Stop Running Your Company Like a Machine

But first, let’s introduce the authors. Phil and Jana bring deep leadership experience from global organizations like McDonald’s, Tesco, and DHL and later joined AWS, where they now help enterprise customers design transformation strategies suited to the AI-driven digital age. In the course of speaking with around 1,500 executives each year from large-scale organizations, few are better positioned to understand the behavioural patterns that drive or prevent change within large corporates.

Tin Man Organisations

“The book started partly out of frustration”, Jana explained. “We worked with these incredibly talented, thoughtful and driven people that were completely stuck in the swamp of their company’s bureaucracy. Increasingly, we came to understand why. So many organizations are still built like machines, based on the scientific management doctrines of Frederick Taylor which were formulated almost 150 years ago. We refer to this as the “Tin Man” paradigm, describing organizations optimized for mass production and conditioned to rely on heavy process and top-down decision-making. Though that may have worked perfectly fine during the industrial age, where environments were complicated but outputs predictable, this current time of high complexity needs a completely different approach.”

So they introduced a striking metaphor: companies as octopuses, “miracles of distributed intelligence.” An octopus doesn’t wait for instructions from a central brain before an arm explores a crevice or recoils from danger. Nearly two-thirds of its neurons live in its arms, enabling fast, local decision-making.

Jana and Phil argue that organizations should stop designing and controlling rigid “machines” and instead cultivate adaptive “organisms” by empowering the edges. To make this possible, they propose that healthy organizations need three biological hearts, just like the octopus has: Clarity, so the arms understand the mission; Ownership, so they have the agency to act; and Curiosity, so they can sense, learn from, and respond to their environment.

The Problem With Total System Reboots

For those of you old enough to remember Zappos’ holacracy approach or Frederic Laloux’ concept of the “Teal Organization”: the Octopus Organization does indeed lean on similar tropes, like decentralization and empowerment. But there is also one huge difference: Jana and Phil do not advocate for a total system reboot. “We’ve seen these types of large-scale transformation projects happen time and time again in our careers and they just don’t work”, explained Phil. “One big reason is that these projects tend to push change to their employees, rather than orchestrate the change with them. That is why the Octopus Organization is less about a rigid structural overhaul and more about influencing behaviours. You can be an Octopus Organization and still have leaders, for instance. You can still have a hierarchy. The difference is how information and decision rights flow through that hierarchy. We focus on their bad habits that Jana and I termed "Antipatterns", because you can fix those one by one without needing to fire all your managers tomorrow. It is an evolutionary approach, not a revolutionary one.”

AWS is a great example of an organization with many Octopus-like characteristics, though Phil was also quick to point out that there is no such thing as a perfect Octopus company. Most of all because it’s not an end state or even a map (“This is how you get there”) but rather a mindset and a set of behaviours that must be continuously practiced and adapted as the organization evolves. “You need to keep mowing the lawn”, as Jana put it.

What makes Amazon so much Octopus-like is its highly distributed approach. “It isn’t a monolith; it’s a federation of independent, "two-pizza" teams”, explained Phil. “Each team has a single-threaded leader who owns their roadmap, their P&L, and their technology stack. They don’t need to coordinate with headquarters to release code. They are the arms of the Octopus and they have the best form of intelligence to make the best decisions.” “We’re also pretty radical in maintaining our core principles”, he continued. “There’s this mutual understanding that it's not good enough to say “we're not going to be a bureaucracy”. You actively have to become anti-bureaucratic. Andy Jassy, for instance, had a mailbox at one point where you could mail any rusty bureaucratic process that was standing in your way.”

Chasing Antipatterns

Phil and Jana’s concept of antipatterns is probably one of my favourite ones in the book: “conditioned, formulaic responses to complex challenges that, despite good intentions and surface-level appeal, consistently make things worse”. They came up with 300 different ones, together with their network of executives, and identified 36 different overhauling categories. It is the identification of these harmful patterns that make the book so practical, because they help identify mindsets and processes that obstruct and can be tackled.

“Lack of focus and priority is one recurrent example of such an antipattern”, explained Phil. “When we ask leaders “What is the one Big priority inside your organization”, they tend to shrug or even laugh it off. “So often, they try to be everything to everyone, afraid of making choices. You know the type: “We are now going to become the most sustainable, most people centric, most customer centric platform-based organization in the world that uses Machine Learning and Agentic AI.” It sounds “leadershippy” to state things that way, but it mostly results in a lack of clear purpose and a meaningful direction.”

Interesting here is that this antipattern concept follows a decluttering mindset, where you find friction inside your organisation and try to remove it. The default mode of human beings, and thus of leaders, is so often to add something - a process, a tool, a service etc. – to fix a problem, rather than to omit or subtract something. So, yes, getting rid of antipatterns is hard, counterintuitive, and requires unlearning. But it’s also not harder than investing time and talent in huge transformation projects that fail more often than not.

Lose The Friction, Not The Value

Jana also made the clear distinction that such a simplifying mindset does not mean blindly replacing humans by intelligent technologies, which seems to be a popular narrative in this accelerating age of AI. I immediately had to think about Klarna boasting that their customer support AI agent was handling two thirds of customer chats after one month, the equivalent of 700 human agents. A few months after which the message followed that it was re-hiring human agents after all because its AI chatbots disappointed customers. “Don’t cut down on value or on humans for reasons of pure cost efficiency, which is a very Tin Man-like approach.”, said Jana. “But lose the clutter, the friction, the things that hold your people down, like unnecessary approvals and guardrails.”

Because of all the former characteristics like unlearning, curiosity or empowerment, the Octopus Organisation requires a specific type of leadership. One that is very much about letting go of Pavlovian reactions to organizational issues. Octopus leaders are system architects, or "culture architects", as Astro Teller, CEO of X, Alphabet's moonshot factory would put it.

"Octopus leaders do not dictate, find answers and solve all problems", said Jana. "They orchestrate and help define clear direction. And that tends to be very uncomfortable for the type of leader that  “grew up” in traditional, hierarchical organizations and have been shaped by that way of operating. Because orchestrating feels like “doing nothing” to them. Their relevance no longer lies in being the lone heroic problem-solver but from pulling value from the entire organization, providing clarity on the end goal and purpose and trusting that their team will get there. It means letting go of the dopamine rush of being the hero and embracing the oxytocin and serotonin that come from making others shine and succeed.”

Humble, Hungry And Smart

“I love Patrick Lencioni’s framing that leaders need to be humble, hungry and smart, with each of these characteristics being mandatory for good outcomes”, said Jana. “The humility part is perhaps the least obvious and most difficult one, but we experienced it time and time again with all the successful leaders that crossed our path. Dame Julia Hoggard, CEO of the London Stock Exchange is a beautiful example of that. Or Benedetto Vigna, CEO of Ferrari.”

“Benedetto once talked openly about his mistakes on CNBC for the very strategic reason of showing his people that failure was just a part of innovation”, added Phil. “He wanted to show that he did not have all the answers (nor should he) and that he realized that he did not need to be the best at everything inside his own company. Andy Jassy, too, is a great example of an Octopus-driven leader. He does not tend to “lead” his teams in the classic sense of the word, by telling them what to do. He trusts them. But also offers them a clear values compass with Amazon’s 16 leadership principles, among which are ownership, curiosity and customer obsession.”

That same customer obsession is also a huge theme in Phil and Jana’s book. “Customers are a bit like the ocean’s current for an octopus”, explained Jana. “Jeff Bezos perfectly described how they should steer an organization’s strategy and decisions:”

There are many advantages to a customer-centric approach, but here’s the big one: customers are always beautifully, wonderfully dissatisfied, even when they report being happy and business is great. Even when they don’t yet know it, customers want something better, and your desire to delight customers will drive you to invent on their behalf. No customer ever asked Amazon to create the Prime membership program, but it sure turns out they wanted it, and I could give you many such examples.

“In other words, staying close to customers ensures there’s always a reason to keep innovating on their behalf,” she continued, explaining Jeff’s intent. “For companies that genuinely listen, this closeness becomes a continuous engine for evolution, a compass that compels them to evolve and keeps their curiosity sharp.”

Clock Problems And Cloud Problems

We obviously also talked about the impact of artificial intelligence on companies and the Octopus approach. “AI is certainly enhancing the complexity of our companies and their context and will therefore only reinforce the need for Octopus organisations with distributed intelligence.”, stated Phil. “Just think about how a fleet of AI Agents working (semi-)autonomously will affect leadership’s knowledge of what exactly goes on inside their organisations. There are so many questions surfacing all at once. Where do you use an AI Agent and what needs human oversight? Do you treat agents like employees? If an agent makes a mistake, who is accountable? This is not about leaders answering all these questions by themselves or, just as worse, expecting the AI to answer all of them, but rather about asking the right questions. So the right people can investigate them, and experiment with them."

"People love to treat AI as an answer-machine", Phil continued, "but it’s not. And neither should leaders be, by the way. AI is a sparring partner and there to help with the drudgery, the dull tasks. More than ever, we will need our unique human characteristics in AI-infused systems. Clarity of purpose, critical thinking and curiosity will only become increasingly essential.”

Lately, I have become fascinated by how philosopher Karl Popper formulated an interesting distinction between “clock problems” and “cloud problems” in the 1960s. Clock problems are predictable and analysable. When something breaks, you look for the cause and fix it. That is the ‘complicated’ domain of machines, and especially of artificial intelligence. You can safely expect AI to make short work of many traditional processes. Cloud problems, by contrast, are fundamentally unpredictable. They change constantly, respond to their context, and cannot be reduced to a blueprint. Organizations are increasingly living in that ‘complex’ cloud world. And yet, they continue to manage those clouds as if they were clocks.

Jana and Phil’s book perfectly lands in that gap, by showing why treating complex organizations navigating a cloud-like context as predictable machines is precisely what keeps leaders stuck. Their Octopus mindset offers a more realistic, humane, and effective way forward: not by imposing control, but by cultivating the conditions in which intelligence, adaptation, and change can emerge from within the organization itself.