The vanguard CIOs I have worked with over the years built their organizations on modern principles of leadership, organization development, team building and diversity. They were not only strong technical leaders, but they also excelled at shaping resilient teams and a strong culture.
A new book by Phil Le-Brun and Jana Werner with the intriguing title “The Octopus Organization” reinforces the importance of understanding the people and organizational sides of leadership.
Le-Brun, now an executive in residence at AWS, previously served as McDonald’s corporate vice president of global development and international CIO. Werner is also an AWS executive in residence; she formerly led the enterprise transformation practice at AWS in EMEA and digital transformation at Tesco Bank.
The book is written for CIOs, their CEOs and fellow C-suite executives. In a conversation with Le-Brun, he made the case that effective CIOs engage directly with their executive teams and boards — both within IT and across the broader business C-suites — to accelerate their learning curves. The mandate for an organization’s top IT expert is to not only translate the technology for nontechnical executives, but also explain how it connects to business outcomes.
Phil Le-Brun, co-author, ‘The Octopus Organization’
“Our core conviction is that the true potential of technology will only be unlocked when the executive leadership understands not just the tech itself, but the organizational and leadership shifts required to become customer-centric, responsive, and resilient,” Le-Brun said.
Werner added, “Our work has a central message for CIOs: You hold a crucial role for cultivating the traits — clarity, ownership and curiosity — that define a continuously evolving organization.”
“Technology is the new leadership mandate,” which has ramifications for every person in the C-suite, she said. “Just as every executive must master the language of finance and leadership, the same is true for technology and data. It is no longer an operational concern; it is a core competency of the C-suite.”
Werner said IT and data competency start with establishing radical clarity around the business outcomes technology must drive. With technologies like AI and machine learning, the only factors limiting an organization from completely reinventing its core value proposition are its imagination and the existing skill sets of its people.
The CIO’s job is to foster a culture of curiosity that relentlessly seeks out these reinvention opportunities, acknowledging that long-term plans and roadmaps normally represent guesswork disguised as reality.
How is that culture of curiosity operationalized amid the rapidly changing IT landscape?
The book is a practical guide to what works — and what doesn’t — in organizational and people development. It captures much of what I learned facilitating conversations in #CIOChat on LinkedIn.
Tin Man vs. Octopus organizations
The authors illustrate the tenets of their approach by contrasting two types of organizations — traditional, mechanistic “Tin Man” organizations vs. modern, adaptive “Octopus” organizations — across 36 management behaviors.
For each behavior, they identify what they call anti-patterns and how to implement corrective action. This guidance is invaluable for leaders who need to quickly assess, adapt, and transform their organizational environment. It should prove especially useful for CIOs, who often have to diagnose situations and then determine what needs to be fixed.
Jana Werner, author, ‘The Octopus Organization’
Six behaviors of Tin Man organizations
Here are the six basically bad behaviors characteristic of Tin Man organizations.
1. Rigid structures. Tin Man organizations are constantly searching for external fixes to operate better. Their business model emphasizes standardization, specialization, control, measuring individual performance, compliance, mass production and predictable outputs — in other words, rigid structures. Even late 20th-century management theorist Russell Ackoff warned that this kind of machine-age thinking reduces people to function like, well, machines and typically leads to reactive or inactive planning.
2. Short-term focus. Le-Brun and Werner describe Tin Man organizations as being built on permission-based structures designed to minimize risk and eliminate variation. This structure, which centralizes control and relies on strict rules, makes enterprise architecture more challenging and creates highly controlled information flow, as IT activities are typically either run or changed by the business. Ultimately, this rigid central control results in short-term thinking and stagnant IT. CIOs have regularly told me that, as bad as the technology stack can be, people are the hardest problem to solve. For this reason, it comes as no surprise that many transformation failures are predominantly caused by organizations having this operating model.
3. Confused priorities. Tin Man organizations rely on jargon, creating a confused workforce, fragmented priorities and wasted resources. Leadership in these environments is frequently seen as evasive, manipulative and dishonest. As the authors note, these organizations “whiffle on purpose statements laden with buzzwords, resulting in a lack of trust, lost opportunities, and difficulty finding talent.”
Tin Man organizations also turn everything into a “strategy,” pursuing vague, ambitious goals that are disconnected from their organization’s purpose. Teams, not surprisingly, struggle to understand what work truly matters. And because actionable goals are lacking, metrics become misused — shifting the focus from creating value to simply hitting the numbers.
I remember visiting one of Italy’s largest banks several years ago. The CIO installed high-definition screens across offices, especially in the director and vice president offices, displaying performance against 150 tracked metrics. When I asked what was most important, the deputy CIO said, “everything.” The response spoke volumes. Measuring everything meant the organization had no priorities.
4. Struggle with teamwork. Even worse, Tin Man organizations have issues with teamwork. Conflicting agendas, turf wars, failed cross-functional efforts and slow decision-making are common. For this reason, decision-making slows, priorities are spread too thin and productivity, morale and clarity all suffer. Moreover, an emphasis on customizing processes in the belief this work adds value is in fact counterproductive. The authors note the Gartner figure that 70% of ERP implementations fail, often because internal processes are made unnecessarily unique and add no enterprise value.
Tin Man organizations also create and reinforce silos by focusing on local inefficiencies instead of enterprise-wide improvement, resulting in fragmented value streams and unpredictable outcomes. These organizations hoard information, resulting in poor decisions, loss of competitive advantage, a culture of distrust and an inability to control outcomes. In turn, this causes these organizations to lean into frequent reorgs, which result in lost productivity and shifting the focus from customers to organizational survival.
5. Breed fear. This environment breeds fear. Team members hesitate to take ownership, voice concerns, share ideas or admit mistakes — fueling disengagement and missed opportunities. Making matters worse, management in Tin Man organizations actually upholds poor leadership. This includes creating gatekeeper approval processes that reduce agility and slow time to market.
Le-Brun and Werner claim that Tin Man organizations fetishize processes. Here, process overwhelms judgment, decision-making becomes perfectionistic and accountability blurs.
Meanwhile, poor hiring practices compound the issue, as individuals are valued over teams and incentives are misaligned. I remember at HP, the emphasis on individual performance once led to me receiving an outsized bonus. Frankly, it was embarrassing — it signaled a broken system, not exceptional performance.
6. Pursue the wrong things. Tin Man organizations prize achieving preset goals and avoiding failure. Instead of listening to customers, they often rely on proxies, causing them to miss opportunities and waste resources. The authors cite General Magic as an example. A former colleague of mine — Apple’s sixth employee — was on General Magic’s leadership team. The company created brilliant technology, but it stumbled during a period when its leaders were convinced they already knew what the market needed. I later advised another company formed by three CIOs with deep market knowledge but no design partners. They, too, missed the mark, never quite delivering a minimum viable product.
Making matters worse, Tin Man organizations avoid hard problems and tough conversations. Their teams are homophilic, and their leaders defer to easily measured data rather than meaningful insights. They separate technology from the enterprise, focusing on systems of record rather than systems of engagement. Meanwhile, they downplay talent development and only pretend to innovate.
3 traits of Octopus organizations
Octopus organizations, by contrast, have the following traits and behaviors:
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Adaptable. Octopus organizations, in contrast, prioritize adaptability, decentralized ownership, interconnectedness, and continuous learning and experimentation. They foster connection, distinctiveness, problem-solving, agency, ecosystems and long-term thinking. Importantly, they are able to pursue a dual strategy — intertwining running the business and changing the business.
Octopus organizations build diverse teams and use language that fosters clarity through shared understanding and collective purpose, ownership and curiosity. This creates an authentic and practical purpose that inspires teams. At the same time, it drives sharp focus on a few durable customer needs that generate unique value. In so doing, Octopus organizations choose where to play and how to win.
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Make strategy a continuous process.Octopus organizations engage in vigorous, ongoing debate about organizational tradeoffs. This helps them identify strategic inflection points early. Another critical behavior? Octopus leaders listen more than they talk, ensuring goals align with customer value and growth. A key part of this is understanding the why before setting goals. And then making sure goals are specific, understandable and clearly owned.
Their measures connect directly to value and purpose, which accelerates learning. By enabling real collaboration among peers, teams deliver greater enterprise value. They do this by ruthlessly prioritizing and deprioritizing — embracing “a less, but better” philosophy. This frees teams to focus on differentiation.
A key enabler of this is enabling team members to immerse themselves in the customer’s world to identify and hone differentiating capabilities. At the same time, Octopus organizations carefully choose what not to do, focusing on the flow of value from idea to customer. They tackle bottlenecks across the entire value stream, not just within departments. They avoid hoarding insights, instead making them accessible to all, creating transparency that fosters innovation.
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Resist bureaucracy. Organizationally, they resist bureaucracy and bloat, instead prioritizing both structural stability and flexibility. They communicate about reorganizations early and ask hard questions about their investments. They strive to develop psychological safety and lead with empathy, humility and curiosity — transforming leadership from a role into a behavior. With clear tenets and guardrails, they replace checkpoints and empower self-sufficient teams that reduce dependencies and increase productivity.
To make this work, they dismantle bureaucracy and accelerate innovation by asking whether work can be eliminated or simplified. They favor “good enough,” reversible decisions that promote speed, learning and growth. They value learning agility and lived experience over credentials. This produces high-performing, cross-functional teams and cultivates ownership and mastery — the strongest source of intrinsic motivation.
Simply put, Octopus organizations pursue rapid, valuable learning, which, in turn, minimizes risk. They are obsessed with understanding real customers to ensure long-term relevance and value. Ultimately, they forge new futures for customers and reshape markets. They love problems, invest deeply in understanding their root causes and use that insight to deliver superior solutions. By tackling the hardest, riskiest parts of projects first, they learn and validate faster.
They use constructive dialogue over superficial harmony, strengthening team performance. They enhance problem-solving through cognitive and intellectual diversity, making data-informed decisions that respect human experience and improve outcomes. By investing in data and digital literacy, they bridge divides and unlock innovation — turning “red people” (technologists) and “blue people” (domain experts) into “purple people,” making innovation everyone’s jobs.
40 fixes to implement today
The authors provide CIOs with a set of concrete suggestions for rewiring their organizations for success. Here were the key ones that I would recommend to the vanguard CIOs I know.
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Connect every initiative to concrete customer or business outcomes.
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Be clear about your purpose.
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Anchor your organization on durable problems.
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Make strategy accessible.
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Communicate continuously.
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Define a small number of critical goals that address a challenge or opportunity
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Focus metrics on learning and improvement.
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Conduct project and metric postmortems.
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Test for business alignment.
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Hold silo-busting problem-solving sessions.
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Create a “stop doing list” and kill criteria for any project upfront.
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Map out your competitive advantage with customer data and validated assumptions.
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Identify bottlenecks, handoffs and wait times, and use this to fix value streams.
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Become a data sharer and challenge a need-to-know culture.
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Decriminalize bad news and mistakes.
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Communicate early and honestly about change.
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Create zero-baseline budgets.
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Ensure that leaders speak last, ask what they are missing, and start meeting with questions.
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Cultivate self-awareness.
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Transform gatekeepers into coaches.
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Accelerate decision speed and think of decisions as bets.
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Create outcome-based job descriptions.
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Broaden recognition methods.
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Reduce the distance between customers and leadership.
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Work to visualize the future.
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Mandate clear problem/opportunity statements.
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Cultivate intellectual honesty with projects.
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Audit meeting practices to reframe conflict as curiosity.
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Encourage cross-pollination in decision-making.
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Elevate data literacy and seek out counter-narratives.
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Seek a common business vocabulary.
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Connect innovation to those closest to the customer.
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Do change with people, not to them.
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Entwine learning and impact.
While CIOs may not always have the good fortune of working in Octopus organizations, they can build one within IT. Of course, it is certainly much easier to operationalize this structure if IT and the business are on the same page. Savvy CIOs will find the right organization in which to work. For those ready to begin the journey, this book offers not only clear contrasts but also the tangible steps for CIOs to drive meaningful change.
