right. You can use the tool effectively or it can run you over.

Speaker B: Right.

Speaker A: And I think you're helping businesses being

Speaker B: able to use it and it's going to fundamentally change agriculture Right. Like, like uh, so that's a good, that's a good metaphor. Sorry to interrupt you.

Speaker A: No, no, it's, it's, that was like my big takeaway from, from reading um, your latest book. I was like man, like this can. This changes the world just the way the Internet did and the people that can adapt it and approach to it are going to win.

Speaker B: And you're starting to see the early trials and impact of this mindset, right? And so you're seeing functions within some companies, you know, this concept of the 10x engineer, right? And marketing like having a productivity boost based on kind of these Gen 1 Gen AI capabilities and everything, right? Like this, this is the starting point. This isn't the ending point on this. This is the starting point on this. And it's gonna, we're tackling kind of the, the work that is really well suited for the superpower of gen AI, which is essentially kind of pattern matching and next best available word, right? Uh, computer science programming that has very strict rules, right? So that's really well suited for the powers of Gen AI, marketing and communications. Those things again, like super, super good fit to the superpowers of gen AI in these early stages. But that's just part of the work that goes on within enterprises, right? And so now you're going to start seeing that I think there'll be a trajectory with jumps and starts, but plateaus also of adopting this into all of the work that goes on within enterprises. But again you're already starting to see the impact kind of these completely redesigned, outcome oriented, built for AI capabilities that are having the impact we're talking about, which is productivity levels that are significantly different than organizations who aren't creative and aggressive in the experimentation process. That's necessary to get the results when,

Speaker C: when we talk about like op, uh, model transformation and you can 100x boost of productivity and the potential pain that that may cause, you know, because of the displacement. How do we have conversations with those teams or those groups that maybe stand to be impacted the most? And, and what can leaders do or say or you know, put in place to um, you know, make it a little less painful?

Speaker B: Yeah, yeah, super important concept. I'm, I'm going to unpack it a bit here and everything. Right? So the fundamental challenge in these transformations is a lack of clarity in our thinking. When you don't have clarity in thinking, then you can't experiment well, you can't communicate well, you can't set expectations well. So the fundamental premise of the book is you have to build A big bet vector.

Speaker C: Right?

Speaker B: A vector has two points, very specific points, well understood points. Our vector has the problem and our hypothesis for what the future state is. So when you have this big bet vector, then one of the things you're able to do is to be a much more effective strategic communicator. And my belief to answer your questions is you have to have authentic transparency, uh, with your stakeholders relative to the journey that you are taking. And if you do that authentically, consistently and in a manner that's actually helpful. And by helpful, I don't mean, um, communication that says we have to change or we have to innovate or we have to have better results. You know, that's kind of like super empty calorie, uh, communication. But that's mostly what's delivered by executives when they're talking about these types of transformations. And the problem is everybody makes meaning of that, right? And so they're taking in all these other signals and they're figuring out like, oh, is, does this mean a big layoff, you know, or what. Whatever the change is a big, a big change. But if you're actually super, super precise and consistent in here's the problem we're solving and why it's worthwhile, and here's our hypothesis about what the future state is, and here's the journey of experimentation that we are going to go on to prove this out, then you're actually taking the guesswork out of the impact relative to this. Now, uh, again, depending upon the stakeholder in the situation, then you have to like complete that story for that stakeholder group. But, but you have the basis for actually calibrating and being, being directionally accurate in what we're doing and that it's fundamentally a process of experimentation. I cannot commit to you that this is going to work or this is going to be the outcome. We are going to test it, but when we do, we will communicate. Like that's the type of communication. And so this is such an important aspect of being a good leader for transformation that we wrote a chapter kind of dedicated to kind of both the culture and communication. And we, we liken it to kind of like the fundamentals of, of good teams. Right? And so this is, this is, uh, chapter five, Championship Habits. And you know, the, the, the quick recommendation is you have to be the chief repeating officer, right? Your job has to be in a story format with, with very intentionally relatable situations. Tell this story again and again and again. And if you look at these big bet legends, people that are systematic, they have A super natural orientation to keeping the main thing. The main thing and part of the way they do that is by the stories and the communication that they tell.

Speaker A: Yeah, we um, we use this concept from your book very recently actually. So we had a client who um, their leadership team would use language like we got it under control, we're taking care of it, we're managing it, I'll handle it. So problems would come up like we're working on it was the reply back. And in that leader's mind it was, you know, I always work and we always give a favorable outcome for, for the people involved. But for the people involved, there's still uncertainty in that gap in finding a way to close that uncertainty is significantly, um, better for your outcomes. And we were basically referencing your chapter in that.

Speaker B: Yeah. And you know, I, I come from a fundamental belief that you know, you should talk to adults as adults and um, if the implications are obvious, don't try to like, you know, pretend that it's not, you know, and everything. Right. And that's part of adult based communication is, is talking about the implications but why we need to do this and everything. Right. And then again, again depending upon the situation, you can come with this, but you know, here's what we're going to do with this extra capacity or this new talent or whatever it is. Right. But you know, the thing I know is you'll sleep well at night if you have honest, intentional, helpful communication. Like that's one of the benefits of going this path.

Speaker A: One of the things I think was when we were talking was in your book, it's starting to blend together. But to that point you were explaining to me a meeting you were having with Jeff, Jeff Bezos, and he asked you a question about the growth in the marketplace and you started to give him the answer and he stopped you and he was like, the answer to that question starts with a number.

Speaker B: Yes. Yeah. Yeah. So this was um, in the Amazon way. And you know we, we launched the marketplace business in, in uh, for holiday 2002. So we launched it in early November, October with just the apparel category in uh, 2002. So it's January 2003. We've come back from m. The holiday. We're, we're doing our S Team Marketplace update. And, and Jeff turns to me and he goes, john, how many, how many sellers have we have we launched this year? Well, it's early January. Uh, and so I start, I start to explain a. We, we, we didn't have any sellers in apparel to uh, to launch and the new categories weren't ready to go yet. That, that was the. What I started with the explanation and he obviously kind of reversed course. Like, no, answer the question. So I said six, but. And then he, he just took it as an opportunity. And he wasn't talking to me, he was talking to the entire organization,

Speaker C: uh,

Speaker B: uh, in that s team meeting that like, we can't let the simple things, the constraints in our business be the hard things in, in the business. Right. And we had, we had allowed some of the simpler things to be the constraints relative to this business. And he was also encouraging me. Like, John, although your title is director of Merchant integration, you need to act like an owner, right? Like think about the entire business and don't worry about putting pressure or ruffling feathers beyond your organizational scope. And it's like, I didn't need to hear it twice. It's like, okay, I've heard this. Everybody else has heard it. So now when I start coming and talking to whether it's the platform team or the business development team or whatever, about things that really aren't tied to m. My job, but they are to the marketplace, people now understand, like I've been told, like, think like an owner.

Speaker A: Right?

Speaker B: And so that's kind of the story. And that is.

Speaker C: Yeah, I was going to say I'm

Speaker B: curious in most companies, which is how to not let organization, uh, structures and job titles are good for some things like essentially business as normal, but when you are driving change, it never works out. Right. And so you, you, if a, ah, good leader, understands the limitations of org structures and job titles and works to allow the messiness of just like acting like an owner and getting comfortable with kind of that internal creative tension that you, that you need to create it. It, it's, it's like a, A uh, songwriting session or you know, a team like, you don't get better by just saying, oh, you know, this is good enough or this is great. Like, you get better by challenging to get to get to better. And you have to be willing to, you know, have those. Like, you want to talk about vulnerability? Like, vulnerability is like saying like a, I'm not good enough. This is what I need to do, and B, this isn't good enough. We have to do better. And that's what good teams do.

Speaker C: I'm curious if, you know, you're mentioning your meeting back. I think you said it was like 2002, 2003, you were sitting next to Jeff Bezos and that's kind of like crazy to think about now just Kind of knowing how large the company's gotten and like how prolific of a, of a person he, everybody knows who he is. So I'm just curious, like, you know what, I guess, uh, my question is like, did you understand like the gravity of like the things that you were doing and did they feel really big at the time or in retrospect, is that something you can look back and be like, oh, that was like we were kind of at the forefront.

Speaker B: Yeah. Um, nobody saw what was coming for Amazon. Nobody saw what was coming for Amazon. Um, and so we had a sense of urgency because at that point the stock was $7. Right. We had gone through a big crash. We were fighting for survival. The marketplace business was the third attempt at kind of this, this orientation or, or need to like, we have to open up more categories and we can't do it as a pure first party retailer. And uh, there was a ton of naysayers, Lauren, like both external but mostly internal people on the board, other senior leaders, Amazon, like, you know, this isn't going to work. But it was, it was really Jeff's willingness to, you know, be strategically patient but tactically impatient to that let the marketplace take another crack. We finally figured out the right tactics to get to the outcomes that we were looking at. But it still took patience and a couple of other big bets m to come into play that weren't on our drawing board at that time. Right. And so, you know, when the marketplace was launching, we didn't, we weren't thinking about prime and we weren't thinking about FBA fulfillment by Amazon. But it took those three things combined and just letting the market develop. Right. Both e commerce market developed, but also customers to realize like, oh, I don't just come to Amazon to buy books, music video. I come there to buy apparel and home decor and sporting goods, equipment and musical instruments and anything. Right. That's that this is the marketplace story is also the story of becoming the everything store and becoming a platform company. And so, you know, he was the one that was willing to take the calculated risk. And at the end of the day, Big Bet leadership is really about how to be smart about taking these calculated risks. Even though the book is called Big Bet Leadership, the big is the size of the ambition. It's not actually the size of the bet.

Speaker C: Right.

Speaker B: It's about experimenting out the, the major concepts before you commit big to them. And, and that's why it, it I've had people point out to me, it's like, oh, this is really kind of the agile manifesto for enterprise transformation. And I, uh, you know, that's somebody else's interpretation. Like, oh, you know, that's an interesting spin on this, is how do you actually have high ambition on a concept but understand that there are risks, dependencies and unknown unknowns that you cannot commit too early. You have to go on this experimental journey. And that is the approach of this book, which is to have an experimental but keep the ambition high. And those are two very difficult things to do.

Speaker C: I think about how that may be challenging, especially for publicly traded companies who have shareholders and boards. And I'm thinking about, you know, you said the stock price was at $7 and Jeff really had to make some calculated risks. But you know, boards and shareholders are not looking for risk. They're looking for like predictable results, you know, or for more predictability. So how do you navigate around something like that?

Speaker B: Uh, great question and there's a ton of context in that question, but, but it can be answered. So on one point it also gets to managing shareholders and your board through this type of strategic communication is part of uh, the playbook. So you have to manage those. Secondly, it's, it's about resource allocation and, and especially with the board and shareholders being specific about a specific amount of resource allocation that is going to go to building the future of our company. And the reason we do that is for long term competitive advantage and for long term benefit. Therefore you are going to see some dollars and some press in this area, all of which may not work and everything, anything. Right. I'm setting expectations now. Right. Um, and it gives them some basis to be calculating in. But this was, you know, big Bad leadership was uh, written by me and my co author, Kevin McCaffrey. Kevin was my client at T, at T Mobile. He ran new business incubation, T Mobile. So think of, you know, T Mobile is essentially this core wireless business. They needed to build businesses beyond the core. And what they did was they allocated a specific amount of resource in the. It sounds like a big number, but in the context of a big business it's not a big number. And that was Kevin's portfolio to take through this process of uh, staged experimentation on new business models. And so we learned a lot of these things and applied a lot of the Amazon approaches and into a company that distinctly did not want to be Amazon either culturally or they were, they were a much more kind of predictable out time come type of organization and shareholder base, you know, and everything. Right. But they still need growth, they still need competitive advantages, they still need to differentiate from their Core wireless competition. And so this is the story and how we manage that situation. Because what you're pointing out is exactly what goes on. But if you, if, if what you just say as a senior leaders like, you know, we're gonna innovate and we're going to deliver growth and we're going to deliver um, predictable uh, results that you know, depends on the business, depends on the context. But that can be a pretty tricky combination.

Speaker C: They're often at odds.

Speaker A: They're often at odds exactly in when I think um, kind of another complication you run in on that if you're not taking a big bet leadership approach is you have people that will say, well innovation happens by a genius. Because I would just give someone a faster horse. They always bring the faster horse argument up. But I feel like what they're fixating on is a type of solution versus the problem being solved. Right. And I think when you're building a big bet vector, you're thinking about problem and hypothesis and somebody is stuck here not getting fully to hear how do you help leaders get back to what's the core problem statement and get them out of what their current solution is to get them to that future state.

Speaker B: And you guys are asking the best questions. Um, I think the art of staying in the problem space in order to really rethink things is a completely unexplored area of like what innovation means. And I, and I did just a little bit in big bet leadership, but there, there are other good frameworks and, and work that's done here, but just the encouragement of staying in the problem space a bit longer and, and then when you're talking about solutions, start with some unconstrained perspectives. Don't always put constraints um, on, on it first. But we have a specific, you know, kind of framework and set of recommendations on how to force yourself to boil down and stay in that problem space until you know the user or the situation well enough that you know the real like what we call the what sucks of the situation. Right? Which isn't just this set of like little pain points and short term desires, but it's a different, deeper understanding of like what's the essence of what they're trying to get done and how could you reimagine how they get to the essence being completed? Right. That uh, we, you know, is the, the killer feature and being able to write this stuff out is kind of the discipline of being able to think and then share in a collaborative way to get the best from everybody in a team into the situation. And you're bringing them along relative to the, to what we might do on the situation. So that, that combination of stuff, but it really does, as you hinted at Derek, is stays with understanding the problem better and rethinking it oftentimes from more, you know, first principles and user empathy standpoint. You know, we reference the jobs to be done framework in our book because that tends to be a good framework in most business situations of really understanding your user better.

Speaker A: Yeah, I think um, I think it's easy for strategists, people that are the smartest people in the room, to dream up the strategy and then not break it down into those jobs to be done, not have the ability to get it into those very tactical high impact things. And then they wonder why things aren't forming the way they need them to form.

Speaker B: Well, um, and because you starting from this very obtuse abstract layer, one of the things you can't do with that strategy is you can't go what are the three to five things that must be true in order to deliver the outcomes that we want that are both high impact and high risk. And so if we had better clarity on these three to five discrete elements we could test before we commit to this big endeavor. Right. And that's that when you don't, when you have just that, that top down view of, of a strategy versus a bottoms up like from the user, the problem we're solving for them, then you can't break this up into a set of small steps to be able to better bring forward the high impact things that should be tested for here. And, and that again is back to the essence of the book is like how to have high ambition but test the critical things out first so that we can proceed in a much better informed manner, fact based manner than, than a guess oriented manner.

Speaker A: Yeah, I really like that. I think it makes a ton of sense and I think too often and

Speaker B: all too often like what the in, in these enterprise strategy teams do and, and big plans and everything is they, they forget that 90% of what they're proposing are assumptions and untested foundational elements. Right. And everybody else forgets that too. And that's where you know, the hockey stick plan comes from and why people sign off on them is because we forget. It is typically conjecture that we are basing that off of. And what we believe is you have to recognize that not that those are bad plans, but you have to recognize them for what they are, which is it's a calculated risk. How do you become the shark at the table. When you're dealing with calculated risk, will you gather more information than the other players at the. The table? That's what we're suggesting you do is gather more information so that you are making better informed decisions on those things that are truly assumptions and guesses.

Speaker A: I think the assumptions and guesses point resonates quite a bit. And kind of an inside joke we have is data science and machine learning. They're written in Python, but AI is written in PowerPoint. Like we see a lot of these things put up in PowerPoint slides of like, what the future is going to look like and, and it's not all factual. It's uh, we used to have a CEO would say, I'm not afraid to take a single data point and call it a trend. There's a lot of that.

Speaker B: Right.

Speaker A: But you have to be able to take that leap to test it. But you maybe don't go, maybe don't go all in. Make it part of your vector, but test it safely.

Speaker B: It is, it's like, trust your instincts. This is big. But don't go all in. Right? Like, our final piece of advice and big bet leadership is be an active skeptic, right? Active meaning like you don't just ignore it, you don't just not apply any resource to it. But skeptic, meaning you test, you fundamentally don't believe stuff until you've proven more of it out. Like, skeptic doesn't mean negative. Skeptic means you, you, you want to pressure test things. You want. You, you, you're, you're a devil's advocate in not believing the hype. And it's the combination of those two things, especially in this era of AI, that the winners are going to be activity oriented, applying resources, uh, and enough resources. But they're skeptical. Like they actually want to see things working and learn. And they also understand is that as an organization you have to build this capacity. You can't just say like, oh, now we want to be this test and learn organization and, and go from 0 to 100. No, it's, it's, it's like any skill, you have to build it up over time. And so you got to start this journey while the business is good.

Speaker C: This is more of a personal question, but just listening to you, uh, you know, you have so many great insights, very much based on your experience. What was it like to sort of sit down and write these books that you've written? And um, what was that process like? And was it different than what you expected?

Speaker B: Well, being a writer Was uh, never on my roadmap, you know and everything. Right after Amazon I was a partner at Alvarez and Marcel. Really nice mid sized consulting, uh, organization. And I left Amazon in late 2005. I became a partner at Alvarez. Marcel started working with my clients and I started to insert all this like these, these little things from Amazon, not preaching the big concepts but the little maneuvers and everything. And I wrote one white paper and it was called Future Ready Self Service. And it was about the power of making a process or a capability self service. And there's a ton of, you know, back to this process design discussion, uh, we had thinking about how would I make it self service so that somebody else could use my capability without ever talking to me and everything like that is a way to do the process design, design uh, and everything. I wrote this one white paper and I sent it to my clients and one of my clients at the Gates foundation called me and, and he was like, you know John, this is really good. And then he gave me like 10 things I should have done better on it because he's uh, an editor by background and everything. And his insight was we're in Seattle, we kind of see and the intensity of Amazon. And So this is 2012, right, like several years after I left Amazon. And uh, he goes, I think you ought to write a book about it because it's a powerful message to others and I've seen how you apply these things for impact in our work and with our grantees and everything. So that was kind of the spark that got me to write the Amazon Way. And I, I've been on a journey relative to how I write these things, you know, and everything. Um, and so I, I worked with a ghostwriter on that first book of the Amazon Way and we self published it and it was ridiculously successful but partially just because we launched it in 2014. We caught the zeitgeist of Amazon like becoming like oh, this is, you know, the company, this is the innovation company and there's so much more than a retailer. Um, and then I just, I, I got these opportunities to start coming and doing keynote speeches and so I started getting asked all these, these more detailed questions about like well how would Jeff think about this? How would Amazon do this? Like what was the trick on this? And that's what led to think like Amazon 50 and a half ideas. So Amazon Way and think like Amazon are kind of paired books together, uh, and everything. And that's the full playbook of like all these mechanisms from Amazon and then big bet leadership, you Know, during the pandemic, AI was partially bored because I couldn't get out and give as many speeches and everything. But I was like, there's more. I need to be more specific in the recommendations I make. In none of my prior books was I specific about this is what you should do. I was more like, this is how Amazon does it. You evaluate how to do it. And so in Big Bad Leadership, one of the big jumps I made in this book was being much more specific about the recommendation to be done. And we had learned all this stuff from T Mobile and a few other situations. It was like more about like, how do you do this? And then the final thing I recognized and the inspiration for the book was large scale transformation or innovation is very different than incremental innovation or incremental projects. And there, there was not a playbook for senior executives on what they need to do differently for these major transformations versus incremental projects. And we saw that as a market need. Right. And this book I wrote with, with Kevin McCaffrey. So I had a co author and that was a he, he was, we had worked together before and one of the reasons we worked well together was because we were both very good at kind of thinking through a situation, setting a commitment, hitting a commitment. And because we, we had that trust of like, okay, I know how this person works and we're gonna, we're gonna create a road map, create a scope, work at this as a project and everything. It, it went really, really well uh, together, uh, and everything. So that, that was a little bit on kind of the book journey and my journey as an author. But I'll tell you, it, it's been as a habit of just writing. I write a newsletter too called the Digital Leader newsletter. Like it is so cathartic and rewarding and helps me through, think through things. And if you can't write it, you actually don't have a point of view is my general perspective. And so it helps me test out ideas and go, John, what's your, what's your perspective on this? Um, hopefully it's unique and interesting and that's, you know, so writing is like, you know, this habit that I've fully bought into to, to think better.

Speaker A: Yeah, I love that. And like, I think um, you know, Lauren's background in journalism kind of uh, lines up perfectly with, with some of those thoughts. Um, and one of the things you talk about, self serving, we're making those,

Speaker B: um, self service, not self serving.

Speaker A: Self service. Yes, the self service processes. We call those dog with a note Workflows.

Speaker B: Oh nice.

Speaker A: Yeah, so, but really similar. And we had to come to that same conclusion again. Like coming up to like, if I'm not here, how can I have somebody else do this without any instruction? It's like if you take a note and you can pin it to a dog's collar and send them off. If they can deliver that message, then you've got the process to find. And if they can't, you probably need to.

Speaker B: And that was kind of our litmus test was can somebody find it, install it, use it and operate it without ever talking to you? Like that's self service in a nutshell. And when you think about what, what's my function and, and build the design of that, what are the inputs, what are the outputs? And then you say it has to be self service. Well, you're gonna, you're gonna have a very deliberate uh, approach to designing the work that goes on. Whether it's automated work or, or human driven work, typically a combination. You're still operating it like a, a uh, well defined capability. And, and I think back to the very start of this conversation that is a super critical underappreciated skill and art in business. If you read um, Amazon's last shareholder letter, so the most recent one that Andy Jassy wrote, he talks about kind of this, this um, fundamental orientation, um, to how they design their capabilities this way.

Speaker C: Really interesting. Maybe let's link to that in our, in our show notes Derek so we can make sure.

Speaker B: And I'll, I'll send you guys the link to my, my newsletter that talked about that um, shareholder letter. So it's the kind of the polls, the, the, the essence of it out.

Speaker C: Oh, fantastic. Um, so the way we typically like to wrap um, each episode is with two questions and this is my personal favorite. If you could have dinner with either the 18 or 25 year old version of yourself, what advice would you give them? What would you tell you, knowing what you know now?

Speaker B: Um, bet on yourself earlier. M. Which ironically is the advice. I've got two boys that are 26 and 24 and that's.

Speaker C: Oh wow.

Speaker B: That's the advice I give them. And that doesn't mean you have to be an entrepreneur, but, but do things that have more calculated risk in them. And so that, that's what the advice I would give to 25 year old

Speaker C: John Rossman because do you feel like you wish you had done that?

Speaker B: I played it too conservative for too long and I thought, I thought you know, having a job was, was the goal you know, and everything. Right. It's like, no, you can always get a job, you know, and everything. Right. Doing the right work is the goal.

Speaker C: I think it's so hard, you know, for, especially for certain people. Like when I first came out of school, it was like, I have $60,000 in debt. We have bills paid, like, I need the job. But to your point, like, the jobs are always there. Um, it's. How do you find the thing that you're destined to do?

Speaker B: I grew up in a very constrained household. You know, I graduated school in 1988 when jobs were scarce. And so, you know, I had a scarcity mentality. Um, and I still work to not have that scarcity mentality. But, uh, it's ingrained.

Speaker C: It's ingrained. Especially when it's, you know, when you grow up that way.

Speaker B: When you grow up that way. You know, my, my parents were, you know, World War II, Depression era, uh, people. Like, they grew up in hard times. And so we always had kind of this, you know, it wasn't, uh, a think big household, let's put it that way.

Speaker C: Yeah, very much understand that with that

Speaker A: mindset, you end up not wanting to explore the paths. You don't want to take the risk. Like, okay, I've got this thing. It's safe, we're going to eat.

Speaker B: Exactly.

Speaker A: I got it. And failure feel, in my world, we came from the same area in Michigan, if I'm not mistaken. But like, in my world, it was like, when you failed, there was no, um, that wasn't great. It wasn't like, okay, we'll try again. It was like, right, so you get. That got beaten out of you fast. Like, failure is negative. And. But to your point, with big bet leadership, like, you make those vectors and you dream big and you test small. So those failures are survivable.

Speaker B: That's exactly the system. Right? Like, they have to be survivable. As a, as an enterprise, you need to be taking these calculated survivable risks. Uh, you need to have a system, like an approach for how you do it. And it fundamentally starts with senior leadership and them understanding the role that they have to do and how it's different than their kind of incremental approaches to things.

Speaker A: Yep. Really love that. And so this is the very last question in one of the other fun ones, like, besides, uh, besides your books, what books are you reading? What, um, what podcast are you listening to? What media is consuming your time these days?

Speaker B: Yeah, so, um, I just finished, uh, the book Surrender by Bono of U2. And that, that was a really interesting audiobook to listen to, uh, and everything because I've always been a YouTube fan and just hearing his personal journey and everything. Um, I'm right now listening to Liftoff, which is the story of SpaceX, the early days of SpaceX, and very much enjoying that. And then the podcast that. One of the podcasts that I really enjoy is the acquired podcast, which is you know, the, the story of great brands and um, and, and founders behind them. And it, they're, they tend to be a three hour plus but you know, it is true history and they do a very good job um, pulling it back into the essence of this discussion. They recently had Howard Schultz, the CEO of, of Starbucks, right? And he gave a clinical diagnosis as to the problems at Starbucks. And I think that this was one of typically you get CEOs or ex CEOs like they're, they're, they play it very safe. They don't really tell you. But, but Howard said, he goes, um, the problem at Starbucks is uh, they stopped going on the offense. And just like a sport, a good sports team, stopping your offense is the worst thing you can do. And then he said, and it's related to another thing that happened at Starbucks which is um, we became hubris and we, we stopped, we started thinking that we had all of this figured out. And um, that's paraphrasing ah from him. But I thought that was just the most clinical diagnosis of like when you stop taking um, calculated risks and when you think like, you know, we're not going to suffer from the innovator still amount like, like we're pretty good, you know, and everything, that's when you are most at risk. Not just from a business model standpoint, but from a culture standpoint, right? Because the culture starts thinking we deserve this. Like you don't deserve this. You only deserve what you earn, you know, and everything, right? Like you've been given a gift. Your job is to make it a better gift for the, for the next employees and shareholders here. When you start approaching that from a stewardship standpoint like you, you, you, you start challenging like how you do things and you know, no matter where you're at, there's a better way to do it. And you keep investing in a long term versus having these short term optics to it.

Speaker A: It's so funny because I was reading in uh, a book a while back about how good management, textbook good management is what generally kills great companies. It's like, you know, they're being, trying to be a steward of finances and resources and they're doing the MBA math and they're looking at the internal rate of return and then they don't take those risks because they're making a proven choice. This is a good choice to make. And that's usually.

Speaker B: And that was absolutely in Howard's longer conversation relative to this, which is, you know, when you start managing to earnings per share as like your North Star versus customer delight, you know, and everything you, you, you, you, you might. Short term, that's short termism, right? Like that, that is the definition of short termism. You, uh, like short term, you, you might deliver better financial results, but long term, you're, you're probably eroding brand and equity value.

Speaker A: Yeah, absolutely.

Speaker C: You just gave me a new podcast to listen to. I just subscribed to it. I can't wait to listen to that episode specifically.

Speaker B: Those are good long road trip podcasts. Yeah, yeah.

Speaker C: Or in my case, walking my dog, which I feel like I'm just constantly doing, so that this is perfect for me.

Speaker A: Well, John, this has been awesome. I think like the uh, the knowledge that we got to get from you, the conversation, hearing the, the journey, really fantastic. Really appreciate the time today and had a lot of fun. Thanks so much for joining us.

Speaker B: Well, you guys are great. Thank you for the conversation. I look forward to figuring out how to put it to work out there

Speaker A: and then we'll link to where we can find you. So your LinkedIn, um, your webpage and the latest book on Amazon of big bet leadership.

Speaker B: Thanks guys.

Speaker A: Thank you so much.