Thursday, September 17, 2026
A Strategic Conversation – Dr. Leandro Herrero and Mike Klein:
Management has a comfort problem. Not a strategy problem, not a talent problem – a comfort problem. And that comfort is built on linearity.
Do this, then this, then this. Declare a state. Progress to the next state. Manage the sequence. The world, in this model, is a machine. The machine has parts. The parts behave predictably. And the job of the leader is to keep the machine running according to plan.
It is a seductive model. It is also increasingly a dangerous one.
Leandro Herrero – organizational architect, psychiatrist, and founder of The Chalfont Project – has spent 26 years watching this model both persist and fail. Mike Klein, principal of Changing The Terms and editor-in-chief of Strategic Magazine, has spent two decades inside organizations navigating the gap between management’s linear assumptions and the lateral complexity of actual human behavior. Their conversation, condensed and edited here, starts with a deceptively simple concept – readiness – and ends somewhere considerably more unsettling.
Leandro Herrero: The reason readiness functions as such a durable organizational concept is that it fits the architecture people are already comfortable with. Things are sequential. You do this, and then you do this, and at some point in the middle you declare either readiness or non-readiness. And then the sequence continues. It has all the appearance of rigor without requiring anyone to define what the declared state actually means.
Mike Klein: And by the time you’ve built the entire preparatory structure – the awareness campaigns, the process work, the governance architecture – you could have done what you were originally trying to do. The readiness process consumes the time that action would have used.
Leandro Herrero: That is exactly correct. And what is underneath all of it is the assumption of linearity. The old-fashioned models of change are still there. They still dominate. You do that, and then you do that, and then you do that. And always at the beginning is awareness, readiness, preparation. Meanwhile life is running in parallel three hundred times faster than your ability to be ready or not ready.
The Machine and Its Discontents
This is not simply a change management problem. It is a model-of-organization problem. The mechanistic view – the organization as a set of coordinated parts, predictable in their interactions, manageable through process – has never been an accurate description of how organizations actually work. It has, however, been an extraordinarily useful fiction. Because what is mechanistic is controllable. What is controllable is comfortable.
Mike Klein: This is symptomatic of a management culture that’s incapable of adapting to external developments in real time. The discourse – on LinkedIn, in conferences, in executive education – is recycling. The same models get relabeled. The same frameworks reappear with new names. The critical thinking required to actually interrogate these concepts is, as you’ve put it, in short supply.
Leandro Herrero: In short supply is generous. The level of recycling and the growth of echo chambers is not just static – in some ways we are going backward. People retreat to the more predictable and comfortable. I think it is partly because when everything feels uncertain, the machine feels like safety. It gives you something to hold onto. A process to follow. A sequence to trust.
Mike Klein: There’s a structural explanation for some of that regression. Experienced people age out of fields. Their successors inherit the models without the accumulated critique. In internal communication – which I know best – you get the phenomenon of the team of one: a single practitioner building a function from scratch, rediscovering the same things the previous generation already figured out, and having the same revelations about cascading communication that someone had twenty years ago. It is a rinse-and-repeat cycle. And the management schools, in the main, are not disrupting it – they are perpetuating it.
The Naming Problem
One of the more pointed observations in Herrero’s work is that naming a problem does not solve it. It relocates it. It creates a box – a concept, a term, an accountable function – and once the box exists, the cognitive work feels complete. The problem has been acknowledged and assigned. The machine can continue.
Leandro Herrero: This is how management has worked. And people have been very happy doing it. You create a concept, you create a box, you put a head on that box, and now the problem is theirs. Engagement has been done this way. Readiness is done this way. Wellbeing is being done this way now. All you’ve done is create another layer of cognitive understanding without solving anything.
Mike Klein: And the function that gets handed the box gets handed it without the power to do anything meaningful with it. Internal communication is a perfect example. You are given employee engagement as a mandate. You have no extractive power. No organizational authority. And when it doesn’t work, you are the ones on the hook. The function becomes a place to absorb blame for failures that were structural from the beginning.
The House That Isn’t a House
There is one context in which the language of readiness makes genuine sense, and it is instructive for what it reveals.
Mike Klein: When you are implementing SAP – a highly mechanized, highly linear system that demands extreme consistency – you can make a legitimate case for readiness. Everything needs to fit neat boxes before the system goes live. That is a genuine pre-condition. That is where the language actually works.
Leandro Herrero: Yes – if you are building a house and you say, I am doing the windows and the roof is coming, it is correct to say the house is not ready to live in. That is a logical use of the term. But we are not talking about houses. We are talking about cultures. About people. About dynamics between human beings. And you cannot apply the mechanics of the physical world to an organization, which is not a mechanism.
This is the key problem in management thinking – particularly in the West. We have a mechanistic view of organizational life. The organization has pieces. The pieces can be replaced. Some pieces need more oil. If you think in those terms, you can manage the parts without confronting the whole. But the organization is not a machine. We are human beings. We think and act in ways that are not mechanical. And forcing us through mechanical sequences is what produces the failures that then get renamed and assigned to a new box.
What Comes Next
The persistence of the linear model is not primarily a matter of intellectual failure. It is a matter of what the model provides that its alternatives do not – specifically, the feeling of control. Organizations do not reward ambiguity. They reward the appearance of managed certainty. That appearance is what linear sequencing delivers.
The question is whether the gap between appearance and reality has grown wide enough – and consequential enough – to force a reckoning.
Leandro Herrero: The life cycle of new concepts and terms is getting shorter and shorter. Things appear and disappear faster than before. That should be a signal. But the underlying thinking has not changed to match the speed of the surface churn. We are still running the same system with new labels.
Mike Klein: Readiness, ultimately, is a 20th-century ERP implementation concept that has persisted into a 21st-century non-linear, accelerated workplace. One of those two paradigms has to give. The question is which one gives first – and under what kind of pressure.
That pressure is building. What it produces is the subject of the next conversation.
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Dr. Leandro Herrero is the founder of The Chalfont Project and the creator of Viral Change™. Mike Klein is the principal of Changing The Terms and editor-in-chief of Strategic Magazine.
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