Introduction
In this third installment from 2017, our cynical protagonists find themselves at the precipice of corporate theater: a kickoff meeting for a “large-scale agile transformation” led by the infamous Mr. Werewolf. What begins as a buzzword-laden executive presentation quickly descends into a revealing behind-the-scenes conversation that exposes the dark underbelly of digital transformation initiatives.
This episode brilliantly captures the collision between genuine innovation and corporate control mechanisms, articulating tensions that have only intensified in the years since. As we look back from 2025, many of these observations appear strikingly prophetic.
As you read, you’ll discover:
- How executives appropriate innovation language while maintaining control structures
- The fundamental disconnect between operational efficiency and true innovation
- Why the “software factory” metaphor fundamentally misunderstands creative work
- The organizational immune system that neutralizes genuine transformation
- How complexity, uncertainty, and human psychology create perfect conditions for transformation theater
This episode operates primarily in the Chaotic domain of the Cynefin framework, where cause and effect relationships are unclear, power dynamics dictate narratives, and contradictory agendas create unpredictable environments. It also explores the boundaries between Complex innovation work and Complicated operational management.
Prologue – Post from 8. August 2017, Updated with 2025 Perspective
Dear reader, a friend and I are starting this story about Mr. Waterfallon and Mr. Aguilero. It is a stage where we can hopefully kick off some not-so-mission-critical but important trains of thoughts about our professional life.
For my whole life, I have seen, perhaps a little too much, the potential for innovation and smart growth. This has a local near-term view where I see new money when the right things are done with the right technology in the right way. It is a painful role, as you are by definition, a minority and have a hard time selling it and getting it done. The new word for this is Digital Evangelist. It also has a long-term view where we, or what can be considered as “we” after the singularity finally happens, are spread out through the galaxy and Mars is just one of the colonies in the solar system. This is my Mad Scientist hat. Keep this in mind when you stumble over some sarcastic, fatalistic statements – it is just a self-protection mechanism.
However, in our professional life, I see an intensifying Filter Bubble that massively distracts us from the bright future and the work that has to be done to get there. Everywhere around us, we read the posts we want to read. This includes travel pics from friends on Facebook, great inventions, success stories on how smoothly the digital transformation works in big companies and of course, as we are so uber-intellectual, spiced up with a well-balanced media mix on political achievements, the permanent critical global threat level, the latest sport results and – weather!
I also see that Deep Work is buried in short-termism and actionism, and people are still happy to pretend they are multi-tasking all the shit flying from all the fans around them. As research shows, this is simply wrong. As research also shows, this is linked to the skills we acquired in our recent near-term history — the ability to build entirely virtual stories, to share those by language and to even believe those.
In this environment, or reality, I have a hard time matching the great success stories with my personal, professional experience and I know nobody who does not admit the same, even though it may take one or more glasses of wine.
So, curtains up for Mr. Waterfallon, Mr. Aguilero, and friends…
PS: The overuse of all current buzzwords is an excellent way to pass through most Filter Bubbles in my network neighborhood. I also apologize for overstressing the average attention period.
Stage
Mr. Waterfallon and Mr. Aguilero are fictitious freelancer project managers, agile coaches, and digital evangelists. Today they attend the kick-off meeting for a large-scale agile project for a big blue chip company.
The CIO Mr. Werewolf is giving a speech to his new digital transformation team. In the past, he was not a true agile fanboy. When he buys a story, he makes sure it will be his story. The crowd is assembled in the conference room on the top floor of the company headquarter skyscraper. The view of the sunset is gorgeous, but all eyes are on Mr. Werewolf. Everyone knows that Mr. Werewolf is not amused if you are not listening.
WEREWOLF
…and the Blockchain will be our new Internet for transactions. My IT-team will lead the transition to a bright future. With Artificial Intelligence, Deep Learning, IoT, and Big Data, we will build the software factory which will transform the whole business model and drive the digital revolution towards a smarter way to work.
Our agile approach is a vital part of this initiative and may become the new industry best practice.
The whole management is dedicated to take control and help wherever it is necessary. You all know, I hate surprises. However, bad news must travel fast. But I am confident, and there will be no bad news.
Mr. Werewolf makes a pause, smiles like Jack Nicholson in Shining, makes eye contact with everyone in the audience, and concludes:
WEREWOLF
We will lead. We will manage. We will succeed. Thank you very much.
The crowd spends frenetic applause. Small talk. Cheap coffee. No one wants to leave the room first. Hand-shaking. Boot-licking.
Mr. Waterfallon and Mr. Aguilero shake hands with Mr. Werewolf, mumble some compliments about the visionary and encouraging speech, withdraw and take a seat in comfortable armchairs to see the breathtaking view of the setting sun.
AGUILERO
You see, it works. He gets the air time for an agile story which he fought against for years. Now he is capturing this agile story and turns it into his very own truth because he is the one controlling the storytelling channels. This truth is then the foundation for even more budget he is allowed to burn, also though it will have nothing to do with the agile mindset.
Mr. Aguilero rolls his eyes and throws up his hands in a gesture that reminds of worshipping ancient gods after an epic defeat.
WATERFALLON
Yeah, he is still the old one. He works on his dark dream of ultimate control in his software castle, why not just follow the alpha male?
AGUILERO
Look, he is just CIO, he is still having a hard time on the board of directors, as he is perceived as the tech guy, even though he has the best handicap. He is just looking to run the shop smoothly in an environment with less budget, less time to deliver, and higher operational pressure. In our days IT has little in common with innovation, which is my part, and you know I have a hard time to find sponsors for this. The real power is the CEO and strangely the COO. I see no reason why we need a COO and a CIO. Both run the company, and you can not isolate IT from the rest. It is again silo thinking, just agiler.
WATERFALLON
The agile manifesto has been digitally transformed, reinterpreted, demystified. You know why I am a fan of agile now! Because it gives us delivery managers the ultimate control over teams, to measure their inefficiency. It provides a wide selection of scapegoats if something fails. I love it, and as Mr. Werewolf, I can put nearly any story in the velocity or other KPIs my clients think are useful for them. They fake us, and I fake them.
AGUILERO
I am not contradicting you. The current agile hype is the greatest danger to the agile idea. The dark powers of dogmas and culture are about to engulf this fragile idea and ultimately kill it as they have done with so many in the past.
WATERFALLON
Backlog items in, product out, and some work accidents in between. A factory, right? In our modern agile world, we do not even need real blood or human sacrifice – it is OK to tell a story. You should be happy, in ancient times you would have been dead so many times!
AGUILERO
Why do you think we are here? Let me guess: you are confident to have mastered the software factory fake story, and you assume to be now immune to his tricks? Never forget you can only control what you measure, you should only measure what you can influence, and you can only affect the people around you. So your delivery job is one predefined story at the very end of a giant beast. Do you know his full agenda? I am confident, against better rational judgment, that I can contribute some few dents in the universe for a better future. In the past, this role has been often misused for propaganda. Future is innovation and requires change – a bad thing for the predominating conservative mindset on C-level.
Creating software has always been part of designing, building, and running organizations. A factory is a part just of the day-to-day operations. Creating and designing is full of risk and uncertainty. It’s for the entrepreneurs and visionaries. The action is for the bean-counting managers. It’s so absurd to organize the creative process of software design and development with an operations management approach.
WATERFALLON
But we are already doing this in oh-so agile projects. Sprints are just sections on the assembly line. WIP management, and this is what we still do. Well, the metaphor sucks, but you know what I mean, right?
AGUILERO
You are right. We do not expect an assembly line to come up with an invention, but that is precisely the dilemma software is facing. Maybe I have to go back in history, to make my point clear.
WATERFALLON
Please do not! Do not re-tell eons to explain why something failed yesterday. Please…
AGUILERO
It has always been a complex world, and it was hard enough to cope with it in the past. It was complex even in times when there was stability. Brick and mortar factories were built on best practices learned at a time before the industrialization started. Steam and electricity paved the first wave of corporate evolution.
WATERFALLON
In those days spirits were brave, the stakes were high, developers were real men coding machine language, women were real women, and small furry creatures from Alpha Centauri were real little furry creatures from Alpha Centauri.
AGUILERO
In the beginning, there was only one variable for business: the counter. It was much more important what to do than how to do. With scaling the denominator came into the game…
WATERFALLON
I am getting tired already. Please proceed!
AGUILERO
Those companies were built to last for decades if not centuries. Then, from the 50ies until Netscape was released, came the digitalization. Most like to call it computerization, and only the current topics digitalization, but it is just marketing. It is typical business lingo bullshit that sounds great and is as wrong as describing great inventions as a quantum leap. How ridiculous is a statement from a company like PwC claiming they are digital?
WATERFALLON
Yeah! We are playing bullshit bingo now! Bingo! Four in a row!
AGUILERO
Shut up and listen! I lost my train of thought. Ah! Digitalization was the next corporate evolution, still with the same mindset of WIP-management. Methods of operations research, which are OK, as long as applied to real-world problems and a set of over-simplifying methods from the not-so-scientific world of economics, rooted in linear models and a deep belief in rational decisions based on facts – the causality misassumption. Correlation is not the same as causality – read Wilmott and Taleb. You may learn stuff you could apply to your world. However, it helped us to integrate SCM, MRP, CRM, PIM, many other TLAs, and to get to the next level of optimized mass production. We were still building cars, incredibly more efficient, but what about effective? The damn vehicles again do not drive themselves or fly.
WATERFALLON
And now we integrate WTF and LOL. Aren’t cars close to autonomous driving? My kids turn into teenagers and may never need a driver’s license.
AGUILERO
Filter Bubble! Do you think that our automotive industry is willing to give up lessons learned in the last century? Do you think our politicians can pave the way for the discussion on new laws that are necessary to make this happen?
In the last century, a business could be planned. When the plan did not fit, marketing mesmerized the masses to carve whatever was pushed into the markets. At the same time, messages were transported from top to bottom – and middle management jerks felt important in doing so. They learned the cooking receipts that worked at that time. Now they are in charge, and the cooking receipts are deeply embedded. Cooking receipts became routines, and routines became the culture – the hidden immune system in organizations. It assimilates all that fits and spits out the dead carcass of anything that is different. As it is so typical for most prominent companies, it also turned into dogmas, the dark matter version of culture, which is embedded in the society itself.
Other as biological entities that have an increased probability of dying, culture and dogmas have an increased likelihood of becoming immortal! This does not match very well with the typical project timelines I am facing.
WATERFALLON
Here we agree. If you say all that too loud, you will be spat out. Preferably from the top story of the corporate headquarter skyscraper. The setting sun will underline the dramatic message: Look at Mr. Aguilero. He denied the software factory. What a creep, but we knew it from the very beginning. We have both witnessed this ceremony many times, and Mr. Werewolf has always surprised us with a new level of unprecedented cruelty.
AGUILERO
Funny. But please do not behave as a goldfish and be patient! Here is the point: Complexity and speed have not just increased; it is growing exponentially – it is exploding! Still, our core brain is mostly reptile. 2% of our thinking is aware. We are mostly on autopilot and driven by the old fight or flight reflex. We are not rational beings, we do not act intelligent, and we have a hard time to assess facts in an objective, unbiased, non-emotional way.
WATERFALLON
I read Kahneman, too. Nice read. So what?
AGUILERO
We cannot assess risk and uncertainty, but we measure and plan on an incredible detail level. Software is soft…
WATERFALLON
so many of your arguments are…
AGUILERO
…but software supports real hardware and the emotional animal inside us, the ideas we try to articulate using a tool that is 50 thousand years old, and the culture of the tribes we live in. Hardware is less virtual and potentially better understandable – it can be engineered. Plumbing can be crafted. Engineering provides the method set for stuff that is already known. It can be planned as long as it is not a real innovation.
WATERFALLON
The software can also be engineered. In complex environments, there is hardly any alternative to do so.
AGUILERO
But then it fails to unveil its real power! As I said, the business has two sides: One side, the denominator part, is about optimizing existing business. It is close to engineering and can be planned. The other hand, the one that counts, when it comes to real substantial growth, requires innovation. This is more a form of art. It requires creativity, and it can not be planned. Large corporations miserably fail at innovation. So they have to buy it.
WATERFALLON
Yeah and please do not forget, they just brought us to create the illusion of a creative process while we’re squeezing the last drop of blood out of our scrum teams – all to meet Mr. Werewolf’s timelines. I am happy to deliver him precisely what he deserves, a sweet story with no link to reality, except my banking account…
AGUILERO
Again why are we part of this excellent transformation initiative? I can not tell why, but I have a terrible feeling. I have the awful sensation we are exceptional guests at a scarification ritual.
What is your actual influence on the package you should deliver? What are my possibilities for influencing the business behind the lighthouse projects we should work on? Why am I not allowed to talk to stakeholders directly? Why is the project site so far away from the HQ? Why is our contract just for the first four months and not longer? Why is he not working with one of his smart asses he is so proud of? What is his real agenda behind the shiny agile transformation story?
WATERFALLON
Ask this, Mr. Werewolf directly. But maybe you want to catch him in the basement of the building for safety reasons. Oh, I guess this sprint is over – without any shippable conclusion, too bad.
Suddenly Mr. Werewolf drops in to collect some more merits for his visionary speech and the two have to stop their debate. But don’t expect this conversation to be over yet.
2025 Retrospective Analysis
The Buzzword Evolution
Looking back from 2025, Mr. Werewolf’s buzzword parade seems almost quaint. Blockchain, AI, IoT, and Big Data have all evolved significantly, with some delivering on their promise and others fading into the background. What remains constant, however, is the executive tendency to appropriate innovation language while maintaining traditional control structures.
The 2020s have seen new generations of corporate buzzwords emerge: Quantum Business, Metaverse Enterprise, Synthetic Intelligence, and Autonomous Operations have replaced the 2017 set, but the fundamental dynamic that Mr. Aguilero identifies remains unchanged – innovation language being coopted by control-oriented management.
The Death and Rebirth of Agile
As predicted in this dialogue, traditional “agile” largely died under the weight of its own contradictions. By 2023, the term had become so diluted that many organizations stopped using it altogether. What emerged in its place were more contextualized approaches – complexity-conscious delivery methods that acknowledged different domains required different techniques.
Mr. Waterfallon’s cynical view of agile as a control mechanism proved prophetic for many organizations that failed to understand the true nature of the transformation required. Studies between 2020-2024 showed that over 70% of “agile transformations” actually increased bureaucracy rather than reducing it, creating what became known as “Agile Industrial Complex.”
The Software Factory Fallacy
The dialogue’s critique of the “software factory” metaphor proved particularly insightful. By 2025, organizations have largely abandoned this framing, recognizing that creative knowledge work fundamentally differs from manufacturing processes. As software continues eating the world, the distinction between “building software” and “creating business value” has blurred to the point of irrelevance.
What replaced the factory model was what became known as “digital gardening” – the understanding that software products are living entities that require continuous cultivation rather than one-time construction. This shift acknowledged both the emergent nature of software development and the need for ongoing care rather than “build and forget” approaches.
Cognitive Biases and Organizational Psychology
The discussion about human psychology, reptile brains, and cognitive biases has become mainstream in organizational thinking. The work of Kahneman that Mr. Waterfallon dismisses became foundational to new models of leadership development, with cognitive science-informed decision frameworks now standard in many enterprises.
What neither character could fully anticipate was how dramatically AI would accelerate this understanding, making our cognitive limitations more apparent while simultaneously offering new tools to overcome them. By 2025, AI-enhanced decision support systems that account for human cognitive biases have become standard in many organizations.
The C-Suite Evolution
The tension between CIO and COO roles that Mr. Aguilero identifies resolved in unexpected ways. Many organizations have indeed eliminated the traditional CIO role, but rather than consolidating under COOs, they’ve created new positions like Chief Digital Officer, Chief Data Officer, or most recently, Chief AI Officer. The boundary between “technology” and “operations” that Mr. Aguilero critiques has indeed blurred beyond recognition in leading organizations.
What They Got Right
- The weaponization of agile terminology against its original intent
- The fundamental incompatibility between control-oriented management and genuine innovation
- The organizational immune system that neutralizes transformation efforts
- The cognitive limitations that make rational planning in complex environments nearly impossible
- The “sacrificial consultant” pattern, where external experts are brought in to take the blame
What They Missed
- The dramatic acceleration of AI capabilities that would transform development processes themselves
- The emergence of truly decentralized autonomous organizations that bypass traditional corporate structures
- The great resignation/quiet quitting phenomena that would shift power dynamics between employers and skilled workers
- The pandemic-driven remote work revolution that would fundamentally change collaboration patterns
Looking Forward
As we proceed beyond 2025, the tensions that Mr. Waterfallon and Mr. Aguilero articulate remain fundamental to organizational transformation efforts. While technology, terminology, and techniques continue evolving, the human, psychological, and cultural challenges they identify persist.
The most successful organizations have learned to embrace complexity rather than trying to control it, focusing on enabling conditions for emergence rather than command-and-control management. This shift requires fundamentally different leadership approaches – something that Mr. Werewolf and his ilk continue struggling to comprehend.
Perhaps in future episodes, we’ll see how our protagonists navigate this ever-changing landscape, continuing to expose the gap between transformation theater and genuine organizational evolution.