Simone Cicero 

Hello everybody and welcome back to the Boundaryless Conversations podcast. This is our first episode of season six. On this podcast, we explore the future of business models, organizations, markets, and society in our rapidly evolving world. Today I’m with my usual co-host Shruthi from Jakarta.

 

Shruthi Prakash 

Hello everybody!

 

Simone Cicero 

Thank you, Shruthi. And I am excited to have with us a legend and master, I would say, of the beautiful mass of product thinking, John Cutler. John is a thought and practice leader in the product management space. He’s known for his deep insights on product development, collaboration, and systems thinking.

 

He is currently an independent consultant but has been working with very interesting and product-centric organizations such as Toast Amplitude or Zendesk and many others. John also writes this fantastic newsletter, The Beautiful Mess, where he explores the intersection of product growth and organizational dynamics. It’s a must-read for anyone looking to understand how to balance, let’s say, strategy, execution, and continuous learning.

 

John, it’s fantastic to have you here.

 

John Cutler 

Yeah, wonderful to be here. Exciting.

 

Simone Cicero 

Thank you so much. So John, as a conversational starter, let’s say, I would like to ask you a question that can be complicated, but maybe we can give it a first stop and then explore the directions. 

 

So let’s say that an entrepreneur comes to you with an established business, maybe several products or many people, and tells you that she’s not coping with the complexity and needs some help in understanding how functions, teams, and capabilities should be organized. What else should she start from? Like rethinking the organization, I guess it’s a condition and a question that many of our listeners have found themselves in. So what would you say and where would you start?

 

John Cutler 

Wow, I love this question. I tend to start by asking them about not directly their belief system. So what I mean is, the most important thing is that I understand, you know, do they tend more on an individualistic kind of view? Do they believe strongly in meritocracies, for example? Do they believe that politics exist implicit or explicit? In their organization, how do they feel, it’s related to meritocracy, how do they feel about skill? Why them? Do they feel they’re the chosen one? That’s why the leader is there. How do they even talk about systems? I think that the complexity community, for example, often takes a very elitist view.

 

They describe the world as if they can see the world and everyone else is either not able to see it or can see it. And so, there’s a lot of what I would call naturalistic leaders who don’t think too much about it. They go home, they have fun on the weekends with their family. They go and ride their bicycle. They don’t read books. They’re not listening to this podcast, unfortunately, or my podcast, or reading The Beautiful Mess. They just don’t care about it, but they’re fairly naturalistic in the sense that they appreciate things. 

 

They might use different words. They might use words like culture or other things like that to understand it. So the first thing I’m trying to do there is just even understand what vocabulary or language we could use to make progress in the discussion. The reason why I mention that is that, for example, the stereotypical enterprise architect who comes in and says, well, you’ve got capabilities and you’ve got this and you’ve got this and you’ve got this and you’ve got this, this, this, this, this, is presenting a language and depending the leader, you the leader looks at them and says, my belief system says I just need to hire smart people and get out of the way. I don’t understand why you’re coming to me with all these words. I don’t need all these words. Talk to me in words that I understand. 

 

So I think that that’s the first question is to understand – their system of beliefs and then the people around them or the people who are advising them or that team of people. I think that I’ve noticed, and it’s probably an Achilles heel or a weakness of mine that even until a couple of years ago, I just sort of assumed there was some sort of one language. The language example I use often is reducing work in progress. You know, I would come in and say, logically, because of queuing theory, you must understand that if you did less work at once, you’d get better results. Obviously, it’s mathematical. See, you see you’re an engineer, even if I’d be talking to an engineer and they’d say, well, what’s wrong with people having more work than they can possibly do? That’s life. I don’t understand why you’re so stressed out about this crazy work-in-progress thing. 

 

Anyway, I’ll pause there for a second. have many, many more directions, but I just want to give you the first thing that I’m going to talk about is understanding their perspectives on systems and people and society so that I can find a language that we can even start talking about.

 

Simone Cicero 

Right. I mean, this makes me think of a couple of things. So first of all, you know, the idea of, you know, the impact that leaders and sources and creators, originators, founders, you know, the past week was the week of the founder mode. So everybody is talking about it. But the first thing is the radical impact that a founder’s belief system has on the product.

 

So that’s one thing that you point out very quickly. So you say as a coach, the first thing I need to understand is what is the belief system of the CEO or founder or whatever to understand how to relate with that. 

 

And the second thing is it feels like you are anticipating that there is a potential diversity on how you can manage a company and still be successful, let’s say. And maybe success is also defined in a different way by different founders. So I’m also curious to understand what are the implications of the product. 

 

So for example, let me say, I don’t know, a certain product with a very strong, I would say, directive founder with very strong ideas and very meritocratic, whatever, I don’t know. On the other hand, you have a founder who is a bit more open to diversity of ideas and experimentation. You end up with really different organizations and products. Am I right?

 

John Cutler 

Yeah, that’s a wonderful way to put it. I think that we don’t want to over-index on startups, because you could argue that those models, the founder, I think it was Mintzberg or someone, he calls it the personal organization or something, these are situations where the belief system of the founders or founder CEO have a huge impact. And it’s very basic, you mentioned what impact might it have, right? And so let’s just come up with a very classic example. 

 

My friends at Google, for example, talk about promotion-driven development, PDD, which is many of the assignments of projects, or when people consider new technologies or what things get greenlit or not is often based on someone saying, I’d like to get a promotion. So I’m going to propose this project. This is what the project’s going to do. And this is what it’s going to look like. And this is what success is going to look like. Go. You know, to do that. So what’s really funny, for example, in Silicon Valley, there’s a reason why in these companies you find eight versions of the same service. Because no one is going to slow down.

 

And no one is going to risk their promotion to let other teams do what they need to do. Now you imagine another environment where think of the exact opposite of that. You know, again, I’ll use the enterprise architect idea. You know, we can’t have more than one version of this service. They say, okay, you’re right. We need to be very efficient here. That’s very wasteful. We wouldn’t want to do that. You know, we wouldn’t want to have duplication like that.

 

So think about how that belief system, you need to move fast. We need to have independent teams talking to other teams. Is either bad. I’ll give you an example from a Silicon Valley company just for the last couple of weeks. I said, well, is that a platform? They said, no, no, no, it’s we’re more of a sales engineering team. And what do you mean? He’s like, well, we just tell managers to work it out.

 

Good managers should just be able to work it out. And I say, you mean you don’t worry about the interfaces between the teams or anything like that, like clean interfaces? They’re like, no, no, that’s for Amazon. That’s not us. Here, we’re moving fast. If you have a good manager, the manager is going to coordinate things for the team so that the team can move fast. What do you spend your day doing as a manager? 50% of the time is dealing with other teams to resolve dependencies and manage to act as a human load balancer.

 

So I’m just giving a couple of examples here in the most extreme examples where this belief system of a founder or this belief system of an early person can have a very strong influence. I think what’s very interesting though is I’ve described these rapid scale-ups where the founder’s philosophy has a very strong bearing. If we flip this and imagine a 150-year-old company or a 75-year-old company, with so much inertia, there’s no real strong opinion or perspective in the culture whatsoever. You begin to realize that having some of that kind of initial philosophy of the founder is actually kind of helpful. So these companies, it’s very hard to get any kind of refactoring of the org. There are so many layers of sort of institutionalized incoherence in those settings. Everyone has their job and wants to keep their job and wants to do these things any type of refactoring or any type of creating a more distributed or more independent model. It just doesn’t happen. So there’s a reason why there’s big companies use SAFe the only way they’re going to get anything done is to do SAFe because they’ve got teams of 1500 people basically because of all the dependencies they have. Meanwhile, at the exact opposite end of the spectrum, you have teams of three, four, or five people where even the mention of process or even the mention of platforms, it’s like, just don’t worry about it now. We’re just. Just go, just go, just go, we need to get it done. So I just find it fascinating. It does make a difference in the philosophies of these companies.

 

Simone Cicero 

I mean, of course, when you work with large companies and especially old companies, as you said, first of all, they tend to be not entirely digital. So I think there are some and I would like to discuss this maybe later, but there are some entrenched elements of culture and management that are hard to connect with the modern lingo we are talking about when we speak about platform engineering and we talk about, I don’t know, product management and so on and agile and whatever. Because when I work with companies, for example, I don’t know, from mobility or industrial printing or I don’t know, digital pathology, whatever, they have a very complex entrenched story that goes into that.

 

But even if we think about digital companies, there are, I would say, there are two types of companies. One is the single product company that is very much focused on a product and can be managed in this very kind of hierarchical and source-centric way.

 

And then there are the multiple product companies. My perception, our perception at Boundaryless is that markets are going in the direction of portfolio companies and multiple product companies. So my question for you is, let’s focus for a moment on companies that are reasonably digital, reasonably modern, multiple products, portfolio companies growing, trying to find new ways to monetize and increase their ARPU (Average Revenue per User), and whatever.

 

My question for you is, to what extent can you really work in this mess without process-ualizing, making an interface, or I don’t know, maybe standardizing? Because I mean, in general, the question of reaching agreements and finding standards and modularizing has been very high in our interest, rather, I would say, for ages now. But it’s really important to understand that finding an agreement is complex. So in your experience, what are the minimum trade-offs that companies really need to have on their desk to reduce the otherwise uncontrollable complexity and messiness of the work they’re doing?

 

John Cutler 

Yeah. I think that, okay, this is so fascinating because let’s go at it from two angles. And so in rapid scale-up companies, the primary driver to add products is you mentioned like ARPU something, you know, just imagine you’ve disrupted a sort of solution and you’re going to keep expanding your product footprint to different parts of that business and that value chain and try to sell them more stuff.

 

Now what’s fascinating though, is that’s very different than something like Cisco just acquiring companies based on a platform premise. One is growing into all that they’re growing, expanding, growing, expanding, growing, expanding something like a Cisco it’s there. It’s big. They’re, just like, we’re going to go and put these, we have a platform hypothesis around why this is going to create economies of scale. So something like a Cisco is thinking goodness. Now that we have the customers, we can sell them other stuff. Let’s just go and buy a bunch of companies to do it. That’s not so dissimilar from the rapid scale-up startup. 

 

The growth intensity is different, as the rate of growth, and the sort of level of chaos in those particular environments. So what’s happening in the scale-up space at the moment is the pendulum is swinging back toward individual products. So you saw, at least conceptualizing it. So I worked at Zendesk at a certain point, we had 15 products or 12. Now there’s Zendesk one. That’s how they package it and sell it to customers, right? You see this pattern in a lot of scale-ups that they went multi-product, but in effect, those products were kind of a combination of a feature and a package and a pricing package. 

 

And then they realized, they hit the wall, they realized they had 40 products and they’re like, we can’t actually continue to thrive and exist efficiently as a business with this many, with this much duplication. Our customers hate it. They’ve shipped the org chart to customers. Now customers don’t even know what product they’re buying. My goodness, this one or that one, or we’ve got all these different things.

 

And so the pendulum is swinging back towards at least conceptualizing. So you’re seeing companies go from the GM or general manager model, which was popular during rapid growth. You’re seeing it switch back to more functional organizations or more sort of centralized ideas to do things. And I just, first of all, I think it’s funny that it’s, it’s the same multi-product motion, but in a very different context, one very stable existing company, not growing very quickly, buying a lot of companies to sell their different products.

 

The other one is a company still growing 10, 20, 30, 40, 50%, 80 % year over year, offering different products to do things. So I think what’s important for people to think about it, and I noticed this in a lot of the discussions of whether it’s team topologies or the org design discussions I hear is the rate of growth of the company at the moment. What’s going on a lot of this discussion is coming from large legacy companies where they are growing very slowly.

 

And so a lot of these ideas of these like clear interfaces and why don’t we do it this way and we’ll have all this modularity and do these things are in environments where they’re essentially kind of reef. You’re going to a company that’s not growing a lot. And if you bang your head enough against enough sticky notes in Miro, you’re going to understand their domain model. You’re going to understand how these parts fit together. You’re going to draw beautiful lines across it and say, this is this value stream and that’s a value stream. And this is this value stream. And it’s going to be amazing. We’re going to just refactor it. It’s going to be great. That’s very, very different from a situation where things are at very different stages of maybe award maturity phase, where a lot of stuff is emergent. There’s a lot of condensing of products to get anything done. Sometimes you need to launch little speedboats, but you need to take the speedboat back into the main product.

 

You have eight versions of the same service. At some point, the company had to decide to take those eight versions because they needed that to move fast. They were not going to move fast enough if they had one version of the API. They needed eight versions and they were fine with the chaos. But now the challenge in my space, this rapid scale-up space is these companies don’t actually have the platform muscle. They don’t really have an ecosystem unless you’re, I mean, Amazon’s 30 years old or plus, right? So, okay, they have that.

 

But a 10-year-old, 15-year-old, rapid scale-up tech company that everyone sort of says, my God, these are amazing products. They, don’t know how to do this yet. Like they do intellectually, but they’ve not had to do it at this rate of growth and scale. The idea of slowing down to speed up or condensing the eight services into one. It’s new. So I don’t know if that’s interesting to the listeners. It’s like, the rate of growth is just an important factor in all these models that we use. And often we don’t include that in the models that we use.

 

Simone Cicero 

Yeah, I know that Shruthi has a question coming up, but I want to just underline a bit of this conversation for our listeners. So what I perceive is that there is a phase in a company, the growth phase, where according to what I understand from your conversation, you’re telling us these companies don’t care about standardization, modularization, optimization, processes and value flows and so on, just because everybody’s busy in growing and creating. And maybe also because this fast pace of growth doesn’t put any pressure on efficiency and so on. And then at some point,

 

John Cutler 

Right. Until the last year, until the last year, then it definitely put pressure on efficiency. Yeah, exactly as you’re saying, perfect summary.

 

Simone Cicero 

Yeah. And at some point, know, the growth plateaus and that’s where you start to consider efficiencies, you know, because your margins, you know, of course, know because when the growth is plateauing is also because your competition is catching up, you are more mature. And so you need to be more efficient and possibly maybe again, you also mentioned Wardley and I think this is interesting to connect.

 

So when the company gets to that level maybe you start to modularize in the interfaces and of course, your organization needs to catch up with that. So you start to maybe put things in the right place and wrap P &L around the right capabilities and so on. This provides the interfaces for the next generation of growth. So at that point, maybe your leadership really needs to show up and say, you know, how is the ecosystem using our services so that we can build the new.

That’s probably the challenge that you have at that point.

 

John Cutler 

Yeah. And the reason why I mentioned this though, is it’s not like a platform. I was a search product manager at Zendesk, for example. So search some kind of, know, we had 15 use cases across the company of people using search ranging from searching for tickets. Like my number ticket one, two, seven, five, then that’s one search problem, a simple search problem. The other search problem is, you know, by arcane ideas, know, show me other tickets related to this so I can find a solution. Those are vastly different problems. 

 

And so one of the interesting parts there is, and I think this example, it’s a very simple example, but hopefully it’s helpful to people is there were these, the sort of Genesis stage for some of the service offerings that we had definitely required my team to get out of platform mindset.

 

And go and get really close to customers, get close to domain experts. We knew the domain of search and what could be done with data science and search, but we weren’t out there with those teams that were going and doing, making the new chat interface or who knew a lot about other domain things. So we’re only a team of six to eight people. And in that emergent stage, we had a whole portfolio of bets.

 

We had a portfolio of 15 use cases with very different characteristics ranging from searching for, you know, number strings all the way to select semantic search and to things like that. And that’s the reality in a rapid scale of things. You don’t have three decades of the problem to go in and do it. And you had to think about, oh crap, you know, okay, this month we have to go and basically go and live with that other team to understand that new surface area, to understand how it’s going to impact search.

 

And we need to maintain our number searching thing to be performant and to make sure it’s doing it. So all the concepts I think relate to the things that you talk about and, it’s popular in the community. But I think it’s like the real world in these rapidly growing companies are, are it’s much more dynamic and you have to, like, if we just jumped ahead towards thinking, we’re going to make everything a standardized API and do that – we would probably not solve the customer problem.

 

So we had to do things that don’t scale. Had to perform almost as to use the team topology things at any given point, we were a platform team, an enabling team, a complicated subsystem team, and not a value stream team. We were three of the team types in team topologies with seven people. So that’s early, early – we’re very, very far away from a nice P &L. We’ve got 10 to 20 people. We’ve got this. Leave us alone, submit our tickets, and everything cognitive load. No, no, no, none of that. Everything was through the roof because it was early. And so I think that that’s just interesting, hopefully that story helps, it can feel real to people.

 

Shruthi Prakash 

Yeah, I mean, just to sort of touch upon that a bit more, right? Like I see that, like you said, right? On the whole, let’s say the shift from growth is happening slowly toward efficiency. Maybe that path is still a long way to go, but there is a necessity to sort of strike that balance between how maybe legacy incumbents are trying to modernize versus digital companies are, let’s say, trying to potentially create standardized practices and so on. 

 

Within this, there is a complexity of multi-products, some of which are traditional products, some of which are new, and so on. So how can companies create that balance and the need for autonomy, especially from a perspective of how new entrepreneurship for product teams is being developed? And is there therefore an alignment required for their broader portfolio of products?

 

John Cutler 

Yeah. The first thing that thinks about, I mean, this is going to get very tactical. There is a difference between pricing and packaging and a product. So just because the marketing team or someone decides to add a price point to it, the problem in my world is everything has suddenly become a product. Everything is not a product. Just because you have six people or eight people thinking about something does not make it a product.

 

And yet I kind of feel bad because my community, Marty Cagan, all these people are telling the rest of the world product, this product, that product, everything. It’s not a product. The customers don’t think of it as a product out in the world. Don’t think of it as a product just because you slap a SKU on something doesn’t make it a product. The people out in the world want to solve their day-to-day problems. It’s very, what’s happening now is fascinating because I mentioned, for example, events storming or DDD or any of this stuff in the rapid scale-up world, they look at me like I’m crazy. They think, what is this stuff? I say to the UX person, look, it’s almost like a journey. It is, wow. That’s amazing. Engineers are thinking about that. Like, yeah, they use that to architect systems that you can do that. These are people who’ve only worked at Meta and worked at places their whole life. They look at these things and they think like, my God, this is a whole other world to do these things.

 

But that’s because they’re in a world where, you know, they’ve just drawn these, the primary organizing principle is speed and growth and selling new stuff. So anyway, back to the actionable thing to do you have to redefine and be honest with yourself about what is a product and what perspective you’re taking on a product. And I think that increasingly in my world of business-to-business software as a service, although they’re not saying it, they are acknowledging that it’s much more of an ecosystem.

 

The whole company is the product. The whole company is the product that helps customers achieve their business goals and do different things with it. We’re not saying that yet. We’re still using this kind of Kagan language and we’re using all these types of things. But realistically, you start to see an acknowledgment from my world that that’s true. And I don’t know if this is helpful, but so then let’s get to the other side. 

 

These sort of big, large digital companies. These pseudo-digital companies realize all these types of things. I think right now the main value of the product-centric language to them is connecting with customers out in the world. Is this idea of like, we actually solved? Remember my Zendesk example, like, are we connecting with the team that’s connecting with the team to make sure that we can make an impact on people out in the world? Like that, that’s the language that you’re trying to encourage.

 

And I think that this is probably what these big companies need at the moment. I think the reason why the enterprise architects and the whole, tech side of the house are scrambling at the moment is like, my God, how are we going to make this happen? How are we going to admit we’re not, we were architected as a centralized IT team. And now they’re saying we need to be able to move fast and get out into the world. And so the language is very compelling. It’s the language we need right now at the moment. However, I think what’s going to emerge in the next couple of years.

 

And if I didn’t answer your question more practically, we can go there back again. You can just say, be more practical. I think what we’re going to see in the next couple of years, in the next sort of five to 10 years or two to 10 years is almost a convergence of this language. The traditions are going to come together in a more sensible way that captures the learnings from these complex environments and applies those to these rapid scale-up companies and then captures the essence of the product stuff without creating almost like a, know, like a cult of product stuff for the other side. And so that’s my hope for the next five to 10 years that we’re gonna get more, we’re gonna get a common language of this, but I don’t know.

 

Shruthi Prakash 

I mean, this is interesting, right? I was in a webinar earlier where we discussed the topic of how leadership itself as a word these days has, let’s say a negative connotation, right? With that being said, like, how do you think, let’s say indexing or the current language that we have on product affects the overall, let’s say, the cohesiveness of a user’s experience?

 

John Cutler 

Yeah, that’s, and this happens in my world too, in this rapid scale-up world, they’re shipping the org chart and they never believed that the support experience was part of the experience. They never understood. Mean, to put it in context, when I was at Toast, Toast does a point-of-sale system for restaurants. Only in the last year two or three were they imagining, do we now have, do they have a product manager of the support experience? VP of, so applying design thinking, data, and engineering skills to the problem of what is it like to have a positive support experience. Now think how funny that is. 

 

You take any big brand, IKEA or whatever, they’ve been thinking about the support experience for the last 15 years in that particular thing because it’s just part of how they had to work. They have service designers, have everyone trying to understand this particular experience. What didn’t they have? For them to make any change in any technology system takes a year. So to me sort of more actionable way of describing how it’s coming together in very clear terms. It’s like these companies, these rapid scale-ups believe that technology would solve anything and that humans don’t exist. If our product is good enough, it’s never going to need support. Or if we want to ship something crappy now, support will deal with it and then we’ll improve the product. And then they won’t have to deal with it anymore. All these economies of scale assumption that was software as a service.

 

It’s unlimited zero cogs once you’ve built this beautiful, that hypothesis has been proven false. The dream of software as a service, it turns out that you need to keep competing with people. You need to add complexity to your company. The dream of SaaS is that you build once and then you never need to build it again. Oops, that didn’t work out so much, right? On that side. However, that kind of product thinking, there’s a – There’s a company in Europe called “theydo” and they’re like a journey management software, but a lot of these modern companies are buying that software because it encourages them to think of these journeys as a product, technology, data, and things. So I think that that’s, in a very clear way, that’s how the disciplines start to come together in an interesting way here as we do this.

 

Simone Cicero 

So if I can try to jump in the question I had in the background was, so if I don’t, let’s say I don’t over-organize to avoid shipping the organization, what is the alternative approach? So do I feel it? Do I perceive it right that you start from the experiences to customer experiences?

 

John Cutler 

Yeah. And I think that’s the only way you can start really. Mean, if you’re not thinking about, if you are not thinking about your customers and their needs and what they’re doing and delivering on all those things somehow, all bets are off, right? So that kind of starts with the first element.

 

The one very, very interesting thing about what you said that we don’t talk enough about in this business is what is just generally the idea of scaffolding. This idea is that strategy and structure will never be in alignment if you are growing. If you have been around for 30 years and aren’t growing, it might not be an alignment, but it’s a much more complicated problem to align strategy and structure. Strategy is not moving. The structure is what it is. You will just align those two things because nothing’s changing. But if you think about any period where strategy and structure are always out of alignment, the question then I think that we don’t talk about enough is how we create the scaffolding to continue to deliver quality customer experiences while managing the emergence of where the direction of the architecture is going in these things. If we just ignore everyone, this is what bothers me on LinkedIn. Everyone will say, that if we just had a strategy, everything would be fine. Really? If you could predict your customer lifetime value for all your customers, you’d be a telephone company. Do you want to be a telephone company? No.

 

Okay, so your strategy next year will be different, right? Because you’re growing, things are changing, you’re in a dynamic environment. We just need a strategy. Do you mean like this? Yes, if we could just have that, everything would be fine. Enterprise Architect, that’s great, the domain’s great, okay, well, I’ve got these things. It’s so amazing, this is good.

 

But if it’s not changing in a year, you’re in a very static environment to do those things. And so the point about the scaffolding part that I bring up is, I think the very important question is, how do we create coherence? How do we create coherence in a perpetually incoherent or out-of-alignment situation so that we can move forward, so we can nudge things into the direction that they need to go, without kind of forcing it? And I know that sounds very theoretical, but in a very practical way, we are going to ship our org chart, whether we like it or not. However, our org chart is not going to be perfect. And we want our customers to be able to enjoy this. So you know what? There will be times when some teams will need a program manager to manage all those dependencies for them. It’s not ideal. We don’t want that to be forever. We don’t want to adopt SAFE in 10 years. But we just, it’s incoherent and we need people and technology to act as the impedance adapter. You could think of it like electronics, know, an impedance adapter takes a charge from one side and a voltage on one side and it converts it.

 

To be able to do it. So I think this is the fascinating question that what you say brings up if we assume strategy and structure will never be perfect. In fact, if it is perfect, it means we’re a dead company. And if we imagine that will always be out of alignment, there will always be a tension between the ideal and the current reality. And so we need to manage what it feels like to be in perpetual incoherence coherently which is a real fun problem. That’s what I think a lot about these days because it’s easy to dream about the perfect architecture and then easy to dream about how shitty things are right now. It’s very hard to imagine what it’s like in that kind of always incoherent zone. Anyway, I don’t know if that brings up any other ideas for you all.

 

Simone Cicero 

Yeah, I mean, again, I would like to maybe ask you a couple of practical elements that we normally use to increase coherence in otherwise distributed organizations and listen to your point of view in terms ofwhetherf you see them useful or not. So one thing you said, you said, first of all, start from the customers and start from the experiences that the customers are seeking and having with your organization’s product, and one thing that we often do with larger organizations in general with portfolio organizations is to map the portfolio visually and also try to consolidate information on the customer in a way that everybody can see the same things. So for example, if I do an interview with a customer, your profile in these customers needs to be accessible to everybody.

 

And then another thing we do. On the other side, another thing we do is taxonomies. So we try to at least have a conversation around what our products are. So what type of products are we building? Sometimess we do not really enforce the taxonomy, but at least having a conversation on the taxonomy itself will to understand how things can plug into each other.

 

And then, of course, there is the question that also Shruthi brought up. So autonomy, entrepreneurship, and we use sometimes thesemicro-entrepreneuriall P &L bearing structures to kind of not just give people fake autonomy, but give people real autonomy. So which of those artifacts sounds interesting or useful to you?

 

John Cutler 

I love them all. Love those. Mean, that’s the tool chest that I’ve been using a lot lately that is just shared. The big aha moment to me was alignment versus coherence, which is all very probably news. It’s, probably very familiar to folks who listen to your podcast, but how many environments I’ve been in where someone says we’ve got to define quality or we’ve got to define value?

 

You’re never going to, those things benefit by having many different interesting definitions, but the macro level idea of creating sort of coherence through shared language or exploring the different languages that people have from things using different frames. I did an activity with a company recently and in prepforo the activity identified over 18 frames for strategy – the technology ecosystem view of strategy, the competitive view of strategy, the customer’s view of strategy, the go-to-market motion view of strategy, the blank view of strategy, the financial view of strategy. 18 different frames. And so the idea that like, we’re primarily in the sort of coherence building business in what we’re doing, where if we just pick one of those frames, it’s going to be impossible.

 

If we pick all of them, it’s going to be paralyzing complexity. And so this idea of dipping into creating shared language and different views, but then coming up with purposely simplified models or some kind of understanding of what’s happening so that we can make any progress. Everything that you mentioned, that’s how I think about those particular ways of doing things. 

 

And I think that the one thing that anyone should take away is that we in this community tend to get attracted to certain frames. We don’t consider the political frame in the organization. We tend to sometimes imagine teams as if they were architecture. We don’t think of the community frame as our team. We think about it as, someone the other day was saying, well, all engineers just want to be left alone. That’s why we need standard interforces for particular teams. They were making a lot of assumptions around the belief systems of the people that we’re in.

 

So the one thing that we can all probably do is challenge ourselves into those different frames to go outside of those frames to create that shared language or those beliefs. But anyway, yeah, in general, those are the techniques that I use. 

 

The thing that I have understood is we’re rare in the grand scheme of things. The people in this community and the complexity community and the architecture community were naturally drawn. I for ould go for six hours. I said this the other day. I could spend six to eight hours starting with a blank whiteboard and just be patient enough in that room and take each of those 18 frames and go down that road. You’re probably exactly the same. And the listeners are exactly the same.

 

But it’s also our job not to be elitist about our frames. And I’ll give you a very specific example. I was talking to someone who’s in the complexity community and they said, well, strategy emerges, you see, we shouldn’t have a clear end state of the thing. Therefore, I’m gonna go and interview all the people and collect all the stories to create coherence in the company. Okay, that sounds interesting. So you’re gonna collect the stories and that’s good. And then they kept saying, but you know, strategy is not a, we can’t know our strategy, it needs to emerge. 

 

And I said to them, well, what’s gonna happen when you talk to someone in the company who is a human being who wants to have a clear vision for the future? You’re gonna say they’re wrong? Or are you gonna be able to step back from your own view of this emergent strategy, this and that? So what you find is that in our community, we privilege certain beliefs.

 

And then we expect people to go down the rabbit holes that we create and the views that we create. And then we get somehow angry at them when they don’t stick with it for 10 hours. So we also need to be in the simplicity business. I hate to say that every, feel terrible saying that, like it makes me lose sleep. I don’t want to be in the simplicity business, but we need to come back from going down these rabbit holes and then create accessible models. Can’t keep the complexity of all these things in ourhead. And I think that that’s untapped.

 

I think that these types of, our job in that, I think is unexplored. I don’t know if you share the same perspective, but it’s something that I’ve been noticing a lot.

 

Simone Cicero

One thing that is lingering in my mind is that, of course, know, accepting the reality of a complex organization, okay, and of a complex world, okay, also deals with a different approach to accountability and managing organizations. So, you you cannot have a complexity-friendly mindset as an entrepreneur and then think that you can manage and create an organization where everybody’s safe, nobody has risks, and everybody can just execute the plan. 

 

Probably at that point, need to give a lot of autonomy to teams, but also they need to get accountability because essentially what I felt when you were speaking is how can you then manage your resources or manage plans or r,oadmaps and then I said, you maybe you just have to make everybody accountable to the customer or to one customer at some point. And that’s the way that you create this forcing function that is really complex, , friendly, and can run the organization on its own because that requirement is that you just satisfy a customer need and you are possibly PNL positive. So what do you think about that?

 

John Cutler 

Yeah. Well, this was just about an hour ago. Had this way to describe it. And it’s with the words, “justand ” “but” “cthere are there’s the jjust We just need to have leadership. We just need to do this. We just need to organize. We just need to, we just need complexity. We just need to have better leaders. We just need to have complexity and form leaders. It’s all it’s like now. The bhinkers are thinking, but what happens? What happens in this context? But what happens with this? And, buat happens with this? And then the third one I realized this morning is the can view. We can’t oversimplify the world and then at the same time,e we can’t drown in the complexity of the world. What can we do? What can we do to move this forward? 

 

So I think that realistically when I’m thinking about it, probably similar to your thinking, I’m imagining there is a balance. Not the, know, Agile tends to focus on seven people and that’s a feature, not a bug.

 

And then, you know, all these scaling frameworks focus on thousands of people. And we realized that that’s not just one group of people, but I do think that you’re the concept putting forward that there is some boundary, probably 20 to 50 people, especially if they’re workingremotelye. And it’s probably one, two, it’s probably two levels of hierarchy or three, maybe max. Cause that’s the most that everyone can know the people and keep some semblance he, the changing realities on the ground. You know, if you go to five levels, by the time you go to five levels, by the time any problem on the front line gets to the person at the top, you don’t know about it anymore. It’s just, it’s just now it is, but there is probably, and that to that point of P and L, like either direct P and L or some proxy that people have a fairly high degree of confidence is linked to P and L. And I think that that’s probably where this all goes that everyone is thinking about where – It’s probably not a two-pizza team. It’s probably like an eight to 12 pizza group, you know, because if you get too specific in most environments, that’s maybe the ideal, but you only get there over many years, perhaps like breaking these things down. 30 to 50, you can be entrepreneurial. You can address a customer problem. You can have a proxy that means something to the business. You’rere still probably going to evolve some levels of some kind of hierarchy or power for some kind of reason, and you can do helpful work. 

 

So I’m probably maybe – If I understood your question, but I picked up on your question was, I think that that’s the, that focusing on this sort of what is that team of teams module size, and then focusing that perhaps it’s bigger once something’s more stable and growing less rapidly. And it’s probably smaller when it’s growing a lot faster and it’s a lot more emergent. That’s probably.

 

And to bring up the technologies like AI and things that I think that these technologies will largely maybe enable these types of groups to work. I think that’s probably, and that’s why I appreciate your work. That’s probably the direction big enough to do meaningful things, but small enough to still be able to hold some parts of the complexity constant to make progress is probably where it’s going, hopefully for organizations.

 

Shruthi Prakash 

I was going to either way ask you maybe to touch a little bit more about, let’s say the effect of technology, right? And all of this, so be it, let’s say AI modularity and so on. How does this impact the journey even in terms of how, let’s say the organization is shaping and evolving, how the role of maybe let’s say product managers is changing. So what’s next in terms of the impact with regards to the organization?

 

John Cutler 

Yeah. There is one specific use case of AI that I think is the absolute game changer. And that’s the, if we assumed before there is a limit to how many ways you can take a central source of truth and recontextualize it for different contexts. Very good example. If you work on a product marketing team – you are not going to have 75 personas. You’re going to have three personas, not because the sales team thinks that’s reality, but because the actual limiter, the cognitive limiter is three. So you’re not going to be able to train a salesperson on 75 different personas. Your most experienced salesperson will know that there’s 75 personas, even if they say it, they won’t say that. They’ll just in their actions, they’re always modifying their actions to do that. 

 

So I think that the absolute game changer in all this is, I mean the, you know, the code completion and, know, yes, it’s going to make people more efficient, but the thing that creates the huge force multiplier is actually being able to create organizations that exceed the bounds of one view of a data. I, I’m not, I’m not an engineer, but you have, you have data and you have many views of the data. And right now we have a limit to the number of views you can have to the data because the consumer is limited. You can make infinite views of the data, but the consumer can only process three views of the data. But what we’re going to have is we’re to have one, we’re going have data and you’re going to have it recontextualized in many different ways. And I think what this allows is it breaks down the central limiter. The central limiter was just cognitive complexity for different perspectives and framing. 

 

So back to our example. Let’s just say you have five dimensions, the seniority of the salesperson, the 72 personas, the stage of the customer journey that they’re at, the culture of where the customer is located and things. You already have 3 million variations or something like that. I don’t know. Like you have to the Nth problem, but now you don’t have that problem.

 

You have something that can go there and say, by the way, you’re talking to someone from Jakarta who’s in an enterprise with 3000 people. You’re a new sales person. You need to get on the call and you need to talk about this as your script to do it. How crazy is that? I’m using sales, but you can imagine for any customer problem. So what it’s going to allow us to do is although we’re never going to, know, complexity is, not this sort of, you’re never getting there but it allows something very, very profound in organizations to enable the type of stuff we talk about. 

 

So the idea that you could spin up specialist teams that would normally be rate limited by the number of times they needed to recontextualize their service across the organization. Now we’ll be able to spin up a specialist team.

 

Because now you can recontextualize what they’re doing across an organization. It’s, I don’t have even the words to describe it yet. Cause I’m not a specialist in that area, but this is just my simple, my simple person’s way of seeing this and how it might make a difference and enable more creative organizational charts. 

 

Like the example I made of the 30 to 50 people in a massive organization of 5 ,000 people, the rate limiter would be how do those 30 to 50 people describe what they’re doing to another thousand teams, 500 teams or whatever. Now that rate limiter might not exist. And it becomes very interesting because it’s not the code problem. It’s not the API to the thing – oh we have a standard interface that 500 teams could use. That wasn’t the problem. It was the contextual problem that was way bigger than a standard interface. And so maybe that problem gets removed or changed even slightly could be a huge thing.

 

Simone Cicero

Well, it generally improves the quality and reduces the cost of internal shared services to some extent, if I understand. I mean, again, it reduces the cost of contextualizing it and makes it much more effective for niches. Just a quick one before Shruthi goes with the breadcrumbs. I feel that lots of people are talking about the impacts that AI, for example, or technology advancements are having on the supply side, on how we build products and so on, how we run organizations. What do you think is going to be the impact on the customer side and in turn how this translates on the product and organization?

 

John Cutler 

I’m not an expert in that. I I think anytime you see technology, you see change consumer habits. And we saw it with mobile and we saw it with different. mean, if we just divide it the last 30 years into.

 

Simone Cicero 

I mean, let me be more clear. What I mean is, how much of the product and the organization goes back in the end of the customer? We witnessed already a major transition of power from the organization to the customer, from the brand to the customers in the last 20 years. I feel it’s going to be much bigger now. There’s a lot of what we produce in terms of value as organizations and products that is going to go in the hands of the customers. What do you feel about that?

 

John Cutler 

That’s an interesting way to put it. That’s making my head explode. I might need to pass on that one because it would definitely mean… No, yeah, I am…

 

Simone Cicero 

We’re going to have another episode maybe on this or I would love to read something from you on that topic.

 

John Cutler 

Yeah, I mean, I think a lot, this is probably not answering the question, but I, I just think about a lot of B2B companies that essentially applied cloud.

 

And created in the B2B space was this idea is called system of record system of engagement. And then they said something like, everyone wanted system of intelligence. That’s what I’ve worked in analytics companies. So we were like system of record system of engagement system of intelligence. And, the idea, I, I don’t think it directly answers your question, but I’m just, I think that this makes that possible. But then to your point, it creates this sort of shift.

 

And I just, yeah, it challenges my head to imagine. So we’ll have to do another, I’ll try to write a blog post about it.

 

Simone Cicero 

Yeah, that would be fantastic actually.

 

Shruthi Prakash 

Yeah, thank you. Yeah. So, I mean, towards the end of our podcast, John, we have a section called the breadcrumbs section where we essentially ask you to share some recommendations on maybe books, podcasts, movies, even music, whatever inspires you in your journey. So our listeners can gain from that.

 

John Cutler 

Yeah, there’s a couple of things. think probably some folks are familiar, but in the last year or so, I read a book called Images of Organization by Gareth Morgan. That had a pretty profound impact on how I see things. It made me realize I was very biased to certain frames of organizations, but I hadn’t really deeply considered like the political frame. And if you read my writing, you can see I’m kind of all over that at the moment. You’re probably getting bored of it by the moment, but I’m really into it direction to be able to do those things. There are some other books and I’m just reading out my list of books which I think would be interesting.

 

This is an older book, but I love by Gerald Weinberg. And Jerry Weinberg, hadn’t read this book called The Fieldstone Method. And in The Fieldstone Method, he presents this beautiful analogy for life, which had a huge impact. And he describes it as, in life, we’re wandering around picking up field stones. Like on the beach, you pick up field stones.

 

This actually has probably a lot to do with AI and book writing and all kinds of stuff too. It’s pretty crazy. So you pick up these field stones like, I found this little thing or found this thing. But, but in our case it’s ideas. And he talks about the idea that eventually, yeah, maybe you write a book or you do something, but you’re taking your field stones and you’re assembling them in a wall.

 

And there’s just something very interesting about that, about distributed intelligence and the idea of, there’s these many note taking books too, about how to take atomic notes. And there’s all sorts of stuff in this sort of second brain community, but Jerry Weinberg, it’s just beautiful how he puts it. Like we’re in life, we’re picking up these stones. You got to kind of keep the stones. Don’t force your, don’t, don’t judge yourself. If you see something that’s interesting, pick it up and make sure you write it down.

 

And then later we can frame our ideas by collecting these stones. So I thought that was a very, very interesting book that I’ve been reading. And yeah, I mean, those are, there’s, there’s a lot. I’ll leave you with one thing. There’s a book by Jeffrey Pfeffer. I think it’s his name called leadership BS. And basically Pfeffer goes through and says all the leadership industrial complex about authenticity and trust and judgment and all those things.

 

If we did indeed value those things, our companies would look very different. I needed to read that book as a reminder. You know, we put a lot of these things out there about, he’s like, if we, you, if you, if we cared about authenticity as much as we talked about it, our companies wouldn’t be, it’s authenticity, it’s very hard to be authentic in the corporate environments that we’re in. He talks about trust and he’s like, actually we routinely, there’s studies, for example, that when companies go against contracts, we think that’s fine. 

 

That’s fine, it’s just business. It’s okay that the CEO changed their mind and now we’re gonna do layoffs, they’re not gonna do that. That’s just what happens in work. So it’s like, we obviously don’t care about trust very much as we we lie, actually perpetually lie, all of us do. And so that was a good book because I needed that level of grounding as sort of a reminder that again, going back to Gareth Morgan’s frames that, there’s more frames to the world than the sticky note frame. And so think that’s really, important. 

 

By the way, thank you so much, John. That was an amazing conversation. I hope you also enjoyed as much as we did.

 

John Cutler 

Yep, absolutely. This was so much fun. Yeah. What a way to spend a Friday. Now I’m ready for the weekend. It’s exciting.

 

Simone Cicero

Yeah, I really look forward to your upcoming post on the discussion we had on the customer powers shift. But again, thank you so much for everything and for our listeners. Of course, you will find as usual on our website, www.boundaryless .io/resources/podcast. You will find John’s episode with all the transcripts, the notes, all the links to the interesting things that John has mentioned during the conversation. Thank you, Shruthi, for your contribution as always and for our listeners. I hope you enjoyed the first episode of sixth season. More coming up until we speak again. Remember to think Boundaryless.